For some reason in our culture — especially in Silicon Valley —

when someone is rich and successful, we collectively ask, "How do

they do it?" Instead of the obvious contributing factors (wealth,
talent, privilege, friends in high places, etc.), we fixate on the
eccentricities: morning routines, juice cleanses, and pilates habits.
Facebook COO Sheryl Sandberg, Sen. Kamala Harris and
Microsoft founder Bill Gates have all gotten the "habits of
successful people" treatment. These days, it's Twitter and Square
CEO Jack Dorsey who's getting all the attention.
Dorsey's schedule has long been the subject of public fascination;
the fact that he routinely tweets about it certainly stokes the
ongoing interest. But earlier this month, an hour-long podcast
interview turned Dorsey's daily routine into a national
conversation.
Appearing on fitness enthusiast Ben Greenfield's podcast, Dorsey
described how he walks more than 5 miles to work, meditates daily,
enjoys a sauna and ice bath routine, and restricts eating to a mere
2.5-hour window every day (except weekends when he sometimes
fasts for 72 hours straight).
In short, it's extreme. And before I go any further I want to make
something clear. A lot of what Dorsey described isn't realistic and
much of it is not healthy. Washington Post columnist Monica
Hesse pointed out that when women act like this, it's considered
an eating disorder — when it's a tech bro, it's glorified.
If you find yourself struggling with disordered eating, or otherwise
unhealthy behavior involving food, see the National Eating
Disorder Association's website for resources.
I subjected myself to this insanity for 24 hours, but you definitely
don't have to.
So here we go, a day in the life of Jack Dorsey.
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6:15 a.m. — Exactly what time Dorsey wakes up isn't clear to me.
Sometimes he says 5 a.m., sometimes he says 6:15. I (obviously) go
with the latter option to give myself as much sweet sleep as possible.
Meditation plays a big role in Dorsey's life, so I start my day as he
does, in meditative silence. He says he meditates for two hours a
day, but I start small, with 30 minutes of guided meditation using a
phone app. I sit up in bed to avoid falling back asleep, but as a
soothing British man tells me to inhale and exhale deeply I start to
sink lower and lower into my warm bed.
6:45 a.m. — Yup, I fell back asleep. But my boyfriend's alarm
wakes me up and it's time to get ready for my big day as a waif-like
tech CEO. Just kidding — I'll be doing my normal job, so I have to
make some attempt at looking presentable. If only I could go into
the office with messy hair and a hoodie. Now I'm running late.
Damn patriarchy.
7:30 a.m. — Here's where things start to get weird (stalkery?). I
hop in an Uber to Jack Dorsey's house in Sea Cliff. As we drive up
Fell Street through Hayes Valley, the inanity of what I'm doing
strikes me. Soon, I'll be doing the journey in reverse, on foot.
See, Jack Dorsey says he walks 5.2 miles to work every day wearing
jeans, a t-shirt and running sandals — except Tuesday and
Thursday, when he works from home. Lucky me, it's Wednesday.
8:18 a.m. — Jack says — now that I'm at his house, I feel like we're
on a first name basis — the walk takes an hour and 15 minutes at his
brisk pace. If I can be like Jack, I should arrive at the Twitter
building at 9:30 a.m., fashionably late but perfectly acceptable for a
sandals-wearing executive.
8:22 a.m. — I see what appears to be a stray white Bichon Frise
dog roaming the manicured sidewalks of Sea Cliff. Must not stop!
Must not be deterred! Must be like Jack. Good luck, floofy boy.
8:36 a.m. — Jack says he uses his walking time to listen to
podcasts and reflect. I'm listening to a podcast about California's
housing shortage and reflecting on how I'll never be able to afford
one of the beautiful homes I'm passing by. I'm not like Jack.
9:19 a.m. — I'm at Fillmore already? At first I think the street sign
is a hunger-induced mirage, but it's not. I'm making great time and
turn to start heading south through Lower Pac Heights.
9:55 a.m. — I'm here! That wasn't so bad. The journey took me an
hour and 35 minutes and it was pretty much all downhill. Not nearly
as bad as I'd thought it'd be. I head straight to Blue Bottle on the
Twitter building's ground floor, as Dorsey is known to do, and
order an iced coffee. I pay with Square, of course. I cherish every sip
as I know it'll be my only sustenance until dinnertime.
10:30 a.m. — I arrive at my office very late (sorry, boss!) and head
straight into a meeting. Oh boy, am I caffeinated. I start working on
a story that's less ridiculous than this one.
11:53 a.m. — My coworker offers me some cheese crackers she's
snacking on. I explain that since Jack Dorsey only eats between the
hours of 6:30 p.m. and 9 p.m., I have to decline. I am not known to
turn down snacks. I'm officially making my coworkers
uncomfortable.
12:14 p.m. — I'm a little light-headed and jittery. My paper straw
looks like it's composting into my iced coffee.
Considering I haven't consumed anything but water and coffee, I'm
not as hungry as I thought I'd be. In a twisted way, I'm kind of proud
of myself for not caving into the urge to eat. I'm acutely aware of
how disordered and unhealthy this kind of thinking is. Yikes.
4 p.m. — Despite the fact that Dorsey has claimed to work 18
hours a day, 6 days per week, I'm not feeling up to an 18-hour
workday. Quite the opposite actually. I have to leave early to finish
all the things I'm supposed to do in a day in the life as Jack. Sorry
again, boss.
4:55 p.m. — Apparently, Jack Dorsey is a believer in the 7-Minute
Workout, a short but high intensity workout made popular by
a New York Times article. It's basically a bunch of bodyweight
movements (jumping jacks, crunches, push-ups) that you do back-
to-back with little rest. Dorsey says he does one to three rounds of
the routine daily.
It's not that hard — much easier than the SFPD workout I
suffered through a year ago — though I do break a sweat. At this
point in the day, I'm fully happy to underachieve and I just do one
round.
5:07 p.m. — It's time for a sauna. There's only one problem: I,
unlike Jack Dorsey, do not have a custom near infrared sauna nor a
custom ice bath installed in my home. I improvise. Instead of going
back and forth between a sauna and custom ice bath, as Jack says he
does, I simulate the experience by cranking the temperature of my
shower way up for 15 minutes, then all the way down for 3 minutes.
I'm supposed to do this three times in a row, but after about 22
minutes I can't bear to waste any more water. I'm over it.
5:40 p.m. — Finally, I get to eat. No, I'm not going to make it to the
prescribed 6:30 p.m. dinner time but I have somewhere to be at
6:30 so now is my only shot. Dorsey says his meals usually consist of
protein and vegetables. I have leftover spaghetti squash and turkey
meatballs that fit that bill, and I can't reheat the plate fast enough.
Dorsey says restricting his eating to only two and a half hours per
day has given him a new appreciation for food and it tastes better
when he does eat. He's not wrong; these meatballs I thought were
far too dry two nights ago do taste a lot better, which of course they
do — I'm starving.
I inhale my first portion and go back for seconds. This is the best
part of my day. I'm glad it's over.
Final thoughts: I'll keep it to under 280 characters as a final
tribute to Jack. This daily routine isn't what makes Jack Dorsey
successful. Few parts of it are worth emulating. Walking is good, but
so is eating when you're hungry. I won't be doing this again. Because
I like myself.