How to Eat Nachos and

Influence People
a guidebook for business (and life)

Obie Fernandez
This book is for sale at http://leanpub.com/nachos

This version was published on 2015-01-17

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©2013 - 2015 Obie Fernandez

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Also By Obie Fernandez
The Lean Enterprise
Programación para Niños
El Libro Principiante de Node
To Lark, always my first number one fan. Even if you
won’t return my calls anymore…
Contents

Introduction . . . . . . . . . . . . . . . . . . . i

The Laser . . . . . . . . . . . . . . . . . . . . . 1

Maximum Impact . . . . . . . . . . . . . . . . 10

Metacognition . . . . . . . . . . . . . . . . . . 16

Perfectionism . . . . . . . . . . . . . . . . . . 25

Purpose . . . . . . . . . . . . . . . . . . . . . . 29

Values . . . . . . . . . . . . . . . . . . . . . . . 48

Power . . . . . . . . . . . . . . . . . . . . . . . 56

Dressing the Part . . . . . . . . . . . . . . . . 75

Never Work With Crazy . . . . . . . . . . . . 91

There Is No Spoon . . . . . . . . . . . . . . . . 121

CONTENTS

Communication . . . . . . . . . . . . . . . . . 130

Punctuality . . . . . . . . . . . . . . . . . . . . 161

The Power of Names . . . . . . . . . . . . . . 170

Introduction
I started writing this book in 2008, at the behest of
my buddy John “Lark” Larkowski. In the years since,
it’s gone through a series of phase shifts. Initially, it
was targeted strictly at consultants and structured as a
collection of power plays, actions that subtly commu-
nicate that you’re in control of a client relationship.
The key word being subtle since overt displays of
power are just going to put off the client, right?
But in subsequent years, as my web design &
development firm, Hashrocket, became successful, I
lost interest in writing simply about power plays. (I
also lost my notes where I had a big list of power plays
jotted down. So much for that idea.)
Instead of starting over, I considered how I might
approach a guidebook about philosophies of con-
sulting in general. And when I mentioned the new
direction to Lark, he suggested that I call the book How
To Eat Nachos and Influence People. I thought the title
was hysterical, and loved its play on the title of Dale
Carnegie’s classic book. So I renamed the manuscript
and carried on.
Introduction ii

That was seven years ago, and I have added a lot of

material during that time. But I wasn’t able to finish
the book.
The thing is, now I’ve also lost the motivation to
write an entire book on just consulting. While I have
a lot of experience on the subject, consulting doesn’t
really gets my creative juices flowing anymore. Sell-
ing your time to others can be a means to a profitable
end, but often lacks any sort of spiritual or emotional
fulfillment, because you’re not usually working on
your own ideas. Given that we spend so many of our
waking hours at work, I’ve come to the conclusion
that it’s much better to work on stuff that you enjoy. If
that happens to coincide with work that clients want
to pay for, more power to you.
I know, I know. Only doing stuff you enjoy is a
total cliche. The purview of privilege. Luckily, I’ve
been one of those people. And I’m a writer, so write
about it, which also constitutes work that I enjoy.
Ain’t life grand?

In getting to where I am today, the universe has

granted me a ton of insight and wisdom. But it has cost
me, sometimes dearly. One of the benefits of being a
writer living a transparent life and having no shame,
is that it’s easy to talk about yourself with little to
no censorship. That means I can talk about those life
Introduction iii

lessons in print, with the ultimate hope that some of

you might be able to learn those hard lessons at a
lesser cost than what they cost me.
Along the lines of my previous writings, the book
you hold in your hands could be called The Obie Way,
because what I’ve ended up writing is part memoir
and part personal guidebook for a successful working
life. Perhaps like me, you are ambitious to be a winner
at this game called life, but don’t necessarily have
a traditional foundation for doing so. Listen, I don’t
have any formal education beyond high school, from
which I barely graduated. So this book is based on
over 20 years of bumbling self-discovery, gradually
building up to the success I currently enjoy. Some of
the minor details are invented because of my spotty
memory, but I swear that the stories in this book
actually happened.
At best you will use some of the information in the
book to fuel your own success, but if not, I sincerely
hope that you at least get a good laugh or two. And
if you happen to run into me at a bar, feel free to buy
me a drink and a plate of fully-loaded nachos.
The Laser
In the summer after fifth grade, my brother and I
made a stunning discovery in the parking lot of the
office building down the street from our childhood
home. There sat, next to the dumpster, a large, dis-
carded Xerox photocopying machine. Calling it large
doesn’t really do this thing justice. Unless you’re my
age or older, you might not realize that in those years
a large photocopier was perhaps 6 or more feet long
and weighed almost as much as a car.
Now, in order to begin to understand where I’m
coming from with the stories and advice in this book,
you should know that throughout early childhood, my
favorite hobby was taking mechanical and electronic
things apart. Discarded old televisions, telephones and
record players were dragged home from the curb,
analyzed and dissected for parts. During the eighties
(and still today, I think) the town where I grew up,
Hackensack, NJ, in northern New Jersey, was chock
full of light industrial and commercial buildings, in-
terspersed freely amongst the modest, working class
houses. When not in school, my friends and I roved
the neighborhood in search of treasure, prowling the
loading docks and dumpster diving.
The Laser 2

Despite our predilection for electronics, treasure

came in many forms. Sometimes it was reams of dot-
matrix report paper, with its characteristic green/white
striping, full of mysterious codes and numbers. Other
times it was thick bundles of wiring harnesses yanked
from (what we imagined to be) exotic machinery.
Most dumpsters were quite a bit bigger than we
were; the term “dumpster diving” is a literal descrip-
tion of the work involved. The bigger ones necessi-
tated cooperation, and equitable dividing of the spoils
afterwards. Negotiation would ensue, after which we’d
all take our pieces of the prize back home for further
investigation.
The 1890’s-era duplex home that I grew up in had
plenty of storage areas in the unfinished basement
and detached 2-car garage. I remember maintaining
at least a dozen distinct caches, filled to the brim
with boxes of old motors, gears, wires of all colors
and gauges, batteries, gear assemblies, mirrors, lenses,
voltage transformers and electronics of sorts and sizes.
Transistors, capacitors, resistors, diodes. You name it,
I had it, carefully de-soldered, categorized and put
away for future use.
Vacuum tubes held special appeal, but not in the
nostalgic way you might expect. Lobbed across the
parking lot at friends during mock battles, they made
a satisfying simulacrum of a grenade, especially the
The Laser 3

bigger ones.
Which is a long way of explaining why finding
an entire photocopier was such a big deal. It was
like an insatiable pack of young lions encountering a
freshly killed moose. The old Xerox was the proverbial
motherlode of STUFF. It was packed full of motors
and mirrors and prisms and lenses. We rushed back
home for our tools and attacked the machine with the
ferocity of fire ants on a dropped honey-glazed donut.
First to go was the outer shell. Picture beige metal
panes being hastily unfastened or pried off and flung
casually over our shoulders. Then we pulled individ-
ual modules and components. And then I spotted the
sticker that made my young heart stop.

LASER WARNING

Holy shit! There’s a laser in there. There’s a LASER

in there!!! A real bonafide laser. And it was all mine.
(My brother wasn’t old enough to claim his own stuff
at this point.) The sun was setting, but we doubled
down on disassembly to dig the laser unit out of the
guts of the beast. It was a two-foot long hunk of solid
machined aluminum, on a steel base, with a thick
black wiring harness coming out one end, and a small
hole on the other.
The Laser 4

The sun was setting, so I carefully noted where the

harness connected to the laser’s power supply, then
walked my prize home. At the crack of dawn the next
day, my brother and I were up before anyone else in
the house. We pulled our clothes on and rushed down
the street to claim whatever else we could. I needed
that power supply. It was heavy, and took quite a bit of
work to remove, but we finally got it loose and carted
it home in our radio flyer.
Remember this was circa 1985, so ordinary people
didn’t have lasers the way they do now. I was super
eager to get this thing put together and try it out.
Problem was, while it was obvious how to connect the
laser unit to its power supply, it was far from obvious
how to connect the power supply to a source of elec-
trical current. This was also pre-internet, so looking
up a technical manual for the machine was out of
the question. After no small amount of nervousness, I
decided to partially disassemble the power supply to
figure out how it worked.
With the cover off, I was able to find which
wires of the harness led to the supply side of a large
transformer. This presumably would accept a normal
electrical current. Impatiently, my brother and I un-
spooled a large stretch of house wiring and patched it
into the power supply. Then we inlined an old light
switch and finally, a wall power plug.
The Laser 5

At this point I remember some argument about

what would happen when we connected the power.
At best we’d be blessed with our own laser beam,
and become local heroes amongst our friends. At
worst it wouldn’t work. Scratch that, at worst the
power supply would explode because we hooked up
the voltage incorrectly. Being somewhat risk averse
and afraid of my father’s wrath, we decided to put
the whole rig outside on the concrete patio out back.
Because, you know, shrapnel.
We also weren’t sure what kind of laser it was, so
we pointed it at the concrete wall behind the garage.
The power cable was hastily hoisted up through the
kitchen window and we scrambled back into the
house to finally run our experiment.
Hunched up and praying as hard as we could, we
dipped below the window sill for safety and click, I
flipped the power on. No explosion. Okay, step one
was a success. But was the laser on? We peeked out the
window, unsure if we’d be blinded. Nope, no blinding
light, other than the bright sunlight of a clear summer
day. Alright, outside we go. We ran out the house and
to the patio. Wait, is that a red dot? Is that a RED DOT?
It is, it is! Hallelujah, it works!
I’m sure at that point my brother and I did our
version of an irish jig, dancing for joy at our good
fortune. I bent down and listened to the power supply,
The Laser 6

humming away quietly. Awesome. Then I picked up

the laser unit and swung it around. The dot folllowed,
wherever I pointed. I swung it around and put it on
my brother’s chest.
“HEYYYY!!!”
“Don’t worry, stupid, it can’t hurt you.”
“You don’t know that!”
“Well, it’s not doing anything to you is it??”
“I guess not.”

I know. Real scientific prowess on display there, right?

I swung the beam back in the opposite direction and

pointed it at the neighbor’s house, about 50 feet across
my backyard. There was the dot. Wow. So cool.
“I wonder how far we can make it go?”
“We can probably light up the moon” exclaimed
my brother.
“Oh my god, probably!”

My uncle’s friend Eddy arrived and asked what we

were doing. We have a laser, man! Instantly, Eddy
regressed from 30-something to our age. That’s the
kind of effect this thing had on people. Seriously, it
was like the coolest thing ever.
The Laser 7

I ran inside and started telephoning my friends to

come over and bear witness to my greatness. Before
long a small crowd was gathered behind my little
house.
Shining a little red dot around the backyard, or
simply staring at the shimmering light that it pro-
jected got old rather quickly. So we carted the con-
traption out in front of the house for further experi-
mentation. Lodi Street was long and straight. So we
aimed the laser down at the old St. Francis church,
about a block and a half away. We could still see the
dot!
Then we aimed it at the stop sign about three
blocks down the street. The whole stop sign lit up red!
My brother sprinted out of the house with our
walkie-talkies, tossed one at me and hopped on his
bike, racing down the street to see how far we could
make the dot go. The fun must have lasted at least
half-an-hour, until we noticed a police cruiser talking
to people on the sidewalk. They pointed in our direc-
tion.
Crap!
My adrenaline surged. We were about to be in
trouble, or even worse, they might confiscate my
treasure! I don’t know why I was so nervous, but
young boys tend to have a sixth sense about those
things. As I remember, over the course of the next
The Laser 8

60 seconds I performed the fastest cleanup job ever.

I pulled the power cord and tossed it down the stairs
to the basement. The heavy power supply was shoved
under my mom’s van. The crown jewel and prime
piece of evidence, the laser unit with its telltale warn-
ing stickers was promptly, but carefully, buried in a
pile of discarded moving blankets in the corner of the
garage. Everyone, myself included, got out of sight,
until danger passed.
When I finally emerged from the garage, my brother
was sitting on the front steps. I asked him what hap-
pened, suddenly realizing that I had totally forgotten
about our walkie talkies.
“They thought someone had a gun.”
“What?”
My brother shrugged. And just like that, it was the
last time we played with our laser out in the street,
although it continued to be a prime attraction at the
Fernandez household for the remainder of the year.

You might be wondering why this story is a big

deal. Well, for starters, it represents an exceptionally
interesting experience in my memory, one that I can
relive about three decades later and still get a rush. A
core part of my philosophy is believing that we are
special, that we are capable of being more than just
an ordinary, useless member of society. That belief
The Laser 9

is bolstered whenever we experience special events,

things that stand out not just for their rarity, but
because we caused them to happen in a way that
others could not.
In the case of this story, the reason that I had a
laser and my friends did not cannot be chalked up
to luck alone. If I hadn’t spent years building up my
collection of tools and knowledge of machines and
electronics, I never would have been able to pull a
laser out of that discarded copier. Nor would I have
had the motivation to do so.
By the same token, it takes years of energy and
effort preparing to capitalize on lucky opportuni-
ties when they arise. Absent that investment, you’ll
probably spend your entire life performing the same
routines over and over again. The routines will define
your life, you’ll get old doing them, and eventually
you’ll die. Not that there’s anything super wrong with
that, and we’re all going to die, it’s the one constant
in life, right? It’s just that some of us will have a lot
more fun and excitement (and lasers!) before we exit.
Maximum Impact
“Only those who will risk going too far
can possibly find out how far one can go.”
– T.S. Eliot

These days, I don’t play with lasers anymore, al-

though I’ve been known to disassemble old electronics
with my six year-old son, Tenzin. But as I will try
to explain in this chapter, no matter what I’m doing,
even if it’s just enjoying some downtime, or preparing
a big heaping plate of nachos, I believe in maximizing
impact. Others might refer to this mentality as no half
measures.
I’m the first to admit that a maximally impactful
plate of nachos is not good for your health. That’s
why I don’t claim to always seek a positive impact,
or always feel secure that I’m doing the right thing,
sometimes I know that I’m not. Those that have ridden
shotgun with me in my Challenger SRT8 around
Atlanta should have a visceral understanding of what
I mean by that. But boasting aside, the point is that
anything worth doing is worth doing in a way that
maximizes return.
Maximum Impact 11

The Gauge
The scale I used to gauge whether I’m achieving
maximum impact from my efforts is internal. I’m
decidedly not advocating a constant comparison of
your own results with those achieved by others, and
I don’t think this is a service that you should seek out
from peer groups or mentors.
When it comes to my work, where I constantly
strive for excellence and perfection, the crafting of my
gauge has been a deeply personal and introspective
activity. Apart from this book, it’s not even something
that I like talking about with friends and acquain-
tances, because I don’t want to sound conceited.
It’s worth mentioning that the pursuit of excel-
lence should not have anything to do with desire for
awards or accolades (although those are nice!) It seems
quite possible, even honorable, to live a life of excel-
lence without receiving an iota of acknowledgment
for it.
To recap, I gauge performance based on my own
perception of how I am living right now compared to
my internally perceived potential for greatness.
Everyone in possession of mental and physical
faculties has the potential for greatness in some way,
despite their limitations. And to establish a foundation
for this belief, let me explain that in my view, great-
Maximum Impact 12

ness is achieved by the magnitude and longevity of

your personal contribution to order in the universe,
meaning the extent to which you fought entropy
along the course of your existence.
Just our mere existence, the improbability of the
life force that defines us, not our bodies, but rather
our unique identity in the universe, is testament to
generations of other souls that have come before us
and fought the good fight against entropy and decay.
Ask yourself: Do my thoughts and actions betray their
fight, or do they honor its legacy?

The New Normal

The potential for greatness is there, whether you
realize it or not. The problem is that with every day
that passes, the world gets more and more jaded about
what I want to call ordinary performance. As Kevin
Kelly says, “The Improbable is the New Normal.”¹
Kevin posits that thanks to the ubiquity of cameras
in our lives, our perception of reality is constantly
bombarded with improbable feats of performance.
Every day our Facebook feeds are filled with examples
of otherwise ordinary humans doing extraordinary
things. This constant exposure is changing us, because
it depreciates normal, steady, ordinary performance.
¹http://www.kk.org/thetechnium/archives/2013/01/the_improbable.php
Maximum Impact 13

You may like this new reality, or you may find it

disconcerting, but you can’t ignore it if you want to
achieve greatness.
One of the best aspects of this new normality is
the ubiquitous nature of self-promotion. The potential
influence that normal people can exert on others is
growing exponentially. As you have legitimate ac-
complishments to share in order to establish your rep-
utation and expand your network of influence, you’ll
be able to leverage affordable media channels to make
the masses aware of your talents and achievements.
As I ultimately want this book to be more than just a
collection of amusing stories, I’ve included as much
information as possible about influencing the way
that the outside world views you so that you don’t go
without work and/or passive income streams. Hence
the title.
No matter how good you get at influencing peo-
ple’s perception of yourself, and mind you, I say this
based on experience, it’s ultimately a waste of time
if you don’t eventually reach mastery of what you’re
promising to be. Who makes that promise? You. That’s
what I mean by measuring yourself against an inter-
nal scale of excellence. No matter what, you have to
be moving up that scale and improving your level of
mastery, and only you truly know if you’re moving
or staying still. Cultivate the mindset that staying still
Maximum Impact 14

equals dying and motivation will never be a problem.

Now I’ve been an ambitious guy most of my life,
so I’m predisposed to keeping that excellence gauge
turned way up high in my head all the time. Beep,
beep…, beep, beeeeeeeeep!
I can’t turn the damn thing off really, at least not
without copious amounts of alcohol! They monitor
my life on a regular basis, helping me subconsciously
track my progress and adherence to values that I
cherish; whether I want to do so or not. As a result, if
I’m idle for days at a time, whether it’s due to sickness
of lack of motivation, or if I’m stuck working on stuff
that clearly does not align with my purpose in life, no
matter the reason, I can be sure that there’s going to
be trouble ahead. Those are the times I get depressed
and sluggish.
Now, nobody can strive for excellence if they’re
feeling depressed and sluggish. Consultants especially
need to be energetic and cheerful on a regular basis (or
at least pretend to be while talking to clients.) At those
times, I’m no stranger to manipulating the chemicals
in my brain to achieve desired outcomes, and I have
strong opinions on that subject that will come up in
the rest of the book. Better living through chemistry us
ravers used to call it. But for now, let’s consider what
it takes to install the gauge and arm the alarms. How
do you become passively aware of your performance
Maximum Impact 15

levels on a constant basis?

Metacognition
My old mentor Roy Singham, the founder of Thought-
Works, spoke often about the cultivation of metac-
ognizance, a background thread that is constantly
analyzing the rest of your thoughts and conscious
actions. It was one of his pet themes that he went
on and on about constantly and I think he was onto
something very important.
Metacognition has been studied somewhat exten-
sively by scientists. It is often defined as thinking
about thinking and we all do it naturally to some ex-
tent or another. Cultivating a strong sense of metacog-
nition is referred to as being metacognizant. You can
be a perfectly adequate laborer or office grunt without
being metacognizant. Good grunts just do as they’re
told and keep their noses pressed to the grindstone.
But grunts, even the good ones, don’t solve novel
problems or suggest improvements to their jobs. They
don’t innovate. They certainly don’t consult.
Consulting can be defined as getting paid to pro-
vide influence. It is different that most other work,
because to be a good consultant you must constantly
refine the way that you give advice and cultivate
the knowledge base that you mine for applied wis-
Metacognition 17

dom. That refinement and cultivation can only hap-

pen once you achieve metacognizance. Thoughtworks
was a world-class consulting firm, which explains
why metacognition was one of Roy’s favorite topics.
Over the years I’ve learned that your metacog-
nition can be constructive or destructive. When it is
constructive, you are constantly searching for better
ways to accomplish the work you’re doing. Over time,
that quest for constant improvement becomes second
nature and your metacognition background thread
goes about its business in a natural flow that feels
very comfortable and intuitive. You might even lose
conscious awareness of it.
A destructive metacognition thread would con-
stantly criticize and tear down your efforts. If you
feel like you have problems with getting the little
voice in your head to build you up instead of putting
you down, you might be suffering from pessimistic
thought habits. In that case, the book Learned Opti-
mism by Martin Seligman is a good starting place for
reorienting your outlook.
The other way that I’ve personally had success
with in controlling negative thought patterns is via
contemplative practices such as meditation. By learn-
ing the skill of quieting your conscious mind, you
can take better control of your thoughts and emotions
even when you’re not meditating.
Metacognition 18

A little meditation goes a long way. Once I got into

the habit, I realized that it bore quite a bit of resem-
blance to the prayer habits that my father attempted
to instill in me as a child. Whether you’re chanting
a mantra or taking a quiet moment to talk to God, it
still represents practice in mindfulness, the exercise of
control over your thoughts. It’s absolutely essential to
achieving success.

Constant Improvement
It’s not hard to imagine that a habit of constant
improvement tends to yield tangible results over the
years. But as with any good habit, it takes time to
learn, practice and requires regular nurturing.
It seems fashionable to refer to a life of constant
improvement as being a lifelong learner. I’ve also
heard it called an attitude of of perpetual learning.
I love those terms because they stress the long term
nature of the undertaking and give it a name that
you can use to discuss the concept with others. The
more perpetual learners you surround yourself with,
the easier it is to maintain that attitude in yourself.

When I started out in the consulting business almost

20 years ago, I was not a perpetual learner and I was
Metacognition 19

woefully unprepared to help anyone with anything

of substance. Any improvement was essentially acci-
dental, I hadn’t yet learned about metacognition and
I did not particularly care about being excellent. In
fact, my happiness in those times sprung from a sense
of good fortune on having obtaining a well-paying job
after a bout of sad underemployment and a disastrous
startup experience. I was young and recently married,
had a newborn baby at home and did only the bare
minimum of work needed to keep myself employed
and in the good graces of my bosses.
In retrospect, I had a couple of things helping me
that are vital for any professional consultant. One, I
knew how to communicate and present myself. Two,
I could hustle and learn quickly. And that was enough
for my first professional job with a consulting com-
pany, Indus Consultancy Services (ICS) in Paramus,
NJ.
Through sheer luck, the first thing that ICS did
after hiring me me was toss me into several weeks
of training for Powerbuilder, an old PC-based clien-
t/server technology. When I was done with that train-
ing there was no projects to work on, so they taught
me how to teach others. That was my first hands-
on proof that teaching something (especially the prep
work involved) is a great way of learning it.
Despite the fact that I could infer certain things
Metacognition 20

and help students work through their exercises, I

had zero practical knowledge to draw from in the
classroom. I know that I wasn’t a particularly effective
trainer. I was often reduced to answering student
questions with a shrug and promises to “get back to
you as soon as possible.”
I was not excellent and I knew it. Yet I didn’t care
because it wasn’t a priority, and I was still getting pay
raises like clockwork every six months.²
When I wasn’t training people, I got to help out on
client projects. Sometimes they were smallish client-
server systems written in Powerbuilder, like for the
Kansas Board of Education to manage student rosters
and who got free lunches. Other, more exciting times,
they were big distributed object systems written in a
powerful technology called Forté. My experiences on
these teams taught me the importance of apprentice-
ship, meaning novice-level involvement in projects,
even when your contribution is negligible.

