In Praise of the Meandering Career

In the mid-2010s, two Harvard researchers conducted a study on what it takes to be successful. They were testing the assumption that success mainly comes from following a straight-forward career path that will inevitably lead to stable employment, social status, and financial security—what they coined the “standardization covenant.” (Think about the CS major to FAANG internship to developer to engineering manager pipeline in tech.)

The researchers, Todd Rose and Ogi Ogas, were interested in people who took a less conventional approach to life. They interviewed hundreds of high-achieving, wildly successful “dark horses”: people who swerved in and out of jobs—and often industries—to find a good fit. From symphony conductors to chess masters, Apple execs to dogsled mushers, every interviewee gave a version of the same disclaimer. “I can tell you about my career journey, but please don’t tell anyone to copy what I did,” they’d say. “My path isn’t replicable.” 

Rose and Ogas each eschewed nontraditional routes themselves. Rose was a high school dropout who took a meandering path, eventually becoming the director of the Mind, Brain, and Education program at Harvard. Ogas dropped out of four different colleges and struggled to hold down a full-time job before getting his Ph.D in computational neuroscience. (He also won $500,000 on Who Wants To Be a Millionaire?)

Their own experiences led them to wonder if there was “some essential quality” that idiosyncratic professionals shared—perhaps a fierce ambition, rebellious personality, socioeconomic background, or approach to education. Instead, the one common trait was one the researchers weren’t looking for: high degrees of fulfillment. Subjects talked about their purpose, passion, and engagement in their work. They spoke of finding their calling and living their dream. “As we dug deeper, we realized that their sense of fulfillment was not a coincidence. It was a choice,” Rose and Ogas explain. “This all-important decision to pursue fulfillment is what ultimately defines a dark horse.”

There’s a common misconception that our résumés ought to tell a linear story, free from breaks, twists, and turns. But this assumption is not borne out in reality. Nearly three out of every four college graduates work in a field unrelated to their major. The average worker holds over a dozen jobs by their fifties. And over half of today’s college students will work jobs that don’t yet exist. 

So I can’t help but wonder why, in an age where two-thirds of workers don’t feel engaged by their work, there isn’t more support for individuals forging their own way. Sure, there’s the Thiel Fellowship and a handful of grants that incentivize people to follow their curiosity, but by and large, we still live in a society that celebrates conformity and stigmatizes peoples whose paths are less legible to others. 

There’s a set of common retorts I hear when I urge people to approach their careers more experimentally. The most common: what about healthcare? What about my next promotion? What about my kids’ college fund? These are all valid concerns. By tying healthcare to paid employment, the United States makes it unreasonably difficult to take professional risks. Companies strategically place incentives to keep employees chasing carrots without ever feeling full. And taking professional risks is easier for those with fewer responsibilities. 

But for a second, I urge you to mute your inner skeptic and consider what might happen if more people had the confidence and ability to experiment with their careers. As Khe Hy, a former Wall Street banker who quit his finance job after his first daughter was born, said in my book, "Compared to the risk of an uncertain financial future, I realized the riskier thing was for my kid to watch their dad be checked out and do something just for money."