On the long road of becoming who you are

Vocation, doubt, and the courage to not know

Author’s note: Ahead of the release of my book, I’m trying something new and sharing some personal writing with the Article Book Club. If you haven’t ordered a copy of How to Not Know, now’s a great time to do so :)

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On the long road of becoming who you are

I’ve known I wanted to be a writer since the second grade. My brother and I went to different schools. One day, he didn’t have school, and my parents offered to let me play hooky so we could hang out.

“My class has a writer’s workshop today,” I told them. “And I’m not missing that!”

Through high school, writing was my main academic interest. I started doing spoken word poetry, and chose to attend Penn, at least in part, because it had won the collegiate national poetry slam the previous year.

But in college, I started to lose sight of the clarity I’d had about writing when I was younger. I started to see friends with varied, quirky interests contort themselves to the interests of the investment banks and consultancies that came to campus to recruit. Looking back, it wasn’t just the money that drew my friends to finance and consulting. It was the certainty.

Finance and consulting each provided clearly lit paths, from intern to analyst to associate to manager to director. Much like school, they offered benchmarks for success and validation for drawing within the lines.

Rather than pursuing uncertain paths in, say, the arts or entrepreneurship, many of my peers opted for the least uncertain route. And after I started hearing about friends who landed prestigious internships at McKinsey and Goldman Sachs, I started to feel anxious about my own career prospects.

I’m reminded of this Paul Graham quote about prestige. He writes that, “Prestige is like a powerful magnet that warps even your beliefs about what you enjoy. It causes you to work not on what you like, but what you’d like to like.” I knew that I loved creative writing, but I wanted the legibility of my peers’ path. So, I decided to study both poetry and economics (hello existential crisis!).

When it came time to look for my first internship, I couldn’t admit to myself what I actually wanted—to be a writer—so I looked for jobs in advertising and tech. After I graduated, the pull toward certainty continued to warp my tastes. I remember one conversation I had with Sam Parr, who was in the early days of starting a media company called The Hustle. We sat in his office, and he asked me point-blank, “So, you studied poetry and econ. I can’t tell: do you want to write or work on the business?”

I let my brain override my heart. “I want to work on the business,” I told him. Maybe Sam could sense the shakiness of my conviction. I didn’t get the job.

The evolution

A job is not a vocation

Elizabeth Gilbert has a great framework about the difference between a hobby, a job, a career, and a vocation. A hobby is something that you do for yourself. A job is something you do to earn a living. A career is a story you build over time, and a vocation is an almost-spiritual calling. The only thing you need is a job, she says. We live in a material world, and you must find a way to pay for your material existence.

But I was one of the lucky few who had a vocation. I just couldn’t admit it. The mental gymnastics I did to talk myself out of what I deeply wanted were remarkable. I chalked it up to realism or being “financially responsible,” but it was just fear dressed in sensible clothing.

Even after I went back to journalism school to get a degree, I still couldn’t admit my desire to myself. It came to a head when I was 27. I was at a career crossroads, deciding between two job offers: one at a trendy magazine and another at a prestigious design firm. The decision threw me for an existential loop. I spent weeks waffling back and forth. I asked the opinion of everyone I knew—and my Uber driver and my yoga teacher. I was insufferable.

Looking back, almost a decade later, I can now pinpoint the source of my ennui: I was looking for certainty where none existed. I deluded myself into thinking there was one right answer, one perfect job that would emerge if I just banged my head against the wall at the right angle. But the truth was, I was so uncomfortable with facing uncertainty that I would rather self-sabotage than make a choice for myself. I secretly wished one of the offers would be revoked, just so I didn’t have to decide.

Maybe you’ve felt something similar—a civil war being waged between different parts of yourself. One reason I believe so many young people in the 2000s and 2010s opted for careers in finance, law, consulting, and medicine is that legible ladders allow you to kick the can on having to reckon with what you actually value. You value what the firm values, which is much easier than having to determine what you value for yourself.

In retrospect, I’m grateful for my quarter-life crisis for the lesson it taught me. In the words of psychologist Rollo May, "Commitment is healthiest when it is not without doubt, but in spite of doubt.” Uncertain moments strengthen our values by forcing us to make choices without knowing how they’ll turn out. Rather than trying to rid our lives and careers of uncertainty, we must learn to live with it.

I think this skill—call it uncertainty tolerance—is going to be more and more important as career ladders and “stable” institutions break down before our eyes. The things about me that I thought were flawed—my inability to hold down a job for more than a few years, my desire to pursue multiple distinct careers, my meandering path—might all become advantageous in a world where nonlinear careers are the norm. I’ve built my tolerance through exposure.

Much like someone with a phobia of spiders can become more tolerant by gradual exposure in controlled environments, we too can become more tolerant of uncertainty by choosing to face it directly. Now, when I think about the uncertainty ahead of me—while trying to support a family as a full-time author in one of the most expensive cities in the world—I think back to past times in my life where I’ve been able to weather the anxiety of not knowing. I’ve chosen to take what my friend Paul Millerd calls “the pathless path.”

I don’t think there’s anything inherently virtuous about approaching your career this way. But I believe those who are able to build their uncertainty tolerance—to see the possibilities that wait on the other side of not knowing—have a leg up in the increasingly uncertain world in which we live.

Next week, my second book, How to Not Know, comes out. I wrote it for that 20-something version of myself, hellbent on finding certainty, worried what he might find if he admitted what he actually wanted. Even now, 28 years after my second-grade writer’s workshop and after having written two books, I sometimes still doubt my desire to be a writer and question how much longer I can keep up the charade.

But I’ve come to learn that on the pathless path, not knowing is a feature, not a bug. Uncertainty is where the magic lies.

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Thank you for reading! If you enjoyed these words and want to build your uncertainty tolerance, please consider ordering a copy of How to Not Know. Publishers Weekly, The Next Big Idea Club, and Adam Grant each named it a best book of the year.

You can order from Bookshop.org, Amazon, or get a signed/personalized copy from my local indie bookstore.

Warmly,
Simo

P.S. The song of the week is a thematically relevant classic from Faces. The full songs of the week playlist is here.