Should you love your job? (The Jay Pritchett story)

What it really takes to "do what you love"

For most of my twenties I held a quiet article of faith about work, which was that if I just thought about it carefully enough, I’d uncover the thing I was meant to do. Some hidden passion would surface, the world would arrange itself around it, and the rest of my life would feel like a slow exhale. I read books, did exercises, made lists. None of it worked, in the way that pure introspection rarely does, and at some point I started reading and listening to people who had spent considerably more time than me thinking about how careers actually unfold. One of those people was Scott Galloway, and he has a line that very much changed my thinking on the matter.

His advice, more or less, is this: don’t follow your passion, follow what you’re good at. Find something the market values, become excellent at it, and let the love come afterwards. You’ll come to love the craft because you’re rewarded for it. You’ll come to love the lifestyle that mastery affords. You’ll come to love being able to provide for the people you care about, which is one of the most underrated sources of meaning in adult life and one that almost no career advice book mentions. Passion, in his telling, is a consequence of competence.

This advice cuts straight through the bullshit of an entire flavour of career advice. The “follow your passion” wing has produced a generation of people staring at their interests like a bag of jigsaw pieces from three different puzzles, trying to assemble skiing, philosophy and a vague interest in design into something that pays rent in London. It rescues you from that. You stop trying to find some hidden vocational truth inside yourself, and start asking the more useful question of where your aptitudes meet the world’s appetites

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As I sat with this idea over the last few months, I kept being reminded of a character from one of my guilty-pleasure shows. Modern Family is a sitcom, eleven seasons, an extended Californian family caught between three households, the kind of thing you put on at the end of a long day because it’s familiar and warm and asks very little of you. The patriarch is Jay Pritchett, played by Ed O’Neill, and on first appearance he’s the epitome of the American dream gone right. Big house, stunning wife, adult children who still call him for advice. The grizzled, golf-playing, slightly grumpy kind of wealthy that signals a man who started with nothing and ended up with everything.

You might reasonably assume, given the polish of the lifestyle, that Jay made his money in property, or in finance, or in some 1980s tech bet that paid off. The answer turns out to be a little more prosaic than that. Jay made his money in wardrobes. Pritchett’s Closets, four decades of designing, manufacturing and selling fitted storage to the houses of greater Los Angeles, and somewhere along the way he became seriously minted on the back of it.

What makes the running joke work is that Jay genuinely loves wardrobes. He really does. There’s a scene where his wife teases him about the closet hall of fame, and he turns to camera, slightly affronted, and says: “I’m sorry, you mean the sanctuary where a man dons his armour in the morning and takes stock of the battle at night?”

He didn’t grow up dreaming of fitted shelving. No nine year old lies awake at night picturing themselves selling sliding doors to suburban families. He fell into the work, gave it a go, turned out to be unusually good at it, built a business around what he was good at and what people would pay for, became extraordinarily rich in the process, and somewhere over the next forty years he fell in love with the thing itself.

There’s one scene in particular where Jay confronts this realisation. His granddaughter Alex, the genius of the family, has been on the science track her whole life, has just been accepted to a top university, and is suddenly wobbling. She tells Jay she’s thinking of pursuing singing instead, that she’d be good at it and she loves it. Jay sits with her in the car for a moment and tells her about a daredevil he once knew called Danger O’Shea. O’Shea had wild dreams of being a stunt rider, jumping cars and motorcycles for a living, the whole Evel Knievel fantasy. He wanted the leather suit and the screaming crowd. But before he chased any of that, he was sensible enough to build a successful business first. He made his money, established himself, and only then went off to chase his motorcycle dream of jumping a school bus, which inevitably went wrong. The point of the story is that O’Shea had a safety net to fall back on when the dream went sideways. He’d built the platform. The romance could come later, and it could go wrong, and he’d still be fine.

Plot twist: Jay was Danger O’Shea. Alex gets the message. She’s going to stick to science.

I’ve subscribed to this advice for a long time. It’s the version of careers advice I quote when friends ask me what to do, and it’s the version I’ve recommended in writing. But after a couple of years of having hundreds of conversations with people who are thinking very seriously about these questions, I think there’s a piece of nuance that this example misses.

When we say Jay “fell in love with what he was good at,” we’re skipping over the more interesting thing happening underneath. I want to caveat that Jay is a fictional character on a sitcom, so all of what follows is conjecture, but bear with me, because the same conjecture applies to a lot of real people I’ve spoken to. Jay fell in love with the specific things the closet business gave him daily access to: the puzzle of fitting storage into awkward spaces, the satisfaction of building a company from nothing, the pleasure of being the best at something most people didn’t bother to take seriously, the swagger of being able to negotiate his way out of any room he walked into, the private authority of running a small empire he’d assembled with his own hands. The wardrobes were the surface of the thing. Underneath was a constellation of drives that were always going to find an outlet somewhere, and happened to find it here

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This is also where it’s worth saying something the “follow your passion” school never quite separates out, which is that passions and hobbies are not the same thing. Telling someone to do what they love often gets heard as “make a living from your hobby,” which is why so many people end up trying to monetise their love of skiing or photography or sourdough and finding the experience considerably more painful than they expected. The passions worth building a career on are almost always one level deeper than the hobby.

