Permission Comes First, And Clarity Later: A Lesson from Cheryl Strayed
When everything fell apart, Cheryl Strayed didn’t cling to what was left. She chose something braver. This is what giving yourself permission to try something wild can look like in real life.
Cheryl Strayed was in her mid-20s when her life cracked open.
Her mother died. Her family unraveled. Her marriage ended. She made choices she later wrote about with brutal honesty; choices involving drugs, affairs, trying to outrun a grief that wasn’t going anywhere.
It wasn’t a tidy rock-bottom. It was just… a mess.
And here’s the part that stays with me: she didn’t fix it first. She didn’t clean up her résumé, or sit down and map out a five-year recovery plan. She didn’t wait until she felt strong to make a move.
She signed up to hike the Pacific Crest Trail.
Cheryl wasn’t an experienced backpacker. In fact, she says she overpacked so badly she could barely lift her pack. She lost toenails. She cried.
But she kept going.
What moves me most isn’t that she finished, but that she allowed herself to begin.
There’s a moment in her book, Wild: From Lost to Found on the Pacific Crest Trail where it’s clear she still doesn’t know what comes next. There’s no promise waiting at the end of the trail. No guarantee that she’ll become a bestselling author. No neat redemption arc.
Just a woman who understands that the life she had is gone, and that staying in the wreckage isn’t an option.
Now, she was 44 by the time Wild was published. The meaning of it took almost twenty years to unfold. Cheryl’s brave act didn’t instantly deliver clarity. It didn’t immediately produce a new identity.
ICYMI:
Giving herself permission to take those steps moved her out of a life that wasn’t working, and gave her something true to build from later.
Midlife has a funny way of bringing us to similar crossroads. The job looks fine. The marriage is “okay.” The house is paid for… from the outside, it all checks out.
And yet something inside becomes restless.
We tell ourselves we need a better plan before we pivot. More savings. More certainty. We need more proof that the next version will work and besides, things aren’t “that bad” so do we really need to make that change at all?
But maybe we just need to admit the truth first, and consent to moving in a new direction without a clear view of what lies ahead.
Maybe your version of the Pacific Crest Trail isn’t 1,100 miles on foot; maybe it’s saying no to the promotion instead. Or booking the one-way ticket without having the entire itinerary figured out.
'Maybe it’s letting the grown kids solve their own problems, or starting the thing you feel wildly underqualified to start.
You might still feel lost while you’re doing it. Cheryl did, in ways that weren’t even clear at the time. But that doesn’t mean you’re wrong.
Courage doesn’t have to look like a giant leap into the unknown. Sometimes it’s just giving yourself permission to take that first step, and believing that clarity comes with experience.
✌🏻 Miranda
Right On Time is our weekly series of lessons in courage, clarity, and change for those rewriting their story — in two minutes or less.