From Clueless to Entrepreneur: Finding Deeper Motivation

The Work Series // Deep Fix №15

Jul 30, 2021

Deep Fix is a newsletter by Alex Olshonsky exploring mental and spiritual health, addiction, work, and philosophy. Thanks for being here. If you were forwarded this email, get your own:

When Substack launched a few years ago and made it easy for a noob like me to start a newsletter, I figured I had nothing to lose. I thought of myself as a writer, but I could list on one hand those who had read more than a hundred words I’d written—

College professors (bro, existentialism is so deep!), ex-girlfriends (forgive me?), tech clients (I Want You to Like Me and Pay Me), HR departments (I’d like to formally submit my resignation), and my dear friend Erica—who read a draft of the memoir I was working on in 2017. I was still in early recovery. While she read, I cowered in the corner in fear of what she would think.

It didn’t take long for this newsletter to become one of the most exciting things in my life. My first year, I had only a tiny sliver of the four-digit readership Deep Fix has now. It mattered not—I was having fun!

I spent far too much time perfectionating, and begging my most literary friends to edit my words late on Thursday nights. Still, it felt good to care about the quality of something. The soul-labor I poured into the newsletter provided a stark contrast from how I felt about the value of my tech work.

I’m hesitant to write this next sentence because its intrinsic air of douchiness, but such is the occasional risk and cost of honesty: today I am living the life I fantasized about and worked towards for the past six years.

I get paid to help people as a coach. At the same time, I am pursuing my writing career—the dream my daimon has been nudging me towards since I was a young, reckless buck. A vibrant community is forming around the newsletter with shared interest in depth and the ancient art of conversation.

If it weren’t for the heartfelt emails I received from my early newsletter readers, my transition to entrepreneurship would have never been possible. So first and foremost, thank you for reading my introspective musings, joining the community, and coming along for the ride.

As someone who was previously trapped in a startup and corporate mentality—feeling like I was unable to escape the Fat Paycheck and Juicy Benefits Penitentiary as I re-stacked piles of sand in Microsoft Office—I’d like to offer some further perspective on how I made it here.

New interests > wanting to escape a shitty job

When I became serious about my recovery from drinking and doping, my interest in mental health became more than just an interest—it became an obsession. The same is true of writing.

Sitting in meetings at VentureBeat about ethical A.I. and the metaverse—topics understandably engrossing to many—I realized I was no longer excited by tech. Part of me mourned what this meant for the identity I spent twelve years cultivating in the Valley. I was enjoying far more my studies in psychology, hosting men’s groups, attending retreats, and writing newsletters.

All the badges and tinsel I had accumulated on my LinkedIn profile would mean nothing if I kept heading in this direction …

Work can be mundane and boring. That doesn’t mean we need to quit our jobs immediately and attempt to become TikTok influencers. Pragmatism is ever crucial.

So often people hate their jobs, but they don’t know what else they’d rather be doing. In my case, my job wasn’t the problem. It was me. One of the clearest signals that I needed to find a way to transition into working for myself was the undeniable evidence that my interests lay in other fields.

It took time to cultivate my interests. It took even more time to figure out “what to do” about them.

Finding mentors doing the things you want to be doing

Most people work for bigger companies, which makes a potential transition into entrepreneurship (or towards a work-free space of personal exploration) feel scary, unattainable, unrealistic.

Moreover, there’s a swath of people—like my former self—who know they don’t love their jobs but have no idea about what a realistic financial path looks like to do something else more meaningful.

So, I started seeking people who were doing things in the world I aspired to be doing. For me, this was finding established writers, podcasters, coaches, and community builders.

James Clear @JamesClear

One of the only true shortcuts in life is finding an expert and apprenticing under them.

I began reaching out to some of my greatest influences. I always tried to offer some value or a deep personal reflection, and my hope was to build a relationship. In many of these cases, I mentioned I was willing to pay for their time in the form of coaching or mentorship. That way, when I reached out, I wasn’t just some unaware schmuck treating the relationship as a take without any give. The give-and-take dynamics are important to honor, especially early on in this type of dynamic.

Throughout recovery, I had done years of therapy, attended support groups, Twelve Step meetings, and more. But I did not elevate to my “next level” until I started working with mentors and coaches who inspired me.

Finding a creative outlet and not waiting until “someday”

Technically, I’m only three and a half months into my entrepreneurial journey. While that might sound wildly premature to write this essay, my transition had been a long time coming.

I’ve been writing weekly newsletters since 2018. I’ve been building my business and community for the last two years, training in yoga and somatic psychotherapy during PTO and on the weekends.

My last day at VentureBeat—during Zoom Covid—was literally the most uneventful thing you could imagine. Leaving felt incredibly natural.