Here’s the critical part, and the reason I think being good at something is incomplete advice on its own. You can’t outwork people who find the work natural. For them, the hours don’t feel like hours. The thinking happens in the shower and on walks. The hard problems get worked on in the background, while they’re doing something else, and the answer arrives later without anyone having to force it. Mastery accrues from those unrequired moments, the small obsessive optimisations they make because the work feels like play and they can’t help themselves. Galloway’s advice tells you to pick what you’re good at, and that’s good advice as far as it goes. What it under-prices is that two people can be equally good at something on paper, and the one for whom the doing of it feels natural will, over twenty years, leave the other one in the dust.

If you don’t enjoy the daily activity of the thing you’re good at, even if eventually you learn to love the rewards it brings, you’re swimming upstream from day one. Every Sunday evening costs you a little more than it should. Every promotion comes with a small private dread alongside the satisfaction. The cost compounds, and you tend not to notice until you’re forty five and trying to work out why the thing that was supposed to feel like arrival feels like a long corridor instead. What’s really happening, I think, is the slow horror of feeling trapped by a decision you made when you were a child whose brain wasn’t even finished developing. Picking a career at eighteen and having to live with it for the next forty years is, in most other contexts, a recipe for disaster.

The good news is that work is broader than it used to be, and it’s getting broader still. The default career ladder our parents climbed was a narrow set of legible options. Most people picked from a list of maybe forty professions, and the wise advice in that economy was to pick aptitude over enjoyment, because that’s the trade-off you actually faced. In an economy with four hundred thousand niches, falling barriers to entry, and AI rapidly dissolving the boundary between what counts as “a job” and what doesn’t, the calculation changes. The intersection between what you’re good at and what you find rewarding to do has more entries in it than it used to.

At Rumbo we use a framework we call the Career Fulfilment Triangle, three circles that need to overlap for work to feel sustainable over the long run. The first is capability, what you’re good at or could become good at with time and reps. The second is alignment, where the doing of the work feeds you and the activity itself fits your temperament. The third is market value, someone willing to pay you well enough that you’re not constantly anxious about money. Most career advice focuses far too heavily on one corner, partly because balance seems to have become a naughty word in self help and productivity literature, with the implication being that anyone aiming for it is settling.

Balance has been so thoroughly captured by wellness influencers and corporate HR posters that using it in a piece about careers feels almost embarrassing. But the older sense of the word is the right one. You’re trying to find a working equilibrium between three forces that pull in different directions, and you don’t need to score a hundred on each. A career that’s ninety on capability, sixty on alignment and eighty on market value is a very good career. A career that’s ninety on alignment, thirty on capability and ten on market value is a hobby you’re funding with anxiety. The goal is sufficient overlap.

The thing it took me longest to understand is that this equilibrium moves. You don’t find it once at twenty two and ride it for forty years. You rebalance. The work that suited you at twenty five might bore you at thirty five, and the work that bored you at thirty five might be exactly what you need at forty. Markets shift, you shift, and the work shifts underneath both of you. Treating your career as a single decision you make once is what creates most of the misery I see in the people I speak to.

Galloway is right that you can learn to love what you’re good at. He’s right that the rewards matter more than people admit, and that providing for the people you love is one of the most underrated sources of meaning in adult life. Jay Pritchett is the proof of concept. What I’d add is that the love came easier for Jay because the daily activity of the work happened to sit on top of a personality that was already wired for it. He got lucky. Most people don’t get that lucky by accident, and what we’ve built Rumbo to do is help people engineer the same outcome on purpose: to understand themselves well enough that when they pick the work, they’re picking it with their eyes open about all three corners of the triangle.

So should you love your job? Duh, yes, of course you should love your job. Or at least aim to. You have one life, and spending the majority of your waking hours on something that doesn’t bring you joy is a great shame. But for most real people, the ones who aren’t celebrities or lottery winners or the rare child who knew at nine what they wanted to do at forty, getting there requires a deep understanding of yourself, what you’re capable of, what you actually love doing once you separate it from the hobbies you do to escape work, and where there are opportunities in the market for someone with that combination. Those are the three corners. The work of finding the overlap, and finding it again as you change, is some of the most worthwhile work you’ll ever do.

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