In Praise of the Meandering Career

Build a compass, not a map

Midjourney prompt/"meandering career"

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“It is absurd that I could achieve what I did in four weeks!” — Henry F., former student.

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.”

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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."

A nontraditional path might not be for everyone, but here are three reasons why it might work for you. 

Taking a nontraditional path will force you to grapple with what matters

The greatest benefit of a nontraditional path is that you have to figure out what you care about. Rather than an employer telling you what you should value, you have to do the hard work of determining what you value for yourself. This may sound self-evident, but in a world where the pressure to chase prestige, status, and money is ever present, it can be difficult to ask whether you are playing a career game you actually want to win

In the book about their research, Rose and Ogas open with the story of dark horse Jennie McCormick, who became an internationally respected astronomer despite never having graduated high school. By age 21 she was a single mother, working at a fast food joint to support herself and her son. Her astronomy journey started with a pair of binoculars, lent to her by a relative. She then spent decades doing “independent study” of the stars, driven solely by her fascination for the subject. She eventually became the first amateur to discover a new planet in over a century, among many other accomplishments. 

Jennie’s foray into astronomy wasn’t driven by recognition or accolades—for years, it was solely about her intrinsic motivation. When you’re not following the markers of a well-worn trail, it forces you to become acutely aware of your own internal compass. 

The traditional path is becoming less reliable

In the past few years, many workers on traditional paths faced a rude awakening: the seemingly secure paths they were on turned out not to be as stable as they thought. From layoffs to furloughs, office closures to the existential threat of AI, the tide of various industries rushed in, and many workers found that they were swimming naked. 

For millennials who had built their lives around their jobs, the pandemic hit particularly hard. “Millennials became the first generation to fully conceptualize themselves as walking college resumes,” Anne Helen Petersen writes in her book Can’t Even: How Millennials Became the Burnout Generation. “With assistance from our parents, society, and educators, we came to understand ourselves, consciously or not, as ‘human capital’: subjects to be optimized for better performance in the economy.” 

But when the economy takes a turn, the promise of a reliable, optimized career falls flat. As one former Twitter employee summed up for me recently, “I used to think that job was my dream. Now I see it was just a job.” 

The truth is that the careers of our grandparents’ generation no longer exist. With the pace of technological advancement, no single job or company can be relied upon to deliver lasting stability. The pillars of institutional excellence are eroding before our eyes, and those who know how to carve their own path already have a leg up.

Our career decisions are more reversible than we think

Humans suffer from what psychologists call the end of history illusion. We tend to understand that we’ve undergone significant personal growth and changes in taste to bring us to the present moment, but we discount the fact that we’ll change in the future. 

The end of history illusion is worth keeping in mind when it comes to our careers: we understand that a meandering path may have gotten us to where we are today, but discount the fact that our paths will likely continue to turn. Rather than cause worry, I believe the fact that our careers are less predictable than we might imagine ought to be a source of relief. 

Particularly when we’re at a professional crossroads, we white-knuckle our career decisions as if they are matters of life or death. But if the Dark Horse Project is any indication, we’d all benefit from lowering the stakes.

If we have chosen to zig when really we should have zagged, we often have the ability to course-correct. But more likely than not, our zags will open us to new possibilities that we never could have anticipated. 

If you are interested in pursuing a nontraditional path, I have two pieces of advice. First, listen to your curiosity. You don’t need a 10-year plan for your career. You don’t need to read a dozen biographies of founders, or reverse engineer successful people’s career paths on LinkedIn. Instead, how might you develop an acute sense of what turns you on? What do you find yourself reading about in the cracks of your day? What are the work tasks that other people find tedious that you enjoy? A strong internal compass is more useful than anyone else’s map.

Second, find the others. This phrase comes from Paul Millerd, who has built an entire community of people exploring nontraditional career paths. Part of the reason why there is still so much stigma around and judgment of people who break the standardization covenant is that dark horses are less visible. As the study illustrates, despite the ubiquity of people who have taken meandering paths, many dark horses feel like they are alone on their journeys. This doesn’t have to be the case. 

People in positions of power have a vested interest in workers keeping their heads down and staying in their lanes. Elite schools and corporations run on the backs of excellent sheep. But when you find other people who are open to less linear definitions of success, it will give you the confidence to keep going. Wander on, fellow traveler. I’m right there with you.


Simone Stolzoff is a San Francisco-based writer and designer. He is the author of the book The Good Enough Job: Reclaiming Life from Work. If you liked this piece, you can follow him on Twitter or subscribe to his free newsletter.