My transition wasn’t a shift into blank space with no idea of how I wanted to spend my time. Or—going to backpack around South East Asia hoping to find enlightenment and pick up a few followers on the ‘gram while slowly cratering towards existential crisis. We’ve all seen sad stories like that, where after quitting a job and traveling, an earnest human is only more lost than when they announced their big decision on social media.

There were many moments these last two years when the balance of two full-time jobs drove me to the brink of burnout, when I wanted to quit my salaried job prematurely. But I’m glad I took my time. Setting the intention—knowing the arc of my life and my work was headed in a direction that aligned with my values—was enough to keep me going.

I benefited from honing my interests and skills over the course of several years, so that when my last day at VentureBeat came, it just felt obvious. Even if you have the financial freedom to quit a job without a “plan,” it makes sense to start dabbling today with new ways to express whatever might be brewing inside you.

Capitalism and Psychedelics

My relationship with money is complex and evolving. I started with little, hustled my way into some (that only provided harmful validation for a destructive lifestyle), spent it all, went into debt, and then over the course of the six years of my recovery, rebuilt it all.

Money comes and goes. I spent the year leading up to my career evolution reflecting on what money means to me. I literally meditated on it—even sitting in ayahuasca ceremonies—feeling into what it would be like to forgo my bi-weekly paycheck. Would the essence of me change? Would I freak out after looking at my bank account a few months in, fearing I made the wrong decision? Would the money-stress trigger my achievement-oriented, holocaust PTSD Jewish lineage? Would I descend into fearful neurosis, repeating the same psychological patterns I’m working so hard to break?

For psychedelic journeys, renegade Harvard professor Timothy Leary talked about the importance of set (your mindset going into a trip) and setting (how comfortable and safe your journeying location is).

In the psychedelic trip that is modern existence, it’s helpful to think of capitalism in similar terms of set and setting.

We are conditioned to want to earn more money than our neighbors. This desire is infused in our consciousness. Our entire physical world reflects capitalism, with stark markers of income inequality visible all around us. And now, for millennials, there’s “performative wealth”—in the form of a “wealth of experiences” displayed on social media.

Even if you’re a self-described neo-Marxist, decoupling capitalism’s impact from your consciousness is not so simple. Some economists and philosophers argue that, in fact, it’s impossible, which is perhaps one reason why so many people don’t ever leave the safety of their jobs.

My contemplation on the capitalist mindset allowed me to recognize that I was not the type of person who could just take the plunge into entrepreneurship without having some evidence it was a good idea. For me, that evidence was the heartfelt letters I received from readers around the world. And it was the fact that people were willing to pay me for my input helping them build their startups, break addictions, or reconnect with a deeper purpose. I created a situation where I had safety of the right setting to make my transition.

More profoundly, I also had evidence that relentlessly pursuing money without a deeper sense of meaning leads to darkness—a never-ending “bad trip.” (Read last week’s piece in my “Addiction Series” for a harsher description of this ; )

Boomers, doomers, and death: Remembering the why

Boomers told us we could be anyone and do anything—and that we’d have more wealth than they did. We know how that promise now meets the most indebted generation in history.

I constantly reminded myself that the reason I was making my transition was not about money. It was about something deeper inside of me that needed to be expressed. Perhaps, I hope, to help people.

Honestly, Covid helped. The global pandemic was the nail in the coffin for my tech career. Our world has too many existential issues to list. I’m not one of these Steven Pinker, or New Age conspiracists who believe that we are heading towards spiritual transcendence!

No. I believe we have a broken culture that mass-produces depressed, anxiety-ridden, addictive, suicidal, and obese people wholly disconnected from nature. If we do not change this radically and quickly, I worry about the world my grandchildren might inherit.

So, if it helps to hear …

Not everyone can—or wants to—quit their jobs. But most people have some wiggle room to experiment in. This space is where agency, freedom, and creativity go to play. When people explore their creative instincts, everyone benefits. Perhaps we even have an individual and collective duty to do so—with a healthy degree of urgency.

As overlooked philosophers like Ernest Becker remind us in his seminal work The Denial of Death, we will all eventually die. We spend our entire lives pretending this is not the case, spinning our wheels in the rat race, distracting ourselves from the “worm at the core” of our existence. Moreover, we forget that we, too, are ancestors of future generations. What sort of elders do we want to be?

Jason Snyder @cognazor

If you're not a doomer, you don't have a head. If you're not a doomer optimist, you don't have a soul

It’s worth it

What I can report thus far is that taking the plunge into entrepreneurship is worth it. That’s the whole point, right? To design a life that cultivates a more joyous and fulfilled state of being, allowing us to deepen our appreciation of—and contribution to—the sum of beauty in the world.

Something else I can’t get out of my mind: There’s one thing that all the greatest writers, entrepreneurs, actors, and scientists share in common …

They submitted their work.

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