Explore a better way to work – one that promises more calm, clarity, and creativity.

Zen and the Art of Investment Banking: When Working Right is More Important than Finding the Right Work

The Seeker

During the summer of 1998, Thomas was working an entry level position in the IT department of a large London investment bank, his days filled with data entry and the occasional light secretarial work. It wasn’t a terrible job, but it wasn’t great either. “I was constantly unhappy,” Thomas recalls, looking back at this period.

The most recent crop of lifestyle advice literature offers a clear directive to 1998 Thomas: Follow your passion to something better!

“It’s worse to tolerate your job than to hate it because, if the pain is painful enough, you’ll make a change,” Tim Ferriss explained in a recent interview with 37 Signals. “But if it’s tolerable mediocrity, and you’re like, ‘Well, you know it could be worse. At least I’m getting paid.’ Then you wind up in a job that is slowly killing your soul.”

According to this philosophy, Thomas needs to escape the tolerable mediocrity of his banker job before it becomes too late. But here’s the thing, Thomas had already tried that — quite a few times actually — and it hadn’t seemed to solve his problems.

Years earlier, right after college, a young Thomas, who was terrified of becoming a Dockers-clad cubicle jockey, followed a “passion” for cycling and quickly moved up the sport’s ranks to join a professional team. He had a tendency to overtrain, however, and admidst the physical grind of professional-level athletics, his mind turned toward greener pastures.

Quitting cycling, he entered academia, earning two graduate degrees, before discovering that his research was too mainstream to be interesting.

Wanting to try something more reflective and less demanding, he tried traveling to Korea to teach English. But even the lush exoticism of East Asia couldn’t dampen his sense that he was destined for something better.

“Every job I did paled in comparison to some magical future passion-fulfilling occupation,” he recalls.

Needing to pay his bills, he moved back to London, took the entry level Banker position, and remained unhappy.

If stopped here, Thomas’ story would be a cautionary tale of the soul-sapping repressiveness of the working world. But it didn’t stop here. Nine months into his job at the bank, Thomas did something completely unexpected; something that would change his life, but not at all in the way he assumed:

He dropped everything and moved to a Zen monastery, tucked into the foothills of the Catskill Mountains, where he would spend the next two years…

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The Pre-Med and Ira Glass: Complicated Career Advice from Compelling People

The Tragic Mistake

Not long into their interview with public radio host Ira Glass, one of the three college-aged interviewers, a young girl, asks, with a desperate smile etched on her face, how to decide “which of her passions” to pursue.

“Like how do you determine, how…”, she begins.

“How do you figure out what you want?”, Glass interrupts.

“How do you not only figure out what you want, but know that you’ll be good at it?”, she finishes.

There’s a pause. In this moment, when Glass prepares his answer, the young girl’s earlier admission that she’s a pre-med, and doubting her decision to attend med school, hangs in the air. Glass can relate: he too had been considering med school when he stumbled into his first radio internship, after his freshman year of college.

He proceeds cautiously, softly: “Honestly, even the stuff you want you’re not necessarily good at right away…I started working at 19 at the network level, and from that point it took me years. The key thing is to force yourself through the work, force the skills to come. That’s the hardest phase.”

One of the other interviewers, a young man in a baseball cap, interjects: “Do you think hard work can make you talented?”

“Yes. I do.”

The students let this sink in.

“In the movies there’s this idea that you should just go for your dream,” Glass continues. “But I don’t believe that.”

By the students’ reactions, this is not what they expected to hear.

“Things happen in stages. I was a terrible reporter, but I was perfectly good at other parts of working in radio: I am a good editor…I feel like your problem is that you’re trying to judge all things in the abstract before you do them.”

A beat.

“That’s your tragic mistake.”

The Roadtrip Nation Revelation

This interview is one of many conducted by the non-profit organization Roadtrip Nation, which sends students across the country to interview “eclectic individuals who have resisted pressures to conform.” They seek advice for building an interesting path through life.

If you explore the full Roadtrip Nation video archive, as I did one recent weekend, you begin to appreciate the nuance and serendipity behind these compelling people and their compelling careers. Amidst this nuance, however, one conclusion is stark: the canonical advice to follow your passion is way too simplistic. As with Glass’s story of toiling for years before finally discovering a niche in radio editing, many of the interviews echo this same theme that passion is not something you discover in a career center.

Its source is more complicated…

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The Passion Trap: How the Search for Your Life’s Work is Making Your Working Life Miserable

The Priest and the Parachute

It began with a joke.