At Andela, we take complete novices and train

them to be world-class software consultants over
.

²My starting salary had been 35 thousand dollars. A couple years later my
paycheck had doubled. Those were the early years of the dot com boom and
everyone was making bank, whether they knew what they were doing or not.
Lucky, lucky.
Metacognition 21

the course of a four year fellowship. After in-

stalling fundamental knowledge, the next step
for a fellow is to be a ghost on an actual client
project. Ghosts are non-billing apprentices. They
work, but do not communicate with the client
or have a formal presence on their project. They
need a lot of hand-holding and are rotated on
and off projects as situations permit. But ulti-
mately, this exposure provides crucial and real-
istic experience that permits fellows to move on
towards their own client engagements.
.

Throughout my time at ICS, I had lots of fun and

learned a lot about programming. My job title in-
cluded the word consultant, but it would take a couple
of years before I would get to do actual consulting:
talking to clients about their problems and helping
to solve them. In the meantime, I had my hands full
with professional development, by which I refer to
learning how to interact with peers effectively in an
office environment. What to do, and what not to do in
order to be respected and given growing responsibility
for anything. Some of those lessons were imparted by
others, like a guy named Anthony who was hired a
few months after I was.
Metacognition 22

Anthony was a somewhat tall and quirky Italian.

He couldn’t have been much older than me, but
something was off about that guy. I remember on his
first day in the office, in the context of a conversation
about our respective commutes, he explained that he
never paid the tolls on the Garden State Parkway.
(They took quarters and did not have toll gates at
that time.) Anthony explained that he had done the
math, and according to his calculations it was more
cost effective to get a fine for toll violation a couple
times per year, than to pay the toll every day. So he
just drove through the toll everyday with impunity.
I remember thinking that Anthony suffered from
a very odd and suspect way of thinking and imme-
diately doubted his moral judgment. To this day he
remains my canonical example of why you shouldn’t
tell people you just met about how you break the law
on a regular basis.
Anthony was a decent enough VisualBasic pro-
grammer, but unsurprisingly he was constantly get-
ting in trouble for stupid shit. Like the time he took
a two hour lunch because he was fixing his car’s
engine, in the parking lot of our office tower, in plain
sight of everyone working in our third floor office. It
was during summer, and when he finally came back
upstairs, he was sweaty and greasy and not exactly
ready to continue working. The boss chewed him out
Metacognition 23

in front of everyone, and a few months later he was

fired. Anthony was not metacognizant.

The Impostor in the Deep End

My first true experience with consulting began when
I moved to Atlanta in 1998 and was hired by mid-
sized national firm named Born Information Services.
Due to my previous job title, they hired me with the
expectation that I knew how to consult clients. Yep,
they threw me right into the deep end of the pool
immediately. And guess what? I was happy to take
up the challenge, since they had just spent a bundle
relocating me and were paying me 80 thousand dollars
a year, a figure that seemed preposterous given my
meager qualifications and humble beginnings. I think
what I lacked in formal education, I made up for in
sheer hubris.
Despite the outward displays of confidence, those
were tough years inside my head. I was plagued
with a terrible case of impostor syndrome, the sense
that I was a fake, that I was not really as qualified
as people thought I was. All highly metacognizant
people that I’ve talked to about it have dealt with
impostor syndrome early and often in our careers.
The more ambitious you are, the more you’ll put
yourself in situations that are beyond your comfort
Metacognition 24

level. That’s where fast growth happens, but that

metacognition thread in the back of your head can
get brutal with self-criticism. Often I would be aware
of exactly what I did wrong in a given circumstance,
or panicking inside because I didn’t know what to do
next, yet the client and/or my co-workers remained
blissfully ignorant of my limitations. After all, I’m
supposed to be an expert. Those times are tough. And
unavoidable when you’re just starting out.

The first step to excellence is believing yourself

to be capable of excellence. Fake it ‘til you make
it. Mistakes are unavoidable, especially early
on in your career. Lack of confidence in your
capabilities brought upon by mistakes will end
your consulting career faster than the mistakes
themselves.
.
Perfectionism
The conscious pursuit of excellence in everything that
you do is a foundational concept for this book, and
part of the reason that I’m writing it is to inspire you
to have the same conscious pursuit in your life. The
correctness of the pursuit may seem bloody obvious
to you, but not everyone that I have met agrees with
it. I’ve been called a perfectionist many times, often
in disdain. I even cried tears of self-doubt during a
workshop about the perils of being perfectionist in
front of the inestimable Jerry Weinberg, one of the
greatest consultants of all time.
I’ve since wiped away the tears and figured it
out. Being perfectionist, widely considered a negative
personality trait, is not the same as being a person who
pursues excellence relentlessly. After all, how often is
perfection actually achievable?

Designers are taught to produce pixel perfect

work. In my experience, only their Photoshop
high-fidelity comps are pixel perfect. Implemen-
tation might come close, but is almost always a
.
Perfectionism 26

work in progress.
.

Perfection is often undesirable, especially when you’re

doing tangible, results-oriented work for clients. In
client work, there are constant tradeoffs between what
they can afford to pay and a high level quality of work
that lives up to your standards of excellence.

Craftsmanship
I work in technical fields where long-held princi-
ples of “craftsmanship” have become a fashionable
metaphor for excellence in programming. It is an
apt metaphor, since great programming encompasses
artistry and technical rigor. My friend Dave Hoover
even wrote a successful book on how to apply the
apprenticeship model to the programming field.
As such, I’ve arrived at the belief that craftsman-
ship implies adherence to excellence and caters to
folks with perfectionist tendencies. People like Corey
Haines and “Uncle Bob” who flog craftsmanship to
the unwashed masses of programmers out there in-
evitably stress religious adherence to techniques such
as “test-driven development.”
Perfectionism 27

Another friend, Brian Lyles, even coined a new

catchphrase during his talk at Ruby Hoedown 2008
when he repeatedly exhorted us to “test all the fucking
time.”
In practice, only programmers with perfectionist
tendencies adhere to high levels of testing rigor.
My counterpoint to test obsession is that many
times perfection is not warranted. Until you know
what kind of reward you’re going to get from a
particular project, perfection is simply not needed or
desirable. Learning this level of discernment is part of
my pursuit of excellence.

Excellence to me entails figuring out what good

enough means in any given circumstance and
pushing to consistently hit that limit.
.

The rest of the book deals with different aspects of

what I consider to be the pursuit of excellence in busi-
ness, with some emphasis on professional consulting,
since that’s what I’ve spent most of my career doing.
I can’t presume to make an overall guide to a happy
life, since context is everything, and yours is surely
different than mine.
Perfectionism 28

Some of the topics are more internal-facing: how I

think you should approach thinking and feeling about
your clients and problems they’ll throw your way.
Other topics are more external and have to do with the
work itself and how I’ve achieved my own material
success.
Absent a strong and guiding purpose in your life,
it doesn’t matter whether you’re excellent at anything
or not, because eventually you’ll find yourself in a pit
of despair. That’s why it’s our next topic.
Purpose
It is absolutely vital that you seek and define a sense
of purpose in your life. Countless books have been
devoted to that subject, so I won’t delve into how you
go about doing that. ³ Just know that you must.
The times that my life goals and behavior have
been driven by a well-defined purpose I’ve achieved
mind-blowing successes and earned tons of money.
My clients have been happiest when I’ve worked in
support of the purpose underlying their own goals.
Other times when I have failed to understand my own
purpose or that of my clients, I’ve fallen flat on my
face. Ouch.

My purpose these days is to be a storyteller

I believe that my story can change your story,
which is one of the main reasons I have written
this book. By telling compelling and authentic
stories, both from my own life and that of others,
.
³I was able to painstakingly brainstorm and document my purpose in life
with ample help of my mentors Mark Shekter and Nancy Botkin. The process took
a couple of months and yielded many insights that continue to shape my behavior
to this day. Mark and Nancy’s system for creative discovery and planning is called
Think8. Google the term to learn more.
Purpose 30

I hope to inspire you to break through whatever

limitations are binding you and reach greater
heights of fulfillment in life.
.

Leading with purpose

From the earliest days of Hashrocket, my partners
and I had this vision of making Hashrocket a great
place to work. But that’s not very distinctive, right?
Plenty of executives have that purpose on behalf of
their employees.
It took me over a year to fully crystallize our actual
purpose as a group and to put it into words. It didn’t
happen until after we had hired over 20 people and
made a ton of rookie mistakes. But once I did isolate
and identify our purpose for existence, we were able
to really take off “like a rocket” and soar high amongst
our top competitors.

Do you lead a group? You must understand the

joint purpose of your group and take concrete
steps to accomplish it if you want to be an
effective leader. The group purpose will be a
.
Purpose 31

combination of the purposes of its members.

Even the goals of the least confident members
of your group need to be taken into account.
.

How did I figure out our joint purpose at Hashrocket?

In early 2009, Hashrocket was whistling past our
initial goals and expanding rapidly, way beyond what
I was equipped to handle on my own. My partner
Marian came aboard as CFO to make sure I didn’t
screw up our finances and to lend some business
maturity to the executive team. The two of us made a
good team, her the more serious and considerate half,
and myself as the passionate bomb-throwing radical.
Nonetheless, given the velocity of our growth,
I was feeling a under qualified and overwhelmed.
That old foe impostor syndrome was stirring from
its Thoughtworks-induced slumber, so I fought it by
delving deep into stacks of modern business books.
Aggressive pursuit of knowledge is one of your most
effective weapons for fighting impostor syndrome.
Purpose 32

The Best Fucking Mission

Statement Ever
During my studies, the importance of enunciating
mission and vision statements kept coming up. Sadly,
most employees consider mission statements to be
bullshit. I think it’s because the mission statements
that corporate committees come up with generally are
bullshit. They sound too much like empty platitudes.
Despite plenty of cynicism and resistance from
my Rocketeer colleagues as soon as I started talking
about it, I was still eager to draft our own mission
and vision statements. I spent weeks trying to come
up with formal statements that we could agree upon.
The results provoked heated email discussions and the
usefulness of the pursuit was debated ad nauseum. It
was difficult to figure out our joint purpose, because
we were a very diverse group with strongly held
opinions. We didn’t actually have a shared purpose.
Uh-oh. We had gotten big enough, at least 25 or so,
where I intuitively felt that lacking a shared purpose
would cause troubles sooner or later.
Let me give you an idea of the earliest draft
mission statement, which I mined out of my old email
archives. I think you’ll agree that they it was a bit
uncompelling:
Transform the world for good via expert
Purpose 33

consulting in web technologies.

Transform the world for good.

Expert consulting.
Web technologies.
Descriptive for sure, but doesn’t get you all fired
up.

Entire books have been written on the subject of

crafting effective mission statements. That’s because
it’s surprisingly difficult to capture the essence of
purpose in a pithy and memorable way that drives
employees to action and makes their hearts pound in
their chest. It takes deep insight and no shortage of
writing skill.
Over the course of several mission statement de-
bates at staff meetings, I was also hit with the realiza-
tion that the goal of establishing official mission and
vision statements was only critical to me. Everyone
else seemed satisfied to just plow ahead with the
status quo.
One day, in a moment of frustration, I typed a
brash statement that I thought captured the essence
of Hashrocket:

To be the best fucking web design and

Purpose 34

development shop.⁴

Since the beginning of the company, with the

zeal of a pentecostal snake-handler, I had tried to
get everyone involved in the company to believe we
could be the best fucking web design and develop-
ment agency in the world, period. Why not actually
enshrine that in our mission statement?
Rocketeers would ask me, “hey does best mean
best place to work?”
“Yes.”
“Does best mean that we deliver results faster than
anyone else?”
“Yes.”
“Does best mean that we come up with the most
creative solutions? The most innovative designs? The
most artistic designs?”
“Yes!”
“Does best mean that we have the most fun?
Charge the highest rates? Throw the most outrageous
parties???”
“Yes! Yes! Yes!”
“Why does our mission statement contain profan-
ity?”
“Because fuck you.”
⁴Emphasis on the period at the end, although we thought adding “, period.”
would be superfluous, so we left it out.
Purpose 35

We cursed a lot at Hashrocket. If someone had

a problem with the profanity they wouldn’t make a
good client.
Hopefully you get the picture. I was attempting to
stake a claim as outliers, out where other brash and
remarkable companies live, and to reap the plentiful
benefits that come along with being recognized as
such by everyone else. We were cool. People were
clamoring to work with us so that they could feel
cool too. Arguably I had accomplished my goal, it’s
just that nobody at Hashrocket sat around explicitly
stating that that was our goal.
So I did what all good CEOs do when they’re
successful: lay awake in bed sweating about how to
keep the good times going for as long as possible.
Since my purpose, my goal, was very clear to me,
I tried to make it clear to the rest of the company
in no uncertain terms as often as possible. In blunt
language, I routinely told Rocketeers that they should
exude passion in everything they did, that they should
quit if their involvement became “just a job.”
During one impromptu company meeting during
which I said exactly that, I also talked about my
own dreams of great mainstream success and wealth.
I told them how the taste of fame that I got from
the strong performance of my book The Rails Way
had intoxicated me. I wanted to take over the world,
Purpose 36

and I wanted all of them to want the same thing for

themselves, to believe that they could achieve it too.
(Sound familiar?)
One problem though. They were employees, and
their own goals were mostly at odds with mine. In
time I realized that it would be impossible for our
goals to align properly, for them to adopt my purpose
for themselves. Not one of them had ambitions quite
as large as mine, I realized. To my chagrin, I came
to the stark conclusion that most of them, even my
partner Marian, pretty much all they wanted was
a steady job and a happy work environment. All
this other stuff they were getting from working at
Hashrocket was cool and motivating, but it was just
icing on the proverbial cake.

Analyzing Purpose
Max Siegel, author of Know What Makes Them Tick
wrote an entire book about analyzing people’s pur-
poses and using that information to your advantage.
I think this paragraph sums up the importance of
understanding purpose succinctly:
Success depends on other people commit-
ting to you, signing on to try things your
way: your job application, your new idea,
your plan or project or deal. You need
Purpose 37

them to tie their success to yours. They’ll

only do that if they feel that you un-
derstand what matters to them, and that
your success will make them successful,
too.

Italics mine. First understand what matters to you,

but then understand what matters to the people you
are working with and make sure that you put helping
them achieve their purpose front and center in how
you work with them.
The worst example I can remember of when some-
one highlighted their own purpose instead of their
client’s? Many years ago, during an important lunch
meeting, an executive I worked for dropped the fol-
lowing nugget on our largest client: that he was look-
ing forward to buying a personal helicopter once we
starting turning a profit. To put it mildly, the client
was not amused. Clients don’t like to think about the
luxuries you will buy yourself with their money. That
executive got canned not too long after that lunch.
So here’s some concrete advice: Don’t ever talk
to clients about what you’re going to do with the
money you get from them, even if they bring it up.
It’s in poor taste and is guaranteed to backfire. Even
if you’re making millions of dollars in profit from
Purpose 38

them, don’t rub it in their face. Often times you’re

bringing home significantly more money than the
client representative responsible for approving the
expenditure. They don’t want to be reminded of that
fact.

Money Ain’t a Thang

If the answer to the question what matters is
money, then I propose that you’re not digging
deep enough. Money is an extrinsic motiva-
tor, a second-order effect of success. Most peo-
ple want to make lots of money, but what is
truly driving them? Just the hoarding of cash?
Definitely not. Unless they’re Scrooge McDuck
swimming in piles of gold, monetary goals al-
ways relate to the freedom that having lots
of money will enable. Experiences and things
that money can buy, or projects that can be
accomplished with copious amounts of money.
Hopefully something altruistic and good for the
world at large!
.

So one of the key things you should do once you get

past the formalities of initially meeting a client, or for
that matter, anyone that you will be working with,
Purpose 39

is to gently probe into their motivations. Try to work

questions into the conversation that will reveal what
their purpose in life is, what makes them tick.
I’m not suggesting you do this in a cynical attempt
to manipulate them or anything like that. The point is
to make it a habit to figure out what motivates people,
what their big goals are in life, so that you can help
them get there. If you make it a habit to help people
achieve what they want, the more they will help you
and the more successful you will get.
Now the tricky part is: The more successful you
get, the harder it gets to stay attuned to the needs
and desires of the people around you. Once you burn
the people that pay your invoices or provide the
labor for your venture, they’ll be waiting for the first
convenient opportunity to bring you down a notch.
Or further.

When Purpose is Lost

For all my success at Hashrocket, towards the end of
2010 and just before the end of my reign as CEO there,
my ambition and inattentiveness to the purposes of
my people caused me huge problems. The deception
and disloyalty that I suffered as a result shook my trust
in friends for awhile.
The Hashrocket brand was very strong at that
Purpose 40

time. We had more business in our pipeline that we

knew what to do with. At the same time, the financial
realities of how we were capitalized prevented us from
making big moves into vital new markets such as San
Francisco and New York. I was frustrated, stifled and
uncomfortable.
Unable to hire additional employees due to cap-
ital constraints, we started hiring out remote sub-
contractors, both freelancers and entire small compet-
ing shops. At our peak we had over 15 extra develop-
ers working with us this way on a regular basis. All
were eager to emulate our work style, using a distinc-
tive set of practices that set us apart from our major
competition. Most of them expressed frustrations with
their fluctuating cash-flow problems and having to
constantly maintain a pipeline of new business. Many
of them were open to discussing how we might join
forces for mutual benefit.
As a result, I started planning a restructuring of
Hashrocket to accommodate faster and more capital-
efficient organic growth. How? By breaking out a
“mothership” corporation to own the brand and in-
tellectual property, and act as a business pipeline for
our regional branch offices in Jacksonville, Chicago
and future locations.
The reason this made sense was that additional
locations could be launched “under the Hashrocket
Purpose 41

umbrella” similar to how franchise businesses work.

These small agencies that were currently sub-contracting
for us would become a virtual part of Hashrocket and
get business from our pipeline. But by taking on some
risk in the equation, they would be able to keep a very
healthy share of the profits.
How healthy? I calculated that a location with 6
billable consultants at 75% utilization would clear over
500 thousand in profit per year on revenues of almost
$1.2 million. That included sending a generous 30%
revenue share back to the Hashrocket mothership to
cover administrative and marketing costs.
Many small competitors really liked the sound of
those numbers. It aligned with their purpose, which
was to maximize profit while minimizing the amount
of non-programming-related work that they had to
do to keep their business running. Assuming that
Hashrocket mothership took care of their sales pipeline,
negotiating contracts, closing deals, scheduling, in-
voicing, collections and even ensuring that client com-
munications were handled effectively… damn, what a
good deal! All they had to do was to deliver quality
software development and cash fat checks. Not to
mention the prestige of being considered Rocketeers,
during a time when Hashrocket’s technical reputation
was sky high and still growing.
The mothership plan matched the purpose of those
Purpose 42

outsiders perfectly. But its fatal flaw was that it was

completely at odds with the shared purpose of my
existing employees. Remember earlier I mentioned
that most of them just wanted a steady job and happy
work environment. The mothership plan represented
a betrayal of the “social compact” long established. It
was seen as increasing their risk and diminishing their
prestige and happiness. Anyone left off the moth-
ership and assigned to work for a regional affiliate
would be subject to fluctuations in demand that could
plausibly impact their pay. It didn’t matter that the
best of them would be principals in the affiliates and
be able to capture much more upside than their usual
salaries, because as employees (not entrepreneurs)
that was the wrong motivator. Employees crave sta-
bility, and there I was carelessly bragging about taking
it away from them and telling them they should be
happy about it. I’m lucky that I didn’t get a literal knife
in the back during those times.
Then there was that prestige factor. Hashrocket
numbered about 35 people. The idea of rapidly ex-
panding that into the hundreds or more just to make
me and Marian rich, that didn’t really sit too well with
the Rocketeers. Worst of all, my Director of Opera-
tions, a good friend that I had known and worked with
for over a decade, sided with the employees against
me and Marian. In his view, he had to defend “his
Purpose 43

people.” During a tense argument in front of the whole

company, he hurled some nasty accusations our way
concerning our motivations for the restructuring.
It was mutiny and a blatant show of disrespect,
so we fired him the next day. Given his position in
the company, and the fact that he had been the one
to hire many of the newer employees, morale hit a
new low soon thereafter. By forgetting to mind the
purposes and motivations of my staff, I had killed a lot
of the magic that made us special. Many Rocketeers
started looking for new jobs, not even hiding their
intentions. It wasn’t too long before the turnover and
morale issues started rocking the foundations of the
partnership itself.
The relationship between my partners Mark and
Marian had been on the rocks for months, but now
things turned downright nasty. Terrified that he would
not be able to recoup his investment in Hashrocket,
Mark started maneuvering to take the company over.
The initial attempts were covert. At one point I dropped
in to visit him at home to discover the entire block
in front of his house, the “Oasis”, covered in parked
Rocketeer vehicles. He had gathered everyone to turn
them against me and Marian. I walked in to the
meeting and was met with stone-cold silence. When
I asked what everyone was doing, Mark replied that
they were having a meeting. I asked if I could join and
Purpose 44

he said, simply, “no.”

