What I’ve Done in My Career Goes Against Everyone’s Advice. It’s Really Working.

Last month, one of my co-workers introduced me to his husband. “Harris knows where the bodies are buried,” he said. We were drinking gin and tonics paid for by our employer, a tech company you (or someone you know) might have heard of. He locked eyes with me over his glass, as if he were expecting me to lead him to the body of our former chief operating officer beneath the bar.

“You’ve been here, what, forever?” he asked.

If forever is a decade, then yes, I’ve been here forever. Technically, I’ve been here eight years full time and two years as a contractor before that. I’m a statistical anomaly, the rare millennial who’s moving through their career the way my parents did. Median job tenure among people in my age bracket is 2.7 years. I’ve exceeded that by a factor of three. I’m 37. Maybe I’ll stay another 30 years and give a brief, tearful speech at a walnut lectern before collecting my tiny brass plaque and retiring to a cottage in the Hudson Valley.

But—and no one ever says this—if you stay at a job past a certain point, people start to look at you strangely. If you’re a millennial, or a garden-variety young person, they wonder what’s going on with you.

“You’re still working at [redacted]?” a friend asked me recently.

We used to sit within each other’s sight lines in an open-plan office. We’d Slack “henlo” just to watch the other person’s eyes dart up. She left after 2.6 years. It was as if an alarm went off somewhere in her brain. A biological clock, but for jobs. I just have to leave, I remember her saying. It’s time.

Most of the twenty-to-thirtysomethings I know are suspicious of job loyalty. (God forbid you pledge allegiance to an entity that can fire you at will!) They flit from one job to the next, giving themselves raises every two or three years. They play the job market as if it’s that level in Super Mario Bros. where the floor is lava and every pipe starts to sink as soon as you land on it.

We’ve been conditioned to believe that this makes economic sense. According to a decade-old Forbes story that still spawns Reddit threads (and YouTube shorts), people who stay at a job for more than two years earn at least 50 percent less over the arc of their careers than those who leave. Job-hoppers have been deemed smarter, more loyal, and more emotionally intelligent than job loyalists. And it makes sense: When millennials like me were dropped into the hellscape of the late-aughts job market (double-digit unemployment and underemployment), we learned immediately that no employer would save us. We would have to save ourselves.

But things are different now. More people are doing what I’m doing. Unemployment is less than half of what it was when I got my first paycheck. Median employee tenure is still shrinking (it was 3.9 years in 2024, the lowest it’s been since 2002), but last year, the number of people who quit their jobs was down by 5 percent. This triggered a slew of stories essentially proclaiming that Staying Is the New Leaving. (One of my main takeaways from reading all of this: People are simply obsessed with generalizing about the state of the labor market.)

Now some employers are beginning to view excessive job switching as a red flag. In a healthier economy than the one that shaped my generation, maybe hopping from job to job no longer looks like survival. Maybe it looks like self-aggrandizement.

Yesterday I was on the phone with a corporate apex predator. She’s a friend who has hired and fired hundreds of people throughout her career. Seven years ago, she was interim CEO at American Apparel. She sold it to a less chic Canadian clothing company and is now on the board of Beyond Meat. She’s 16 years older than me and makes five times as much money as I do.

“Your generation loves to lily pad,” she said, “but they never learn anything beyond how to do their one job. They never go deep.”

This is the gift of staying somewhere a Very Long Time. Think of your tenure as a path toward increasing your situational awareness. Stay somewhere for a year, and you know what your job is. Everyone else knows what your job is too. Stay for two years, and you’ve made the job your own in some small way. By three years, you’re fluent in the unspoken norms and social patterns of wherever you are. In Years 4, 5, and 6, you start to dissociate (and I mean that in a productive way). You float above the Slack channels and see how it all kinda fits together. After a decade, you attain something I’ve come to think of as clairvoyance.

