My Job Looks Good on Paper. Why Do I Want to Leave?

A few years ago, you would have been thrilled to land the job you have now. The salary is solid, you like the people you work with, and when someone asks what you do, the answer sounds respectable.

Yet you keep opening job postings.

Then you remind yourself how many people would want your job, shut the tabs, and return to work. A week later, you're browsing again.

It is difficult to explain wanting to leave when staying seems so easy to justify. You may wonder if you're ungrateful or asking too much.

You can appreciate what the job provides and still wish something about it would change. Naming that change precisely can help you sort out what to do.

Look at an ordinary working day

A job description lists responsibilities and qualifications. It tells you much less about what it's like to spend Wednesday coaxing five people into approving the same paragraph.

Try describing your day without using your job title.

“I work in marketing” becomes “I spend most of my day coordinating feedback on documents.”

“I manage a team” becomes “I help people solve problems, but rarely have enough uninterrupted time to finish my own work.”

Those descriptions give you something concrete to look into. You may enjoy marketing but dislike chasing approvals. You may like managing people and need a workload that leaves enough space for that.

Also include what you enjoy. Which parts of your week would you gladly do more of? What are you doing when you lose track of time?

Pick three moments when you wanted to leave

Look back over the past couple of weeks and find three times when you thought, I can’t keep doing this.

For each one, write down:

• What was happening?
• What specifically bothered you?
• What did you wish you could do instead?
• How often does this happen?

Draw on moments you remember clearly. “I felt stuck on Wednesday” is much harder to work with than “I spent Wednesday rewriting a presentation after three people gave me conflicting feedback.”

Imagine you are a project manager with reasonable hours and a supportive boss. You have begun to wonder whether you chose the wrong career.

Looking back, you recall a meeting about a deadline nobody could change. Then an afternoon spent updating a tracker you would have to chase people to update again tomorrow. You also remember helping a colleague fix a spreadsheet, enjoying yourself, and feeling let down when you went back to your own tasks.

There is a thread worth following: you like solving concrete problems, while much of your role is about coordinating work you cannot directly affect.

You could look into jobs with more hands-on work. You could also talk about changing your responsibilities. Either way, you now have something more useful to say than “I hate my job.”

What are you hoping leaving would give you?

Picture yourself in a new job somewhere else. Six months later, what do you hope has changed?

“More freedom” is a start. Freedom to do what?

Maybe you want to solve problems without asking permission at every turn. Or you want to finish at six and feel fine ignoring your phone. Those wishes would lead you to ask different questions about the next role.

Try finishing this sentence:

I want my next job to give me more room to…

Then think about what would need to be true for that to happen. If you want to create things, learn how much of the role involves making them yourself. If you want more family time, ask what happens when deadlines slip.

I wrote about leaving Google to work for myself in How Did I End Up Here Again?. I gained the freedom to work from anywhere and eventually found myself coding for a customer deadline at 3am in a hostel in Spain. Some familiar demands had come along with me.

“What happens when someone is on holiday?” may tell you more about the freedom you’re seeking than a promise of flexible working.

Consider what you can change from where you are

After you have described what is bothering you, think about which changes would address it.

If you like the work but are overloaded all week, a conversation about priorities and responsibilities might help. If the tasks themselves leave you uninterested, look into roles where the daily work looks different.

Your life outside work belongs in this conversation as well. Maybe the job is reasonably satisfying, but you have stopped doing nearly everything else you enjoy. What would happen if you made room for one of those things again?

You might need a different job and want more life outside it. Those possibilities can overlap.

Money and obligations matter. A salary that supports your household is a substantial reason to stay while you explore. Looking into alternatives does not require setting a resignation date.

If you struggle to imagine what else you would want, I Don’t Know What to Do With My Life: How to Find Your Next Step offers ways to explore possibilities through small experiences.

Choose something that will help you understand more

Go back to the moments you wrote down. In the next couple of weeks, what could you do to explore what they suggest?

Our project manager could ask to own one concrete piece of a project and notice how that changes the experience. They could also talk with someone in a role they're considering and ask about a recent working day, including the tedious parts.

Before you try something, write down the question you want it to answer. Afterward, note what you learned while the details are still fresh. Did you enjoy having more responsibility for the work? Would you want more days like that?

The answers may be mixed. You can want more autonomy and still value the security of your current role. Talking through how those things fit into your life can help you figure out what to try next.

That's part of why I'm building Hazel. She's an AI you can talk to about your life. Bring her the moments you wrote down, what the job gives you, and what you keep wishing were different. Hazel can help you connect those details and explore a next step. When you try something, you can come back with what happened.

If you'd like help working out what you want to change, talk it through with Hazel.