The Anti-Valentine's Post: Love Your Work (Or Leave It)

I was having coffee with someone last week who told me they’ve been at their job for four years and they’re “pretty happy.” Pretty happy. The words sat there in my coffee cup like a stone. I wanted to ask: if you were in a relationship where you were “pretty happy,” would you stay? Would you plan for the next decade? Would you introduce your partner to your family?

Probably not.

But we accept “pretty happy” at work the way we’d never accept it anywhere else in our lives. There’s a whole narrative built around this—the idea that work is different, that you shouldn’t expect love or passion or excitement, that contentment is something to aspire to. You’re not supposed to adore your work. That’s what Instagram influencers and motivational speakers sell, and we’re too cynical for that now, right? So we settle for fine. We settle for bearable. We settle for the paycheck and a few good colleagues and the assumption that nobody really loves what they do.

Except some people do. And when they talk about their work, it sounds different. Not in the Instagram way—there’s no performance to it. They talk about what they’re building, what they’ve learned, where the work is leading them. They show up with intention. And the question isn’t “How do I make this work?” but “Why wouldn’t I want to do this?”

Here’s the part everyone dances around: loving your work isn’t a luxury. It’s a choice about what you’ll accept for a third of your life.

I know someone who stayed in a job they were “pretty happy” with for six years. Good company, decent pay, smart people. On paper it was fine. But something was missing—not in a way you could name in a resume critique, but in the way you feel when you’re spending your time on something that doesn’t actually matter to you. They knew other people who were excited about their work. Genuinely excited. Not in a naive way—these people knew the job had hard parts, boring parts, tedious parts. They just cared enough that the hard parts seemed worth it.

It took a forced leave due to burnout for them to finally ask the real question: why am I staying?

The answer wasn’t “because it’s safe.” It was “because I haven’t given myself permission to want more.” Because somewhere along the way, they’d internalized the idea that needing work to feel meaningful was greedy. Adolescent. Unrealistic.

What they realized in the months away was that they weren’t too old, too practical, or too experienced to care. They were just tired of pretending that fine was enough.

They left. Found something that aligned with what actually mattered to them. Is it perfect? No. But it’s not “pretty happy.” It’s engaged. It’s a choice they actively renew, not a default they’ve resigned themselves to.

There’s a specific thing that happens when you’re in the wrong work situation. You spend energy on negotiations instead of execution. You optimize for staying comfortable instead of moving toward something. You become an apologist for your own life. Well, the pay is good, so I can’t complain. At least I have flexibility. Everyone’s job has hard parts.

It’s all true. And it’s also a trap.

The uncomfortable truth is this: if you don’t love your work, you need to get honest about why you’re staying. Is it the money? Is it fear of change? Is it the fantasy that this job is somehow protecting you from something worse? Is it that you’ve already invested so much time that leaving feels like failure? Each reason is legitimate, but they’re not the same, and they don’t all lead to the same answer.

If it’s money, you already know what needs to happen—either the job itself pays more, or you find something else that does. If it’s fear, that’s real, but it’s also not actually about the job. If it’s sunk cost, that’s when you really need to listen—because sunk cost is the worst possible reason to spend the next five years of your life somewhere.

What I’m not saying is that work needs to feel like love at first sight. Good work is usually built, not found. But there has to be something—the direction matters, or the problem you’re solving, or the people around you, or the way the job actually lets you do your best thinking. Something that makes the hard parts feel like they’re worth the effort.

The question isn’t whether you love your job right now. The question is whether you could. Whether the structure of the work, the nature of the problems, the kind of people involved—whether any of that speaks to something in you that’s worth developing.

If the answer is no, then you’re not staying because you’re practical. You’re staying because you haven’t decided you’re worth more.

I wrote about why your dream job might be a trap—how the fantasy of perfect work keeps people stuck. That post is about the danger of waiting for something imaginary. This one is about the danger of accepting something mediocre.

The real gap isn’t between perfection and settling. It’s between work that has direction—that’s pulling you somewhere you want to go—and work that’s just moving time forward. Between something you choose and something you’ve resigned yourself to.

The dark side of hustle culture captures the other extreme—when people pour everything into work that doesn’t deserve it. But the opposite problem is just as real: staying in work that doesn’t deserve you because you’ve confused stability with contentment.

And if you’re thinking this is about balance, about work-life integration, it sort of is. But it starts before balance. It starts with the choice: am I willing to spend this time here? Does this matter to me? And if the honest answer is no, then it’s not about working harder, managing better, or thinking differently. It’s about leaving.

Not because perfect exists. But because it’s February, and Valentine’s Day is here, and if you wouldn’t love a person who was “pretty okay” with you, why are you loving a job that you’re only “pretty okay” with?

The answer deserves to be better than “because I haven’t left yet.”