Flash back to 2021, when I’d been at this job for six years. We were planning a website redesign. We’d done it before, but this one was more dramatic. I sat on Zoom as my boss explained it to me. He was 10 years older than me but had worked at this place for only two. He seemed calm. Unbothered. I was—and I remember feeling surprised by this—irate. The redesign was heinous. I’m not a designer, nowhere near one, but I had Opinions. Turns out I … cared? A lot?

In a burst of insight that seemed to have been delivered to my brain directly from God, I knew exactly what would happen. We would ship the redesign. We would do this against 70 percent of the company’s wishes because the CEO wanted us to. Our numbers would spike momentarily. An onslaught of bouncing emojis would briefly overwhelm the #general Slack channel. My co-workers would performatively celebrate the launch. A year later, when a new design leader arrived, we’d tear it all down and pretend that it had never happened.

That is how it played out. And the next time something like that happened, I trusted my instincts even more. Months ago, when we were ignoring a core feature I knew that die-hard customers adored but staff tended to dismiss, I (politely) sounded off about it in a company all-hands. Comments flooded the Zoom chat: People felt the same but hadn’t been moved to speak up. It’s something I never would’ve had the chutzpah—or even the background knowledge—to do a few years ago.

“When everyone in your generation is bouncing around,” this friend said to me over the phone, “there’s value in stealth. Stay in one place and watch it change.”

In the way one of my divorced friends says she can now clock how long a friend’s marriage will last based on their response to a simple “How are you?,” I can tell how long a new hire will last. The buzzier their arrival—the more people talk up their exploits before they even log on—the shorter their tenure. (A relationship analog: The more someone gushes over their marriage, especially on Instagram, the sooner it seems to end.)

When you keep a job this long, it gets interesting. You don’t just get to watch a few episodes; you track the arc of an entire season. You can predict layoffs based on a very specific pattern of cagey silences, sort of the way some people who’ve lived in one place long enough can intuitively predict rain. You’ve attended buzzy launch parties for features that would take years to reveal themselves as monumental failures. You’ve felt the subtle yet pervasive influence of a single brilliant new hire (and a single terrible one), stretched over several quarters.

I realize not everyone can have this experience. Layoffs happen. But I’ve seen too many of my peers jump to something new just because they’re vaguely bored. And I’m beginning to realize, standing here on the cusp of 40 with a decade of a single Slack handle behind me, that longevity unlocks something else you can only get the hard way: care. It’s impossible to stay anywhere this long without caring so deeply it seeps into your bones. I don’t mean caring just about your job performance, like the job-hoppers do—I mean obsessing over the bigger Thing, the business itself.

Some friends would think I’m delulu for this. Caring about your job is fine, but caring about your company is gauche. We’ve all seen Severance, right? Yet, drinking at least a little bit of Kool-Aid makes your work better. It’s undeniable.

Which brings me to a lesson that I think applies equally to jobs and relationships (because, really, they’re the same thing): If you’re going to stay, it needs to be an active choice. Just like how some couples renew their vows in front of their friends and family every year, you need to constantly remind yourself why you’re still committed to this idea, task, or skill. If you don’t, you’ll just be coasting—and you’ll have a hard time keeping your job anyway.

A few years after college, I was the executive assistant to a CEO. My boss was a guy named Davi, who—and this will be familiar to anyone who has ever been an EA—was not the executive I was assisting. His role was similar to Emily Blunt’s in The Devil Wears Prada. He’d ascended from a lowly scheduling peon to more of a superassistant. I don’t know exactly what he did, but he would chide me for booking the wrong Lincoln Town Car.

At the time, he’d been there four years. Even that seemed too long.

I left that job after a year, but in 2019 we met for burgers and Coronas at a bar near my apartment. He’d surpassed a decade at that point. Sometimes I google, just to check in on him. He’s still there.

For a long time, this baffled me. Why would a smart, capable person languish at basically the same job he’d had since the Bush years?

Now I am him. And I know what happened. He found a job he likes and, through a mix of tenacity and self-awareness and the witchy ability to detect unforeseen changes, he managed to keep it. There is some kernel of purpose that keeps him there. He’s probably so great at what he does.

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