My Path to Entrepreneurship: Leaving “Follow Your Passion” Bullsh*t for Curiosities
Deep Fix №3
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:
Is this just a phase? I asked my therapist.
What do you mean by phase? she responded.
As in, I seem to be really into all this spiritual stuff. You know, meditation, yoga, even 12 Step work...
What’s wrong with that?
Nothing. I just thought my interest would have waned by now. It’s been a year of recovery work non-stop, and I don’t seem to be slowing down.
Phases certainly happen, Al. But, like we’ve talked about, you’re past the pink cloud stage of recovery, where everything is bright and new.
No, this doesn’t feel like the pink cloud.
What does it feel like, then?
It feels like I’m more interested in all of this than anything else in my life! And I don’t even know what it is, or what to fucking call it! Maybe growth, or psychology? Recovery?! Ugh.
And, I guess what I’m saying is—what does it all imply? It’s not like I’m gonna quit my job and do this full-time!
Well. What if this is not just a phase, Al? she asked with twinkling eyes and a knowing gaze.
What am I going to do, go sell essential oils in Bali? Ha!
I’ll never forget that moment four years ago, sitting in her office in San Francisco, her eyes clearly seeing something in me that I was not yet ready to own. The identity I slaved to maintain throughout my life was beginning to dissolve. All the things I thought I wanted—a big-time tech career, pretty wife and the picket fence, tinsel atop my Chrismukkah tree—lost their luster.
I was unraveling towards a set of interests and desires not defined by others, but by what the ancient Greeks called the Daimon—a voice inside all of us that drives us towards fulfilling our soul’s purpose. My Daimon was sweetly whispering into my ear, telling me to keep following the scent of my budding obsession with psychology and consciousness. Yet, I faced a mountain of internal resistance, afraid of becoming just another tech-disillusioned “wounded healer” trope.
The scene with my therapist has been playing back vividly for me this week. After five incredible years at VentureBeat—the first “sober” job I’ve had from start to finish—Thursday marked my last official day.
I’m doing precisely what my younger self couldn’t even imagine: quitting my tech job and going all in on the things I’m in love with: writing, working with curious humans as a coach, and creating. But more than anything, it feels as if I’m going all in on being a student again. Perhaps for the first time in my life.
My transition to becoming a solopreneur (yes, apparently this is a term now) is a big one. I’m leaving behind the comforts of bi-weekly cash infusions, FTE benefits, a known career path, yada, yada. It’s also a transition that feels undeniably natural. I’ve been building and planning for this moment over the last two years.
Quitting a job to “follow your passion” is an appealing, yet illusory Millennial Dream. In many ways, my journey simultaneously embraces and rejects all of this Modern Manifest Destiny Mythology. (To read more on how millennials have been sold an obsession with WORK stemming back to the Puritan days, read my essayThe Religion of Work).
Despite the internet being filled with unsolicited advice, I’d like to offer perspective on how I landed here. Not to say I have it figured out. Or that I will be successful at this transition—talk to me in a year, my friend.
Perhaps I only have a perspective to lend because I’ve made more mistakes than most. Not small mistakes, either, like some Stanford MBA quitting his job at Google upon realizing his true passion was to build a ML-enabled customer analytics startup. No. My mistakes were the costly, self-destructive, privilege-adjacent, blundering-idiot type.
Here’s what I’ve learned.
The Startup Myth
I was young, ambitious, and surrounded by all the access afforded in Silicon Valley. For years, I wondered, where’s my big startup idea? Where’s my breakthrough technology that will land me a seed announcement article on TechCrunch—or VentureBeat?
Ideating from “the top” is a challenging proposition. I thought, I want to have the next paradigm-shifting idea. I want to start a company! It felt like the natural thing to do. My friends were founding companies, unicorns were being birthed all around me, and venture money was flowing. I had been swept by Silicon Valley’s startup myth. (Note: “myth” does not mean untrue. Myths always carry truth).
What I did not realize: the mere desire to birth a company is not enough, and does not mean you know how to provide a product or service that is truly valuable for users. Solving from “the top” might work for some, but generally speaking, most successful companies start at the bottom. Founders use their expertise or passion around a specific problem, and build upon it.
As in my case, when you’re not even on stable footing as an individual, searching the clouds for a big idea only further compounds a lack of existential alignment. You lose sight of crucial questions—like why am I doing this, and whom am I serving?—necessary to unearth your underlying motivation.
Mimetic Theory, “Follow Your Passion” Bullshit, and Curiosities
Becoming clear about underlying motivation is impossibly difficult. René Girad’s mimetic theory—which teaches us that humans instinctively and unavoidably copy others from birth—has become so popular on “trad Twitter”and red pill newsletters, it’s almost getting old.
The silver lining is that folks are finally recognizing how much of their lives are already pre-programmed for them. The advertising industry spends billions of dollars attempting to subvert your very basic hominid desires into bold, abstract, material dreams.
Go into a WeWork or peruse any beachside boardwalk, and you’ll find signs and T-shirts that say Follow Your Passion. For millennials, work is no longer just a job: it’s supposed to be our calling—a singular purpose in which failure equates to a wasted life.
“Follow your passion” sounds great in theory. But how the fuck do you make money from your passion? And what if you don’t even know what your passions are?
I’m a (major) advocate for what Elizabeth Gilbert—author of Big Magic and Eat, Pray, Love—calls following your curiosity. Curiosities are subtle. They might stem from interests in things that feel basic, silly, or mundane. These quiet whispers from the Daimon can be cultivated and explored without the risk of failure. Over time, curiosities can become passions. And then, maybe, someday, they become “callings.”
