Fulfillment FOMO

And alternative paths to passion. What to do when “find your passion” fails. [Not Obvious: Part 5]

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The Way of Work explores stories of where we fit in the world of work. This is part of the series, Not Obvious, exploring why work advice fails us:

• Part 1: Why Work Advice Fails Us (intro)

• Part 2: Burnout, Balance, and the Bullshit in Between (on “hard work”)

• Part 3: You Will Never Feel Done (on “productivity”)

• Part 4: Welcome to Management: Please Proceed With Delusions of Control (on “management”)

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Has any advice created as much hopeless misery as “find your passion”?

Modern workers are infected with a disease: Fulfillment FOMO.

The gnawing anxiety that you’re not quite where you’re supposed to be. That something better is out there, just beyond your grasp. You’re in the wrong job, the wrong career, maybe even the wrong life. And if you haven’t found it? You’re stuck with visions of what could be.

For a while, I bought into the hype, believing that others had it all figured out. Not anyone I knew personally, but people were out there, for sure! They told me they were living their perfect life and I bought it:

“Do what you love and the money will follow.”

But I’ve come to see this as the online version of a late-night infomercial selling miracle juice. A classic bait-and-switch: vague enough to intrigue, empty enough to disappoint.

The problem is that the alternative – suppressing your dreams – sounds way worse. So we’re supposed to endure a life of drudgery, meaninglessness, and regret? That’s what life is like?

In a choice between heaven and hell, we’re holding out hope for a heaven. So we continue on with Fulfillment FOMO, overlooking that purpose might be found in paths that don’t require a perfect fit. I explore those alternatives later.

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The career fantasy that won’t set you free

I blame Ikigai.

Even if you don’t recognize the word, you already know the promise:

• Do what you love.

• Do what you’re good at.

• Do what the world needs.

• And get paid for it.

Ikigai dangles a fantasy in front of your face: a “sweet spot” where your ideal life is custom-fitted, purpose-filled, and waiting just for you.

What you get when consultants sanitize ancient wisdom

It’s a beautifully simple formula for fulfillment… until it becomes a high-stakes hunt for the holy grail, where any wrong move results in failure.

If your work doesn’t check all the boxes, you’re settling. You’re successful, but unfulfilled. You love your work, but never make enough money. You’re doing what the world wants, but not what you want. You haven’t searched hard enough, self-reflected enough, or micro-dosed enough.

While Ikigai is theoretically possible, in reality, it’s a perfectionist’s nightmare:

“…this diagram frankly had the opposite effect, it was paralyzing. It made me miserable, and I wasted a lot of time trying to figure it out… What is my ‘one thing’ at the center of my universe that meets all these criteria? I thought about it a few different ways, but ended up giving up in frustration.” -

Dave Kang

, from Ikigai Ruined My Life

The concept of Ikigai (and others like it) sells you a fairy tale and then makes you feel like an idiot for not living up to it. For many, it doesn’t solve career anxiety, it creates it. The framework is right, just you aren’t.

The main problem, as I see it, is you can rarely jam a paycheck into a passion, let alone get the stars to align across all four categories.

“The truth is that the market doesn’t give a damn about your calling. You’re deluding yourself if you believe the system is organized around helping you find your perfect work.” - from When you don’t have a “calling”

And even if you find your thing, who says it will last forever? Most athletic careers are over soon after they begin; even Tom Brady (at 47) needs to figure out his next act. Artists have short creative peaks; there’s more one-hit-wonders than Billy Joels. Founders (who I salute but whose contentment is over-glorified) work themselves out of what they love when they sell their company (if they’re lucky), scale so big they no longer do what they love, or burnout in the process.

Callings, Ikigai, or whatever you want to call them, are actually quite fragile. Because no one tells you the small print: results may vary.

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Paths to Passion

So if the apex is out of reach, now what? Do we settle for a joyless grind? Accept that work will always suck? I don’t think that’s the right answer either.

Because fulfilled people do exist! I know a few. Maybe you know some too. But in my experience, they find meaning, not nirvana. And it’s that slightly-lower-than-heaven part that’s a bit more in reach for the rest of us.

So at the risk of tearing down a flawed diagram, and then replacing it with my own flawed diagram, I’m going to share some options (not answers) I’ve noticed over time. I’ve studied people on these paths, especially looking to understand the trade-offs, not just the sugar coated sales pitch. There may be more options or more precise options-within-the-options or ways to remix them and so on. Naming this type of thing is an imprecise science (hey, just like finding your passion, which is kinda my point…).

So with full awareness that I might be doing exactly what I just critiqued, here are some imperfect, but real, paths to passion:

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The Practical Path

Here, work is primarily practical and transactional. We first orient toward opportunities profit (e.g. income and savings). Passion is put on hold until later, either because it hasn’t revealed itself yet or because financial independence is required first.