“Okay, I’ll just wait outside then.”
I stormed out and called Marian, who had no
idea what was going on and was furious to find out.
Didn’t take long… a few minutes later everyone came
pouring out of the house and made a bee-line for
their cars. Many avoided eye contact. Big Tiger was
crying. Luckily, Wes, one of my original hires and a
good friend, motioned for me to get in the car with
him. We drove around the block a few times as he
tried to explain what was going on. Essentially, Mark
was trying to rally a vote of no-confidence in the
leadership of Hashrocket, in order to justify taking
over as new CEO.
“Wes, he can’t do that. We have equal shares, and
we won’t allow it.”
The explanation fell on deaf ears. I supposed Wes
had cleared his conscience and was now very eager to
drop me off and get back home.
Marian and I got together and told Mark to back
the fuck off, that he was just making things worse
with the staff. His stunt promptly caused another four
Rocketeers to resign, turnover that we could ill-afford.
Soon afterwards, I called a company-wide meet-
ing to condemn Mark’s actions and assure everyone
that if we all just calmed down, everything would be
okay in the long run. I also canceled the “mothership”
Purpose 45

plan and hoped that this would be a first step in

regaining a sense of control.
Marian suggested that maybe it would be good
to get out of town for awhile, so I did. My girlfriend
Desi was running the Chicago office and had recently
moved into a new apartment high up over Greektown
on the west side of town. I decided to move in with
her and pray for the best. Due to their geograph-
ical distance from the poisoned well that was my
Jacksonville headquarters, the morale and demeanor
of the Hashrocket Chicago team was still relatively
pleasant and optimistic.
Things did settle down a little bit, but it was the
calm before the storm. The overt turmoil in Jack-
sonville had stopped as some of the most disgruntled
people left or were culled out, but the relationship
between my partners reached a new low. Not a month
had passed before I was woken early on Monday
morning by a phone call from Mark.
“This can’t be good,” I remarked to Desi. Mark
never called me, especially not at 7:30 AM on a
Monday morning.
“I demand your resignation, or I will announce to
the company today that you have stepped aside and
I’m the new CEO.”
“Mark, don’t be crazy you can’t do that without a
board vote.”
Purpose 46

He would not listen to my protests, so I demanded

to talk to Marian. She was in the room with him
but wouldn’t talk to me, at which point I suspected
something was really wrong.
“I’m on the next flight down, don’t do anything or
you will regret it.”
I booked the next flight back to Florida, but while
I was in transit Mark went ahead and announced that
he was taking over as CEO anyway. Now the thing
you have to understand, is that while people harbored
no small amount of resentment towards me about
the whole “mothership” thing and a whole other raft
of issues that happen during a fast-growing startup,
most of them were not fans of Mark either. So the
announcement did not go over very well at all. I’m
sure at least another handful of employees sent out
resumes at that point.
While on my way to the airport, I finally did get
a call back from Marian. Mark had pressured her to
go along with the plan, but now she regretted it. We
decided to confront him together that evening. We
would reverse his actions and call an emergency board
meeting.
Hashrocket, my pride and joy, was falling apart
in my hands. Lots and lots of drama ensued. But
in the end, Mark and I sold our shares to Marian,
shook hands and walked away with our dignity intact.
Purpose 47

And for her part, by taking on the risk of Hashrocket

failing, Marian ultimately made out like a bandit.
It didn’t fail, because Marian’s purpose was pur-
posely aligned with the employees. She cared about
being the best, but she cared about running a stable
business with happy employees first.

Despite numerous growing pains and dramatic episodes,

I think that Hashrocket did eventually fulfill the pur-
pose that I laid out for it. With regards to our own
internal gauge of capabilities and accomplishments,
we had achieved the pinnacle of success. During early
2010, despite a persistent global recession, our pipeline
of incoming business was strong and our public image
was top-shelf. We pushed towards a run rate of over
6MM in revenue for the year and surged past 35
employees. The mission was accomplished, and it was
time for a new one. Painfully, that meant ceding my
leadership role to someone new.
While purposes shift over time, our values are
what define us the most. Values don’t change as much
as other critical factors in our lives, but have just as
much impact on our ultimate success and influence.
Values
My personal values define me at home and on the
road. Discussion of values is undervalued in business
contexts. Sometimes it seems like everyone would
rather talk about the latest Silicon Valley gossip or
mobile technology instead! But I’m going to buck
the trend and devote some words to values, the old-
fashioned kind that make you stand apart from the
pack and feel great about it.

Honesty
My devout Christian father drilled it into my head
from an early age that lying is completely unaccept-
able. Out of all the possible transgressions, lying was
the worst, because it broke his trust the most. (Lies
of omission included.) Even little white lies to save
someone’s feelings were considered bad. Satan, it was
explained to me in detail many times over, was the
father of the lie, and I didn’t want to be like Satan, did
I?
Umm, no. I didn’t want to be like Satan. And
although later, in the depths of my teen rebelliousness,
Values 49

I was convinced that my dad was over the top about

everything and hated him for it, for some reason his
teachings on honesty stuck. As I write this, having
shed almost all vestiges of my religious upbringing,
Dad’s approach was still very effective in making me
an honest person. Thanks, Dad.
So how much honesty is appropriate in the busi-
ness world? I’m embarrassed to admit that I’ve had
moments of dishonesty, with myself and others. But
the thing is, I’ve always paid a heavy price in lost trust
and opportunities. So I think the answer to how much
honesty is appropriate is a value that remains the same
no matter the context: Always be honest. Period, full
stop.
Every little lie that you put out there into the
world is a ticking time bomb, waiting to explode in
your face at the worst possible moment. If you don’t
adopt a principled stance about honesty on merits
alone, then try to consider it a selfish favor to your
future self.
Of course, the devil (haha) is in the details. For
perpetual and persistent honesty to work out in your
favor, your communication skill set must include
techniques that mitigate the consequences of telling
someone something that they don’t want to hear.
You’ll also need to refine your sense of timing. You
must be able to shut up when continuing to talk would
Values 50

lead you into divulging uncomfortable or inconve-

nient truths.
When people think that someone is too honest,
they say that he is honest to a fault. Many times
honest people just don’t know when to shut up.

Integrity
Okay so I have strong, fundamental values like hon-
esty. But how faithfully do I reflect them? How well
do I integrate my ideals and values when it comes to
the way that I treat myself and others? That measure
is called integrity. Without it there can be no trust
and without trust there cannot be influence. Integrity
comes into play with both small and large decisions.
That way of thinking was hammered into my head
from an early age.⁵
Integrity is an essential aspect of excellence, and
honesty is the most important aspect of integrity.
Honesty starts with number one – yourself. Without
the compulsion to be honest with yourself about how
well you are adhering to your values, it is too easy
to slack off. The same goes for being honest about
your performance, whether you’re winning or losing.
⁵Whoever can be trusted with very little can also be trusted with much,
and whoever is dishonest with very little will also be dishonest with much.
http://bible.cc/luke/16-10.htm
Values 51

Remember metacognizance.
It seems that the more monetarily successful you
become, the harder it gets to keep your integrity
intact. I’m reminded of that thing that Jesus said about
camels and needles. Or Puff Daddy regarding “mo
money, mo problems.”
The stakes get higher. Temptations come more
often and with bigger stakes. The pressure to violate
your integrity grows in lockstep with your worldly
success. And the penalties grow too! Now you don’t
just face prospects of embarrassment or relationship
difficulties, you might find yourself facing big finan-
cial losses or legal troubles. There is no easy solution
for this dilemma — to some extent, I think that keeping
your integrity could mean opting out of material
success that is not needed.
On the other hand, personal growth, the pursuit
of excellence and perpetual learning requires constant
challenge. Forsaking the challenges and taking the
easy way out, means getting stagnant and leads to
depression. Often the greatest accomplishments of
your life will happen when you’re under the greatest
pressure to perform, and when the challenges to your
integrity are most intense. When things are easy, the
temptation is to coast, to conserve energy.
Values 52

Work Ethic
I always thought I was a lazy person, because ever
since I was a kid, people told me I was lazy. (Be careful
what you tell your kids, they might believe you!)
Everyone told me I wasn’t living up to my potential
and I believed it.
It wasn’t until I was well into my twenties, after
repeated bouts of depression, a failed marriage and a
building sense of desperation about my prospects in
life, that I figured out that I had undiagnosed ADHD.
Turned out I wasn’t lazy, I just had trouble focusing
on boring shit, because I didn’t have the same levels of
dopamine in my frontal cortex as most people. I don’t
consider it an impairment, per se, because that same
deficiency made me much more creative than most
people!
But due to ADHD, it takes the right kind of
motivation to make me do things I am not keen
about doing. Sometimes I provide that motivation in
chemical form, like copious amounts of caffeine or
even Adderall. Other times I just have to really, really
convince myself that I want a particular outcome.
Guess which is easier?
The nice thing is that once you begin to exhibit
a strong work ethic, it is self-reinforcing. You gain
confidence about what you can accomplish when you
Values 53

dedicate yourself to a cause, which makes it easier to

follow through. It also lets other people deepen their
trust in your ability to overcome challenges. I just
wish I had figured it out ten years earlier than when
I did.

Fun
So far, lots and lots of what I’ve written about are
egocentric things. They have to do with our created
identity, the personality that we wear in our internal
and external interactions. But buried under the ego is
our id, the simple being that delights on simply being
a child of the universe.
To the extent I’ve figured out how to be happy,
I know that an essential part of it is keeping our id
satisfied. And the way that I know how to do that is
by making sure that fun is a core value in everything I
do, from naming this book, to the way I style my hair,
to playing innocent pranks on my friends and family.
Everything is better with a bit of fun thrown in,
even a funeral! It’s why we tell jokes to break the
tension, or play games for team building. The desire to
experience fun is a universal human trait that is often
buried in the name of being professional.
Ever notice how very egotistical people are not
much fun to be around? Egotistical people that have
Values 54

achieved success are even kind of scary, intimidating.

I mention it because fear is the opposite of fun, and
ego is the part of your personality that drives fear.
Fear of having our carefully constructed and managed
identity exposed as a fraud. Fear of being signaled as
an impostor. Fear of losing our family, friends and
possessions, the material things that define our iden-
tity. Walking around being afraid means not having
any fun.
Being able to let go of fearfulness entails getting
to know your id. It means practicing blissful states
of minds where you set your normal personality con-
structs aside and concentrate on just being one with
the universe of all living things. This bliss of unity
with others, setting the ego aside, is the foundation
of love.

Love
Ego is a relative thing. I think mine is above average,
but people with bigger egos remark on my humility.
At the same time, people with smaller egos think
I’m an egoist asshole. When it comes to establishing
romantic relationships that actually work, I’ve found
it’s helpful to seek partners with egos of comparable
magnitude to my own.
There’s romantic love, which I adore and prioritize
Values 55

in my life, but in contrast to it there’s also the power of

love as a value that is shown towards all others in our
lives. We are surrounded by people all the time. Some
are more pleasant and helpful than others, but beneath
their egos, all have a pure and child-like being similar
to our own. The love that you cultivate for those
pure beings, and really, the entire universe of living
things that surround us, regardless of circumstance, is
the foundation of spirituality, which I consider as the
ability to elevate your mindset and tolerate setbacks
with grace and serenity.

In my experience, there is no boundary between the

values that I cherish in my professional versus my
personal life. To a certain extent that’s because I don’t
draw that distinction very well, but that would imply
that the failure is a detractor from my success. It isn’t.
I believe that it makes me a better integrated person,
more consistent and trustworthy.
Over time, the devil that consistently tempts me
to violate my values is one that every professional
must manage carefully: power. Which is why it is the
subject of the next chapter.
Power
Power, or to put it another way, the exercise of our
will over the will of others, is a natural human at-
tribute. Some of us are dominant, which means we
are predisposed to seek and derive gratification from
exercise of power. Others are naturally submissive,
and are happiest when delegating their will to others.
Most fall somewhere in between or switch depending
on circumstances.
In the business world, it’s essential to study the
exercise of power and accrue wisdom about how to
wield power yourself. In other words, it’s a skill. All
skills entail techniques — practical application of the
skill.
The seeds of this book are techniques related to
applying power in professional relationships. I called
those techniques power plays as a catchy way to
categorize and disseminate them. I don’t claim to be
the originator of the term by any means, but for
awhile there at Hashrocket it was a thing that we
discussed. And the way that it all came about was the
time that Jon Larkowski and I kicked off a new client
engagement with Thompson Reuters.
Power 57

It was a crisp springtime morning in Times Square.

Jon and I were in town to meet executives from
Reuters, an important new client for our new business,
Hashrocket. To be clear, the deal was closed, but this
was our first day consulting on site and kicking off the
new project.
As we hustled over from the hotel to the Reuters
building, just a few short blocks away, I decided
we should buy some authentic New York bagels for
breakfast.
Thing was, we didn’t quite have time (nor space
in the cramped bagel shop) to actually eat the bagels
and enjoy our coffees before 9 am, the scheduled time
we were to meet the client people. Instead of waiting
to eat breakfast later, or skipping a meal, we took our
bagels to go, in little brown paper bags, and continued
on our way.
At the lobby of the Reuters building, we were held
up by the fact that the person we were meeting was
delayed and unavailable to let us up to the appointed
floor. So we stood there, hungrily, debating the timing
of our breakfast.
One the one hand, a warm bagel tastes much
better than a cold bagel. On the other, it would be
easier to sit down for breakfast once we made it
upstairs to an office, rather than awkwardly chowing
down in the Reuters building lobby.
Power 58

I told Jon, “You know, we could just wait until we

got upstairs and then we could eat our bagels as we
met the new clients.”
“That… would be quite a power play,” responded
Jon, with his signature wit, adding “there’s nothing
like eating during personal introductions to really
establish who’s in charge.”
He was right. If you think about it, in situations
where you’re meeting a new client or business partner
for the first time, polite protocol dictates that you
dress well and be on your best, most attentive be-
havior. You are paying attention to the person you’re
meeting – they are your main priority, at least until
introductions are over.
How does eating during an introduction alter that
equation? Well, it essentially says to the person that
you’re meeting: “See here, I was hungry, and satisfy-
ing my hunger was more important than respecting
protocol regarding introductions, even at the risk of
pissing you off.”

Power Plays
A power play is a behavior that tips the balance
of power within a business dynamic in your favor.
Please note that I don’t recommend power plays for
interpersonal relationships, just business. I like fun
Power 59

power plays and shun dishonest ones, for reasons

that should be clear if you read the chapter right
before this one. Power plays are especially useful with
consulting clients, who I’ve found will usually try to
take advantage of you in any way they can.
It seems like the actions and modes of thinking
related to subtle power plays come spontaneously to
assertive, confident individuals, as they did to me, but
it wasn’t until that particular morning in the lobby of
the Reuters building that the concept of naming and
defining particular power plays crystallized, and the
original idea for this book came to life.
The underlying principle is that your behavior will
constantly affect the power dynamics of your business
relationship with your clients. From the moment you
first interact with a potential client, you are either
helping or hurting your ultimate chances for success
and satisfaction. Both parties can be happy with the
balance of power resting on the vendor side, your side,
as the consultant, the provider of services, as long as
you manage the power dynamic with a measure of
respect and wisdom.
Conversely, I believe that you will never be happy
when the balance tips over to the client side, because
their temptation to screw you over is ever-present
and extremely tempting. Rational, even… which is
one of the main reasons that I maintain a measure of
Power 60

contempt for untempered capitalism.

Assuming you are a moral person and skilled
consultant, and you want to do a good job, I advise
you to cultivate a healthy fear in your client. They
should have an ever present concern of pissing you
off, and causing you to fire them, not the other way
around.
Normally, clients do always have the upper hand,
because no matter how much they depend on your
services, no matter how afraid they might be of losing
you, they are the ones that pay you, and not the other
way around. You depend on your clients to make
your money, your living, and that leaves you at a
disadvantage right from the start.
In fact, given the nature of billing cycles, you’re
always one or two mistakes away from not getting
paid – and collecting after a disagreement can be near
impossible in practice. (If any of you reading this have
discovered a foolproof way to always get paid up-
front, please let me know.)
“But wait a minute,” you might counter to this line
of reasoning, “isn’t pissing off your client with power
plays a mistake?”
That would assume that power plays result in
anger, but power plays should not draw the ire of any
client when properly executed.
The rest of this chapter identifies some examples
Power 61

of power plays what I consider essential aspects of ex-

ecuting them with finesse. The most important aspect
of a power play is undeniably subtlety! If something
is too obviously a power play, then you’re doing it
wrong, and putting your client relationship at risk.
At its most fundamental level, a power play is simply
a way to send a subliminal message about who is in
charge.

The Breakfast Meeting Power Play

Let’s go back to the bagel example. If Jon and I had
started eating in the atrium of the Reuters build-
ing, not only did we run the risk of being inter-
rupted by our due-to-arrive-at-any-minute client, we
would also subject ourselves to the undeniable in-
convenience of eating in a public place, standing up,
bundled up in jackets, and carrying backpacks and
briefcases.
We can extrapolate the messages that course of
action would send to onlookers and the thoughts it
might provoke:
• We didn’t leave enough time for breakfast prior
to arriving, perhaps betraying lack of prepara-
tion or foresight. Are we late risers, or did we
party too late the night before, or maybe we’re
just lazy?
Power 62

• We didn’t budget enough time to finish our

meal, since we might get interrupted. We might
not be able to finish eating until much later, if
even at all, which means we might be working
hungry. Nobody likes to work while hungry.
• We don’t mind inconveniencing ourselves in an
embarrassing way, which might betray lack of
confidence or self-esteem issues.
• Scarfing down a bagel, loaded down with gobs
of messy cream cheese, particularly in a highly
visible public place, might betray a lack of social
refinement.

Risking a mess before an important meeting without

an easy way to clean up is a potentially foolish course
of action and certainly risky. When broken down this
way, almost any social interaction can yield insight
into power dynamics at play.
So we waited to eat once we got upstairs, and
I think it made for a successful power play. (Fair
warning, it takes years of practice and hubris to do
this sort of thing without making a fool of yourself.)
“Man, we’re hungry. Mind if we eat our bagels
as we talk?” I inquired once our bags were on the
floor and we were settling into an impromptu meeting
space within the office of a vacationing executive.
Power 63

It was a reasonable request, and the client granted

it without any obvious displeasure. Why not, we’re all
friends, right?
The context makes all the difference in the world.
Just play it like you meant to do this all along, and
here are some of the subliminal messages you are
broadcasting:

• Sleep (your comfort) was more important than

waking up early to be able to have breakfast
before this meeting.
• Satisfying your hunger is more important at
this moment than waiting for introductions and
meetings to break or be over
• You’re okay with the risk of talking with your
mouth full, or leaving crumbs on someone else’s
desk or meeting table.
• You are not a slave to generally accepted social
protocols. Might indicate above average will-
ingness to drive innovative solutions to prob-
lems.

Awesome! Bet you didn’t know you could do all that

while enjoying a yummy bagel, eh? Seriously though,
what you want to do with any power play is to gently
send the message that you’re in control, that you’ll
Power 64

manage this relationship the way that you want, and

that you can break unwritten rules whenever you
want to do so. You’re special, just like your Mom told
you when you were a child.
On the other hand, you never want that message
to come across in a crass manner. Convey it matter-
of-factly, as if it’s the most natural thing in the world
for you to get what you want.

The Pause Power Play

Here’s another, more serious power play. Inevitably,
you will find yourself in a situation where you’re
doing some work for a client and they decide that
they can’t pay you. However, they still want you
to continue working on whatever important thing
you’re doing for them. They’ll probably promise you
payment at some later date when it’s more convenient
for them. Perhaps they’ve run out of funding, or are
having cash flow issues.

Problems with payment are so common, that the

best approach for a consultant is to always get
paid upfront on retainer. A retainer is a regular
pre-payment for services, usually on a monthly
basis. It’s like a deposit for time you will bill in
.
Power 65

the future, but it has to be replenished whenever

it runs out.
You usually need to have a great reputation and
a lot of nerve to ask for a retainer. So most
people make do with invoicing their time for
payment, and it’s common to grant so-called Net
15 or worse terms, which means you don’t get
paid for your work until two weeks or more after
you invoice for it.
.

Say a client informs you that they won’t be able to pay

you on time. Except that doesn’t usually happen, does
it? More like when a client’s payment doesn’t arrive
as expected, they are using a power play on you. They
are hoping that your fear of confrontation or fear of
losing their business will cause you to ignore the non-
payment or at least put up with it for awhile.
Intolerable!
When clients fail to pay, they might actually in-
tend to pay you later or they might not. Obviously, not
everyone is equally honest. I’ve dealt with both situa-
tions, and can tell you that some people are downright
evil. But either way, they are making their problem,
lack of cash, your problem. And if they expect you
to continue working, then they are essentially trying
Power 66

to force you to give them an interest-free loan. How?

Because absent a smart late payment policy, your
labor is essentially free working capital for them.
No good. Which is why you should use the Pause
Power Play. As soon as payment terms are violated,
you call or email your client and inform them that
work will be paused until such time as payment is
received. Ideally, your ability to stop working upon
breach is enshrined in your contract with that client;
usually it is, but you should make sure. Need a con-
tract template? I have an entire online store full of
them⁶.
It is of utmost importance that you use the word
“pause” instead of “stop,” in fact, this is what makes
the whole affair a power play. Do not under any
circumstances refer to it as a work stoppage. Stopping
work implies that it may never start back up again,
and unless the client is a real pain in the ass, you
probably want to avoid that outcome. Pause, on the
other hand, implies that work will start back up again,
perhaps quickly. It is the client’s choice of when to
press play again, just as soon as you get paid.
⁶http://msabundle.com
Power 67

The “No Asshole” Power Play

It’s a good policy to avoid working with assholes,
period. Don’t hire them to begin with, or fire them
as soon as you figure out that they are assholes. (That
goes for employees and clients equally.) However, the
realities of cash-flow will keep you from following
that advice 100% of the time, especially when it comes
to clients. After all they’re paying you, so you might
be inclined to take the abuse. This is where you have
to get tough and make sure you and your team get the
respect you deserve. If you’re being excellent then you
have leverage. So use it.
Once when I was running Hashrocket, I found out
that a client had yelled at Adam, our project manager,
during a status call. Poor Adam, who had one of the
more stressful positions in the company to begin with,
was pissed off and trying to calm himself in my office
when I walked in.
“What happened?”
“Mike (name changed) just totally lost his shit on
the phone with me and called me a bunch of names.”
“Seriously?” I asked. But I was not shocked, given
Mike’s reputation for being an asshole.
So I collected the details from Adam and gave
Mike a call on speakerphone. When I connected, I
calmly told Mike that Adam was sitting in my office
Power 68

and had just told me about their earlier phone call.

Mike tried to cut me off, but I did not let him. In
fact, I didn’t even ask Mike if he agreed with my
assessment. I did not ask him for his point of view of
what had happened, or why he had lost his temper.
I did however, inform him in no uncertain terms,
that this would be the last time that such behavior
would be tolerated and that we would immediately
terminate our contract if it happened again.
After a brief pause, Mike began apologizing pro-
fusely and promised that it would never happen again.
I told him I was on speakerphone and that Adam
was present so he could address his apology to Adam
directly, and he did so.
Pleased with his reaction, I told Mike I was glad
we had sorted that out and that we needed to get back
to work. Believe it or not, we had no further conflicts
with this guy and we did some great work for him.
The incident had the side benefit of becoming part
of a canon of stories related to our high standards at
Hashrocket. The way I handled it won me points with
employees and clients alike. Nobody respects a wimp.

