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.