“Anyone who tells you to follow your passion is already rich.” – Scott Galloway

Strengths

• Financial stability: income is predictable, bills get paid

• Clear trajectory: structured paths, makes planning easier

• Skill-building: can find fulfillment from mastery over-time

Trade-offs

• Life deferral: “I’ll do what I love later,” but later may never come

• No guarantees: that patience will be rewarded

• Habit-forming: you might never pivot (never knowing enough), career exits (voluntary or not) can become an existential crisis

Examples: stability-first careers (e.g. lawyers, doctors, accountants), FIRE (e.g. MadFientist), later career passion pursuers (e.g. Sara Pendergast, Cathy Foerster, me?)

Read next: Waiting Decades to Finally Follow Your Dreams

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The Passion Bet

The leap now, figure-it-out later path. They prioritize fulfillment over finances, jumping headfirst into work they love, even if it doesn’t pay well (or at all). It’s not that money doesn’t matter, but it’s secondary to doing something meaningful.

"Follow your bliss and the universe will open doors where there were only walls." – Joseph Campbell

Strengths

• Live now: no waiting or deferral, intrinsic motivation can fuel long-term persistence

• Less regret: don’t have to wake up later wondering “what if?” (at least the passion part)

• Potential upside: if break through, the rewards can be big (financial or otherwise)

Trade-offs

• Financial instability: many struggle for years (or forever)

• No ladders: lack of defined paths to success

• Social outlier: can appear too risky or irresponsible to outsiders

Examples: creatives, artists, activists, mission-driven workers

Read next: The Pathless Path by

Paul Millerd

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The Work-Life Split

The work-to-live path. Work is a means that pays the bills, funds interests, and, ideally, takes up as little time and mental space as possible. Passion isn’t monetized or careerized, it exists separately from any job.

"Not everything you love should be turned into a career. Some things are better left as hobbies." — Paul Jarvis

Strengths

• Unlimited passion options: because passions don’t need to pay

• Clarity in work’s purpose: it just has to fund life + take as little time as possible

• Like with like: no need to force passion into work (or vice versa)

Trade-offs

• Partial passions: must fit into the margins of the day

• Job is a slog: work feels like a distraction away from what you really want

• Either/or thinking: over-compartmentalize, not realizing that work can sometimes be fulfilling even if it’s not a passion

Examples: 9-5er who’s an artist on the side, weekend warriors, amateur hobbyists

Read next: The Good Enough Job by

Simone Stolzoff

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The Passion Pivot

Like The Practical Path, but with less waiting. Instead of grinding toward financial independence, they build career capital (which creates a base), then pivot toward passion when they have enough leverage. Rather than climbing a single career ladder forever, they trade wins for freedom; shaping their work on their own terms, sometimes one move at a time. Money isn’t the goal; it’s the bridge to something better.

"Become so good they can’t ignore you. Then, use that leverage to do what excites you." — Cal Newport

Strengths

• Have it both ways: build security, but don’t wait forever

• Accelerated: to partial-freedom at midlife where you choose work you prefer

• Optionality: once you gain leverage, you have more choices

Trade-offs

• $$$ left on the table: pivot during peak earning years (a crime against capitalism!)

• Living in limbo: not maximizing either side, no single-minded clarity

• “What if?”: should you have gone all-in earlier or waited a little longer?

Examples: Successful-to-independents (e.g.

Khe Hy

,

Kris Abdelmessih

), Portfolio Careers (e.g.

Dave Kang

), CoastFIRE

Read next: Just Enough to Walk Away

Which trade-offs could you live with? What do you think I missed or messed up? Let me know in the comments.

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Let go of the FOMO

The happiest people I know have made peace with imperfection. They shift between priorities, adjust to life’s trade-offs, and adapt instead of agonizing. They build a life that works for them, not one that fits neatly inside a Venn diagram.

I’m not going to claim any one choice is right. Every path has risks. Exactly zero are easy. But the biggest risk may be wasting your life chasing something theoretically possible, but practically out of reach.

Careers evolve (and end). Interests change. What excites you at 25 might bore you at 50. There’s rarely a "eureka moment," but always another step forward.

It turns out you can live out your passion. Just maybe not in the perfect, heavenly form you hoped for.

And if you are able to pair your passion with a paycheck… then go for it! Just think twice before you tell all of us it’s possible too.

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Bonus: Ambiguous Advice

▸ “Just do what you love and the money will follow.”
- guy selling B2B accounting software.

▸ "The only way to do great work is to love what you do." – Steve Jobs
Steve, I’m so glad tech guys understand this. Because I really love my work and excited for a long, stable career at USAID.

▸ "Look for a job you love, and you will never have to work a day in your life."
Because they aren’t hiring.¹

▸ “Find your calling.”
My calling is to not work, then come back and tell you all about it.

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Next up, I’ll be exploring the office politics.

The Two-Party Trap (in office politics)

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1. This is not my joke, but I can’t find a source to attribute it to.