In retrospect, it was easy to be tough on Mike because

his project was small. Later on I would learn exactly
how difficult it is to follow my own advice.
My biggest client at Hashrocket dragged their
Power 69

feet on payments again and again over the course of

several months. I spent lots of energy trying to get
them to pay, but ultimately let them get away with it
because half of my shop was on the project. At that
stage in our history, it meant about a dozen people
billing 60 thousand dollars per week.
To make matters worse, the CIO of this company,
the guy I was dealing with, was an asshole. Not just
any old asshole, he was passive aggressive. He would
purposely avoid my calls and do everything possible
to keep me in my place. I could tell I was being played,
but couldn’t figure out how to deal with it.
This evil client nearly ruined me in the end. They
waited until we had delivered a working version of
their project (and owed us almost half a million dollars
in late payments) before suddenly pulling the plug. No
warning given, just termination. Ultimately we only
got them to pay 90 thousand of what they owed and
wrote off the rest of the amount as a loss.
Could we have sued them for the balance? Sure,
but we demoralized and afraid of throwing good
money after bad in a trial. We knew it would present
an ongoing distraction and had an uncertain outcome.
Sometimes you get checkmated.
Now here’s the thing: if I had conjured up the
balls to pause work the first time they were late, that
never would have happened. If I had never tolerated
Power 70

asshole behavior, it probably wouldn’t have happened

either. Sure, we might have forsaken the big project
revenue, but given the frothy condition of the market,
we probably would have just earned that money from
someone else. To this day that one fiasco represents
the most expensive business lesson I’ve ever learned,
one which would have paid for a Harvard Business
School degree a few times over. It decimated our profit
margin for the year and was one of the factors in
Mark’s decision to stir up trouble later that year.
Clients sometimes get very angry at you for paus-
ing work. They may scream or foam at the mouth.
They may make threats of legal action or worse. Or
they might plead with you for mercy, calling upon
your generosity or loyalty to their cause. I had one
client tell me once that we were forcing him to draw
down his daughter’s college savings. What a sob
story! After all, we didn’t force him to overcommit
to anything.
Don’t fall for the threats and excuses. As long as
you maintain your resolve, the power rests with you.
Nobody deserves to get taken advantage of, especially
not someone who is working hard to do a good job.
And actually I say don’t fall for it based on experi-
ence, because time and again, I witnessed clients who
had “run out of money” figure out how to make pay-
ments in order to restart their projects. Maybe they
Power 71

had been lying, maybe they put their own personal

money in, maybe they really did use their kids’ college
funds, I didn’t actually care where it came from, as
long as we got paid.
Learn to use this power play early and often. It’ll
save you a lot of money and grief.

The Long Vacation Power Play

If you’re able to afford taking a long-distance va-
cation, definitely consider using this power play. It
works especially well when you’re friends with your
clients on Facebook. Give them a daily stream of how
much fun you’re having on your trip. Ideally you want
them to be stuck back home working while you’re out
having fun.
The reason that this otherwise banal power play
packs a punch is that so many ambitious people don’t
actually take time to enjoy their success. They’re
always trying to infect you with their workaholicism.
They’ll demand that you work continuous overtime
or hound you with calls and emails outside of normal
work hours. Depending on how much you need the
work, you’ll put up with it to some degree or another.
(Don’t be an enabler! It’s useful to set boundaries on
overtime, but that’s outside the scope of this particular
discussion.)
Power 72

First give the relationship at least a few months to

build trust, then go on a 2-3 week vacation. I’m not
talking about a trip where you make sure you have
internet connectivity and continue doing work even
though you should be relaxing at a beach or ski lodge.
I’m talking about an honest-to-goodness, completely
disconnected vacation.
To be clear, I’m not saying to disappear suddenly
for a few weeks or anything like that. Give your client
enough notice to not be caught off guard and then go
enjoy yourself. Make it seem as normal as a gray day
in Seattle.
Like the others, this power play communicates
confidence in your worth and abilities. You are not
intimidated by your client’s opinion about your vaca-
tion, nor are you worried about losing their business.
But you are making it crystal clear that your needs
come before theirs.

On Being a Cynic
The whole notion of power plays might seem quite
negative to some people. Why play games, or risk
coming off as an asshole, when good work and in-
tegrity should be enough? Actually the least you can
do is to arm yourself with a confident attitude and
some psychological techniques for protection.
Power 73

I agree that doing good work, exceeding expec-

tations and holding up your end of your business
agreements should be enough for success. But the
realities of the ruthless capitalist business world that
we inhabit have made me cynical over the years.
There is little loyalty left out there. It’s every man
for himself, and even friendly business partners some-
times succumb to the temptation to screw each other
over if given the chance. Time and again I’ve been
knifed in the back by people I trusted. I’ve witnessed
clients shamelessly try to weasel out of hundreds of
thousands of dollars of debt incurred for legitimate,
high-quality work.

Trust, but verify. — Someone wiser than me

.

Learn as much as you can about everyone you con-

sider working with. If you’re in a position to hire
employees, strongly consider a strict contract-to-perm
policy. If you take on clients, especially for big projects,
do yourself a favor and invest in background checks
and credit references. And if you work for a corpora-
tion, fully expect to be shafted as soon as it’s in the
shareholder’s best interests to do so.
Power 74

Bleak outlook, I know. But I think it’s better to

be pleasantly surprised when things go well. Don’t
believe me? Research why Denmark has the highest
levels of happiness among nations while being some
of the most pessimistic people on earth.

One of my favorite kinds of power plays involves

a super obvious way of telling people that you’re
confident in yourself and your abilities: the way you
dress. It’s fun and can entail being true to yourself.
I like the subject so much that I devoted an entire
chapter to it.
Dressing the Part
Over the years and in the course of much exper-
imentation, I’ve come up with some best practices
for dressing myself. I don’t mean the mechanics of
dressing myself; I put my pants on one leg at a time
like everyone else. But the way I look says a lot about
who I am and what I’m about. It does for you as well,
so definitely put some active thought into it.
Personally, I have two wardrobe modes: default
and message. These are modes, not styles. In default
mode, I primarily want to minimize the decision
time involved in getting dressed. In message mode, I
purposely pick a look that sends a message to clients
or other associates. Depending on how aggressively
my message contrasts with the way people around me
are dressed, I might even consider it a power play. But
before getting into that, let’s first consider our default
mode.

Default Mode
Did you know that denim is highly bacteria-resistant?
Unless you’re especially sweaty, smelly or prone to
Dressing the Part 76

bouts of bladder control issues, you might be able to

wear the same pair of jeans for a week at a time before
airing them out. I wash most of my jeans maybe a
couple times a month.
When I’m on trips that do not involve formal
wear, I pack two pairs of jeans: one classic or dark
blue denim, and the other black. They match with
everything else in my basic wardrobe.
I don’t wear dress shirts, or any button-down,
collared shirts on a daily basis. I only own about 2 or
3 such shirts that get any sort of regular usage, and as
I write this out I’m questioning whether those belong
in my closet or not. The problem I have with them is
that they require dry cleaning.
Ain’t nobody got time for that.
Fancy clothes, for lack of a better term, also tend to
go out of style very quickly. Too quickly for my tastes.
Thus in default mode I wear nice t-shirts instead
of anything fancier. The problem with most T-shirts
is that they shrink in the dryer and get unacceptably
short. Having portions of my midriff peeking out over
my belt is not a desirable look, not for me. Probably
not for anyone, especially in a business context. Luck-
ily I figured out that Gap actually sells “tall” T-shirts
that are extra long in the midriff. When they shrink,
they remain long enough to tuck into my jeans or at
least cover my waist. However, they are not available
Dressing the Part 77

in retail stores. You have to order them online. I tend

to order a dozen of them at a time, in different colors,
but mostly black. They’re cheap enough that you can
replace them once a year, or whenever they get too
faded in the wash.
As a tech guy, I’m constantly picking up free logo
t-shirts at conferences or other events. I admit that at
times, especially during the Hashrocket years, I wore
these shirts almost every day. But nowadays I find
that plain t-shirts are a lot classier and make a better
impression. Leave the promo shirts for the gym or
events where you need to identify yourself with a
particular company.
When it’s cold outside I layer a heavy knit sweater
on top of my t-shirt. Really cold? I add a gray coat,
either waist or mid-thigh length and double up on
the T-shirt. Score bonus style points by using slightly
different color shirts. (Warning: wildly contrasting
colors might look okay on the mannequin in the store,
but usually don’t work on real people.)
Socks are a really important part of your wardrobe.
Usually, I try to limit the variety of athletic socks in
my drawer at any given moment so that I don’t have
to spend a ton of time matching them up after doing
the laundry. But since the rest of my default wardrobe
is plain, I add some flair using colorful striped socks.
The brighter and wilder the color combinations, the
Dressing the Part 78

better. Don’t hesitate to wear different colored (color-

ful) socks on each foot, in fact some brands naturally
come that way. It’s a super subtle power play of the
“don’t care about conventions” variety.
Default mode means keep your basic wardrobe su-
per simple. It means easier laundry and less decisions
to make in the morning when you’re getting dressed.
An artifact of this scheme is that I end up buying
certain items in bulk when I like them.
Most people have some amount of trouble finding
shoes that fit comfortably. In 2009, I happened to
buy a pair of extremely comfortable, black, fully-
lined leather, rubber-soled moccasins by an Italian
designer. They were so comfortable and versatile that
I found an online retailer that sold them at a good
price and ordered four more pairs. I unpacked one
of the extra pairs and put the others in the closet
for safe keeping. Other than leaving a pair in a hotel
room somewhere a few years ago, the rest are still in
rotation. They’re versatile too; I’ve worn them with
everything from big baggy linen shorts on the beach
to formal suits.
Default mode works especially well for me when
I’m working from home. I have nothing to prove to
anyone. I just want to be comfortable enough to not
think about what I’m wearing. Pajamas or sweats
might be more comfortable, but being too comfort-
Dressing the Part 79

able is not conducive to concentration on work. It’s

conducive to naps.
The most well-known proponent of default wardrobe
strategy is Steve Jobs, who turned his black mock
turtleneck and Levi’s 501 jeans into a Silicon Valley
guru uniform. The Japanese designer Issey Miyake
made Steve enough black shirts to last a (too-short)
lifetime.

Message Mode
Default mode works best when you’re working from
home or mostly by yourself. In a nutshell, I do not
advocate dressing the same as everyone else in your
office environment. It’ll send the message that you’re
just like them. And you’re not, right?
I was in my mid-twenties when I got divorced.
Under the weight of family responsibilities and pres-
sure to fit in from my very conservative wife, I had
never really taken a chance to express myself via my
personal appearance since being a teenager. And even
then my choices were severely limited by my overly
religious parents. If I remember correctly, when I
left my ex-wife I packed up a closet full of Dockers
khaki pants and button-down casual dress shirts, the
standard uniform of boring office grunts everywhere.
That shit promptly got donated to Goodwill.
Dressing the Part 80

On my own for the first time ever, I went a little

nuts with my appearance. Goth? Yep. Skater punk?
Yep. Big flare-bottom raver pants? Yep. Piercings?
Yep. Bleached hair? Hey, it was during Eminem’s peak
popularity!
I admit, I was going through what you might call
a quarter-life crisis. And despite the fashion hijinks, I
was still gainfully employed as a six-figure technical
architect at my employer, MediaOcean. For a couple
of years after being acquired by clueless corporate
overlords in New York City, it was common for Jim
Freeman, our slave-driving Director of Development,
to make us spend 60-70 hours or more per week in the
office.
During those times my life turned into a vicious
triangle of work, drinking and sleep. Picture this: I
literally lived across the street from the office. Our fa-
vorite drinking establishment, Halo, was in the base-
ment of our office building. It was a classy joint, so
you had to look good to be in there. Particularly when
happy hour turned into dinner, turned into drinks,
turned into dancing, turned into shots, turned into
stumbling back across the street to collapse into bed
at 2-3am in the morning.
I lost a lot of weight during those days. When
my marriage fell apart I weighed about 260 pounds
and had a size 38 waist. I look at old pictures of me
Dressing the Part 81

from that time and I look bloated. Over the course

of the next two years of hard partying, drinking and
drugs, I dropped down to a svelte 175 pounds. Not the
best way to shed pounds, but it was a much healthier
weight for my 6 foot frame.
For a brief time, slimmming down to a size 28
waist opened up a whole new world of fashionable
opportunities. Now I could rock hipster skinny tshirts
and purple velveteen Dolce & Gabanna jeans. Frankly,
I looked gay and loved it.
Over time, the more outrageous my outfits be-
came, the better I performed. It was a reflection of my
confidence.
My bosses at MediaOcean did not care what I
looked like, or what I did in my spare time, as long as I
kept producing work. During the most intense times,
I have a feeling I could have come in decked out in
full S&M leather bondage gear and a bright orange
mohawk and nobody would have cared.

My next job was at ThoughtWorks (TW), one of the

best tech jobs in the world at the time. I was hot shit
and acted like it. (Ahem, sincere apologies to everyone
who had to work with me in 2004.) My work environ-
ment changed significantly from the wild, anything-
goes attitude at MediaOcean. During my tenure at TW
I consulted at McGraw Hill, Barclays Bank, Daimler
Dressing the Part 82

Chrysler, and John Deere, all Fortune 500 corporations

where people really did care what you looked like.
Most had corporate policies to make people comply
with their ideas of proper appearance.
Did I buy a new wardrobe? Ha! Far from it. I kept
the big piercings in and continued dressing the same
as I had before. I no longer bleached my hair, but
instead let it grow out until it touched my shoulders.
My facial hair continued to change on a monthly
basis. Sometimes a full bushy beard, sometimes a
well-trimmed goatee. Whatever floated my boat. And
all around me? The same sea of boring casual dress
shirts and khakis.
And that’s the point. My look sent a clear message
to the ordinary people surrounding me, including
some of the tech managers I was consulting: “Zero
fucks given about how you normally do things here.”
Reason I could get away with it, besides confi-
dence, was because the way they were doing things,
illustrated by their boring, sensible, eminently main-
stream fashion sense, well, that wasn’t working, was
it? Otherwise they wouldn’t be paying tens of thou-
sands of dollars per week to have me and my team on
site rescuing their project. Simple logic.
That said, I did care very much about solving
their problems, about living up to the ThoughtWorks
reputation for excellence. I also did care about com-
Dressing the Part 83

municating with them so that I could effectively do

my job. What I didn’t care about so much was their
opinions about how to do what needed to be done. Or
their personal opinions about me. To most of them, I
was arrogant and got away with it.⁷
More than once my flaunting of dress code did
provoke quite a bit of butthurt among those with less
confidence or power. Griping emails were sent to su-
periors. ThoughtWorks client executives were alerted!
I was never seriously reprimanded, but meetings were
had about the importance of maintaining peaceful
relationships with our client’s employees. I thought
the notion of us being sensitive to inconsequential
restrictions put on rank and file employees was ridicu-
lous. Let them gripe. They’re lucky to still have jobs,
right?
⁷Mercenary, results-driven consulting in corporate America, if you can
get it, is one of the most intellectually satisfying jobs possible. Executives pay
exorbitant fees to bring you in and get shit done that their own managers and
teams have failed to do. But they don’t fire those managers and teams! So you
get the perverse pleasure of coming into a hostile situation and rubbing their
noses in their failures. I figured out that being an asshole is a prime asset in those
situations, and I dressed the part. No subtlety needed. Dress-casual dress code? I
wore ripped jeans and a tshirt. Dress-down Fridays? I wore beach shorts and flip
flops.
Dressing the Part 84

Unpredictability
Mixing it up is an important aspect of dressing to send
a message. If you become the guy that always wears
swim trunks and flip-flops no matter the weather,
people can start to write you off as “that wacko down
the hall with the flip flops.” Avoid being typecast by
mixing things up on a regular basis.
On one particular client engagement, at Barclays
Bank in Wilmington, I dressed up instead of down.
My good buddy Jay Fields was working with me and
brought his NYC sensibility when it came to dining
choices, drinking habits and fashion sense. So what
did I do? I added some nice suits and dress shirts to
my wardrobe. I invested in some ties and fancy shoes.
It was a different kind of fun. More refined. I could
afford it, so why not?
Jay and I overdressed the onsite employees that we
were working with by a mile. Although it was a bank,
we were in their tech center, full of programmers and
misfits, operating under no discernible dress code.
You could argue that we were showcasing our
arrogance by dressing so much better than everyone
else every day, and we kind of were, however that’s
missing the point. The reason it’s a power play is
that it sends a clear message to your peers that you
do things differently. Again, I stress that this attitude
Dressing the Part 85

must be coupled with excellent work or all bets are

off.
How do you find your own style? The office
uniform, whether it’s blue dress shirt and khakis, or an
ironic t-shirt and jeans makes you fit in to the crowd
in a predictable fashion. That’s no good. See if you can
find a style that fits your personality without copying
what everyone else is doing. And do it right from
the beginning of the working relationship, to establish
that you’re different. You play by different rules.

While Steve Jobs personifies my default wardrobe

concept, the message wardrobe is Facebook CEO
Mark Zuckerberg with his hoodie and Adidas
slide-on sandals.
.

What it comes down to is that if you’re a high-value

asset to your employer, all sorts of trivial rules and
practices do not need to apply to you. Ignore them
and prosper in happiness. Bask in the glory of being
special! Depending on your appetite for confrontation,
dealing with the inevitable pushback can even present
opportunities for fun, but harmless mischief.
Dressing the Part 86

Getting away with it

There are a couple of approaches that I’ve successfully
used to get my way with employers. It helps to dig
deep into your memories of teenage rebellion, if you
have any. Note: I’ve said this half a dozen times
already, but it’s that important: this advice only works
if you’re truly good at your craft. If you suck or prone
to bad luck, then following any of this advice will
probably get you fired. Don’t say I didn’t warn you.
So you’re in a meeting with your boss and she’s
pissed off that you’re flaunting the rules and disobey-
ing conventions. First, try to wipe that smug grin off
your face. Second, decide on an approach.
1) The Adversarial Approach
“Why does it matter what I wear? Does it affect
the quality of my work? Don’t you understand that I
need to be comfortable to do my best work? Why are
we wasting time with this conversation?”
Especially, notice the “why” questions. They are
rhetorical and purposely confrontational. They don’t
really have a correct answer. If you have the personal-
ity for it, you might just rattle off a rant on conformity
and dysfunction and whatever other pet topic you
want to throw into the mix. See how long you can
keep the rant going — my personal best is around
20 minutes. Preloading with caffeine helps. Berate
Dressing the Part 87

whoever has been complaining for wasting your time

with such nonsense, especially if they’re your boss.
“Fire me already if you have such a big problem
with how I dress. Or move me to another project
where people are focused on the work at hand instead
of trivial bullshit.”
Your boss may be angry that you’re power playing
them, but deep inside they must begrudge you some
respect. You might even give them a vision of what
they were like before they submitted to corporate
shafting on a regular basis. Visions of when life was,
you know, fun and worth living.
You might be limiting your upward mobility, but
as long as you’re awesome, most bosses fear losing
you to another employer most of all. I’ve pushed the
envelope very far before facing disciplinary action
using this approach.
2) The Conciliatory Approach
This approach is fun in a subversive way and
better suited for you introverts and fans of passive
aggression. Ready? Just agree with the advice you’re
given. Look your boss earnestly in the eye, nod and
agree with everything they are telling you. Apologize
profusely for your digression. Promise it won’t hap-
pen again. Ask if they would like you to go home and
change into more suitable attire. (They won’t.)
Go back to work and pretend like the meeting
Dressing the Part 88

didn’t happen. Just ignore it. Note that you shouldn’t

adhere to the dress code for a day or two and then
revert to your old pattern, just disregard it completely.
I had fun with this one at MediaOcean. Everyone
hated Jim Freeman for his arbitrary rules about when
and how we could take breaks and what time we had
to be in the office. The thing is that when you’re slave-
driving your team to put in 70 hours or more per week,
you better be prepared to let them work whenever and
however they see fit to be productive.
Jim didn’t see it that way. I can’t even begin to
count how many lectures we got from Jim every week.
He spoke about responsibility. He spoke about honor.
He spoke about entitlement mindsets and the crucial
importance of not developing a sense of one.
I can only give Jim credit for one thing, which
is that he spent the time onsite with us when we
had to work late. But then he would insist on getting
there early in the morning the next day. Sure man, I
understand that you’re going home and ignoring your
wife and kid and going straight to bed so you can get
back up at the crack-ass of dawn to do it all over again,
but not all of us are like that! Me and the crew, we
decompressed by going down to the bar and getting
drunk. You can’t really expect us to be here at 9am
and actually get any work done, can you?
So we’d shuffle in at 11am, cursing our hangovers
Dressing the Part 89

and expecting a lecture from Jim. We’d get one, and

we’d apologize and promise to never do it again.
Rinse. Repeat. Over and over. An exercise in futility,
and nobody ever got fired.

Sales Mode
There’s actually a third mode related to messaging.
First impressions are critical, and there are longstand-
ing rules that govern the way you are perceived when
you’re out in the field having a sales meeting, raising
money, etc. Do your homework. Find out how your
prospect dresses and what their corporate dress code
is, even if it involves calling the receptionist and
explicitly asking about it.
Armed with information about your prospect, your
goal is to dress one step up. If they’re in jeans and t-
shirt, then you wear slacks and a collar shirt. If they’re
wearing sport coats with no ties, then you wear a
suit (but still no tie.) Strike the right level of dress
above theirs and you’ll come off as having respect for
their time and solid authority. Don’t overdress, or you
might come off as unrelatable.
Also, this should be obvious, but details matter!
Shoes should be clean and (if applicable) nicely pol-
ished. Don’t forget your belt. Tuck your shirt in. Get a
manicure or at least make sure your fingernails are
Dressing the Part 90

clean and filed properly. Need a haircut? Go get a

haircut. The nicest outfit can’t fix needing a haircut.

In conclusion, whether you’re dressing up or dressing

down, or sending a message, at least take care that
you don’t look like a slob. Go through your wardrobe
on a regular basis and pick out anything that is faded
or that has shrunk or that has holes where they’re
not supposed to be. Keep an eye out for subtle stains
that don’t wash off. Throw all that stuff into garbage
bags and donate it to Goodwill or your local Salvation
Army for a quick little tax write-off and karma boost.
Even when you’re in default mode, the one thing
you never want your dress to communicate is that you
have no pride in yourself. And speaking of pride in
yourself, one of the fastest ways to lose it is to work
with crazy people. As you’ll see in the next chapter, it
pays to avoid crazy people at all cost.
Never Work With
Crazy
Crazy people will make you crazy, so don’t work
with them willingly. It won’t always be immediately
obvious that someone you’ve gotten involved with is
crazy. Or a situation that starts out rosy might turn
on your when you least expect it. Be alert and get
out of crazy situations as quickly as possible, lest their
insanity rubs off on you.

