How to Know When It's Time to Leave a Job

14 Mar 2025 #career

I’ve stayed too long at stagnant jobs, and I regret it.

Staying too long at jobs cost me years and thousands of dollars. I left lots of money on the table. It made some of my skills get rusty.

But after connecting the dots, there were signs I failed to notice:

1. You’re not learning anything new

This is the #1 sign to look for. If your daily job becomes boring, that’s a sign. Or stay but diversify your source of joy.

2. There’s no room for growth

“You can build any role you want,” I was told.

That happened at a past job. I rejected the idea of being a team leader. I didn’t like how the role was designed at that place. It was a “wear all hats for the same pay” role.

And when I brought my ideas to the table, they got rejected with a “somebody else is already kind of doing that.” Staff Engineer? Software Architect? Right Hand? All of them.

It was a red flag I failed to notice.

3. It makes you sick

If your job makes you sick, physically or mentally, what other sign do you need? It’s time to take action. It’s time to run. Run, Forrest, run!

You can always get a new job, but not a new body.

4. You’re learning coping mechanisms

“OK, I just sent a message without a period at the end and without capitalizing the first letter,” my friend told me.

He was working from home and I stopped by for a coffee. In the middle of our conversation, he got a message from work and replied from his phone. There’s nothing wrong with that.

But to make sure his boss didn’t notice it, he didn’t add a period at the end of his message. Oh boy! I had just left that job no more than one year before that.

5. There’s no more money

The last time I heard “There’s no more money this year” when asking for a raise, the Hunger Games of layoffs started, until only a few ones were left standing.

I tried to convince myself I could stretch that job for another year or two. Wrooong! Eventually, layoffs knocked at my door too.

6. You have a bad boss

Often it’s hard to leave work stuff at work when going back home. A bad boss (whatever that means to you) will make you feel bad along with the people around you.

7. There’s no willingness to change

If after raising flags with your boss, you only hear “that’s fine. It used to be worse” or anything along those lines, that’s where change dies. Don’t waste more time bringing ideas.

Either you accept things the way they are or disagree with your feet.

8. It’s more important to find who to blame

If something goes wrong, it means there’s a flaw in a standard procedure or a process that let it happen. Finding who to blame only create a toxic work environment. Don’t waste time blaming. Fix the process.

From Brent Ozar, the SQL Server master, I learned that by the time we ask ourselves if we should leave, it’s too late. The best time to look for a job isn’t when you’re desperate. It’s when you don’t need one. Start updating your CV, reflect on what you truly want, and take control of your career. And don’t forget to read the fine print in job descriptions.