The Art of Letting Go
Founders tend to carry everything— ideas, deadlines, client expectations, screenshots, old notebooks, unresolved team tension, a folder labeled “Someday,” and five others labeled “Important.” You carry not only what you’re doing, but everything you haven’t done yet.
But what if letting go is exactly what creates space for your next great move?
At our recent ELEVATE: Founder Wellness session, we explored this exact topic—not from a theoretical perspective, but as a practical, embodied strategy for sustainable leadership and inner stability.
And truth be told, we approach this topic in a way that is simply human, key for living a thriving life in general, whether or not you give yourself the “founder” title.
Let’s dig in.
“What If Letting Go Is Actually the Leadership Move?”
That question from guest facilitator Regina Carey, M.Ed. got us going.
Letting go doesn’t mean giving up. It means creating room—for clarity, creativity, and energy to flow again.
“Burnout doesn’t come from doing hard work,” Regina reminded us.
“Burnout comes from carrying too much—yesterday, today, and tomorrow’s weight all at once.”
Letting go is a power move. It’s the conscious decision to stop white-knuckling your life. It’s about asking yourself:
What am I holding onto that’s no longer useful?
Things We Hold (That Hold Us Back)
During the session, we did something deceptively simple. Each participant was asked to grab the nearest item that could be classified as clutter. A stack of business cards. Desktop files. A junk drawer of mental tabs. A complicated relationship. A guest bedroom filled with unfolded clothes.
What shows up when you try this exercise isn’t just physical—it might be emotional, digital, interpersonal. It requires you to ask yourself why you have those things, and what you’re waiting for before doing something about them.
“Even the tabs we keep open or the files we dump into a folder and pretend don’t exist—we feel those. Sensitive people, especially founders, carry it all.” Regina told us.
The Three-Part Practice: Pause, Purge, Promise
Regina outlines a simple 3-step framework for release:
Pause – Carve out a moment to breathe, move, notice.
Purge – Identify one thing—digital, emotional, physical—you can let go of today.
Promise – Make a decision and commit to action.
Letting go doesn’t require a dramatic life change. It can start with deleting old desktop files. Having an overdue conversation. Emptying one box in your closet. You can commit to getting rid of 1 physical object, or spending 5 minutes a day cleaning out your camera roll.
“When you release even one thing,” Regina said,
“you free up energy for the things that actually matter.”
Closing Wisdom: The Fall, and the Flight
One quote shared during the session still echoes:
“To be fully alive, fully human, and completely awake is to be continually thrown out of the nest.”
— Pema Chödrön
That’s what growth looks like for founders. You don’t always get a map. You just get the push—and the choice to trust the freefall.
Whether you're cleaning out a closet or closing a chapter in your life, the act of letting go is what lifts you.
Take This With You
The other half of Regina’s framework was:
Delete
Delegate
Decide
This is the call to action. So, here’s your challenge this month:
Choose one thing to release.
Maybe it’s a habit, a digital pile-up, an emotional weight, or literal clutter in your office that’s clogging your mental space without you even realizing it.
Then—decide how and when you’ll release it.
Letting go isn’t weakness.
It’s clarity.
It’s strength.
It’s the beginning of something better.
Join us for more.
If this content resonates, make sure to get connected for more Flying with Founders resources.
Sign up for next month’s ELEVATE event.
Curious about a deep dive into founder wellness, goal-setting, and leadership strategies? You should probably be on our next Founders Retreat. Get in contact today to learn about El Salvador - Jan 2026!
