How to Know When It’s Time to Leave Your Job (And What to Do Next)

Q: How do I know it’s really time to leave?

“Maybe you start to think, huh, I’m kind of stagnant here and I’m no longer really growing. There’s nobody here that I can learn from and I don’t really see a position that I can grow into.”

That line from The Unconventional Part hit me because I’ve felt it too. The moment you start saying, I’m not learning anymore, that’s your answer. Growth stops when curiosity does.

You don’t need a dramatic reason to justify leaving. You just need an honest one.

If this sounds familiar, read You’re There for a Reason (Even If You Don’t Know What It Is Yet). It’s about finding meaning in the middle of uncertainty.

Q: What if I’m scared to start over?

“It is so much easier to stay where you are because of all of the things that I have just said that you have to do to find another job.”

Leaving feels impossible until you do it once. The fear doesn’t disappear; you just stop letting it lead.

The trick isn’t to erase fear. It’s to give curiosity a louder voice. The moment you focus on what’s possible instead of what’s predictable, you start moving forward.

Check out How I Turned My Fears Into Reality (And How to Avoid the Same Mistake). That post breaks down how fear quietly shapes your choices if you’re not paying attention.

Q: What if leaving makes me look flaky?

This one gets in your head fast, the fear of what people will think. But here’s the truth: no one’s tracking your timeline the way you think they are.

You’re not supposed to build your career like a staircase. It’s a mix of steps, pauses, and pivots. Some of the most successful people I know have “messy” résumés because they followed growth, not rules.

If you’ve been worried about how your choices look, read How to Show You Care (Without Going Overboard). It’s technically about relationships, but it’s the same principle: authenticity over approval.

Q: What if I have no idea what I want to do next?

“You are at what I am calling the unconventional part. The part where you don’t know what you’re supposed to do or what you want to do or what’s out there for you.”

You’re not broken for not knowing. You’re just in between versions of yourself. Most of us figure out what we want by first finding out what we don’t.

Start by paying attention to what gives you energy again, even outside work. Curiosity isn’t random. It’s direction in disguise.

If you’re figuring things out, start with 7 Lessons I Learned About Confidence from Talking to Girls at Bars. It’s about how small risks build confidence over time.

Q: How do I stop comparing myself to people who seem ahead?

“Why does it feel like they’ve had a promotion and a raise and climbed the ladder to success while I completely don’t?”

Comparison kills clarity. You stop asking “What do I want?” and start asking “What do they have that I don’t?”

The truth is, no one’s ahead or behind. They’re just on their own track. The more energy you spend comparing, the less you have for creating your own momentum.

Read How to Talk to Girls at a Bar (Without Making It Weird). It teaches presence, not performance, which applies to every part of life.

Q: How do I know if I’m making the right choice?

You don’t. And that’s kind of the point.

Every decision that feels uncertain is a test of trust: in your gut, in your instincts, and in your ability to figure it out as you go.

There’s no “right time.” There’s only your time.

When you feel ready, you’ll know.

Notes From Josh

If you’re standing in that in-between space right now, give yourself credit for noticing it. Feeling unsure doesn’t mean you’re off track. It means you’re paying attention to what’s no longer right for you, and that’s where real change starts.

Want to hear the full story? Listen to The Unconventional Part: Figuring Out Your Career When You Feel Lost on Spotify or Apple Podcasts.