Sometimes an entire company is crazy. Back in 2004,

I got my first full dose of corporate-wide insanity
when I landed at DaimlerChrysler’s Dealer Technical
Services. Not only were my bosses there insane, the
project itself was one of the worst death marches I’ve
ever experienced.
Ray was a grizzled veteran of Chrysler and Michi-
gan native. He was a short heavyset man, with dark
circles under his eyes, and a big salt and pepper beard,
mostly salt. I’m guessing he was in his fifties or later.
We’re talking about someone that’s been around the
block in corporate america. The group he led was
Never Work With Crazy 92

in charge of producing StarScan devices, a handheld,

Linux-based tablet computer used by dealer techni-
cians to diagnose problems with Chrysler vehicles.
Myself and another sharp ThoughtWorks con-
sultant named Aslak were parachuted into Ray’s at
Chrysler’s massive headquarters in Auburn Hills, Michi-
gan at short notice in late autumn, just as the days
were getting dark early and snowfall becoming a more
common occurrence.
The scale of the Chrysler headquarters is mind
boggling. They don’t actually build cars there, but
they do everything else from engine design and test-
ing to financing. At the time perhaps 16 thousand
employees worked at headquarters. They inhabited a
network of large buildings interconnected in such a
way that you could get from place to place without
having to brave the fierce Michigan winter climate.
My first week onsite was exciting, even just from
wandering around the massive 50-foot hallways dur-
ing lunch, innocently peeking into the different lab-
oratories. One of the alcoves I’d tuck into to make
personal phone calls was loaded up with dozens of
high-performance HEMI engines on pallets. There
were literally cool things to see around every corner,
and as far as I could tell the mood was upbeat too.
The economy was starting to turn around from the dot
com slump, and Chrysler itself was in full integration
Never Work With Crazy 93

frenzy from their recent merger with DaimlerBenz of

Germany.
It was clear from the very first week that this
was not going to be an ordinary client engagement
for me. To begin with (even though I didn’t hear
about it until weeks later) ThoughtWorks had a long,
rocky history with Chrysler. A few years years prior,
a TW employee had violated security protocol by
plugging in his laptop computer into the Chrysler
LAN and dialing in via modem into the internet at
the same time. The malicious worm that entered their
network as a result brought down over half of the
companies’ Windows-based computers and several
manufacturing plants, causing millions upon millions
of dollars in delays and other problems. IT security
traced the breach to the TW consultant’s desk almost
immediately and caught the guy redhanded, still con-
nected to the Internet. After the embarrassment of
a physical altercation during which security tried to
take possession of the offending laptop and threatened
to physically detain the TW consultant, the Thought-
Works contract was summarily canceled and the CIO
made a personal promise that ThoughtWorks would
never be allowed to work for Chrysler again.
Not exactly fertile ground for a growing, healthy
relationship to take root. And yet here we were,
because not only was Ray a bit of a rebel, it turns
Never Work With Crazy 94

out that he was also good personal friends with Bruce,

the Global Vice President of Sales for ThoughtWorks.
Their secret deal to continue staffing ThoughtWorkers
on Ray’s team lasted a couple of years before I arrived
on the scene. I never did meet the guy staffed before
me, a Thai programmer named Koson. He had quit
ThoughtWorks (and by extension, his contract with
Chrysler) a week before Aslak and I landed on site to
take over his work. The somewhat suspicious disap-
pearance should have given me a clue that something
fishy was going on, but at that point in my career I
was in full-on hubris mode, so I plowed ahead with
my usual headstrong confidence.
The StarScan system we were to take over main-
taining was written in Java, mostly by Koson. It ran
on a custom commercial J2ME runtime on the Linux-
based StarScan device. As it happens, the first issue
we ran into was that Koson was a C programmer
and this was the first code he had ever written in
an object-oriented language. We ended up with the
distinct sense that Koson was no ordinary Thought-
Worker. First of all, nobody had ever heard of him
before, and he had been working on this project all
by himself, partially from his home, without any help
or monitoring on the part of other TW personnel. That
was very unusual.
The project itself, given the history of the client
Never Work With Crazy 95

relationship was pretty much a skunkworks. (Near as

I could tell, nobody else at TW even knew this project
existed.) Koson did not follow our normal Agile prac-
tices, and although Ray, the head of the department,
professed to be a fan of extreme programming, he
actually didn’t follow any Agile practices with any
sort of consistency.
If you’re not a programmer yourself, I’ll clue
you in to the biggest problem with a C programmer
writing a mission-critical system for the first time in
Java without any supervision. It’s madness! Koson had
no idea what he was doing. It would be like taking
someone that only spoke English his entire life, giving
him a crash course in Latin grammar and then sitting
him down by himself to write an opera in Italian. It’ll
be a miracle to get anything usable at all and the result
is going to be painful for everyone involved.
There were other consultants involved in giving
birth to the unholy beast that was the StarScan system
too. A fellow by the name of Rod Johnson, who
later achieved massive success with his Spring Frame-
work, was an early contributor to the project via
his consulting company named Interface21. He had
a dependency management framework by the same
name, which relied heavily on XML configuration
files to organize the components of a large, modular
Java system. It was essentially a predecessor to Spring.
Never Work With Crazy 96

A clunky one at that. Koson and friends organized

the entire StarScan system around the Interface21
framework. The definition of a particular vehicle’s set
of computerized controllers was specified in an bean-
config.xml file.
If you’re an old Java programmer like I am, and I
hope at least some of you are, let that sink in a minute.
Yah.
So over the course of what must have been years,
an army of low-skill, low-wage, cargo-culting grunts
copy-pasted bean-config files, producing an ever-expanding
blizzard of tweaked numbers and letters to support
additional vehicles as they were introduced. It was the
biggest exponential explosion of craptastic code I had
ever seen in my life.
Koson’s StarScan implementation limped along
and mostly worked until the merger with Daimler
started to bear fruit in the form of brand new au-
tomotive collaborations. The new small scale Jeeps
and highly-anticipated Chrysler 300 platform vehi-
cles were hybridized little monsters, at least from
a technical perspective. They incorporated a bunch
of Mercedes Benz components, including advanced
drivetrain and safety CPUs in otherwise plain-jane
American cars with older Chrysler-designed CPUs.
The vehicles handled well and impressed critics, but
behind the scenes, the new vehicles demanded new
Never Work With Crazy 97

releases of our diagnostic devices capable of speaking

extra protocols. The controllers originating from Benz
sat on the the same “car-area network” (CAN) wiring
harnesses, but they might as well have been talking
German and ours English; the binary specs of their
communications protocols were completely different,
everything from baud rate to binary data patterns
involved.
Koson didn’t anticipate these sorts of changes, so
he had coded all sorts of implementation details about
legacy CAN communication protocols directly into
the screens and buttons of the StarScan software, in-
stead of abstracting that knowledge out into modular
components that would be easy to modify. During
my first meeting with Ray, he described the goals for
our engagement. We needed two accomplish two key
outcomes:

1. Support communications with the new Benz

modules in the hybrid vehicles
2. Split the StarScan software in two, so that the
user interface could run on commodity laptop
computers that interfaced to the vehicle via a
wireless-enabled “pass-thru” box connected to
the OBDII port.
Never Work With Crazy 98

The requirements seemed reasonable to me, because

I made the (tragic) assumption that the system had
been written in a well-structured, modular fashion.
ThoughtWorks only employed superstars, so it wasn’t
wildly inappropriate for me to assume that would be
the case. Then again, I didn’t personally know Koson
or the circumstances of his sudden departure. (Sorry
buddy, I realize now it wasn’t your fault.)
I don’t want to get any deeper into the technical
details of this monstrosity of a project, just trust me
when I tell you that the two key outcomes Ray wanted
ended up being almost mutually exclusive. Koson had
made such a mess of things that once he realized shit
would hit the proverbial fan, he didn’t even try to fix
it. He didn’t even bother to try getting reassigned, he
just up and quit ThoughtWorks with zero notice and
got the hell out of the country, presumably back to
Thailand. (I know this because my team spent the next
six months unsuccessfully trying to get a hold of him
to ask him tough questions about his code.)
Let’s see, so far I haven’t mentioned a third key
aspect of the project. Time pressure! The changes
needed to be finished by the spring EPA deadline for
diagnostic software updates, or Chrysler would be
fined a MILLION dollars PER DAY until we delivered.
Unbeknownst to me that first week, I was about to
Never Work With Crazy 99

embark on the first real death march of my life.

It took a few days for Aslak and I to begin figuring out

that we were in deep doo-doo. We called Bruce, the
TW global VP of sales to give him a heads up about
what was going on. “You guys just do the best you can
and be sensitive to the fact that we made this mess for
them.”
I can only describe my reaction as yeah, boss…
sorry what? We pleaded, to no avail.
“But you don’t understand, this is mission impos-
sible!”
Bruce was unfazed.
“Ray’s a good guy, just talk to him and figure it
out. You’ll do fine.”
“Okay,” we sighed, and went back to our desks.
Ray dropped by and asked for our opinion so far.
Well, we were in a little over our heads here given the
amount of work that would have to be undertaken.
We’ll need additional help for sure. “No problem!”
exclaimed Ray. Over the course of the next few weeks
we got another handful of TW consultants onsite.
Now were a team. A team in deep, deep doo-doo.
The first couple of weeks involved desperately try-
ing to add test coverage to Koson’s code, so that we’d
have some sort of safety net for making sweeping
changes to it. No best practices for writing testable
Never Work With Crazy 100

code had been followed, so it was HARD work. We

had half-a-million lines of untested, procedural Java
code on our hands and no way to figure it out. Not
only that, but its author was missing-in-action, so it’s
not like we could get him to explain things to us.
We kept uncovering one crazy obstacle after another.
Within another few days it was clear that we needed
to do a rewrite from scratch. We worked up some
courage and took our concerns to Ray.
He was indignant.
“Every new team I’ve ever worked with said the
previous team’s code was shit and needed to be rewrit-
ten,” Ray informed us flatly.
“No, but this time it’s true.”

This is when we first heard about a deadline. “There’s

no time to rewrite, we have to ship in February.”
Uh-oh, this wasn’t going to end well, so we shifted
tactics on the fly.
I broke it down to Ray: “Okay so maybe a rewrite
is out of the question, but we should start breaking up
the work into stories and estimate them, and do some
high-level release planning, so that we have a handle
on how long it’s going to take.”
Ray was not happy about that suggestion. He told
us that we could spend time planning or working, and
he would prefer us working. That was an extremely
Never Work With Crazy 101

troublesome position to take. Without a plan we’d be

working blind, something disorienting to anyone, but
especially to us, the creme de la creme of Thought-
Works talent. We were not used to being treated this
way, so we continued to protest.
For the first time of many instances to come, Ray
got agitated with us. He used what you might call a
screaming power play.
“Just fucking get it done, you guys are Thought-
Works, you are the best. You can get it done, just
fucking do it already.”
Well that just happened. Ten years into my career
and had never been screamed at before, especially not
by a client.
Let’s recap: It’s a few days in, Ray’s dropping F-
bombs and the project is already off the rails. De-
jected, we shuffled back to our workspace and de-
briefed the rest of our small team. Greg, the meekest
member of the team shrugged and got back to work
on whatever he was doing. He had preceded us on the
project for a few weeks and was already acclimated
to the abuse.
Aslak and I plowed ahead with the rewrite, pulling
strands on the biggest hairball mess of code that I’ve
ever encountered. No progress. We were stuck and
every week brought new nightmarish revelations and
additional requirements for the system. The runtime
Never Work With Crazy 102

platform for our software didn’t work on our laptops

very well. To run our nascent test suite, we had
to copy it onto a USB stick, load it onto an actual
StarScan tablet device, and run it there. Furthermore,
the StarScan device itself needed to be connected to
a large plywood board to which an assortment of
vehicle controllers had been bolted onto and wired
together to approximate an actual car.
As an aside, it’s unusual (at least in my experience)
to work on software that talks to hardware, without
having software emulations of that hardware. Using
actual hardware outside of its native environment
seemed unconventional, to say the least. When I men-
tioned this to Ray, he told me that the car controllers
were massively complex beasts that could not be
modeled in software for our use. That some of the
engine controllers were implemented in decades old
C code that was only understood and maintained by
a single individual Chrysler engineer. I’m guessing
that old guy was treated very well by the company
indeed. But truck-factor of one for a crucial engine
component? That’s some industrial grade crazy right
there, son!
Over the course of the next month or so I com-
plained incessantly about the inefficiencies were be-
ing subjected to, especially given the serious deadline
looming. However, in a union-dominated industry,
Never Work With Crazy 103

I should have realized sooner that inefficiencies are

accepted as an inviolable fact of life. One evening I
worked late with Aslak and Dave Hoover, one of the
newest members of the team. All of us were big fans
of extreme programming and wanted to facilitate pair
programming on the team. But the cubicle seating we
were crammed into made things very uncomfortable
for pairing. Once everyone else around us was gone
for the night, we busted out our own tools and took
apart the under-desk filing cabinets and work sur-
faces. We moved things around so that we actually
had space for some whiteboards and to sit side by side
at our desks to pair program.
The next morning Ray almost burst an artery in
his neck when he found out what we had done. “You
can’t even hang a fucking clock on the cubicle wall
without getting union-members to do it for you, ARE
YOU FUCKING CRAZY???”
We were lambasted for our idiocy in front of
the whole department. As we stood there red-faced
and shuddering with disbelief, Ray stormed off in a
fury and we didn’t see him for the rest of the day.
A member of his staff explained the separation of
labor between white and blue-collar staff at Chrysler.
Anything involving tools, you were absolutely not
allowed to do it, unless you were union. There would
be hell to pay once the union boss caught wind of our
Never Work With Crazy 104

reorganization of the workspace.

That wasn’t the only craziness abounding. Ray
himself was responsible for most of it. He was a rebel
and he wasn’t dealing very well with the apparently
disastrous politics of the Daimler merger. I don’t think
their honeymoon period lasted very long at all. In par-
ticular, Ray was worried about the Germans’ diamet-
rically opposed approach towards “dealer services.”
Ultimately one would have to emerge as a winner. The
chances of compromise? Nil.
Why? Our StarScan device cost about $800. By
reducing it to an even less complicated pass-through
device, they hoped to cut the cost of this tool in
half or more, all the better to open new markets
in third-world nations with their exorbitant import
duties. On the other end of the spectrum, Mercedez-
Benz diagnostic stations were huge rack-mounted,
PC-based affairs with multiple racks of custom elec-
tronics equipment. The base cost of an MB station was
$30,000 not including annual maintenance fees.
I think underneath the gruff, confident exterior,
Ray might have been terrified of what the merger
would do to his department. The Germans clearly had
a lot of money and power. On their part, they were
probably also terrified of losing the battle between
these two drastically different approaches, so they
were brutal in their power plays. We had to keep al-
Never Work With Crazy 105

most everything about what we did under tight wraps

or we’d get sabotaged, from within! For example,
when the Germans found out we had our eyes on a
particular ARM processor for our new devices, they
secretly bought the manufacturer along with all of
their manufacturing capacity for the following years,
just to screw us over!
To say that the atmosphere in that department was
poisonous would be putting it lightly. The pressure
was mounting to unbearable levels. My team was
patiently hacking away at Koson’s mess, yet making
very little progress. It would be very clear that the due
date was impossible, if only Ray would allow us to lay
out a release plan!
At least a month passed by and Ray starting
making it clear that he was not happy with our
progress. He went behind our backs to TW and asked
them to assign a project manager to the project, ap-
parently thinking that would help get us in line. A
pretty blonde from Chicago named Renee showed up.
She was awesome, but powerless to change anything
about the project. A week or two later, TW hired a
well-known Agile expert and he showed up on our
project too. I was relieved to be getting some heavy
artillery help, so to speak. We got Dave up to speed on
the situation and integrated him with the rest of the
TW staff. Privately, I clued in Dave on all the problems
Never Work With Crazy 106

we had on the horizon, especially if we didn’t make

the critical due dates early next year. During a “lunch
and learn” meeting with the rest of the department,
Dave presented a talk about his specialty, the subject
of his recently published book: Test Driven Develop-
ment, a disciplined approach to programming that we
were definitely not following during our hacktastic
adventures in StarScan spaghetti code. During the
obligatory Q&A session following his talk, I prodded
Dave to pipe up with his observations and opinions
about changing direction of the project. He sat there,
silent. It dawned on me that I was going to get no help
from dear Dave.
Fuck.
About two months into the madness, Aslak and
I got the team together and considered our options.
It was the beginning of November and our work was
due in February. This was do or die time. We had a
good grasp on the system and trusted our ability to
crank out code, if only we were allowed to start with
a clean slate. We were sure we’d bang out it in no time
and save the day, if only we were allowed to do so.
We took our plan to Ray and explained the pros
and cons of a rewrite. We showed him some of our ini-
tial stabs at a revised architecture that would support
the requirements. Our story was solid and we beamed
with confidence.
Never Work With Crazy 107

Ray gave us a surprise this time. With a patient

demeanor and a rare smile, he sighed and told us to
go for it. Once again, we returned to debrief the team,
this time barely able to contain our excitement. We
would get to rewrite this beast correctly! Koson’s folly
could be relegated to the dustbin of history where
it belonged. We immediately stopped what we were
doing and buckled down on the new codebase.

The next four weeks were a blur. We pair programmed

and practiced Test-Driven Development (TDD) reli-
giously. Everyone was super excited. Our shiny-new
test suite actually ran on our laptops, and quickly
too! The iterations flew by and we were actually
having fun for the first time on this project. Since
were doing proper story carding and estimation, we
were beginning to have accurate velocity metrics to
feed into our long-range planning. But the picture that
was emerging from our velocity metrics was troubling
from a schedule perspective. We obviously had too
much scope to get finished before February, especially
taking into account breaks for the upcoming holiday
season. I started pestering Ray about doing release
planning on an almost daily-basis. He shot me down,
every single time. About a month after the course
correction, my anxiety level was beginning to reach
record levels. Our fresh rewrite approach obviously
Never Work With Crazy 108

wasn’t going to work either.

Before going to much further, I should mention
that throughout the preceding months I was con-
stantly trying to get a hold of Bruce, the TW Global
VP of Sales, to let him know what was going on at
his client. I could not get a call back from that guy
to save my life. I went through other channels and
found out that Bruce did not have any other clients
himself, being that he was a couple levels removed
from actual account managers and salespeople. He
owned the Chrysler relationship simply by merit of
his relationship with Ray and high position in at
ThoughtWorks. The times that I actually got Bruce to
email me back, the answer was always the same: just
talk to Ray and work it out.
Or as I understood it, “go fuck yourself.”
Around Thanksgiving, the situation was becom-
ing untenable. Ray was disappearing for days at a
time, to parts unknown. His admin claimed to not
know where he was. I was starting to hear rumors
from his own employees that Ray’s temper was leg-
endary, that he was bipolar. The Chrysler employ-
ees that worked on the system were no help either.
They had their hands full with a full gamut of other
things related to the upcoming release of the updated
software, and disturbingly, they wanted nothing to do
with our rewrite. Michigan itself didn’t like us either
Never Work With Crazy 109

and blanketed us in a deep layer of gray snow. As non-

Chrysler workers without Chrysler vehicles, we had
to park in the non-preferred parking lots and trudge
through the snow every morning and every night. The
bottom of my pants and my feet were constantly wet
and cold. Hell had frozen over.
We returned from a couple days respite due to the
Thanksgiving holiday. Maybe we could turn this thing
around somehow? And what do you know, Ray was
actually in the office and seemed to be in a good mood.
He also wanted to meet with the entire team! Maybe
he had some good news? Maybe he was firing us? No,
the actual subject of the meeting was much worse.
“As of today, you’re halting work on the rewrite
and getting back to the refactoring(sic) of the old
code.”
I started to pipe up in protest and Ray slammed
his fist down on the conference table to let us know
he meant business. I exchanged a nervous glance with
Renee and she shook her head, telling me to let it go.
This was the worst possible outcome. We had
thrown away a month of work when we didn’t have
enough time to begin with. I waited a little while for
Ray to calm down and went to talk to him. I argued
in vain against the change in direction, assuring him
that there was no way we’d be able to make our dates,
that we had no idea how long the changes would take.
Never Work With Crazy 110

That throwing away a month of work was the worst

possible decision.
“Listen, you can’t rewrite the system, period. Even
if I thought you had time to finish it, which you ob-
viously don’t, because you have no way of regression
testing it.”
“What do you mean?”
Ray broke it down for us: “How do you propose we
test that you didn’t break the last 5 years of vehicles
that work with the StarScan, eh!”
I was like a deer in headlights. “I… I don’t under-
stand. How did you test them in the first place?”
“On the damn cars, obviously.”
But couldn’t we just… and it all started to make
sense. They didn’t have any sort of regression testing
facility. Those trips down to the garage to connect
our StarScans to the new hybrid vehicles for testing.
The large pieces of plywood with twenty controller
units jerry-rigged together and wired to a 12 volt
power supply. The weekly email blasts to tens of
thousands of employees asking “if you have a 1999
Dodge Caravan with VIN ending in 12KH” please
bring it in to DTS next week.”
Motherfucker.
“My god, Ray, why on earth did you let us waste
a month??” I stammered.
“Cause you wouldn’t leave me alone about it!”
Never Work With Crazy 111

But. But that was crazy. Absolutely batshit crazy.

Exactly. And that’s when it hit me.
*you can’t work with crazy

When confronted with a situation that is literally

insane, it just doesn’t make sense to stay in it. Leave.
Actually, don’t just leave — run for your life! Just like
our dear Koson, once the shit hits that fan, get outta
there and don’t look back.
Dejected, I went for a long lunch with the team.
We needed out of there. It didn’t matter what the
personal cost to our reputations was, it just didn’t
make sense to stay and sacrifice our collective sanity.
I made the call to Bruce and he actually picked up.
I took my time re-explaining the situation and why we
needed to fire this client and move on.
“Listen Obie, I understand, but just do the best
you can, okay? We can’t lose this account. Ray will
understand, as long as you put in the effort. I have to
go.”
There have been a few times in my life when
I wanted to reach through the phone and strangle
someone. This was one of those times. I hung up in
abject frustration.
We actually took Bruce’s advice and went back to
work, resigned to our fates. As the weeks wore on,
Never Work With Crazy 112

Ray’s behavior got more and more erratic. He started

screaming at us in the office for random stuff, even
things out of our control. One day he dragged myself
and Aslak into a small conference room. He informed
us that he has been inspecting the team’s commits to
the codebase for the last few weeks and that we had
not been commenting our code. He told us that we
needed to comment our code.
The issue of commenting code, that is, adding
non-executable, human-readable lines of text to code
while you’re programming, is contentious at best.
People on the Agile end of the development philoso-
phy spectrum (like the ones at ThoughtWorks) despise
comments. Not only do we not add comments to
new code, we have a habit of deleting old comments
when we find them. The problem with comments is
that they LIE. You see, when a programmer comes
along and modifies existing code, they have a habit of
changing the executable parts of the code and forget-
ting to update the comments to reflect those changes.
Since comments are non-executable, it doesn’t matter
that the programmer neglected to change the com-
ments, because the system will still work. However,
the next programmer to come along trying to figure
out what is going on will read the comment and
potentially get very confused and waste a lot of time
figuring out that the comment is wrong.
Never Work With Crazy 113

We calmly explained to Ray what I just explained

to you. He sat there taking it in. Yes, he indicated that
he was familiar with that line of reasoning. Okay, then
we shouldn’t have a problem. But Ray was about to
make it a big problem.
“I don’t care about your reasoning, I want you to
add comments to everything that you touch in the
system,” he sputtered.
Aslak piped up and started repeating the reason-
ing behind our dislike of comments. Ray cut him
off. I interjected, explaining that were writing the
code in an expressive fashion, that it would not need
comments to be understandable. He cut me off too.
This was a battle we were going to lose. I exchanged
looks with Aslak, who was starting to get a bit hot
under the collar.
“Okay,” I said.
“Yes, okay that’s fine,” said Aslak.
“What is fine?” asked Ray.
“That’s fine, we’ll add comments,” we both said
almost in unison.
“No, you won’t,” Ray told us.
“What?!”
“You’re not going to.”
“I don’t understand, we just said we will,” we
protested. The next lines out of Ray’s mouth are
etched permanently in my memory.
Never Work With Crazy 114

“I. AM. NOT. A. GOOD. COMMUNICATOR!!!!”

bellowed Ray, while violently slamming his palm
down on the little round conference table again and
again. Spittle and dry erase markers went flying. I was
sure people outside would be hearing the commotion,
maybe even calling security. I was agitated and rather
confused.
Aslak was a little cooler under the pressure and
piped up: “I agree with you, Ray, I have no idea what
you’re trying to communicate.”
“I fucking know you guys. You’re not going to do
it. You’re going to tell me you’ll do it and then you
fucking won’t.”

