I've Hated Every Job I've Ever Had

I remember my first day at my first job with uncomfortable clarity.

I'd finally made it. College degree in hand. Interviews survived. Offer accepted. It was an IT help desk role—not glamorous, but it was the start. The path forward.

I ironed my uncomfortable corporate casual outfit that morning. Drove to the office. Got shown to my desk.

And about 45 minutes in, reality set in.

I couldn't believe this was what a job actually was. That you put on clothes you'd never wear under any other circumstance, drive to a place you'd never go otherwise, sit in a chair, and stare at a screen. For years. Decades, maybe.

I looked at my colleagues—heads down, typing, occasionally answering phones—and I thought: People actually do this. This is what everyone's been doing. And now I have to do it too.

I couldn't leave. I was stuck.

Looking Back, Looking Forward

There's something naive about that story. Entitled, even. What did I think was going to happen? Did I expect my first day at work to feel like a vacation?

But that's exactly the point. I'd never stopped to think about it.

I was on a track. Good grades led to a good school led to a good degree led to a good job. I did all the things I was supposed to do. I followed the path that was laid out. And it never occurred to me to ask: What does this actually mean? What does a job actually feel like?

A few months before graduation, I'd run into some people who'd just started at Microsoft. This was Seattle in the late 1990s—Microsoft was the pinnacle. The dream job. They'd made it.

A few of us gathered around them, starstruck. "What's it like?" we asked. "Is it amazing?"

One of them looked at me with what I can only describe as dead eyes.

No excitement. No pride. Just a flat acknowledgment that this was his life now.

I should have taken that as a warning. Instead, I filed it away and kept following the path.

The Jobs That Followed

That IT help desk role was the first job I hated. It wasn't the last.

I moved on to other positions. Better titles. More money. More responsibility. I worked as an IT manager for seven years. And I hated that too.

Here's the strange part: I was good at it.

I had incredible autonomy. Universal approval. Positive reviews. I built systems that worked. I managed teams that performed. By any external measure, I was successful.

Why I'm Telling You This

If you hate your job, I want you to know something: you're not alone, and you're not broken.

Job satisfaction surveys consistently show that most workers are disengaged. Depending on which study you read, somewhere between 50% and 80% of employees don't like their jobs. The specifics vary, but the direction is clear: most people are not thriving at work.

That's not because everyone made bad choices. It's because jobs are complicated. They involve people, politics, incentive structures, and thousands of small frictions that can grind anyone down.

Maybe you hate your job because the work itself doesn't fit you. Maybe you're good at it but you don't care about it. Maybe you enjoy the actual tasks but the people around you are impossible. Maybe the expectations are unreasonable, the meetings are endless, your boss is terrible, or you're just... tired.

All of these are real. All of them are common.

The Trap

Here's where it gets tricky.

Hating your job is uncomfortable, but it's also familiar. The dissatisfaction becomes part of your identity. You're the person who complains about work. You're the one who sends cynical texts about your boss. You bond with coworkers over shared misery.

And the deeper you sink into that dissatisfaction, the heavier it gets. The complaining becomes a ritual. The cynicism becomes a lens through which you see everything. The job you hate becomes an immovable object in your life—so big, so permanent, that it feels impossible to change.

It seeps into everything. It affects your relationships, your health, your sense of what's possible.

And the worst part is: it doesn't actually lead anywhere. Complaining isn't a strategy. Cynicism isn't a plan. You can spend years being unhappy and end up exactly where you started, just older and more bitter.

The Opening

But here's what I've also learned: hating your job can be an opening.

Not a dead end. An opening.

Discomfort is information. When something feels wrong—persistently, deeply wrong—it might be telling you something important. Not something you need to suppress or complain about, but something you need to pay attention to.

Maybe you're in the wrong role. Maybe you're in the wrong company. Maybe you're in the wrong industry. Or maybe you've been following a path that was never actually yours—doing what you were supposed to do instead of what you were meant to do.

That IT help desk job taught me something, even if I didn't understand it at the time. The feeling of "what have I done?"—that wasn't weakness. That was signal.

The seven years of IT management taught me something too. The success I had was real, but it was someone else's definition of success. I was optimizing for outcomes I didn't actually want.

Two Things at Once

I want to hold two ideas at the same time, because I think both are true:

Both things. At the same time.

The trick is knowing which one applies right now. Are you in a temporary rough patch that requires patience? Or are you getting persistent feedback that something needs to change?

I don't know your situation. I can't tell you which one it is. But I can tell you that the first step toward figuring it out is to take the discomfort seriously—not as something to complain about, but as data to examine.

What's Coming

In the next part of this series, I'll dig into what hating your job actually tells you. Because it's not always obvious. Sometimes the problem is the work. Sometimes it's the people. Sometimes it's you. And sometimes—often, in my experience—it's a mismatch between who you are and what you're being asked to do.

We'll look at aptitudes and talents. We'll look at fit—not just whether you fit the job, but whether the job fits you. We'll look at that feeling of exhaustion that goes deeper than tired.

And in Part 3, we'll talk about what you can actually do about it. Not in a self-help, positive-thinking way. In a practical way.

Because this gets better when something changes. Maybe you need to change. Maybe your circumstance needs to change. Maybe both. But the first step is understanding what you're working with.

One More Thing

I titled this post "I've Hated Every Job I've Ever Had" because it's true. And because I think there's power in saying it out loud.

Not as a complaint. Not as a badge of suffering. But as a fact that opened up possibilities.

If I'd loved those jobs, I'd probably still be doing them. I'd be comfortable, stable, on the path. But I didn't love them. I hated them. And that discomfort—eventually—pushed me toward something better.