Leavers vs. Stayers
Hi! I’m Molly. I write about what it actually takes to lead inside growing, changing companies: the frameworks that help, the honest truth about what it feels like, and the messy work of shaping a career that actually fits.
Lessons is where those ideas live — both the writing and the conversations around it. (If you want to learn more about how Lessons and the community work, you can read more here.)
A close friend of mine was raised by a mom who had one firm rule: you don’t quit what you start. Not piano lessons. Not soccer. Not the miserable summer job he hated.
Decades later, he’s spent most of his career in long tenures — ten years at one company, eight at another. He was taught to endure. And he does.
He’s a stayer.
And I’m not.
Over the years, I’ve come to see that many of us fall loosely into two career archetypes: the leavers and the stayers.
Leavers walk away. When they’ve done what they came to do, when misalignment creeps in, when the mission no longer feels like theirs, they go. It can look impulsive. Sometimes reckless. But for most leavers I know, it’s rooted in something deeper: a fierce internal clarity. This isn’t mine anymore.
Stayers endure. They weather bad managers, strategy shifts, reorgs, and leadership changes. They dig in when things get hard. Sometimes too long. Sometimes just long enough to shape what comes next.
Neither is better. But each comes with a cost, and a different currency of growth.
Leavers: Pros and Pitfalls
Leavers are often builders. They show up with energy, ideas, urgency. They catalyze change. They’re clear-eyed about when things no longer fit — and they’re willing to act on that clarity.
