Inspiration: Leader Identity Narrative

Josh Jackson
College of Integrative Sciences and Arts
OGL 482: Pro Seminar 2
Professor Brent Scholar
October 20, 2021
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Introduction

The ability to look back is a powerful thing. When we do so, so long as we are honest, we

can discover what kind of character we play in our own story. Are we the kind of character that

develops from weak to strong over a long arch? Are we the kind that is defined by a fixed set of

traits that remain static over time? Or are we like the classic Greek heroes of old, beset by a fatal

flaw that causes us to need to relearn a valuable lesson over and over again? When I took this

opportunity to graph my leadership journey, I learned that in reality, I was a mix of all three. At

the time of writing this, I am wrestling with several leadership challenges that loom over the

horizon. The following stories serve as fuel for engaging that ominous future. Here’s where it

begins.

Leadership beginnings – Discovery in Australia

I have always been a late bloomer. In almost every way, my talents, sense of self and

developmental experiences have emerged later than most of my family and peers. My discovery

of a capacity for leadership echoes this pattern. From sophomore year of high school until about

two years after graduating in 2000, my sense of identity was very much rooted in an enclave of

close friends. This enclave started as a tight-knit crew of 4 or 5, but as each of us started

discovering the unknown horizons of girlfriends (them, really. I wouldn’t share in this

experience until far later. “Late Bloomer,” remember?), that enclave grew into a crew of 12 to

16. My house became our hub, and my mom became the ad-hoc tribe-mommy. 

At the time, my extroversion-fueled motivations were very satisfied by the constant

social dynamics, and I was happy to live a life defined by minimal work responsibilities taking a

backseat to maximized social activities. I still pursued creative endeavors, namely in the form of
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drumming in metal band projects that could never quite get off the ground, but as a whole, I

coasted through my early 20’s. 

That all came to a violent stop in September of 2002 when my mom suddenly took ill and

then died within seven days. The next year would be defined by fall-outs with the core members

of the tribe, aimless wanderings, shuffling from host family member to host family member, and

several gruelling graveyard shift service jobs.  I would eventually start drumming for the worship

team at my aunt’s church, which would lead to me becoming an informal family member of one

of the congregants and her family.  Over the course of several months, they introduced me to an

organization called Youth With A Mission (YWAM), a world-wide missions organization with a

range of ministry focuses depending on each chapter’s location. After learning more about me,

they suggested that I would enjoy the Newcastle, Australia “base,” a team notorious for its punk-

rock flavor.  In January, 2004, I made the trek from California to Newcastle to take part in  their

initial five month course/ministry outreach, with no clear idea about where I would go after. It

was in this strange new environment where my capacity to lead would finally emerge.

I would, after some initial bumbling, find a kind of home in Newcastle. After taking part

in two courses and subsequent mission trips, I joined the staff and became a full-time missionary.

Our focus was local Newcastle youth through outreach and activity programs. My group’s

specialization was mentoring kids in the context of a music program. Over this first year in

Australia, a new set of skills and motivations took shape in the absence of the slacker culture of

the tribe back in California. I was given challenging tasks from superiors, and found that I was

easily able to rise to the challenge. I had always prized my artistic abilities, but in this

environment, I was learning that I also possessed a talent for big-picture, systems oriented

thinking, a heart for mentoring others, and an ability to activate other people. What’s more, I was
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actually receiving affirmation for it, something that was always lacking in my past environment.

Over that first year, I became aware for the first time that I wasn’t truly a slacker, but a leader.

An Early Low: Outreach in New Zealand

My lowest point in this leadership journey would ironically take place the following year

in 2005. It was always my hope to get to be on staff for one of the adult courses our “base” ran. I

wanted to serve as a mentor and support for other students who would experience what I did the

year earlier. I was finally getting my chance, but the result would be one of the great

disappointments of my life, both in what I experienced from my own leaders, as well as what I

would discover within myself. The culture in YWAM Newcastle was very performance-based.

