"Don't quit" is pretty terrible advice.

Hello Friend!

I heard someone tell a story recently that I can’t shake.

She walked into her boss’s office almost ten years ago to resign. Stable job. Good trajectory. She was leaving it to chase something most people had never heard of.

She expected a lecture. The gap in her resume. The sunk cost of her degree. The talk about being sure.

Instead, her boss congratulated her. And then told her about the thing she had never done decades earlier because it seemed too impractical at the time. Something that caused her great regret.

That’s the part that got me. The boss wasn’t worried about her employee’s future. She was still carrying her own past.

I’ve sat across from a lot of executives who are carrying the same thing. They’re 44, 51, 58. They’ve built something impressive by every measure that shows up on a resume.

And somewhere in the last two years, a voice inside started asking whether any of it still fits.

They don’t say “I want to quit.” They say “I’m just tired.” Or “I think I need a sabbatical.” Or my favorite, “It’s probably just a phase.”

It’s not a phase. It’s data.

We’ve confused stamina with tenacity

Somewhere along the way, we decided that staying is the virtue and leaving is the failure. That grit means gripping. That the person who endures the longest wins something.

But look at what actually gets rewarded on the other side of a hard decision.

Show me the 44-year-old who walked away from the stable job everyone told her to keep. The 51-year-old who quit trying to be someone she wasn’t, no matter how long she’d practiced it. The 58-year-old who quit the title he’d spent two decades collecting, the day it stopped meaning anything.

People call that giving up. It’s the opposite.

Real tenacity isn’t staying somewhere long after it stopped serving you. It’s having the nerve to quit the wrong thing so you can finally chase the right one.

Stephen Covey wrote about climbing the ladder of success only to discover it was leaning against the wrong wall. Everyone nods at that line. Almost nobody acts on it. Because unlearning a ladder is harder than climbing one.

I know this personally. When I left my C-level role after eighteen years, I didn’t feel brave. I felt exposed. My identity had been fused to a title, an org chart, and a badge that got me into a building. Take those away, and I genuinely didn’t know who I was for about eighteen months.

In fact, my LinkedIn headline read, “4x CIO” for the longest time!

That’s the real fear underneath all of it. Not the money. Not the health insurance. It’s the question of who you are when you stop being who you’ve always been.

What’s actually worth quitting

The instinct is to quit the big thing first. Blow it up. Announce it.

Don’t. Start smaller and pay attention to what fills the space.

Quit the identity, not the job. Before you touch your employment status, notice how often you introduce yourself by your title. Try this: At the next three social events, describe what you’re curious about instead of what you do. Watch what happens to the conversation. Watch what happens to you.

Quit the thing you’re good at but don’t love. Competence is a trap. We keep doing the thing we’re praised for long after it’s stopped feeding us. Try this: Look at your calendar from the last two weeks. Circle the meetings where you were valuable. Star the ones you were alive for. If those don’t overlap, you have your answer.

Quit predicting the future. Most executives I coach are stuck because they’re trying to see the whole staircase before taking one step. Try this: Name the smallest experiment you could run in the next 30 days that gives you real information. Not a plan. An experiment. Fifteen minutes of doing beats fifteen hours of thinking.

Quit the comfort you’re clinging to. There’s something you hold onto that isn’t serving you. You already know what it is. Try this: Write it down. Just the one thing. Then tell one person you’re putting it down.

Here’s what I want you to hear. Don’t quit because something is hard. Hard is often exactly where the growth lives.

Quit when it’s no longer serving you.

You will almost never regret quitting the wrong thing so you can finally chase the right one. What people regret is the years they spent being loyal to a version of themselves that expired a long time ago.

The nervousness you feel reading this? That’s not a warning.

That’s a signal.

Live fuller. Love what you do.

Your coach,
Chris

P.S. If you’re sitting with something you know you need to put down but can’t quite say out loud yet, that’s usually the conversation worth having. You can grab a clarity call with me here, and I’ll happily be your brainstorming partner.