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@luispaisbernardo 8 months ago

hey Simone. this is the first time I have posted. I'm 38. A kid. A temp job at a mediocre college in backwater Portugal. A PhD I can't remember. A marriage I'm fully committed to but with a stance I'd liken to a mixture between Munch and the Matrix. I've meandered. I've worked with refugees out of an unspoken sense of kinship (I know, it's shameful, but I can't help it). I've been a journalist. I try being a good, helpful, diligent academic, but I can't help feeling stupid in this most esoteric of worlds. So I read a shitload. Fiction, nonfiction. Sci-fi and ridiculous essays trying to prove how smart the author is.

So your essay drops. I'm halfway through a wine bottle - red, cheap, unassuming, just like me flying through midnight. And I find that I'm just a bit less desperate. And it's a fine notion. So thanks.

Tintin 8 months ago

@luispaisbernardo I'm currently living in Portugal. If you need a friend, message me or contact me on Every's discord.

Simone Stolzoff 8 months ago

@luispaisbernardo what a beautiful and well-written late-night note! Luis, it feels like you're an old friend. Appreciate your honesty and kind words.

@luispaisbernardo 8 months ago

@Tintin I'll get in touch! But don't worry, my desperation is Thoreau in ironic mode. Trying to cross into epicurean territory, which would be a midlife crisis I could enjoy?

@luispaisbernardo 8 months ago

@luispaisbernardo 8 months ago

@simonestolzoff Deleted the damn comment, no clue as to why. I did feel a sense of kinship towards you, so, truly, thank you. about the note, English is my third language, so I guess we found a sentient wine who used me as a vessel? Anyways, thanks. I read Every occasionally; I'll now bookmark.

@sheshallconquer 8 months ago

This piece aligns with my own career journey.
I am reticent to call it meandering though, because it hasn't had the whimsical, casual feeling I associate with meandering. I've begun associating it with the concept of Bricolage though. When asked about "job-hopping" or "swiss-cheese knowledge" or how "interesting" my CV is, I worry that meandering feels too non-committal. Bricolage being a practice of using the tools and resources that are available to me right now to address the problems and opportunities in front of me is a way of introducing that:
1. At times I've had less tools and resources that I would've liked, so I've had to make do,
2. I've picked up new tools that I can apply in a deeply transferrable way because to learn and adapt one must abstract and understand quickly,
3. Responsiveness to problems and opportunities is more valuable than a pedigreed training—this includes learning, adaptation, and centring the needs of the various people rather than bureaucratic procedure

It's been 5 years since completing my small honours thesis on meaning, agency, and empowerment for workers and it's such a relief to find more and more pieces like this that inevitably hit the same notes! As my world grows bigger, so does the validation that we are not alone in this journey of navigation. Thanks, Simone!

I'm intrigued by the final paragraph, about the resistance one will encounter in response to this journey of self-discovery. I'm wondering if this path of connecting to the work that we do will make those checked out kind of jobs more intolerable, that if we are truly invested in the work we are doing, we will take it more seriously, ask more questions, be less willing to just do what is asked if it doesn't make sense—does this not make us then less employable for most work that exists?

Control / power is such an insidious faculty of many organisations large or small, has anyone encountered resistance? and if so, are there good methods of soothing the discomfort or anxiety of control seeking managers? Or ways of communicating and asserting needs /boundaries so that it is well received? Does the pool of opportunities just shrink drastically to only allow for people who are tolerant or on the same path?

Resources in case anyone is seeking: Paul Millerd (and Anne Helen Petersen) is a great recommendation! Here are a few others I've found inspiring and like a homecoming.
1. David Whyte's Crossing the Unknown Sea,
2. Hunter S Thompson's Ninth Path letter to Hume (Masterfully discussed by Russel Max Simon),
3. Kahlil Gibran's On Work from The Prophet,
4. Ed Zitron (on an org level),
5. Dr Gena Gorlin's substack,
6. Gabor Mate on work (recommend the Bioneers talk on Toxic Culture to start, pretty sure this is covered by the Myth of Normal),
7. My greatest source of inspiration has probably been the work of Mihaly Csikszentmihalyi, starting with Creativity (as the kind of work I aspire to), Flow, and currently Good Business—which unpacks everything from societal and cultural factors to the individual habits, tasks, and ways of shaping a life that is fulfilling.

--- adding this post as well to the list! Thanks again, Simone!
Also, regarding: "Wander on, fellow traveler. I’m right there with you."
This reminds me of the Keri Smith's sentiments in The Wander Society, and perhaps this is an apt space for her "Solvitur ambulando" exhortation. I certainly would like for work to become more fulfilling and meandering rather than desperate sprints to survive.

@stevo1971 8 months ago

It makes sense to carve your own path... because you learn transferable skill sets no one else can take away from you.

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