This was a precious bit of madness to throw into the

mix. I mean, maybe we were, maybe we weren’t going
to start commenting the code, but at this point it didn’t
do any good to continue talking about it. The next
step would be a fistfight and it was a rather small
conference room with glass windows. I think Aslak
and I could take Ray out but the consequences of doing
that were a bit scary to contemplate.
“GODAMMIT, WE WILL DO IT RAY,” shouted
Aslak.
“NO, YOU FUCKING WILL NOT. I WANT YOU
TO BELIEVE THAT YOU NEED TO ADD COM-
MENTS!” shouted Ray back at him.
Never Work With Crazy 115

This was too much. I’d had my share of difficult

meetings in my life until then, but never one where
the feeling that a fight might break out was so palpa-
ble. Ray was literally egging us on. I was not about
to lose my job and potentially get arrested because of
this raging asshole.
I stood up and mumbled something to excuse
myself and as I turned the corner, I spied Aslak leaving
too. When I got back to my desk the rest of the team
was staring at me.
“What the hell was that?” asked Greg.
“I don’t know, it’s crazy.” I told them.
“What does he want?”
“I don’t know, to add comments I guess.” I offered
and slumped in my chair, depressed.
“Where the heck is Aslak?” asked Hoover.
“Probably smoking a cigarette.”
Now the poor guy had been trying to quit, but this
situation could not be helping his resolve. Not too long
afterwards, Renee asked to speak to me privately.
“I just heard from Chicago that Ray is trying to get
you thrown off the project. He says it’s your fault that
we’re not making progress.”
Of course. Ray needed a scapegoat and I was serv-
ing myself up perfectly to take the fall. Undeterred, I
told Renee not to worry about it and to make sure we
kept working as usual. I took a long walk and called
Never Work With Crazy 116

up a fellow ThoughtWorks guy named Greg that was

supposed to be my official mentor in the company.
He’d been working there for awhile and might know
what to do. I managed to get him on the line and on the
borderline of tears explained the whole thing, from
the confidence we came in with, to the craziness, the
latest altercation.
“I’ll be there tomorrow,” replied Greg.

To his credit, Greg did fly up to see us in Michigan

the next day, leaving whatever he was doing to try
helping us out. He showed up and met with Ray. Then
he met with other Chrysler people that worked for
Ray. Then he met with us, individually. Then he met
with Ray again. They spoke for about 15 minutes and
then Greg calmly walked back over to our desk.
“Pack your stuff, we’re done here,” he told us.
I could have hugged him right there, but he’s a
rather serious old dude, so I held back my excitement.
We literally packed up our stuff and left immediately.
We all drove back to the airport and back home.
Later on I asked Greg what happened and this is
what he told me:

1. Everyone was in agreement that Ray was crazy.

2. During the first meeting, Ray had insisted that
I was to blame for everything wrong with the
Never Work With Crazy 117

project and that ThoughtWorks should pull me

off the project immediately and replace me with
someone that could get the job done.
3. Greg had proceeded to interview everyone else
involved and ask them who they thought was
to blame for the state of the project. Everyone,
including the Chrysler people, said that Ray
was the problem.
4. Greg sat back down with Ray and informed him
of the results of his interviews. Ray backpedaled
immediately and said that it was okay for me
to stay that he would work with me to make
things work. If he had not backpedaled, my
goose probably would have been cooked, but
once Ray reversed position, Greg knew he was
full of shit.
5. Greg informed Ray that he was pulling the
entire team and wished him luck on his project.

A week later I was on a plane to London for an easy-

going six-week gig at Dixons, during which I would
teach myself Ruby on Rails. Negative repercussions
from the Chrysler fiasco? Zero.
Shit happens, right? Undoubtedly. Sometimes it’s
random, and other times you bring it on yourself. But
it’s definitely going to happen whether you want it to
Never Work With Crazy 118

or not. So you best learn from it when it does. Find

the positive.
There are plenty of positives I can point back to
related to the Chrysler project, not least of which an
interesting story to put in this book, but I at the time
it drove me close to a nervous breakdown. I don’t
regret the experience, but there are plenty of more
productive and happy things that I could have been
doing instead.
The final move to bring in Greg was done in a
moment of desperation, only because I came to the
startling realization that I was in the process of being
scapegoated.
It wasn’t until years later and with the benefit
of hindsight that I realized we could have pulled out
of the project much, much earlier. From the moment
that Ray started acting crazy, which objectively was
within the first week or two, I could have unilaterally
opted myself and Aslak off the project. After all, we
made our own travel arrangements, so it would have
been trivial to just fly to Chicago instead of Detroit,
show up at TW headquarters and explain the situation
to whoever complained. It wasn’t like we were going
to get fired about it, we were two of the hottest young
superstars at the company at at time that we were
hiring dozens of people per month. The last thing on
their mind would have been firing us – they would
Never Work With Crazy 119

have put us on a different project and sent other

people instead.
The takeaway is that the ultimate power play is
standing up for yourself. Don’t just accept disrespect
from crazy people, because once you take it once,
you’re going to have to take it again and again and
again until everything comes to a head and you get
the final blow to put you out of your misery. If Greg
hadn’t saved us from Chrysler, I might have been
tossed off the project in disgrace and faced disci-
plinary action back in Chicago.

Beyond crazy, run from death marches, and avoid

working with unhappy and unlucky people too. The
same kind of logic applies. Their misery can quickly
precipitate your own disaster and leave you in a state
of mind that you can’t recover from. That’s especially
true if their problems were not caused by you to begin
with — the futility is maddening.
Chrysler represents one of the times in my life that
I let my pride and fear of reprisals override my instinct
for self-preservation. I had come in aggressively and
made bold promises about how we would be able
to fix the situation, but my expectations were based
on false assumptions about the state of the existing
codebase. When I figured out I was wrong, I should
have accepted my error, run for the hills, and let some
Never Work With Crazy 120

other loser be forced to deal with it. Not the most

honorable approach perhaps, but I don’t really see
the point of acting otherwise. ThoughtWorks would
not have necessarily suffered either, since if everyone
acted rationally and opted out, they would have cut
off the engagement sooner. When it comes down to
it, I don’t think Ray ever even paid for our time there!
So thrashing about for six months before pulling out
abruptly was probably one of the worst of the possible
outcomes. And that is crazy.

Sometimes a situation is crazy, other times it only

seems crazy. Solving problems that have driven others
to madness or worse is one of the ultimate forms of
power.
There Is No Spoon
One of my favorite scenes in The Matrix movies is
where the lead character, Neo, is in the Oracle’s apart-
ment and he is amazed by a young boy performing
what appears to be an illusion.

Boy: Do not try and bend the

spoon. That’s impossible. In-
stead only try to realize the
truth.
Neo: What truth?
Boy: There is no spoon.
Neo: There is no spoon?
Boy: Then you’ll see that it is
not the spoon that bends, it is
only yourself.

Over the years, my most enjoyable and successful

consulting jobs have been when I get to bend the spoon
for the benefit of my consulting clients.
My favorite was a three month project at a major
credit card bank. Myself and a strong ThoughtWorks
There Is No Spoon 122

team worked on location at the client’s technical cen-

ter, right on the waterfront in Wilmington, Delaware.
Riding high on the success of Ruby on Rails and my
hand in growing the ThoughtWorks Ruby practice, it
was one of those times when everything fell into place
and I could do anything I set my mind to, including
bending spoons.
The way I look at it, attempting to bend a spoon
with only your mind, represents a seemingly intractable
problem, one that no matter how hard you try, you
just can’t solve. Our client had one of those seemingly
intractable problems on its hands.
The bank had a lucrative business going signing
up major consumer-facing companies and organiza-
tions to be credit card partners. Their logo would
decorate the card and those partners proved to be
an excellent marketing channel for acquiring new
credit card subscribers. In return, the bank would
compensate those partners by sending them a small
percentage of the charges made on those cards.
Robert, the head of development and client repre-
sentative, was in charge of a group of programmers
responsible for calculating partner compensation. At
first glance it might seem like a relatively straight-
forward task, but it was complicated by the nature
of the partner contracts. Each one was individually
negotiated and had subtle variations. There was also
There Is No Spoon 123

the complication of calculating reimbursement for

different perks associated with the cards. For instance,
their airline partner issued frequent flyer miles in
exchange for hitting certain spending limits, as an
incentive for use of the card. Those miles cost the
airline money, so they had to be compensated for
them.
Robert had quite spoon in his hand, so-to-speak.
As the partner program got underway, they imple-
mented the calculations for partner compensation
using Oracle stored procedures. These are scripts that
run inside of the massive Oracle database servers
that process and store the millions upon millions of
transaction records received by the bank on a daily
basis. During a brief 3 day window at the end of
the month, Robert’s team would run their scripts to
spit out reports detailing the amount of money that
needed to be sent to the partners.
The stakes were high for this task. Send too much
money back to the partners and you took a hit on
profits. Trying to explain to a partner that you miscal-
culated and needed money back was a certain way to
wreck the relationship. Not sending enough money?
Well, that was even worse since it was a surefire way
to get sued at some point. Either would trash the
trust relationship and send the partner off packing to
another bank.
There Is No Spoon 124

Everything might have been okay except that…

1. The sales department for the bank was going

gangbusters and wanting to add partners to the
system many times per month.
2. Every addition of a new partner entailed adding
logic to the stored procedure, and doing a pro-
duction release of the system.
3. Oracle stored procedures are notoriously hard
to test and maintain.
4. Every release of the system had to be tested,
reviewed and approved by the bank’s informa-
tion security (Infosec) group prior to production
usage. Infosec routinely took 2-3 weeks to com-
plete review of a new release.

You might think that the bank’s sales people could

just hammer out a deal with Infosec to speed up their
review process. You’d be wrong about that.
Furthermore, after patching in conditions for over
a dozen partners, the Oracle stored procedure that
powered the partner calculations was starting to col-
lapse under its own weight of maintenance. It had
been written by a DBA (Database Administrator)
rather than a programmer, so it was not exactly the
paragon of extensible, modular software even from
There Is No Spoon 125

the start. Even if Infosec had allowed them to release

the software more often, there was not much of a hope
that they would be able to keep up with the pace of
changes.
Meanwhile, a huge amount of pressure was build-
ing from the top executives of the bank for this
situation to be resolved so that sales could actually,
you know, sell freely and expand the bank’s profits.
These sort of intractable pressure cooker problems
pop up everyday all over corporate America. You
don’t solve them with a traditional approach. You
have to summon your inner Neo and learn that it is
your own limitations that hold you back from finding
a solution.
ThoughtWorks won this consulting contract on
the strength of my proposal, and the sheer audacious-
ness of our plan. We quoted them a half million dollar
price tag for three months of work with five people
and they practically dared us to pull it off.
Here’s how we did pull it off and leave them
begging for more.
Our CEO had convinced Robert that he should
consider Ruby for his shop, which had resulted in me
being flown out to the bank to take a look at their
issues for a few days. During my analysis, I realized
that Infosec made an important distinction between
code and data.
There Is No Spoon 126

Code consists of the lines of programming logic

that reside in files comprising the system in question.
Those files are bundled up in a particular way and
transferred to the production servers whenever the
system’s behavior must be updated. Changes to code
inevitably introduce defects to the system. Banks,
needless to say, are very concerned about defects,
especially those that can cause the bank to suffer ir-
reparable financial losses. Therefore banks have some
of the most stringent policies related to quality as-
surance (QA) and information security. Hence the 2-3
week delay in producing releases.
Data is also important to the bank. Without it,
there would be little point to having any code. How-
ever, all major transactional systems produce reams
and reams of data on an ongoing basis. In our case,
the bank’s servers were receiving millions of rows of
transaction entries every day. Literally, multiple rows
of data would be created every time that a customer
swiped their credit card at a store somewhere. No
formal review dictated for data that is added to the
system.

Fans of the programming language LISP have

this saying: code is data, and data is code. I
don’t think too many of them go into careers in
.
There Is No Spoon 127

QA and Infosec departments.

.

My special insight was that if I was able to build them

a system where the details of the partner contracts
were entered into the system as data by the sales
department, then they could do an end run around
QA and Infosec policies and procedures and speed up
the process of on-boarding new partners.
The key to bending this spoon was to build a
system that was fast and flexible, but to do so in such
a way that prevented those tragic errors we discussed
previously. Under no circumstances could we allow
mistakes in the configuration of the contracts to cause
bad payments to partners. And we had three months
to build and deploy it into production, under the
assumption that Infosec wouldn’t stop us dead in our
tracks.
During this project I got to exercise a bit of soft-
ware wizardry by creating what is called a Domain
Specific Language for specifying partner contracts.
Here’s where my budding expertise in Ruby really
paid off. Instead of implementing the language from
scratch, something that would potentially take months
to implement just itself, I implemented it using Ruby
syntax.
There Is No Spoon 128

Ruby is legendary for the flexibility of its syntax;

it’s one of the things that makes Ruby a joy to program
in. So my team and I created a very fluent and
readable style of Ruby code, that looked as close to
English as I could get it and read like a well-structured
interpretation of the partner contract language.
My design goal was that you could take the con-
tract and put it side by side with my program speci-
fication written in Ruby, and that a layperson could
scan down line by line comparing the two, verifying
that they said the same thing.
That specification, would be saved to a database
belonging to the new Partner Compensation System.
It was data, but crucially, it was also code. Since it was
data, it was maintainable by the salespeople them-
selves, on a daily basis, without needing to involve
the programmers, QA or Infosec.
It only took a bit of hubris to bend that spoon
further! Instead of building a user interface (think
buttons and drop down lists) for creating the contract
specification in my new domain specific language,
something that I was sure would take well over three
months to properly design implement and test, I took
a different approach.
I had non-programmers write the specification
themselves. Yep, I had legal/financial analysts asso-
ciated with the sales department writing Ruby code
There Is No Spoon 129

into big text boxes! My rationale is that these were

smart people who were adept at plugging complicated
formulae into their Excel spreadsheets. It would only
be a small step further to teach them how to write
some simple programming code to define contracts.
The system was a roaring success and we got
follow-on contracts to bring this DSL approach to bear
on other spoons at the bank. I rode off into the horizon,
quite literally, since my next adventure was half a
world away in India.

Looking back at common success factors across my

career, the ability to communicate effectively stands
out. It doesn’t matter how excellent you are if you
can’t talk to other people about it. That’s why com-
munication is the subject of the next chapter.
Communication
To succeed as a consultant you must cultivate strong
communication ability, especially effective writing
skills. You must have the ability to get to the point
and describe situations with clarity and punch. When
the occasion calls for it, you must be able to tell
compelling stories that provoke action in the listener.

Writing
Being able to write well is a primary skill. Writing
not only makes you effective in your day-to-day job,
it is the most important factor in long-term career
viability. Why? The overarching life goal of a consul-
tant should be to grow beyond selling your time for
money. That evolution powers your ability to build
up wealth. Selling value instead of time enhances
stability and opens up the possibility of fun pursuits
outside the work sphere.
In order to sell value (instead of time) you must
create products that convey the maturity of your
wisdom and knowledge on your behalf, without the
need to be present in person. The traditional way to do
Communication 131

that is by authoring books and other expert material

valuable to consumers in your field.
At the start of your career, you don’t have the
basis to be an authority on anything, so you have
no business writing expert books. However, as you
mature in your field of expertise, you should be able
to prove it via your writing.
The easiest way to start down this path is via
blog posts. Then you graduate to books and other
training materials targeted at wider audiences. The
aim is always to influence more people than you could
ever reach face to face. As your products stack up,
you build up a recurring revenue stream. And when
that stream becomes a powerful river, you can retire
in comfort. By retirement, I mean that you no longer
have to work every day if you don’t want to. Your
area of focus is now dictated only by what you find
interesting.

The benefits of strong writing skills should be self-

evident. Eloquence breeds trust with the reader. Bad
writers sound dumb. They breed distrust. Especially
with people who themselves are good writers. Noth-
ing gives me an immediate bad impression of someone
like getting a cold email containing typos.
There are no valid excuses for spelling and gram-
mar mistakes in your business communications. If
Communication 132

your spelling and grammar skills are weak, you must

find someone trusted to proof your work for you.
Could be your wife, business partner, or even a parent.
My dad is a gifted writer and I’ve relied on him over
the years to proof my work. I’ve also done this chore
myself for many of my friends.

My friend Kevin Dubienski uses the popular

Reddit website as part of an innovative approach
to editing his blog posts. He finds sub-reddits
relevant to his subject matter. Then he picks the
third or fourth most relevant forum and posts
an un-edited version of his writing. Inevitably,
the community harasses him with replies for
at least an hour or two. Then he deletes the
post and thanks everyone for their input. Armed
with valuable feedback, he posts the revised
writing to his own blog. In his words: “easy-
peasy crowd-sourced editing.”
.

It doesn’t matter how you get your proofreading

and editing accomplished. Always compare revised
drafts with your original. Take mental notes of the
corrections made. Those of us with weaknesses in
our writing often make the same mistakes over and
over again, year after year. Thoughtful examination
Communication 133

of revisions to your work yield meaningful improve-

ments. Metacognition does not only apply to thoughts
and feelings. Knowing yourself involves constant and
methodical analysis of your work output also.

Practice
Personally, I learned to write by 1) reading books
about writing and 2) lots and lots of practice. Most
business people write tons of verbiage in their every-
day work activities, but not all of them are effective
writers, because they lack focused practice. Like many
people, I can bang out Chopsticks on a piano. I could
play it every day for years and it would never make
me into a good pianist.
Reading and learning about writing skills gives
you tools for exercising your communication skills
in a disciplined and effective manner, similar to the
way that a musician would learn to practice their
instrument.
And daily practice is of utmost importance. My
personal rule of thumb is 750 words per day. On good
weeks, my other workload is light enough that I can
hit my goal several days in a row. The longer the
streak gets, the easier it is to continue, and the more
satisfaction I derive from the practice.
At times when I’m not working on a book, I
Communication 134

exercise my writing using 750 words⁸. The topics that

I write about when I’m practicing vary wildly, from
deeply personal journal entries to ideas for blog posts
to poetry and (terrible) song lyrics.
As you get more and more into writing, you
should consider using software other than Microsoft
Word. I recommend iA Writer for Mac, for its focus
mode and well-integrated statistics features.

Practical Matters
Quiet. Turn the music off. Turn off Twitter. If you can
get away with it, go ahead and turn off the network
interface. Leave your phone charging in the other
room. I used to get a lot of writing done on planes.
(Damn you, in-air wifi!)
Find solitary times and spaces. I’m writing this
right now on a Saturday morning while the rest of
the family is still sleeping. Productive writing sessions
involve more than just inspiration. You must create an
environment conducive to letting your creative juices
flow. Everyone’s situation is different. My favorite
times are early in the morning and late at night,
especially on weekends. Those are the times that I
don’t have to be thinking about work and I can focus
on putting my thoughts in words. Morning times,
⁸http://750words.com
Communication 135

right after waking up work especially well for me.

Quite often I lay awake in bed, the thoughts tumbling
over and over in my mind. Does it happen to you? See
if you can make a habit of forcing yourself out of bed
and putting your thoughts into written form.
My writing style is to pump out as much raw
writing as possible in a given sit-down session. I’ll try
to capture all the inspiration I’m feeling, if not in full
sentences then as bullet points. When I’m done with
the session I want to be spent. No more to say on the
topic. It doesn’t even matter if it makes sense. It’s just
a rough draft and I’ll come back to edit it later. How
much later? Sometimes days later. Other times it takes
me years to come back. This book itself has taken me
years to complete.
Practice your writing every day. Common advice,
commonly ignored. I try to follow that advice and it’s
one of the reasons that I like to have a big pool of
rough draft material available at all times. Because
most days I’m decidedly not inspired to write. Those
are the days that I edit and revise. Tighten up lan-
guage. Research and add citations. Flesh out stories.
Throw things away, add new things. Many times the
act of revision gets your creative juices flowing again
and you end up adding new reams of rough draft.
Good. That’s how it all comes together.
I like writing when I’m hungry. That’s one of the
Communication 136

reasons that morning sessions are so productive for

me. Comfort is the enemy of creativity. I can’t sit here
in front of the keyboard feeling full and satisfied. It
just doesn’t work. I need to be uncomfortable. I need
to experience urgency. There’s a primal urge to create.
I feed on the writing, but it doesn’t satisfy me so I
need to write more and more. How deep inside can I
go? How long can I last? How long can I ignore the
outside world. My family? My own physical needs?
I push to get the words out because every day that
passes is a day less than I have on this earth. Breakfast
does not add to my legacy. Breakfast does not yield
immortality. Words do.

Blogging
Posting to your blog on a daily basis provides practice,
with the added benefit of critical feedback from your
readers. Daily updates are also a proven formula for
growing the readership of your blog. A popular blog
serves to credentialize you in the minds of your read-
ers. Potential clients will see the activity on the blog
and assume that you must be very good at what you
do, otherwise you wouldn’t have such a successful
blog.
I started blogging before the term blog was used
widely, using a website called LiveJournal. The con-
tent, much of it protected from the public, dealt pri-
Communication 137

marily with my personal life and times. Unwittingly,

I got into the habit of sharing bits and pieces of myself
on a regular basis. I developed a rhythm and got
comfortable with transparency, gaining the ability to
convey my inner thoughts and emotions in writing.
I’m a big believer in honest transparency in your
writing, but many people cannot deal with the vul-
nerability of putting themselves out there. You need
confidence and occasionally, hubris, to open yourself
up to criticism and scorn from the wide internet
community.

Find your authentic voice

You are not a journalist. Your writing should reveal
personal details that give the reader a sense of who
you are and what your style is. Those little details,
hints of your true self, are what make your writing
engaging and interesting to the reader. Impersonal
writing gets skimmed and quickly forgotten. Even
when you are writing technical material, you should
strive to make your writing sound like your own
voice.