In 1968, Richard Bolles, an Episcopal priest from San Francisco, was in a meeting when someone complained about colleagues “bailing out” of a troubled organization. To remind the group to return to this topic, Bolles jotted a clever phrase on the blackboard:  “What color is your parachute?”

The line got a laugh, but as Bolles recalls in a 1999 interview with Fast Company, “I had no idea it would take on all this additional meaning.”

Two years later, Bolles lost his job as a priest and was shuffled into an administrative position in the Episcopal Church, advising campus ministers, many of whom were also in danger of losing their jobs. Noticing a lack of good advice on the topic, Bolles self-published a 168-page guide to navigating career changes, which he handed out for free. Looking for a catchy title, he re-purposed his blackboard one-liner. The initial print run was one hundred copies.

The premise of Bolles’ guide sounds self-evident to the modern ear: “[figure] out what you like to do…and then find a place that needs people like you.” But in 1970, this concept was a radical notion.

“[At the time], the idea of doing a lot of pen-and paper exercises in order to take control of your own career was regarded as a dilettante’s exercise,” Bolles recalls. It was also, however, a period of extreme workplace transition as the post-war industrial economy crumbled before an ascendant knowledge work sector. Uncertain employees craved guidance, and Bolles’ optimistic strategies resonated. The book that began with an one hundred copy print run and a clever name has since become one of the bestselling titles of the century, with over 6 million copies in print.

This story is important because it emphasizes that one of the most universal and powerful ideas in modern society, that the key to workplace happiness is to follow your passion, has a surprisingly humble origin. What began as a quip jotted down on a blackboard grew into the core principle guiding our thinking about work. “What color is my parachute?”, we now ask, confident that answering this question holds the answer to The Good Life.

But when we recognize that this strategy is not self-evident — and in fact not even all that old — we can begin to question whether or not it’s actually right.

And when we do, it’s dismaying what we find…

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The Danger of the Dream Job Delusion

The Ivy League Farmer

Earlier this summer, Julie and I attended a dinner at Red Fire Farm, a 110 acre organic farm in rural Granby, Massachusetts. The dinner celebrated the strawberry harvest and the farmhands had setup tables under a tent overlooking the fruit fields. As we poured our wine, the farm’s owner, Ryan Voiland, stood up to say a few words about this year’s harvest.

Ryan is young, only in his early thirties, a fact he tries to hide with a grizzled black beard. As he spoke, his few words stretched into an enthusiastic dissertation on rain fall and cabbage yields. Eventually, Ryan’s wife, Sarah, took over, leading the group in a prayer to the “earth goddess.” As we sipped strawberry gazpacho, a group of college-aged farm interns formed a song circle in a patch of grass near the chicken coop.

In the comfort of cynical Boston, the event would have felt over the top, but in the shaded fields of Granby, it made sense. When I looked over to the main table, I saw Ryan take in the scene. He was smiling.

What makes Ryan’s story canonical is its start. Ten years earlier, he walked out of Cornell University with an Ivy League diploma in his hand and headed straight into the offices of the Farm Service Agency, where he secured a loan to buy his first farm property. A decade later, Red Fire is a success: it sells organic produce straight to the consumers through farmers markets and a sold-out CSA. When I last visited the farm, in mid-August, they were installing a $200,000 solar array. Ryan loves what he does and does it well.

The Dream Job Trope

Ryan has a dream job — which I define to be an occupation built around a hobby or casual side interest that you enjoy.  (Growing up, Ryan loved to garden, so, naturally, he started a farm.)

The dream job is a powerful trope in the job satisfaction literature. For example, here’s the opening paragraph from a popular career advice guide:

“[A] New York investment banker becomes a small-town college chef. A college professor becomes a chocolatier. An entrenched corporate exec…converts to the ministry.”

These are all dream jobs. When Tim Ferriss tells his famous story of an attorney who drops everything to open a Brazilian surf shop, that’s also a dream job, as are most of the examples touted in the perennially popular quit your terrible cubicle job to start a business advice guide niche.

You like to cook? Become a chef! Love chocolate? Open a chocolate shop! Like surfing on exotic beaches? Open a surf shop! And so on.

We’re entranced by dream jobs. When we hear stories like the one that opened this post, we feel a rush of aspiration. Hundreds make a living writing books and blogs about mustering the courage to pursue dream jobs, and millions dedicate their day dreaming to the topic. In this post, however, I want to argue that this is a problem.

The dream job trope isn’t the path to job satisfaction, and it’s not just harmless wistful thinking: it’s instead downright dangerous.

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