As a religious organization, and one that was staffed almost entirely by young, virile twenty-

somethings, there was a heavy emphasis on living at a high moral standard, but under the

surface, what was even more valued was not giving any opportunity for anything to appear like

it wasn’t up to a high moral standard. I had finally earned a position I really coveted, and having

earned it, I immediately became afraid of making any mistake that would cause me to lose it. For

this reason, throughout the course, I would make leadership calls that did not align with what I

believed were wise decisions, but were motivated by what I thought my superiors would approve

of. I felt very conflicted and insecure. I rarely truly led but often reacted, mostly by withdrawing

and removing myself emotionally from my director, co-leaders and students. I would receive

conflicting messages from my own leaders, who in retrospect were probably dealing with their

own internal conflicts, and because I hadn’t yet developed the organizational or communication

skills necessary to clarify and execute their goals,  the results would often be anger and

confusion on their part as well as my own.

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The ultimate sting would come when it was time to delegate leadership roles for

missionary outreach. My director had such little confidence in me, she placed me in an assistant

role under my peer, while a student in the course actually received a leadership role for the other

team. My peer would then go on to delegate other leadership responsibilities to our students,

leaving me to spend the next two months in New Zealand with no clear purpose, taking

instructions from the very students I was supposed to be leading. It was humiliating.

After a series of events during a brief furlough in the states following the end of the

course, I would cut my time as a YWAM staff member short and start a new life chapter in

Nashville, TN. It would take months to process what I had experienced in that last year in

Australia. Eventually, I would recognize the life lesson of leading out of courage and integrity,

rather than letting myself become hamstrung by fear and insecurity. Over the following fifteen

years, I would get many opportunities to practice this new leadership lesson in ways that were

less dynamic than that in Australia, but by their nature, would serve as training grounds for the

exercise I severely lacked back on the base.

Rediscovery: A New Chapter in Nashville

The first year in Nashville was harrowing. I was held up and pistol-whipped by three

masked men days into being hired at my first job. A week later, the timing belt on the Astrovan I

purchased would snap, and I would roll to a vulnerable stop in the middle of the interstate. Due

to many doors of opportunity slamming shut simultaneously, I would end up serendipitously

taking a job at Starbucks, a decision that would eventually color every aspect of my life, from

child-rearing to social networks to the impetus that would lead to me writing this very paper. 

Within that first year, I would end up becoming a member of a small but earnest church

in a nearby suburb. It was in this environment that I would slowly build back my capacity to lead
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once again, and the foundation for my current-day leadership identity would be laid.  It was in

this period that I would begin to enjoy the freedom to experiment with my natural proclivity for

short term projects, namely in the form of music events and performance-oriented fundraisers.

Unbeknownst to me, what I was really engaging in was the craft of Project Management and all

that it would entail. I was exercising my ability to engage others with a vision, delegate roles and

responsibilities, balance differing stakeholder motivations and measure progress, all in the

context of these very modest projects. Simultaneously, over the next several years, I grew in

stature at my church, taking on various leadership roles like rotating childcare leader, and leader

of a rotating setup/teardown team.  This would ultimately culminate in the head pastor letting me

launch a 3-month long weekly men’s discussion group centered on discussing a leadership book

called Ordering Your Private World by Gordon McDonald. At work, after many months of

receiving coaching and feedback, I was finally promoted from barista to Shift Supervisor, where

I would experience a more formal setting for exercising practical leadership skills.

By 2011, I was becoming very established, both in the minds of others as well as myself

as a reliable contributor to my community and as a servant-leader to my peers. For my effort, I

was being rewarded with more opportunities to influence and serve in my community, my

workplace and in my creative endeavors. Inadvertently, I was also being set up for my next

valuable lesson in leadership.

