Dealing with Doubt on the Pathless Path

Last month, I quit my job at IDEO, a job I loved for nearly four years. I had known I was going to leave for months. I drafted the company-wide goodbye email weeks before my last day. But the second I hit send, I felt a pang of doubt. 

Had I made the wrong choice? Should I have stayed six more months to vie for my next promotion? Who leaves a good job with nothing lined up on the other side?

I’ve heard these voices before. Truth is, I’ve always been a doubter. Whether it’s a life decision or sandwich order, I often have to unpack some combination of buyer’s remorse, Jewish guilt, and millennial fomo before I develop the nerve to make up my mind. 

In the weeks since I left full-time employment, I’ve interrogated the source of those voices in my head: why is it so difficult to break from standard ways of working? Sure, there are logistical barriers, such as figuring out healthcare and retirement savings, but I’ve found the gnarliest obstacles have been psychological.

In a now famous commencement speech, Yale English Professor William Deresiewicz observed how many of his students were “world-class hoop jumpers.” They had been trained to achieve any goal set out for them. They could memorize any formula, ace any test, and “climb the greasy pole of whatever hierarchy they decide to attach themselves to.” As one of Deresiewicz’s students put it, Yale students were “excellent sheep.”

I, too, am an excellent sheep. For the majority of my life, my sense of purpose extended only as far as the next hoop set out for me—whether that be getting into college, landing a job, or grabbing the next rung of the career ladder. Underneath my achievements, though, lie a few prominent fears. 

My first fear is that if I don’t get ahead, I’ll somehow fall behind. On one hand, I see how this is somewhat irrational. I have a combination of privilege and resume virtues, which means even if things were to go terribly wrong, my floor is still relatively high. 

And yet as a millennial, I’ve also been raised on a cocktail of workism, economic precarity, and hustle culture. It’s a strange milieu that inspires both risk-seeking (“Jump on the rocket ship!”) and risk aversion (“Recession is coming!”). I’ve had a front-row seat to the systemic forces that have rattled the careers of many in my generation, and yet still believe my success is up to me.

I recently interviewed an older millennial journalist who has won a Pulitzer Prize and worked as the top editor of some of the world's most prestigious publications. She told me it wasn’t until recently—more than 15 years into her award-winning career—that she truly believed she’d be able to get another job if she were to lose her current one. Leaving a job is scary when you’re not sure when the next one will come 

My second fear is that if I don’t have a job, I’ll somehow be less loved. Having a job provides an enormous social utility. Our jobs are like enamel pins we can choose to wear when convenient. They help at cocktail parties and Thanksgiving dinners, on social media and first dates. Leaving full-time employment means losing an easy answer to “What do you do?” 

I know that my loved ones don’t love me because of my job (and if they did I could probably use some new loved ones), but I still have a fear that without an employer beside my name, they’ll somehow think less of me, irrational as it may be. 

When you leave a job, you also leave a community. I’ll be the first to say that your colleagues aren’t your family, but they are people who know and validate you. They’re people with whom to banter and ask out to lunch. It’s scary not to have a consistent group of people to depend on who depend on me. 

My last fear is the most personal: I’m scared that by losing my job I’ll somehow lose part of myself. There’s some irony in that I’ve literally written a book on the dangers of conflating who we are with what we do. And yet, even more than the judgment from others, I’m afraid of the judgment from myself.

A job can be a sort of existential balm. For my entire career, jobs have given me a purpose, a steady paycheck, and a structure for my days. Now, as I try my hand as a self-employed person, I’ll no longer have an employer to distract me from myself.  

The conventional tips for overcoming entrepreneurial self-doubt—Reflect on your progress! Don’t worry about what others think! Surround yourself with believers!—are falling on deaf ears at the moment. Trying to ease my existential angst with a gratitude practice feels like trying to shield myself from the sun with a cocktail umbrella. 

Truth is, going out on your own is scary. There aren’t two ways around it. But, I think that’s the point. When there isn’t a performance review to define what success looks like, a boss to tell you what to work on, or a company to tell you who you are, you have to figure those things out for yourself. 

So far on this pathless path, the thing that’s helped me the most is faith. Faith might not be as concrete as ruthlessly budgeting or starting a freelancer support group. But if the greatest challenges on this path are, in fact, psychological, perhaps spiritual antidotes offer the most potent salves.

I like Martin Luther King’s definition of faith: faith means taking the first step even when you can’t see the whole staircase. I have faith in myself, and I have faith in this experiment. On the days when I’ve felt down, I’ve tried to remember that. 

In the words of psychologist Rollo May, “Commitment is healthiest when it is not without doubt, but in spite of doubt.” I’m standing on the first stair. I’m scared and excited to keep going.

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If you liked this piece, you should order Simone's book, The Good Enough Job, and follow him on Twitter.

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The cover art for this piece was created by Midjourney with the prompt: "a man dealing with doubt on the pathless path"