In 2005 I wrote an incendiary blog post called

Top 10 Reasons That Java Sucks Ass. It was over
.
Communication 138

the top and crass, even by my low standards.

Some of writing didn’t even make that much
sense. I set out to provoke a response from the
community, and man, did I get it. Java apologists
wanted to burn me at the stake for my heresy.
They ranted and raved and wrote up their own
lists of why Ruby sucked too. I caught flack from
the other direction too. Nice Ruby people told
me that I should be nice to the Java people, on
principle.
The thing is, that blog posts remains one of
my most popular pieces of writing ever. It still
comes up in conversation, occasionally in the
most embarrassing manner. People remember
it, because it was raw and it touched a nerve.
Like it or hate it, that piece of writing put me on
people’s radars and paved the way for additional
success down the road.
You know what else? It was an accurate re-
flection of who I was when I wrote it. Back
then I was brash and arrogant and kind of an
asshole. I used expressions like “sucks ass” with
no remorse and no apology. Would I do the same
today? No way, I’ve grown up quite a bit and
I am more conservative than I used to be. If
back then I had worried about the effects of that
blog post on my future self, I would have never
.
Communication 139

written it in the first place.

Are you afraid of how the public will perceive
you if you let your true personality shine through
in your writing? Why? What’s the worst out-
come if your fears are realized?
.

Write about stuff you’re passionate about

Not sure what your passionate about? Write about
yourself. Most everyone cares about themselves. Some
people only care about themselves, and that isn’t too
interesting, but when you’re starting out and when
you need to practice, keeping a journal where you
note down your observations and opinions is a good
place to start. (They’ll also be very helpful the day you
decide to write a memoir masquerading as a business
book!)
If you care about your subject, then that passion
is going to come through in your writing and engage
the reader. If you don’t care about your subject, no
amount of linguistic gymnastics or precise grammar
will save you from irrelevance.
Communication 140

Communicating with Clients

Clear and constant communication with your clients,
particularly around expectations, is essential to main-
taining a good working relationship.
On the other hand, communication with your
clients carries a burden that your other writing does
not: If that client ever decides to become your enemy
or sue you, then anything you’ve written to them will
potentially come back to bite you in the ass.
Therefore, you need to balance the need for con-
stant communication with the risks of over-communication
or antagonizing your client. When things are going
right then it is difficult to over-communicate. I don’t
think I’ve ever had a happy client tell me to send them
less email updates. If things are going badly, then it’s
a whole different story.
In fact, there will inevitably be times where your
client makes you very angry. Those are the times
when you should step away from the keyboard and
take deep, cleansing breaths. These are the times when
you should save drafts for sending later when you’re
calmer. These are the times when it’s useful to involve
a surrogate, whether it’s a business partner or trusted
advisor, to communicate on your behalf.
Communication 141

Pro-tip: If you’re going to write an angry email,

go for it, rant away to your heart’s content. Just
don’t enter the recipient addresses right away. If
it’s a reply, go ahead and delete the contents of
the to: box before writing anything. That way
you can’t send it by mistake. And never, ever
write angry emails while intoxicated. No good
can come of it. I speak from experience.
.

Avoid Loaded Language

When I was at Hashrocket, a once happy–as measured
in terms of revenue: over a million dollars billable–
client dragged their feet on a payment. During the
back and forth email conversation that ensued with
their CEO, I used the expression:
“I do not play games.”
And that’s what I mean by loaded language. It was
the verbal equivalent of loading a .45 caliber revolver,
putting it in her hand, and raising it to my face. She
was pissed and replied:
“ARE YOU IMPLYING THAT I PLAY GAMES?!?”
Yeah, in all caps. You might wonder how I got out
of that one gracefully. Well, the truth is I didn’t. They
did pay their late invoice, and never paid late again,
Communication 142

but my relationship with their CEO was ruined. She

never forgave me for the insult.

Unsent Drafts
Over the years I’ve littered my drafts folder with
unsent emails to clients, partners and my ex-wife. If
I had kept the ones to my ex-wife, I’d probably be
publishing them as dark comedy.
Drafts can help you keep your sanity. I consider
them a private release valve. Weeks or months later,
when I’ve calmed down and got over whatever riled
me up, I go through and delete them. Hopefully at that
point I can do so with a grin or a chuckle.
The following letter is a draft from a few years ago
that was so grand in its ridiculousness that I kept it for
posterity. Here it is, with minimal redacting, for your
enjoyment.
Note that this letter is a vivid example of what
not to say to your client. I might have been somewhat
drunk when I wrote this. Enjoy.

Dear XXXX,
A trusted business advisor has assured
me that you are a devout Christian. I
think it’s a shame that we don’t know
each other very well, because we may
well have avoided the problems that are
Communication 143

now plaguing the business relationship

between our companies. Nevertheless, the
current situation calls for brave action
and I’m not typically one to back down
from a challenge. Since we’ve barely got-
ten to speak to one another, you may not
know this about me, but I was privileged
to have a strict Christian upbringing. I
understand this is is something we have
in common.
The principles of honesty and integrity
were drilled into me by my father, a de-
vout and hardworking pastor. Above all, I
was taught to be honest, to never lie, that
more than anything else, God hates liars.
Why? Because according to the bible, the
devil was the original liar and it was a lie
that set original sin in motion.
Colossians tells us to do whatever we do
excellently, as to God and not to men.
Hashrocket is a manifestation of my com-
mitment to excellence. I strive to run a
learning organization that not only per-
forms to the utmost of its abilities every
single day, it also invests time in organi-
zational learning and improvement of its
processes on an everyday basis.
Communication 144

My christian upbringing has stuck with

me all my life and served me well in
my career. It’s also made me highly in-
tolerant of liars and deceitful business
people, as well as people who wield their
power and position carelessly or without
regards for who they might be hurting. If
the price for being relentlessly honest and
demanding integrity from all of my peo-
ple and business partners is to be occa-
sionally called “arrogant” then it is a price
I’m willing to pay. My friends, employees
and trusted partners know that in reality
I strive to be humble and am more than
happy to admit when I am wrong.
To get to the point, I am writing this letter
to you personally to warn you about a
grave danger to your business and its in-
vestors. Simply put, your CIO, XXXXXXXXXXXX,
is grossly incompetent and unqualified
for the position with which you have
entrusted him. Also, based on his last
official communication to my firm, I be-
lieve that he is a false accuser, literally a
“Satan” in your midst. Not that my words
leave much room for misinterpretation,
but just in case, I want to be crystal
Communication 145

clear: I am calling XXXXXXXXXXXX a

liar and a menace to your business. He
is perpetuating a deception in order to
cover his incompetence as CIO of your
company. He is attempting to scapegoat
Hashrocket for his own errors in judg-
ment and mismanagement of your project,
as well as the incompetence of his staff.
He has called into question the most im-
portant architectural decision that we made
in order to deliver your project success-
fully under crushing time pressure. He
has impugned our integrity by accus-
ing us of maliciously introducing bugs
in your software and then charging you
extra to fix them. He maligns us while se-
cretly conspiring with one of Hashrocket’s
competitors, spitting in the faces of my-
self and a world-class team of designers
and programmers.
XXXX, you should know that my team
has sacrificed for you. We have shed blood,
sweat and tears to bring the rewrite of
your software to fruition on time and on
budget. We felt a great degree of honor
in doing so. I’m not saying that we’re
perfect, but perhaps we’re as close as
Communication 146

you can get to perfection in this indus-

try, which is full of disgustingly ineffec-
tive people. The one big mistake I will
admit to was to agree to working with
XXXXXXXXXXXX to begin with, de-
spite evidence of his incompetence man-
ifesting itself early in the relationship.
I recognize that it is unconventional busi-
ness sense to write this letter and I also
fully understand that my accusations against
XXXXXXXXXXXX are very serious. I
also suspect that you might consider XXXXXXXXXXXX
a friend, and that this letter might anger
you. I pray that you believe me, that
my intention is not to antagonize you
or poison the relationship between our
companies. It’s just that given the unfor-
tunate circumstance that we’re in at the
moment, I cannot think of an alternate
way to maintain my integrity to you as
my client. If your company is to sur-
vive, I believe you must take immediate
steps to save it from the menace that is
XXXXXXXXXXXX’s mismanagement.
As your consultant I feel ethically bound
to present you with the facts as I see
them. I assure you that I have every in-
Communication 147

tention of backing up my claims with

hard evidence, assuming that you would
allow me to do so. However, I feel it
is pointless to get into a tit-for-tat with
XXXXXXXXXXXX, particularly with re-
gards to the more outlandish criticisms
that he has launched against us. We will
not dignify XXXXXXXXXXXX’s last of-
ficial communication to Hashrocket with
a formal reply, but I am willing to meet
with you in person at my office in Jack-
sonville to discuss the contents of this
letter and advise you on how to proceed.

Over the top? Yeah.

It was late when I wrote this letter and I didn’t
dare send it. However, I did email it to my business
partners, for their amusement. They called into ques-
tion my sanity. And told me to stop writing business
emails while drunk.
It’s never a good idea to write business emails
while drunk.
Communication 148

Fear Factors
Writing for an audience beyond yourself and close
associates is scary. Speaking to a group of people, par-
ticularly when the cameras are rolling, can be outright
terrifying. On the other hand, personal conversations
are easy. Small group discussions or one-on-ones are
of a transient nature. The memory of those words will
only live on as concepts and perhaps sound bites in the
memory of your listener. That is, if they live on at all.
Almost everything that we utter during our lifetime
fails to register in the long-term memory of anyone.
Not scary at all.
Why do we worry so much about non-transient
communication? The reasons are myriad, but I think
I’ve identified a unifying theme: Fear of exposure
as incompetent or worse. Fear of undermining our
reputation and career prospects. Fear of effort wasted,
of time better spent on more profitable pursuits. Fear
of feeling embarrassed in front of people we respect.
Fear of offending people and exposure to dangerous
reactions.
Danger? Yes, you never know who is out there
reading your words, or how they will react. It’s easy
to shrug off threats as an abstract concept, but when
words can have real world consequences, fear of
saying the wrong thing can become paralyzing.
Communication 149

My online activities have provoked strong reac-

tions on more than one occasion. Usually I enjoy the
attention, but once in awhile people cross the line and
make me nervous. For instance, a few years ago, while
I was still blogging on a weekly basis, I received the
following email:
My name is Abo Moldova and I just
wanted to tell you that you’re one of the
biggest fuck ups I’ve ever seen in my life.
If I met you in real life I’ll break your
hand and tear of your ear. Hope you’ll die
a slow painful death as goats shit down
your fat spick neck.

Now I can tolerate name-calling, but threats of vio-

lence cross the line. Even bizarre threats in broken
English. Some would have shrugged it off, but this
malicious missile hit its target and detonated my
peace of mind.
It didn’t take much hacking skills to uncover the
real identity of the hate-mail author as a Java pro-
grammer based in Paris. I indulged my rage. How dare
this guy disrupt my life in this fashion! I set out to
make him pay for the transgression.
Over the course of the next 48 hours, to the chagrin
of my friends and family, I exposed the true identity of
Communication 150

Mr. Abo Moldova on my blog. I published his hateful

email along with identifying information, meant to be
picked up on the radar of his employer and clients. I
didn’t necessarily expect a response, but I trusted that
Google would give high ranking to this information
whenever someone researched this man in the future.
Payback time!
My loyal blog readers and fans were outraged by
the incident too. Coincidentally, one of them had a
business relationship with Abo’s employer. He con-
tacted that firm and threatened to break ties unless
action was taken. Unsurprisingly, the man I accused
of hiding behind the Abo pseudonym replied to my
blog post, protesting unfair treatment…

I know this will sound like spam but in fact

it’s not (I’m going to send you an email as
well). I am Andrei (the guy in the photo) and
I was pretty shocked when I saw this post. I
never wrote that message there, and I don’t
own the adress abo.moldova@yahoo.com. I’ve
actually tried accessing it with some of my usual
passwords just to see if it was some mailbox I
created at some point. I couldn’t access it.
.

On the lies, damned lies and statistics scale, this

Communication 151

was clearly a damn lie. All it took was comparing the

IP address associated with Andrei’s blog comment to
the IP address in the headers of the original offensive
email. Same address. Coincidence? Nah.
I shot back an email.

Andrei,
I know it was you. Everyone knows it was you.
There’s no sense in denying it. You fucked up,
not me.
Would you like your photo removed from my
site? Just apologize and it’s done. Because you
can call me racist names. You can call me a
fuck up. You can call me incompetent or a
goat fucker or whatever else you want, to your
heart’s content. In private. In public, I don’t
care. But you do not, under any circumstances,
threaten violence against me. That is completely
unacceptable in civilized society.
.

A few days later, the angry Mr. Moldova had a change

of heart and sent along a contrite note:
Communication 152

Sir, yes, you are right, I fucked up. I didn’t even

mean to write that stupid message, it was a
mistake and I sent it by accident. Believe me, I
regret it with all my heart and I cannot describe
how horrible I feel. Please believe that I am not
a racist, nor am I violent. I’ve worked in many
different countries, with people from Africa,
India, Arabia, and I’ve always gotten along well
with everybody, some of those people are my
friends. Please, forgive me, that’s not who I am,
I slipped, I made a mistake, I feel horrible. Please
take that page with my horrible deed down.
Please.
.

I acknowledged his apology, took down my blog post

and we both moved on with our lives. I actually felt a
little bad for the guy. (Maybe he was drunk when he
wrote the offending email?)
The reason I mention this story at all is to illustrate
the chilling effect that the threat of violence had
on my creative output. Even though the threat was
couched in hyperbolic, almost nonsensical language,
it still had the desired effect, which was to terrify and
censor me. It provoked self-doubt about whether it
was worth being such a public figure. Could harm
Communication 153

come to my family? I wondered whether it was worth

writing provocative material. Maybe I should tone
things down in the future?
Ultimately, the doubt he provoked in me is what
made me so angry and made me lash back with
such vengeance. My career was partly built on an
incendiary, thought-provoking, public persona and
here was a random internet troll undermining that.
Unacceptable!
Not all writers with a public persona are so lucky.
Kathy Sierra was a beloved star of the technology
blogsphere for years. Through much hard work and
creativity, she established her credentials, built a large
fan-base and published bestselling, award-winning
programming tutorials. Then the internet trolls de-
cided to take her down.
In early 2007, in an incident that registered on
mainstream news channels world-wide, Sierra abruptly
canceled her appearance at the O’Reilly ETech confer-
ence in San Diego. The reason? Harassment via blog
posts and emails, including death threats. One blog
post included an image of Sierra next to a noose. She
wrote: “I have cancelled all speaking engagements. I
am afraid to leave my yard, I will never feel the same.
I will never be the same.”
One of the most talented and creative voices of
my generation, silenced. Her words were accurate –
Communication 154

she has never been the same since.

So there are risks to extending your communica-
tion to the public sphere, sometimes even severe risks.
The question is how do you deal with that fear and
turn it into something productive and motivating?

Storytelling
Notice that throughout the book, I try to tell stories as
much as possible.
Storytelling is not exactly a natural talent. Let me
revise that statement. The ability to tell a compelling
story is not a natural talent. (My five year old tells
me stories all the time. They are cute sometimes, but
I’m not sure they’re ever compelling.) Becoming a
good writer and storyteller takes constant, dedicated
practice. It can become a lifelong pursuit.

The whole concept of natural talent is starting

to seem like a myth
http://www.gladwell.com/pdf/talent.pdf

When you are telling a story you are sharing your life
experiences. Given the opportunity to teach, recon-
Communication 155

sider giving direct, prescriptive advice. Instead, tell a

personal story related to the issue at hand. The most
compelling stories you can tell will be your own true
anecdotes. You lived them, so it’s easier to conjure up
vivid emotions to give them color. The more often you
tell the story, the better you become at telling it. A
friend calls them “polished river stones.”
Every telling of a story makes it smoother and
more beautiful.
But what if you don’t have a deep well of experi-
ence to draw stories from? Then you’ll have to make
do with the stories of others. This is a case where it
helps to be a voracious reader yourself. I learned my
joy of reading early in life.
When I was born, my dad Marco already worked
for Public Service Electric & Gas company in New
Jersey. He toiled for them over 35 years before retiring.
Starting as a meter reader and working his way up
the ranks of middle management didn’t make for a
particularly noteworthy career. (Sorry, dad.) But as
far as I can remember, he always had a sales gig on
the side. Hustling to make ends meet for his growing
family. I’m the oldest of five kids.
My favorite item that Dad sold during those days
was the Encyclopædia Britannica. The massive set
of brown volumes prominently occupied a full two
shelves or our massive bookcases. Half was the blue
Communication 156

Micropædia of short topical entries. Its companion

was the red-label Macropædia comprising long-form,
in-depth articles.
Dad did not allow us to express feelings of bore-
dom. We would catch a scolding or worse if we
complained about not having anything to do. As a
result, I spent a lot of time with my face buried in
books. When I didn’t have anything else interesting,
I’d study a random Britannica article. I didn’t know
it at the time, but I was arming myself with loads of
random facts and stories to draw upon when talking
to people.
Later in life, I spent an inordinate amount of time
acquiring random bits of knowledge on the web. (I
still do, I guess.) You might also. You might even feel
guilty about it. Don’t. Much of that knowledge will
fail to be useful on its own. But the interesting nuggets
of narrative that we pick up on a daily basis become
part of our own unique tapestry of stories. When
you’re trying to make a point, nothing is as persuasive
as metaphor. That random knowledge, those stories,
what are they? They are your metaphorical ammuni-
tion. Without them it becomes difficult to craft stories
that make deep and lasting impacts on the minds of
your listener.
Communication 157

The Power of Storytelling

It’s almost like humans have evolved to find stories
appealing. Stories are particularly powerful at influ-
encing people because they activate more of the brain⁹
than just straight up factual information.
When you tell a story, especially if you employ
metaphors, the reader’s mind lights up in delight,
making the experience much more memorable. As
you recount experiences, the reader’s mind reacts as
if it was having the same experience. You are literally
putting them through the paces of your reality. Gives
you an idea of why scary novels are actually scary,
right?
It turns out that our brains are wired to think
in patterns of cause and effect. Narratives, the dis-
tinguishing elements of a story, are essentially state-
ments of cause and effect. As we hear them, our brain
subconsciously tries to relate them to narratives of our
own, and a part of the brain called the insular cortex is
activated. This part of the brain is considered respon-
sible for process convergent information to produce
⁹Researchers have long known that the “classical” language regions, like
Broca’s area and Wernicke’s area, are involved in how the brain interprets written
words. What scientists have come to realize in the last few years is that narratives
activate many other parts of our brains as well, suggesting why the experience
of reading can feel so alive. Words like “lavender,” “cinnamon” and “soap,” for
example, elicit a response not only from the language-processing areas of our
brains, but also those devoted to dealing with smells. Excerpted from NY Times
article
Communication 158

an emotionally relevant context for sensory experi-

ence. Functional imaging experiments have revealed
that the insular cortex plays an important role in the
experience of pain and basic emotions such as anger,
fear, disgust, happiness and sadness.
Because of the effect of stories in the mind of the
listener or reader, they are the most effective way to
influence people and persuade them to come around
to your own point of view. According to neuroscience
researchers such as Uri Hasson from Princeton, a story
is the only way to activate parts in the brain so that
a listener turns the story into their own idea and
experience.
If you don’t have enough interesting life experi-
ence to use stories of your own in your communica-
tion, don’t fret. You can produce the same effect in
your reader by using someone else’s story. Just make
sure you get permission or learn the rules of fair use.

Tenzin says: “How do you write a picture?”

I write a story. The words of my story paint a
picture in your brain.
.
Communication 159

Keep It Simple Stupid

Unless you’re writing a novel, or a business book with
a silly title, you’ll want to keep the stories you use in
your business communications short and to the point.
For example, here is a simple story illustrating why as
a male you should never joke around with anything
related to weight to a female.

While I was at Hashrocket, I bought an

expensive Nikon SLR camera and a col-
lection of professional-grade Nikkor lenses.
I was so thrilled with my new kit, that
I took it with me almost everywhere I
went. One afternoon, I treated a bunch of
employees to lunch at Casa Marina, one
of our favorite restaurants on the beach a
few blocks away from the office. On the
walk back along the sandy boardwalk,
I stopped a few of the girls that were
with me and asked them to pose for a
photo. They cheerfully agreed, except for
one, who sidestepped out of the shot and
became visibly uncomfortable.
“Don’t worry, my camera will take 20
pounds off you!” I offered up with a smile.
Her ample cheeks flushed scarlet red with
anger and she glared at me with sheer
Communication 160

contempt as she stomped away. I realized

my mistake, but not before making that
girl hate me.