Another Low Point - Starbucks Shift Leader

I would only last as a Shift Leader for a year. Much like my time as a staff member at 

YWAM, I came into the position with a misplaced set of expectations about what the role would

entail, and was quickly disillusioned. I thought I would get more opportunities to influence daily
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operations and experiment with time management practices for myself and my fellow baristas

with the intent of making the day-to-day more efficient and rewarding. I was very mistaken

about the level of influence my position held. I was mostly relegated to closing shifts, which

meant my days were mostly spent rushing through closing tasks, restocking and cleaning with a

minimal staff. This schedule also conflicted with my other interests, like church functions and

local shows, adding to my frustration. I was quickly becoming resentful, burned out and

withdrawn in my work life, culminating in my very first all-negative yearly review in my five

year tenure in 2012. It was here that I learned a critical leadership skill that would influence the

rest of my life, albeit the hard way. I realized in retrospect, that I was overemphasizing the

“authentic self” of the emotional life of a leader. I was wearing all my emotions on the outside

for all baristas, managers and customers to see, thinking that, on some level, I was living out

what it meant to be an authentic leader. What I realized, sometime after getting some emotional

distance from the experience, was that there is psychological power in a leadership position that

exists outside of the person that occupies it. Intrinsically, subordinates take cues from whoever is

in a leadership position and assess their own outlook based on them. When I was being resentful

and visibly stressed out on the job, simply because of my position, that emotional heat was being

amplified and was radiating out to the rest of the team, making them feel unsafe. Had I done

better at regulating myself and privately taking steps to ensure my own self-care, the exact

opposite would have been true. The amplifying effect of the position would have resulted in my

positive emotions radiating out to others, giving them a sense of security. It took years to fully

absorb the lessons from this bleak experience, but thankfully, in other areas of my life, my

leadership journey was yielding more positive results.

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Taking Up the Practice Again

2012 marked the beginning for several facets in my life simultaneously. In January, I

launched a private bartending service, meant solely to be a modest side hustle for myself. Little

did I know that ten years later, it would blossom into a robust business with thirty bartenders, a

full-time executive manager, and a yearly calendar of over two hundred events. In March, I

married Stephanie. Like my business, we’ll celebrate a decade together in 2022. The year also

marked my membership in a new church, which would prove to be a true spiritual home for me

for the next nine years.

Much like the span of time following my somber return from Australia which culminated

in my embittered (first) exit from Starbucks, the next nine years would serve as one long

ascending exercise in leadership. In my small business, I was regularly learning the ins-and-outs

of time management, effective communication, recruiting, training, long term forecasting, and

most importantly, learning how to manage myself professionally even when things were shaky in

my personal life. For example, in 2014, we were given very short notice towards the end of our

lease that our landlord was selling our house, which set in motion a turbulent span of months

where Steph and I had no established residence. Simultaneously, my company’s reputation was

growing, and I was experiencing higher volumes of inquiries and new professional situations, all

while still holding down a full-time job. No matter how strained I was, clients and other

bartenders were counting on me. It was a season of toughening up and learning how to deliver no

matter the personal circumstances.

In my church community, I was thriving in the culture that colored that season in the

church’s history. Over the next nine years, Stephanie and I would lead in the worship band,

pioneer arts discussion groups and writing seminars, and lead a neighborhood group that
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remained dynamic and vibrant for several years up until the fall-out of Covid lockdowns in 2020

(More on this later).  For nearly a decade, I experienced a window of time defined by

invigorating community, and steady growth in my business that would lead to the freedom to

eschew regular employment in 2017. It was also a time tinged with many challenges, but they all

contributed to a theme of learning, maturing and an accrual of wisdom and practical experience.

The Zenith: January, 2020

The zenith of my leadership journey thus far took place in January, 2020. I was a father of a

beautiful one-year-old boy, a child we had begotten through an adoption that went sour, and then

miraculously went through after all a month after he was born. My business experienced an

amazing level of growth in 2019, culminating in the partnership between myself and Kelly

Tinnin, who joined as Head of Operations and still serves in the role to this day. The team was

expanding, and our hard work was opening up the doors for 2020 to be the most fruitful year yet.

