by 8020thinking | 2025-11-11 17:13:32+00:00
You’ve done it before.

Things are getting tense. Your manager is pushing back on your recommendations. There’s a reorganization coming. Promotion cycles are starting.

This is exactly when you’d have to advocate for yourself. Risk being told no. Make your case. Be visible about what you want.

And this is exactly when you update your resume.

You tell yourself: “This place is going downhill anyway. Time to move on before it gets worse. I deserve better than this.”

And you’re probably right. The company might actually be a mess. Your manager might actually be difficult. The situation might actually be unstable.

But here’s the question you’re not asking: Why do you always leave right before you’d have to fight?

The Pattern You Keep Repeating Let me guess what happens next:

You start interviewing. You get an offer. The new place seems better (clearer leadership, more resources, a role that “really values” what you do.)

You leave. You feel relieved. Validated, even. “See? I made the right call. That old place was a disaster.”

Six months later, you’re doing great work at the new company. Really great work.

Then comes the next reorganization. Or the next difficult conversation with your manager. Or the next time you’d have to ask directly for what you want.

And you start feeling that familiar itch. “Maybe this isn’t the right fit after all...”

The problem isn’t the companies. It’s not even the managers.

The problem is you keep leaving before you find out if you could win.

What You’re Really Avoiding Here’s what staying would require:

Scheduling time with your manager to discuss your future (uncomfortable)

Making a case for why you should lead the new initiative (vulnerable)

Asking directly for the promotion (risking a “no”)

Negotiating for the raise you know you’ve earned (being “difficult”)

Advocating for your ideas when leadership pushes back (conflict)

All of that feels risky. Exposing. Like you’re demanding something you might not deserve.

Leaving feels clean. Leaving feels like taking action. Leaving means you never have to hear “not yet” or “we’re going in a different direction” or “you’re not quite ready.”

If you left before asking, you never have to know if you would’ve gotten it.

And if the place falls apart after you leave? Perfect. You were right to go. The situation really was unstable. It wasn’t about you at all.

Except it was always about you.

What Happens If You Stay Let’s say you don’t leave this time. Let’s say you do the uncomfortable thing instead.

You schedule the meeting. You make your case. You ask for what you want.

Scenario 1: They say yes.

You get the promotion. Or the project. Or the raise. You realize you were more valued than you thought, you just never asked.

All those times you left before? You might have gotten it then too. You’ll never know.

Scenario 2: They say “not yet.”

This is what you’re most afraid of. But here’s what actually happens:

You ask why. You get specific feedback. You learn what would need to be true. You have a roadmap instead of a mystery.

And you have a choice: Work toward it, or decide it’s not worth it and leave with information instead of running from fear.

Scenario 3: They say no.

The hardest one. They don’t see you the way you see yourself. The path you want isn’t available here.

And yes, that hurts. But you know. You’re not wondering. You’re not telling yourself stories. You can leave with clarity instead of running from discomfort.