On one hand, I see how this is somewhat irrational. My first fear is that if I don’t get ahead, I’ll somehow fall behind. Underneath my achievements, though, lie a few prominent fears. 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. 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.” 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. 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. 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. 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? But the second I hit send, I felt a pang of doubt. I drafted the company-wide goodbye email weeks before my last day. I had known I was going to leave for months. ![]() ![]() ![]() Last month, I quit my job at IDEO, a job I loved for nearly four years.
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