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“What are three things you’re struggling to jettison?”
That’s the question we posed to the thirty people who attended last year’s Simplehaven retreat in Ojai, California.
On the first morning—under the oak trees and dappled sunlight at the Ojai Art Center—we asked each participant to write down three things they wanted to let go of that weekend.
Some answers were familiar:
“My attic is full of my dead parents’ stuff.”
“I want to ditch my fifteen-year career.”
“I need to let go of a toxic family member.”
Then one woman, Gina, wrote something that stopped me cold:
“My hair.”
Huh?
Gina was a beautiful woman with a beautiful head of hair. I didn’t get it. Why let go of something that seemed to serve her so well?
Over the weekend, Ryan, T.K., and I worked through each person’s list. When we finally got to Gina, it became clear: it wasn’t her hair she wanted to release—it was the identity tangled up in it.
Her hair was just the symbol.
She wanted to let go of who she had been so she could move forward as who she was becoming.
That realization felt familiar.
Fifteen years ago, when I began minimizing my possessions, I wasn’t just decluttering stuff—I was untangling stories. My belongings had entwined with my identity, and I couldn’t move forward until I loosened that knot.
On the final day of Simplehaven, I predicted that Gina would email us in a few months saying she’d trimmed a few inches off her hair. That felt like a win.
Then something unexpected happened.
As everyone was preparing to leave, after the retreat’s capstone musical performance, Gina asked if anyone had a pair of clippers.
Someone did.
Without ceremony or prompting, Gina shaved her head right there under the oak trees.
For a moment, I considered stopping her—Are you sure?—but I didn’t want to interrupt an act of letting go.
Everyone gathered as her hair fell to the ground.
With it went her old identity.
She looked lighter. Freer. Radiant.
Sometimes letting go isn’t subtle.
Sometimes it’s decisive.
Sometimes it’s exactly what you need.
Of course, you needn’t shave your head.
But you might ask yourself:
What am I holding onto that no longer reflects who I am?
And what would happen if I finally let it go?
On May 2–4, 2026, thirty people will spend three days in Ojai with Ryan, T.K., and me—creating space to let go and make room for what matters. If you’d like to join us, you can learn more about the Simplehaven retreat here.
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