The Inescapability of Imitation

My circular path to starting a newsletter.

Dear Family and Friends,

Since you are in the unfortunate circumstance of residing within the interior ring of my social web, I took the liberty of including you in the beta test of a side project I’ve been working on for the last several months. If you don’t consider yourself to be one of those two things—my family or friend—please stop reading, unsubscribe and delete this email. Don’t make it awkward. If someone forwarded you this email and you had considered yourself my family or friend, please don’t get all butthurt. We are family. We are friends. Mistakes happen.

Fallow is the name of this creative experiment; a newsletter in which I intend to share some things I’ve noticed about human nature through my struggles to improve my own. Think of it as a hazy mixture of philosophy, psychology and mental health (hazy because the distinctions between those disciplines seem a bit arbitrary to me).

Below is the story of how this project came to be. If you like it please subscribe and share it. I’d love to hear how the story resonates with you either via a direct email reply or by leaving a comment. This newsletter is my first attempt at sharing my writing—which I’m finding to be a vulnerable experience—so thank you in advance for helping me shape it.

-Gerald

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The Inescapability of Imitation

Midjourney prompt: Elevated view of a young man walking through a mystical labyrinth in the shape of a nautilus.

I was sitting in a lounge chair in a dimly lit office, legs bouncing in rapid micromovements like a neurotic hummingbird hovering in front of a feeder. Heather, my therapist, was facing me, seated five feet away. Her solemn facial expression intentionally mirrored my own, but her body was still. We were stuck. I had been seeing her for about a month, once a week, making it our fourth session. Her specialty was cognitive behavioral therapy (CBT)—a set of techniques that help to change thought patterns (that’s the cognitive part) and, subsequently, actions (that’s the behavioral part)—but the techniques had just been glancing off the surface of my distressed gaze. I was in a perpetual state of panic and, as a result, my mind lacked the flexibility to engage with the material. I was there because I was unemployed—going on nine months—and the desperation I was feeling to shed that label had taken over my nervous system.

In late August 2018, I had been fired from the hedge fund I worked for after a brutal first half of the year in which every investment idea I had turned out to be wrong.

Heather reached for the handouts on her desk that were intended to guide today’s session, but her hand paused, hovered above the pages, and fell back to her lap. She sighed and leaned backward in her chair, not so much out of frustration but capitulation.

“So why did you decide to go into finance to begin with?” she asked in a let’s-start-from-scratch tone.

My eyes widened slightly, reflecting surprise at such a rudimentary question, then shifted to my lap in search of a response. My mind flashed back to being a senior in college, fifteen years prior, when I had accepted my first job in investment banking. What surfaced were fragments of memories from the recruiting process:

• Reading the job description “building excel models” to my dad, a seasoned pension fund manager, and hearing his sincerely enthusiastic response (“That’s my kind of fun!”).

• The interview, in which a 29-year-old vice president put me on the spot with a brain-teaser: “A bunch of cubes are placed together to form a larger cube with the dimensions 10 cubes x 10 cubes x 10 cubes. How many cubes have no face on the outside of the larger cube?” (Confession: I flubbed it. My boss later told me, “You did the least bad.”)

• The elation of hearing the words “we’d like to make you an offer” when I took his call from the front porch of my off-campus rental house.

The silence extended as I crossed off each of these anecdotes in my mind, realizing them to be downstream of an answer to Heather’s question. She was asking for the why—why did I choose this—but all I could recall was the what of it.

“I’m not sure,” I mumbled as I shifted in my seat. “I was in undergraduate business school. I was a finance major. I remember someone telling me the best jobs are in investment banking”.

Heather nodded her head, eyes narrowing, unsure how to respond. She didn’t realize it, but she had just handed me the red pill. More like shoved it down my throat.

There aren’t many redeeming qualities to my experience of intense psychological suffering, but one of them is that it makes me incapable of bullshit. It’s like my mind is too broken down to maintain the narratives of my ego. Heather’s question was fundamental. I had answered some variation of it dozens of times throughout my adult life, probably starting with that interview process my senior year in college. But the timing of it at that moment—a moment in which all my sacred beliefs about myself had disintegrated into chaos—was revelatory. I have no idea why I’ve been doing any of the things that have been consuming my life. And I never have.

As I rode the subway home, staring blankly at the floor in front of me, holding the chrome support bar as the train wobbled its way south toward the West Village, I noticed that the anxiety that had been compressing my lungs for the past year had eased just a bit. And I chortled. The involuntary sound of a drowning man the moment his flailing legs touch bottom, realizing the water he’s been thrashing in is only chest deep.