According to my calculations, that story clocks in at

157 words and will take the average reader less than
a minute to consume. I did my best to keep it simple,
while preserving the colorful elements that make it
memorable.
The bulk of this book consists of stories from
my life. Many of them are pretty simple and have a
primary moral or takeaway. The stories you tell in a
business context should be the same way.
Like me, you might have tendencies to be long-
winded in your storytelling. If that’s the case, just
make sure you stay aware of the effect your story is
having on your audience. Take drafts of your writing
and read them aloud to your trusted friends and asso-
ciates. Are they yawning or losing interest? Looking
at their phone? Best get to the point quickly! Don’t
make the mistake of getting so caught up in your tale
that you bore the listener.
Punctuality
I have no doubts that making people wait is the basis
of certain kinds of power plays. Nothing makes you
feel smaller than sitting and waiting for something out
of your control to happen. Just think back to the last
time you were sick and had to visit the doctor. The
nurse leads you to a room, maybe does something or
another with you, but then you have to wait for the
doctor to see you. Things happen on his schedule, not
yours. Because he has the power, not you.
In fact, it’s probably one of the myriad reasons that
I hate doctors.
But I digress. Basically I don’t like power plays
that involve time, because making people wait unnec-
essarily feels like bad karma. Everyone has a limited
amount of time on this earth — why waste your own
or anyone else’s? I think the golden rule applies in this
case.
Still, knowing when it’s okay to be late and when
it’s not is one of the finer skills involved in profes-
sional success, as consultant or any other kind of
business professional. It’s also a skill that many people
have trouble mastering.
Punctuality 162

Kingdom Hall
My earliest experiences with punctuality and lack
thereof involved going to church. Or more accurately,
Kingdom Hall, since I was raised in a devout Jehovah’s
Witnesses (JW) family. I am the oldest of five siblings,
and raised the most hell. My dad was an Elder in
the congregation, what other churches would call a
Pastor. I’m told that I fit the pastor’s kid stereotype
perfectly.
Church was BORING. Twenty years have passed
since I’ve attended a JW service and I still have to put
BORING in all caps. That’s how bad it was. There
were many remedies for the boredom, but the one I
want to talk about is shortening it. The way you did
that was by being late.
How do you control being late or on time if you’re
just a kid? Passive resistance and sabotage.
In my era, JW’s had meetings three times per
week. They’ve since adjusted to people’s busy lifestyles
and cut one of those meetings. But for my family it
was two weeknights, plus Sunday. Depending on how
many congregations were competing for use of the
Kingdom Hall, sometimes we had to have our Sunday
meeting on Saturday night. That was the worst! There
were also meetings for door-to-door service every
morning and special occasions, like assemblies or the
Punctuality 163

Memorial.
Many of the meetings required studying the JW
literature in order to be prepared to raise your hand
and participate in the group discussion. Studying con-
sisted of reading an article in the JW literature, and
using a fluorescent highlighter to denote answer to
the questions in the footnotes of every page.
The only good thing about studying was doodling.
I would fill the margins of my books and magazines
with squiggles, stick figures, geometric shapes and
fractal patterns, and use a rainbow palette of high-
lighters to color them. Plus the occasional glasses and
mustaches added to illustrations of biblical figures.
But what I’m trying to convey is that everything
related to the Kingdom Hall was an ordeal in some
way or another, especially getting ready for them, and
super-duper especially getting ready for them on a
weeknight. You see, all of these church events required
dressing up in formal attire. Suits and ties for the boys.
Dresses for the girls.
Church was about a 15 minute drive away, and
the meeting started at 7:30pm. You were supposed to
get there at least 10-15 minutes early to secure a good
seat and have fellowship with other members of the
congregation, so basically should have been leaving
the house at 7 pm, latest.
Have I mentioned yet that we were seven people
Punctuality 164

in a 900 square foot, 3 bedroom, 1.5 bath apart-

ment? Okay, more accurately it was a duplex that
we shared with my grandparents and my father’s
younger brother; they lived upstairs from us. But
that’s still 10 people sharing two bathrooms. Why is
that important? Well, my dad’s day job involved phys-
ical exertion, so he needed a shower before dressing
up. Same for my mom. As for us kids, we were a rough
and tumble bunch that spent most of our waking
hours outside, so we generally did as well. That’s a lot
of showers. Say we’re talking 15 minutes each, total
bathroom time, and I’m being conservative with that
figure, that’s at least 2 hours total. I’m not counting
time for getting dressed, brushing teeth, combing hair,
and finding shoes that have gone missing, etc.
Remember that I said we needed to be leaving
the house at 7pm. That means that everyone should
probably start getting ready around 5pm, just to be
safe. But we didn’t really get home from school until
2:30 or 3pm most days, and dinner certainly wasn’t
ready before 6, even on a meeting night. So things
start to get real interesting, because while the adults
are doing their thing, there’s a lot of room for passive
resistance. In fact, thinking about it, Mom was my
favorite parent growing up, because she was almost
always to harried or stressed out to even notice or
respond to passive resistance, she just went with the
Punctuality 165

flow.
My dad was a different story. The only saving
grace there was that he did not want to be late. Ever.
The man was punctual to a fault, so even if he was
cursing us all to hell while dragging my half-dressed
brother upside-down the side-door stairs on his head,
he’d be out the door by 7pm.
I hated being ready to go by 7pm because it meant
I had to ride with my Dad. The nights we were down
to one car, all hell would inevitably break loose. My
dad could not be late because he was in charge. He
was literally the boss of the congregation, and he was
compelled to set a good example for others to follow.
But he couldn’t just leave his family at home either,
that would also be a bad example. It was a recipe for
frustration. And fury too.
At Hashrocket, I learned what it felt like. Over the
course of a few years, I could tell that when I was
punctual, then the staff tended to be punctual too. If I
slacked off, then people seemed to feel the freedom to
slack off too. Sometimes if I was going to be late, I felt
like it was better not to come in at all. The freedom to
set your own hours is not actually free.
Punctuality 166

Boiler Room
My first serious job after graduating high school was
working at a boiler room operation called Investors
Associates. I thought I was destined for a glamorous
life of riches. Instead I found myself in a telemarketing
job from hell, pitching crap stocks over the phone to
people that really, really didn’t want to talk to me.
My employer was actually one of the notorious firms
that inspired the movies Boiler Room and Wolf of Wall
Street.
In order to land the job and be allowed to so-
licit people to buy the stocks we pitched, I had to
go through an intensive two-week unpaid training
period. It prepared me for Series 7 and 63 certifica-
tion, according to SEC regulations. That cost me $800
dollars that I had to borrow from my parents. Half
was for the study materials, and the other half was to
register for the exam itself.
The night before the exam, my part of New Jersey
was hit by a monster snowstorm. Given that I was
going to need to drive 30 miles to the testing center,
I decided to set out the evening prior and stay at a
motel closer to where I needed to be in the morning.
The driving conditions were brutal. It was a near
total whiteout, but somehow I made it out of the
neighborhood and most of the way to where I needed
Punctuality 167

to go along Interstate 80.

Disaster struck once I tried to get off the freeway.
I was unfamiliar with the exit and due to the poor
visibility, I drove my aging Audi sedan perfectly up
the center of a gradually sloping median that divided
the two lanes of the split exit. The snow and ice let
me slide just far enough that all four wheels ended
up suspended about a foot or more off the ground. I
had no traction and was going nowhere fast. Worse, I
managed to effectively block both lanes of the exit.
The year was 1993 and I didn’t have a cellphone.
Neither did anyone in the slowly growing line of
cars stuck behind me. I couldn’t abandon my vehicle,
so what the heck was I supposed to do? My body
grew colder and colder and my spirits dampened
significantly. I imagined myself missing the exam and
losing the money I had borrowed. The people stuck
behind me got angrier and angrier too, occasionally
plodding up through the blizzard to yell at me.
After an hour or two, a tow truck showed up! I
remember his blinding headlights as he drove down
the exit from the wrong direction. My burly savior
connected some chains up to the car and rudely
dragged it off to one side and down off of the median,
almost ripping off two of the wheels in the process. I
was shaken and freezing cold, but happy to finally get
to my hotel and get some rest.
Punctuality 168

The next morning I passed my exam with flying

colors. A week later, I was housed in a nondescript
office building working unpaid 12 hours shifts. My
task was to make 400 phone calls per day, slinging
shares of America Online and riverboat casino com-
panies. In the beginning, my main job was just to get
the target buyer on the phone and run through a basic
introductory script to hook him in. If that succeeded,
I could transfer him over to my boss to close the deal.
Speaking of bosses, mine was named Chris. He
was a stocky man with slick, gelled-back hair and a
flawless white toothy grill. Chris was a real ballbuster.
He drove a blazing red Ferrari on sunny days and a
Porsche Carrera 4 on rainy ones. He dressed impecca-
bly and his temper can only be described as volcanic.

On my first morning at work, Chris was standing in

front of the reception glaring at every new arrival
and shunting us off into a small conference room.
Minutes passed and one-by-one, a handful of other
new hires joined me, and finally Chris. He closed
the door and informed us that we were all late, and
that lateness was absolutely not tolerated under his
watch. He pointed at the clock, which read 8:05am. We
were told we were lucky this time, because everyone
showing up after us would be fired. He sent us on our
way and warned us not to be late again.
Punctuality 169

Then he went back to his watch in front of recep-

tion. If I’m remembering correctly, he fired at least
four of my cohort that day. Guys that had just dropped
hundreds of ill-afforded dollars and weeks of their
lives getting ready for the job.
Lesson learned. I was never late again.

The first 20 new customers we turned up would go

into Chris’ book, meaning he would get the com-
mission, not us. So he drove me and my cohort of
new stockbrokers real hard. We had to memorize his
script, along with myriad answers to all the blocking
objections that callers would throw up in our path
to making a sale. I quickly realized that I had signed
up for a telemarketing job in hell, there was nothing
prestigious about it!
The Power of Names
Sometime during my first week in the boiler room,
Chris parked himself on my desk and listened to me
fumble nervously through a call. One look at the veins
bulging in his face and I could tell he was seriously
pissed off. I hung up the phone, disappointed in myself
and cursing my life choices.
“What are you waiting for?” he asked, as I sat there
forlorn, waiting for instructions, “Keep dialing!”
I picked up another Dun & Bradstreet card from
the top of my stack and reluctantly punched the
number into my phone. There was an answer and I
introduced myself, “…my name is Obed Fernandez…”
Click.
Well that was quick. Chris had hung up the call
for me. I looked up at him with a pained grimace.
“Jesus H. Christ, your name sucks! I think it’s the
worst name I’ve ever heard. You’re never going to
fucking sell anything with that name. You need a new
fucking name. Pick a new name before you fucking
call anyone else.”
Chris cursed a lot, especially when he was angry.
He was furious.
The Power of Names 171

As I stared at my phone, he stalked away from

my desk in a haze of utter contempt. Michael Smith,
another new guy sitting next to me snickered, “he’s
right your name does suck.”
Gee thanks for the observation you asshole. You
must have the most common white guy name in the
world.
Now, I didn’t particularly like my name either,
especially since it was weird and from the bible.
People were always asking me where it came from
and whether I was Arabic or some shit like that. Even
worse I had to repeat it over and over again, since
the listener had almost never heard of it and couldn’t
make out what I was saying. Huh?
Dammit. Who was I kidding? Chris and Michael
were right. My name did suck for this job, but having
it trashed like that in front of everyone else in the
office was still one of the bigger humiliations of my
young life. I sat there fuming for a minute. Then I went
to take a pee, pondering my options for a new name.
What name would you have picked?
On the way back to my desk, I borrowed a legal
pad from the receptionist and started writing down
common names. Names that sounded like a stockbro-
ker, whatever that meant. Names like John, Michael
and David. Last names like Roberts and Johnson and
Foster. Wallace. Cash. Yeah, cash! Umm, no, probably
The Power of Names 172

too obviously fake. I did like Johnson as a last name,

but I didn’t want my new name to sound ordinary and
forgettable. After writing down a few more options
and nervously checking my watch, I somehow fixated
on the thought of sounding Jewish. Jews are good with
money, right? (Mind you these were the sensibilities
of an uneducated kid from north Jersey.) I gave the
process about five more minutes before deciding that
my new name would be: Levi Johnson.

Levi Johnson
I picked up the phone with a renewed confidence and
tried my new name on for size.
Hey, not too shabby! It had a good ring and the
person on the other end of the line did not ask me to
repeat it. I was pleased with myself.
Chris came back about an hour later to check on
me again. When he heard the name I had chosen, he
reamed me out good.
“Are you a fucking moron or what???”
“Levi… Levi! What the fuck is Levi! Are you re-
tarded? John or Michael. Hell, John Michaels. I told
you to pick a good name and you pick Levi,” he
screamed in my face.
My eyes welled up uncontrollably as he stomped
off in disgust.
The Power of Names 173

I must admit, being reduced to tears in front of

your peers is probably the worst feeling in business.
Despite my stints in janitorial work, this was now
officially the most degrading job of my life. And I
knew that I could feel either feel sorry for myself or
keep it together out of sheer spite. I shot a sideways
glare at Mr. Michael Smith, thinking that I would
probably punch him in the face him if he started
giggling again.
Back to the phones, since after such a bad day, it
could only get worse if I missed my target number
of calls. That would mean yet another reaming from
Chris and possibly getting fired. I didn’t have time
to pick another name, so I didn’t. I kept using Levi
Johnson as my alias. It did have a nice ring to it, is
what I told myself.
At this point, you might expect me to tell you
that the name Levi Johnson was good after all. But
actually, it sucked too, mostly because a significant
portion of the people I called hadn’t heard of anyone
named Levi either. So it became a talking point –
one that was definitely not on my script. Still I kept
calling. The second week whizzed by; dialing 400
phone numbers a day has a way of making time fly.
By the end of the third week I was not feeling
very well. I hadn’t made any sales and some of the
other guys in my cohort already had ten or more.
The Power of Names 174

They had figured out how to follow the script. They

had understood it was a numbers game. In my mind,
I understood that it was numbers game, I just had a
hard time making the numbers. (Year later I would be
diagnosed with ADD.) My calls were taking too long.
I would deviate from the script too much.
My upbringing was religious and very moral. Like
I mentioned earlier in the book when talking about
values, my dear father had instilled an ironclad sense
of honesty in me. It didn’t take me very long to figure
out that we were a “pump and dump” operation. Chris
and the rest of the brokers did not care in the least
whether a stock that we sold went up or down, they
just cared about the commission. Which meant that
sometimes we had to lie to the potential clients with
a straight face.
The job was even making me physically sick.
We worked brutal shifts, from 8am to 8pm, with
two 30 minute breaks for lunch and dinner and as
a result my eating habits became atrocious. Lacking
time to go elsewhere, I frequented the lobby conve-
nience store for lunch and adjacent T.G.I.F. restaurant
for dinner. Happy hour buffet was complimentary as
long as you bought a drink. I wasn’t old enough to
drink alcohol, so I’d order a coke for about a dollar
and chow down on the greasy goods in the buffet for
free.
The Power of Names 175

One evening after dinner, my stomach started

doing somersaults. I couldn’t get up to take a break
because I was already dragging my call count and
running out of time to catch up. So I’m sitting there
doing the best I can while cold sweat streams down
my pale face like a pregnant nun. To make matters
worse, here comes the boss man striding down the
aisle.
Shit.
No, don’t sit on my desk. Don’t sit on my desk,
please! Not a good time for a spot check, not at all.
And yet here he was. Argh!
“What?” asked Chris.
“Nothing,” I mumbled, a crisp feeling of panic
seeping up from my gut.
“What? asked Chris again, starting to show some
exasperation.
I blinked, and the telltale bittersweet taste reached
the back of my tongue.
No. Not now. My chest heaved and my hand
instinctively flew to my mouth as I tried desperately
to hold back. Where is the trash can?
And then, the inevitable. In slow motion. Just like
it would in a movie. As Chris realized what was
about to happen, he started clawing backwards on the
desk. I couldn’t hold it back any longer and bent over
trying to aim anywhere relatively safe. Unfortunately,
The Power of Names 176

it wasn’t even an ordinary puke. I had managed to

get one of the older grunts in the group to buy me
a couple of beers that night, and they had made
me super bloated. So it was high-velocity projectile
beer vomit loaded with way too many greasy T.G.I.F.
buffet nachos.
Unfortunately, the puke didn’t exactly hit Chris,
but the aisles of our desks were covered in plastic chair
mat material so that we could roll around, material
that provided for quite a bit of splash damage, if you
know what I mean. Everyone in my general vicinity,
including Chris, got puke on their shoes and bags and
pant legs, etc.
I managed to find the wastebasket and heaved
again and again, as one half of the office laughed their
asses off and another ran out of the room in abject
revulsion. It was one of the worst moments of my life.
In retrospect, I wish I had taken aim squarely at
Chris’ chest. No half measures.

Miraculously, the incident got me sent home, but did

not get me fired. At the end of week four I finally made
a sale. And then I quit. Levi Johnson was a failure.
I’m not about to say that the name was to blame,
because I was just not cut out for such a dishonest and
demanding job overall. Not at that age, if ever, but
calling myself Levi Johnson did have something to do
The Power of Names 177

with my ultimate failure as a boiler room stockbro-

ker. The naming decision was hasty and quirky and
made under pressure. Instead of listening to Chris and
changing my name again, I let my pride and a weird
sense of attachment set in. It was, to use his term, a
moron thing to do.

Hashrocket
Years afterwards, in late 2007, John Larkowski and I
would come up with the name Hashrocket as one of
the potential band names for our fledgling musical
collaboration that never went anywhere. The only
song we ever recorded was a cover of Michael Jack-
son’s Dirty Diana featuring vocals by a cute waitress
named, yep, you guessed it, Diana.
When it came time to name our new consulting
venture, we looked at the whiteboard with the list of
band names. We had some good ones on there, like
God Fodder, but Hashrocket really jumped out. It was
cool and sounded like a drug reference. But it was also
relevant to our craft, which is creating software with
the Ruby programming language.
This is a how you define a hash mapping in Ruby¹⁰
:key => value
¹⁰Prior to Ruby 2.0 anyway, when they changed => to :. I suppose we could
have updated our name to ColonRocket, but it’s not quite the same imagery.
The Power of Names 178

The => symbol (or to be precise, operator) in the

center of that hash notation was in 2007 known col-
loquially as a rocket. It is meant to portray an arrow,
since a hash mapping is an association of keys with
values. Hashrocket sounded cool and it had a good
backstory, so we went with it.

Obedient to God
Relevant backstories are great. (So are thinly veiled
drug references, but we’ll get to that later.)
When I was younger and went by the name Obed,
my backstory sucked. Obed means obedient to God as
my devout JW parents pointed out time and again
during my rebellious teen years. Having to explain
that backstory to people I had just met was terrible. If
they themselves were religious and familiar with the
bible, then the name would usually ring a bell. Many
would ask me where the name comes from.
“From the book of Ruth,” I would reply, flatly.
“Oh, that’s right,” they might say, or “No, I’m not
familiar, are you sure?” As if I would be wrong about
my own name.
Sigh. “Obed was the father of Jesse, who was the
father of King David,” I would offer up.
“Yes, that’s right!” they would say. Whoopdie,
fucking, doo.
The Power of Names 179

No offense, but while I don’t consider myself an

atheist, I am not religious at all. The conversations I’ve
just portrayed are ones that I’ve had way too many
times in life already.
In 1998, I moved to Atlanta to get a fresh start
and put some distance between myself and my wacky
religious family, I decided I was done with the name
Obed. I had occasionally been called Obie growing up,
especially as a term of endearment from close family.
Obi Wan Kenobi is a famous and powerful Jedi
from the Star Wars stories. What’s not to like about
the name Obie?
So from day one of my new job in Atlanta, I told
everyone that my friends called me “Obie” and that
was that. It helps to execute a transition like that when
you move 800 miles across the country to start life
over again. Otherwise, it can be very disruptive to
your social life.

I have a friend that was Bruce when I first met

him, then he changed his name to Michael. Or
maybe that was his first name and he went
back to it, I’m not sure. But then he changed
his name to Singing Arrow. When I reconnected
with him after a lapse of several years, we had
the following conversation.
.
The Power of Names 180

“So Bruce, ehrm, I mean Michael, uhh… shit, I

mean, what should I call you anyway?”
“You can call me Singing.”
“Ehh, sorry I have trouble calling someone a
progressive verb.”
“That’s totally understandable. You can call me
Arrow.”
Much better.
.

And so it goes with naming, if you don’t choose

carefully then you end up having these meta conver-
sations with people, that if not necessarily awkward,
do chew up otherwise valuable time and confuse
matters for all involved.

Drug References
Back to Hashrocket, since I did promise I would
broach the subject of its being a thinly-veiled drug
reference. The term “hash rocket, at least in theory or
according to Urban Dictionary, could refer to a joint
filled with hash, which might be one of my favorite
drugs in the world. If I did drugs. Ha.
The Power of Names 181

Therefore, our thinking went, a certain demo-

graphic of people hearing the name Hashrocket for
the first time would naturally think of drugs, and
many of them might mention that. Now here’s a meta
conversation I love, because then I get to be coy about
it. “No, no, it’s not a drug reference,” I say, “it’s because
we do Ruby and a hash in Ruby is defined with a
rocket symbol, yada yada…”
Cute, right? I think so, and besides being clever,
it gives me a segue for discussing one of the pri-
mary ways that we segmented potential customers
at Hashrocket while I was in charge: coolness factor.
Meaning, if you had a problem working with a firm
that may or may not be named with a drug reference
then we probably didn’t want you as a client anyway.
Because you would surely be a pain in our ass in other
ways that were yet to be revealed.

Name it like you mean it

Sometimes a name you want has subtle or not so sub-
tle functionality problems. For instance, certain peo-
ple would inevitably want to split the name Hashrocket
into two words: Hash Rocket. Ugh. No, please no don’t
do that. Or camel case: HashRocket. Nope, also bad.
I’m a details guy and lapses like that drive me crazy.
The name is Hashrocket, people! Get it right!
The Power of Names 182

My startup DueProps had naming issues through-

out its history. Its original codename when it was just
an experimental app at Hashrocket was DueProps.
But when I went to register the domain for it, the
dot com variant was already registered by someone
else. Fixated on having a proper dot com address
for my masterpiece, I decided to go with the name
RightBonus instead.¹¹
The problem that I faced with the name Right-
Bonus is that we were focused on peer-to-peer appre-
ciation, not bonuses. Our name was actually detract-
ing from our marketing message and usage. People
would literally hear about the product and tell us they
didn’t need to or want to change their bonus plans. Or
that they didn’t give bonuses, so they didn’t need our
product. It was killing us, slowly.
Finally, one day I was demoing the product to
Parker Thompson, one of the smartest guys at Pivotal
Labs at the time, and a good friend. He didn’t care for
the name RightBonus, which led me to describe how
it was originally called DueProps and all that jazz.
“Oh, DueProps, that’s a great name for it,” said
Parker.
“I know, but the dot com is taken,” I told him, sadly.
¹¹RightBonus had a lot of things going for it, and I’m a fan of RightX naming
in general. In fact I have over a dozen RightX.com domains sitting there in my
DNSimple account waiting to be used. My friend Jonathan, creator of RightScale,
RightCart, RightRentals, and RightSignature literally has hundreds of them.
The Power of Names 183

Or was it? On a whim, I checked the registra-

tion and it turned out the name was now available.
Whoever had it before me had let it expire! From
that moment on, even though it was a huge pain in
the neck to transition the codebase, I switched all the
naming over to DueProps.

Identity Confusion
Throughout the history of DueProps, I kept the un-
derlying corporation name the same: RightPay, Inc.
Which leads to my final piece of advice about naming.
If you start a company, be it product or service-
oriented, be mindful of the difficulties of having your
public-facing identity be different from your legal
identity.¹²
First of all, you’ll constantly be clarifying your
naming scheme. You’ll introduce yourself as so-and-
so from [Corporate Name] but the person will only be
familiar with your product. After a bout of confusion,
a totally maddening conversation will ensue in which
you clarify your naming scheme.
When my company Lean Startup Machine entered
the Tech Stars accelerator program, we launched a
¹²This is a problem I personally face from time to time, when people give me
checks or airline tickets made out to Obie Fernandez instead of my legal name.
Note that I’ve learned it’s possible to register aliases with your bank rather easily.
The Power of Names 184

product named Javelin. After endless rounds of dis-

cussions about our name, my co-founder and CEO
Trevor Owens started walking around telling every-
one he was CEO of Javelin. This confused the heck out
of everyone who knew us as Lean Startup Machine, or
“LSM” for short.
Javelin might indeed be a better name for the
company, for a number of reasons. For starters, the
lean startup trend might lose steam and we don’t want
our fortunes tied up with it. Then there’s a matter
of trademark. The term lean startup is trademarked
by Eric Ries, and we have a license agreement with
him to use it in conjunction with our business. If that
relationship were to sour, we might find ourselves
having to change names very suddenly. That’s a scary
thought!
Still, the shift from LSM to Javelin was painful. For
the longest time, nobody knew exactly who we were.