How to Know It’s Time to Let Go
There’s a moment every leader faces — and every human, too — when holding on starts to feel heavier than letting go.
Sometimes it’s a role that no longer fits.
Sometimes it’s a plan that doesn’t serve you anymore.
And sometimes, it’s a person or season that shaped you deeply… and is now gone.
Letting go isn’t weakness. It’s wisdom. But it’s a wisdom that comes wrapped in grief.
The leadership myth of endurance
We’ve been taught to equate leadership with endurance — that “strong” means staying, that quitting means failing.
But real leadership isn’t about clinging to what was. It’s about recognizing when the chapter has ended and choosing to honor the story anyway.
Because sometimes, the bravest thing you can do is put the clipboard down, unclench your jaw, and whisper, “This is complete.”
The personal side of letting go
This lesson has been especially present for me this season.
As we move toward the holidays, I’m grieving my mom — my Thanksgiving partner in crime.
We always spent the day together, just the two of us, in some cozy restaurant that didn’t require dishes or drama. We’d order a pescatarian meal for her, something decadent for me, double the dessert—and toast it all with a glass of pink champagne. 🍾
This year, even though I’ll be surrounded by friends who feel like family, her seat will be empty. And my heart will be full.
And while the world rushes toward celebration, I find myself learning again what it means to release — to let go of traditions that once defined “home” and to make space for something new.
How leaders know it’s time
Whether you’re letting go of a role, a relationship, or a rhythm, a few truths tend to surface when it’s time:
You’re managing more than you’re leading. You’re maintaining instead of moving forward.
You’re constantly justifying your effort. You spend more time convincing yourself to stay than feeling glad you did.
You’ve stopped growing. The challenge has turned into a cage.
Peace feels farther away than it should. You’re successful on paper but restless in spirit.
If any of these feel familiar, it might be time to loosen your grip — not because you failed, but because you’ve fulfilled your part.
Letting go with gratitude
Here’s the paradox: letting go doesn’t mean erasing what came before. It means acknowledging its impact and its impermanence.
I’m grateful for every Thanksgiving with my mom — for the laughter, the pink bubbles, her sweet smile that made the waiters smile back. I carry all of that forward, even as I set down the expectation that holidays will ever look the same again.
Grief and gratitude can hold hands. They often do.
A reflection for this week
If something in your life or leadership feels like it’s asking to be released, try this journal prompt:
“What am I holding that’s already done its work in me?”
You don’t have to let go all at once. Just notice what wants to loosen.
Sometimes the first act of freedom is simply admitting you’re ready.
Because leading with heart means leading through change —
and trusting that what falls away creates room for what’s next.
If this resonates, forward it to someone else in a season of release. We’re all learning to let go of something — and no one should have to do it alone.
