Permission to Become Someone New for the Twenty-Third Time

For most of my twenties, I thought I was lost.

To be fair, so did everyone else.

I had a messy car.

I lost my keys.

My shoes routinely disappeared.

I bounced from hobby to hobby, business idea to business idea, dream to dream.

The adults around me worried.

They wanted me to pick something.

Stick with something.

Finish something.

Find my path.

I wanted that too.

I remember feeling like everyone else had somehow been handed a map while I was wandering through the woods hoping to stumble onto mine.

At one point, I enlisted in the Army.

In hindsight, it feels like a spectacularly permanent solution to what was probably a temporary feeling.

I thought maybe what I needed was discipline.

The Discipline I Didn’t Know I Had

Structure.

Someone else to tell me where to be, what to wear, and what came next.

If I could just become disciplined, maybe I’d finally become successful.

Maybe I’d finally become…someone.

But here’s what I’ve realized years later.

I wasn’t undisciplined.

I was simply disciplined in ways no one around me knew how to measure.

I could spend hours teaching myself something new.

I’d become completely absorbed by a project that fascinated me.

I’d throw myself into a new hobby with an intensity that looked suspiciously like obsession.

I read.

I created.

I explored.

I wondered.

I wandered.

People saw inconsistency.
I was practicing curiosity.

People saw distraction.
I was following inspiration.

People saw someone who couldn’t settle down.
I was becoming.

Thankfully, not everyone saw me that way.

Whenever I worried that I wasn’t following the “right” path, my dad would shrug and say something I’ve never forgotten.

“There Is No Yellow Brick Road”

At the time, I don’t think either of us realized how much I needed to hear that.

There wasn’t one correct career.

One perfect identity.

One straight line I was somehow failing to find.

There were just choices.

Experiences.

Detours.

Curiosities.

Turns out, there was never supposed to be a yellow brick road.

There was only the one I made by continuing to walk.

Maybe I Was Never Lost at All

For years, I described myself as lost.

Now I think I was something else entirely.

I was the wandering woman.

Learning.

Experimenting.

Collecting pieces of myself before I knew what picture they would eventually make.

The older I get, the more I think we’ve done ourselves a disservice by treating wandering like failure.

Children wander because they’re curious.

Artists wander because they’re looking.

Scientists wander because they’re asking better questions.

Gardeners wander.

Writers wander.

Travelers wander.

The people who discover new things rarely walk in straight lines.

Why did we decide adults weren’t allowed to?

When I look back now, I don’t see a woman who couldn’t make up her mind.

I see someone trying on lives until she found the ones that fit.

Every business taught me something.

Every hobby became part of me.

Every version of myself left behind a useful piece.

The woman who quit drinking.

The woman who started gardening.

The woman who fell in love with golf.

The woman who writes essays instead of business plans.

None of them erased the versions that came before.

They simply added another layer.

Maybe that’s what becoming yourself actually is.

Not uncovering one final, authentic version.

But giving yourself permission to keep meeting the next one.

I’ve become someone new more times than I can count.

And if I’m lucky, I’ll do it twenty-three more times.

Because becoming someone new isn’t an admission that the old version was wrong.

Sometimes it’s simply the reward for having the courage to keep wandering.

Permission to Wander

🎟️ Permission Slip

Permission to wander without calling yourself lost.

Not every detour is a mistake.

Sometimes you’re simply collecting the pieces of the person you’re becoming.

Every Monday morning, I send one honest letter about midlife, reinvention, Storybook Hill, sobriety, slow living, and the messy process of becoming more yourself.

No productivity hacks. No manufactured urgency. No pretending certainty comes first.

Just a thoughtful place to land before the week gets loud.

Join 550+ women who have made Mondays something worth opening again.

Every Monday morning, I send one honest letter about midlife, reinvention, Storybook Hill, sobriety, slow living, and the messy process of becoming more yourself.
No productivity hacks. No manufactured urgency. No pretending certainty comes first.
Just a thoughtful place to land before the week gets loud.

Join 550+ women who begin their week here.

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