I hit my number. My manager told me to do it three more times. I quit.

38 weeks.

That's how long we've been doing this together — you opening this email on a Tuesday, me showing up with the part of the story I haven't told anywhere else.

Today's is one I've sat with for a long time.

My manager sat across from me, smiled, and told me I'd had an incredible year.

He wasn't wrong.

I had done the thing. Hit the number. Proved — to myself and to everyone in that glass-walled office — that I belonged there. That the high school diploma hadn't been a liability. That the woman who walked in nodding at words she didn't know had figured out the Microsoft engine.

My best year ever.

And then he said it:

"You'll need to do this again. At least three more times. Then we can talk about promotion."

I kept my face still.

I said thank you.

I walked out of that office and sat in my car for a long time.

Because here's what he didn't say out loud — what everyone on that team already knew:

Three more years at that performance level, in a cyclical sales environment, was almost impossible. The math wasn't in my favor. The system wasn't designed for the timeline I needed.

And I had other math happening outside that office.

My personal life was in freefall. The equity I had spent years building — staying late for, believing in, deferring other things for — was being divided in a courtroom. All at once, my dream company didn't feel like my dream anymore.

It felt like a ceiling with good lighting.

I loved my boss. Genuinely, deeply loved working for him. I flew to Las Vegas for his wedding. I believed in what we were building. I was proud to be on that team.

Leaving wasn't relief.

It was grief.

And I think that's the part nobody talks about when we discuss career transitions.

We talk about the bad bosses. The toxic cultures. The layoffs that made the decision for us.

We don't talk about leaving something good — because it wasn't going to become great. Because the ceiling was real, even if it was polite. Because you finally did the thing you set out to do and the reward was being told to do it again. Three more times.

That's not a performance problem.

That's a misalignment between your ambition and the system you're inside.

And no amount of working harder fixes a structural problem.

I've told this story from stages across the country. And every single time, someone finds me afterward — a VP, a managing director, a GTM leader — and says some version of the same thing:

"I've never heard anyone say that out loud before."

That's how I know it's not just my story.

Not a pep talk. Not a LinkedIn post about betting on yourself.

I wish I'd had a clear-eyed way to look at what I was actually feeling — separate from the grief of leaving, separate from the fear of what came next — and answer one honest question:

Is this discomfort telling me to push through — or move on?

Those are two completely different instructions.

And most high performers I know — including the ones I work with today — can't tell the difference in the moment. Because the feelings are the same. The doubt sounds identical whether you're about to make the right call or the wrong one.

That's not a weakness. That's what it feels like to be someone with real options and real stakes.

What I eventually learned — the hard way, over the years that followed — is that transition isn't a moment.

It's a process.

And the people who navigate it best aren't the ones who make the fastest decision. They're the ones who get clear on what they're actually moving toward — not just what they're leaving behind.

That clarity doesn't come from thinking harder.

It comes from having the right structure, the right questions, and someone who has sat in a version of that parking lot and can help you see what you can't see from inside it.

Thirty-eight weeks of showing up in your inbox has taught me one thing: most of you already know what needs to change. You just need the structure and the permission to move.

That's exactly what The Activated Leader Transition Program is built for.

It's a 6-week 1:1 experience — 3 coaching calls, 2 video modules, and a framework that helps you move from "something has to change" to a clear, confident next step.

Whether you're navigating a role transition, building something on the side, or sitting in a parking lot trying to figure out if what you're feeling is data — this program was built for that exact in-between.

If you're ready to stop sitting in the parking lot, reply to this email with the word TRANSITION, and let's talk about what's next for you.

See you next Tuesday.

P.S. I've been getting messages from people asking if there's a group version of this work — a cohort where you go through the process alongside other senior leaders in similar transitions.

I'm exploring exactly that for later this year.

If that interests you, reply COHORT, and I'll make sure you're first to know when it opens.

1. The Activated Leader Transition Program
6 weeks. 3 calls. A clear next step. Reply TRANSITION to get started.

2. Keynote Speaking
Bring The Activated Leader to your next event or offsite.
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3. Leadership Workshop
Half-day intensives for teams navigating change.
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