The next morning, I opened a Word document, saved it as "Life Journal”, and began a practice that I continue to this day of emptying my thoughts onto the page for 30 minutes. The internal chain of realizations that unfolded from the time I left the therapist’s chair that day to my first journal entry went like this:

For the entirety of my career, I have never been motivated by anything resembling genuine interest.

I’m mostly just terrified (of what I’m not sure) and have been perpetually imitating people within my orbit that seem to have their shit together.

Straining desperately to salvage a career that’s the product of fear and imitation is absurd.

Living an absurd existence probably means dying with regret.

Dying with regret is probably the only thing worth fearing (despite every nerve in my body screaming that unemployment is infinitely more terrifying).

Stop looking for a job and figure out what I really want to do so I don’t die with regret.

Start journaling as a tool to help me figure out what to do.

Makes sense, right? Logical. Insightful. Well that was four years ago. Had I known it would take this long, I probably would have kept up the job search. Buried within these pages—now numbering in the thousands—is the coaxing-into-existence of half a dozen creative projects, side-hustles and business ideas, some of which have flamed out, others still works in progress. But none have advanced to the point of providing a living wage.  

“I want to develop a meditation retreat concept!”

“I want to start a jiu-jitsu gym!”

“I want to be a health coach!”

“I want to be a stand-up comedian!”

“I want to invest in small businesses!”

The fact that a sustainable vocation remains elusive has, at times, been frustrating. Not due to financial pressure—I’m well aware of the irony that this whole project of reinvention is being paid for by the version of me I’m trying to leave behind—but because I feel enduring insecurity from not yet having found entrepreneurial success in a culture that equates work with self-worth.

There’s an aphorism I came across early in this journey that I find soothing: The only difference between entrepreneurship and unemployment is your mindset. But the anxiety of not having an automatic, confident response to the question “What do you do for work?” still reverberates throughout my body every time I walk into a social environment. To be clear, in the five years since losing that job, my career anxiety has dampened from a five-alarm fire to a steady background hum, like tinnitus, but felt in the chest not heard in the ear. I interpret this gradual lessening of discomfort as the slow callousing of a mind that’s been constantly gripping the reality of an uncertain future. It has always been true that I have no idea what my life will look like in five years, but that truth was much easier to ignore with my name resting comfortably beneath the logo of a multi-trillion-dollar asset manager on a business card.

A few months ago it occurred to me—while journaling, of course—that my motivation for continuing the journaling practice has evolved with time. Instead of earnestly pursuing the singular goal of deciding on a new career path, my motives are more multi-faceted. For starters, I now just enjoy the experience of sitting at my desk with a cup of coffee, filtering inchoate mental chatter and imagery into comprehensible, linear thought with movements of a pen. It’s fun. Second, the need to answer the question “What do I want my career to look like?”, though still prevalent, is underscored by a deeper fascination—perhaps an obsession—with the question “What does it mean to live well?” And for that, I’m starting to realize, 30 minutes stream-of-consciousness is no longer satisfying. I need to linger on an idea for days—or months in the case of this first essay, my attempt at explaining why I’m starting a newsletter—to work it out.    

I realize that’s kind of a heady, post-hoc analysis of why I decided to send you this essay. Admittedly, it’s not the whole story. If all I was looking to do was develop and clarify a worldview, I could do that work on my laptop and keep it there. Why seek an audience? I’ve ruminated on that question for more hours than I care to admit, and here’s what I’ve come up with:

• To get feedback on my ideas in order to refine my thinking (i.e., to grow)

• To connect with people who, like me, grapple with the big “meaning of life” questions using a form of expression that’s sufficiently nuanced (i.e., to be seen)

• To create an accountability function (i.e., to combat my inherent laziness)

• To test my hypothesis that [cringe] I have talent (i.e., my mind has reconstituted its capacity for bullshit)

I know all these reasons are real for me; their relative weightings unclear. But as I’ve perseverated for weeks on this question of why I want to write and share my writing, I’ve recognized that the above answers are tangential to something more fundamental: The people I’ve come to admire most are writers. And this is what writers do.

[chortle]

In a lot of ways, it feels like I’m back on the subway coming home from therapy, waking up to the way in which imitation dictates my desires. But something feels different. I’m ok with it now. Maybe I’ve just been asking why-questions long enough that I’m gassed out. Or maybe my admiration for writers comes from a healthy need to express myself creatively while my admiration for financiers came from a destabilizing status-obsession. Either way…

“I want to start a newsletter!”

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