In lieu of a Christmas party, we had invited all of our bartenders to join us for an End-of-Year

party at a private residence. We ate, drank, competed in games and revelled in our success. The

exact moment that marked my zenith was when I grabbed a drink and sat next to one of my long-

time bar team leaders, Taylor. We were making jokes about something, and she made a remark

that left me stunned. She said “I’ve found my people. I’ve found my place.” Her statement was

the culmination of almost a decade of my life striving to create a job for others that was devoid

of all of the dehumanizing elements of my previous service jobs. I had worked so hard to create a

culture that honored people, that made them feel like their contribution was valued, and now, my

bartenders were actually showing me that it was happening in their words and deeds. More than
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the rewards of turning a side hustle into a thriving business, this single statement was the

culmination of my  journey as an entrepreneur and leader. 

Fall Out and Rebuilding

As one could imagine, 2020 was not the cascading fountain of growth and success that

we had all projected it to be. 2020 and 2021 have been a crucible, testing me in every aspect of

my character and leadership ability. Postponements, cancellations, fear and confusion would be

the themes of last year. My ability to project forward and create innovative solutions to navigate

the new landscape was taken to a challenging new level, and any success we would experience in

2021 is owed in large part to Kelly’s loyalty and commitment. We were wise to largely ignore

the siren song to “pivot” our business model, and instead, spent all of 2020 retooling our

processes, poising us for a projected rush of inquiries we anticipated would come in 2021.

Though I do not gloat over the misfortune of my peers, I look back in gratitude that I followed

my instincts, and chose to spend the downtime further leveraging our strengths instead of

developing new products that would be irrelevant in a year. Time has been on my side in this, as

2021 did in fact bring about unprecedented volume, greater rewards and even greater

opportunities to grow still further in years ahead. 

My leadership development within my church community did not yield such optimism,

however. My church was dealt a series of blows that led to near disintegration. First, East

Nashville experienced a devastating tornado in February. A week later, the elders fired our senior

pastor, a startling decision but one that had been coming for a long time. Thirdly, our community

along with the rest of the world experienced the ravages of the Covid lockdown. Over the next

several months, I would be buffeted by disappointment after bitter disappointment, attempting to

hold my neighborhood group together in spite of the confusion and fear that gripped us all. The
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group was disintegrating. People were moving away, or they were retreating into their houses.

The elders were no different. The church had silently nurtured a passive culture over the last six

years that culminated in a policy of inaction that lasted well past the initial shock of the Spring. I

finally had to walk away from my beloved church in dismay that Fall, when a bungled attempt to

bring about in-person worship again made clear to me that I could no longer trust these elders  as

my leaders. My time as a servant-leader in my church was over. Stephanie and I are still without

a new church home to this day.

Looking Forward

It is now the tail-end of 2021. I am still steeped in the emotional mix of an astonishing

recovery for my business coupled with the bitter disappointment of my disintegrated

community.  After ruminating over a leadership journey that took visible shape some seventeen

years ago and continues to evolve today, I can point out some clear patterns that remain

consistent. First, I thrive when I feel a sense of ownership over an endeavor. When I failed most

in YWAM and Starbucks, it was brought on by a feeling of having little control over my

environment. I know now that many of those disappointments were due to my own mistaken

expectations and in some instances, character failings, but it is apparent that in environments

where I had authorship, I was in a healthier emotional state to take the hard lessons and absorb

them. Second, I need to remain confident about my own abilities. I don’t physically resemble

many model leaders and sometimes feel insecure because of it, but by now, my story is full of

evidence that I can in fact lead others and make lasting contributions to my community. There

are several looming challenges for me to engage in 2022, and this exercise in documenting my

leadership journey gives me renewed encouragement, knowing that I have the capacity to tackle

those challenges just as I have these obstacles that marked the last seventeen years.
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