Still, we need a new vocabulary for how we talk about work. “Passion” is so overused, it’s almost become a dirty word. “Calling” is equally elusive, sometimes even belittling. My preference is the suaver vocation:
“A strong feeling of suitability for a particular career or occupation.”
Sounds like a more realistic goal, no? In a sense, my very first step towards finding the vocation I’ve landed today was letting go of the Millennial “Do What You Love” Dream. I made a conscious decision to stop worrying about whether my curiosities would earn income. It wasn’t clear or easy; it created inner turmoil. I had to remind myself, over and over again, that what I was doing was deeper than my hard-wired conditioning around money.
Reject the Paradigm: Inner work and #VanLife
I had been told that I was supposed to found a company or climb a career ladder of sequential acronyms (eg. VP, SVP, MD, and CEO). It wasn’t until I rescued my head from the clouds and began exploring the infinite expanse of my internal world that things began to shift for me. In order to subvert my mimetic desires and discover what I truly wanted outside of my tech career ladder, I had to do loads of this “inner work.”
Most critically, I invested in working with professionals: licensed therapists, healers with years of experience, and groups led by skilled practitioners. (Inner work should not mean “on your own.” Be wary of any ableist social media influencer who tells you otherwise. And if you cannot afford therapy or coaching, there are numerous free support groups.)
These teachers granted me permission to explore my curiosities without judgment of how they might impact my career. I learned how to distinguish my Daimon’s whispers from fearful mind viruses imposed by a reductionist society. After all, the Daimon is an intelligence churning inside us that knows our destiny better than anyone else. And to my surprise, I discovered that my love for inner work was more than a curiosity. It eventually became obvious that I wanted to guide individuals and businesses through it myself.
“Doing the work” is not the only way to reject the paradigm and get closer to your Daimon. Sometimes, the simplest thing to do is take the most direct path possible. For instance, when I wanted to “be a writer,” I committed to publishing a weekly newsletter on Substack (because it was the easiest platform to get started on). When I wanted to plunge deeper down the ancient yogic well, I signed myself up for a teacher training (with no idea what I’d “do with it”). And so on.
Rock climbers are an excellent example of those who throw a middle finger up to the paradigm and pursue what excites them. With the growing popularity of #VanLife, climbers have essentially re-branded homelessness into something affordable, empowering, and ‘gramable. Climbers design a life in which they are constantly surrounded by the thing they are most suited for: nature. Thus, a thriving community has formed around #VanLife with others who share a “passion” for taking the most direct route possible to the mountains.
Embrace the Paradigm!
One must be practical. There are many paths to the mountain top. Some quit everything and go travel the world before achieving their breakthrough moment in a hut in Nepal. My path was the classic work a “9-5” and tackle the side project at night.
I hustled in this way for five years—by day a VP of Sales in Silicon Valley, and by night a CEO of Inner Exploration. I spent my PTO on retreats to the Amazon jungle and ranches scattered across California. At times, it felt like I was living a double-life—but this time, the healthy, non-addicted type.
(Also, worth noting: I now ironically understand how all of my “spiritual” and personal development work has made me far more valuable in the business world than ever before. All business, relationships, and even PPT presentations are spiritual.)
I did not scorn my day job. It put food, health insurance, branded fidget spinners, and vacations on my proverbial table—all worth something profound on top of a base salary. I had to remind myself (and may I remind you, sweet reader…) that we do not yet live in a post-work gift economy. Before deciding to leave my job this week, I did what we in the Valley call proving “Product-Market Fit.” I built my “side hustle” into a business that earns enough to cover my living expenses.
Derive Meaning From Each Moment
If I’ve learned anything, it’s that the entrepreneurial journey is not about accomplishing your wildest dreams. It’s about becoming the type of person who has curiosities. Whether we call them Daimon whispers or not does not matter. What matters is that we simply possess the courage to follow them. Just as Arjuna is instructed in the Bhagavad Gita, we must pick up the sword and go into battle—without concern for the outcome.
To keep waxing on this, it’s about embracing a life so drenched in meaning, nothing’s ever left undone. The ultimate mode of being is surrendering to life just as it is. To be entirely engaged in our metamodern world in 2021, yet completely unattached to it. To understand we are starlight dressed as matter, yet also be able to laugh at the messiness of our human selves.
As for me, I’m chuckling at the absurdity of the entire journey. Laughing at myself, wondering if I’m the caricature selling essential oils I suspected I might someday become.
Community + Worthwhile Elsewhere
🌎 Community Dialogue. We are meeting next Wednesday to discuss “gender in today’s world”—a big and important topic. I expect to learn a ton from our community on this one. All voices and ears welcome. Click here to add the invite to your calendar.
🤔 The Psychological Risks of Meditation. This Harper’s article is making a huge splash, shared by many writers with massive platforms (Tim Ferris, Mark Manson, etc.). From my conversations with meditation teachers, the article misses the fact that most legitimate teachers or retreat hosts are trained to handle psychological breakdowns, which yes, do happen on retreats. That said, it’s important to understand all aspects—good and bad—of any practice. But let’s not forget that sitting alone in silence in today’s world is perhaps the most radical thing one can do. We need more, not less of it.
✝️. The Pope vs. Lulu? “Other brands, as well as religions, lean on our insecurities to get us to participate in community building.” A witty essay comparing Lululemon’s marketing during the pandemic and the Catholic Church. Jared Holst’s newsletter Brands Mean a Lot is my new favorite discovery. Subscribe here.
Thanks for reading, my friend.
A major reason why I’m transitioning into working for myself is to create more space and time to write you these emails (and finish my book!).
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There are infinite options for content consumption vying for your attention. Enormous gratitude for spending a slice of your Fridays with me.
Until next week …