When Freedom Feels Like Regret

What Happens After You Choose Yourself

Everyone talks about making the choice (including me). Leave the relationship. Quit the job. Set the boundary. Choose yourself. And yes, that moment matters. The decision is everything.

But here’s what almost no one tells you: Freedom initially can feel like regret.

The brave choice you finally made? At first, it might feel like the worst mistake of your life.

The Mythology vs. The Reality

We’re sold this story that when you finally choose yourself, you’ll feel liberated. Empowered. Free. The Instagram version of transformation: You walk away, the sun comes out, you feel light and clear and certain you did the right thing.

Maybe eventually you do feel that way.

But first? First you feel unmoored. Untethered. Like you’ve lost all your reference points and you have no idea who you are without the structure you’ve been living inside of.

The Death of “We”

When I divorced, I knew it was the right thing. I knew it. And yet I felt incredibly untethered.

I went from 35 years of “we” to “me” — and I had no idea who I was. That’s not just a logistical shift. That’s an identity death.

For decades, my life was oriented around us. Our plans. Our home. Our story. My role as wife, as partner, as the person who held things together. And suddenly: none of that existed anymore.

I wasn’t just losing a marriage. I was losing the entire architecture of my identity. Who am I when I’m not half of a we?

When Your People Can’t Hold You

And then there was my family. They didn’t know how to be supportive. At times they did things that made me feel like he was more important than I was. The person I was trying to survive leaving was the one they were protecting.

That’s its own kind of assault.

The moment you realize that even the people who love you might not be able to show up for your liberation — because it threatens their comfort, their story, their own avoidance. Family systems can’t always metabolize one person’s transformation. Because when you change, it destabilizes everyone else’s equilibrium.

They want you to be okay. But they also want things to stay familiar. And your freedom feels like a threat to their stability.

The Necessity of Witnesses

I was fortunate. I had a couple of friends who held me up. They told me I was brave. That they were proud of me.

In the free fall, when every external signal was telling me I’d made the wrong choice, I needed someone to mirror back: No. You’re not crazy. This is hard because it matters. Keep going.

That’s sacred.

When you can’t yet see your own courage, you need people who can see it for you. Not people who tell you what to do. Not people who try to fix it or make it easier. Just people who witness you and say: I see you. You’re not alone. This is what bravery looks like.

The Book That Changed Me

I found a book. Spiritual Divorce by Debbie Ford. The first few pages brought me to my knees. Not because they were comforting. Because they were true. They named what I was feeling — the grief, the shame, the terror, the desperate need to understand how I got here and who I was going to become.

That book was the beginning of more for myself. Not more answers. More willingness to ask the questions. More capacity to sit in the void without trying to fill it. More trust that this falling apart was also a falling together.

I found a therapist. Eventually I found coaching. And slowly, slowly, I started to rebuild — not who I was, but who I was becoming.

Becoming Your Own Cheerleader

But here’s the thing that surprised me: The lack of applause — the absence of my family’s support, the silence from people I thought would celebrate me — it didn’t break me.

It inspired me to keep going.

Because I realized: I couldn’t wait for external validation to know I’d made the right choice. I had to become my own cheerleader. I had to learn to approve of myself. Not in some self-help, affirmations-in-the-mirror kind of way (although I use those too). But in a bone-deep, I trust myself even when no one else does kind of way.

That’s the real work of choosing yourself. Not the initial decision. But everything that comes after.

The Free Fall

Choosing yourself can feel like free fall. You leave the familiar — even when it wasn’t working, even when it was harmful — and you’re suspended in mid-air with nothing to hold onto. You don’t know who you are yet. You don’t know what comes next. You can’t see the ground.

And everyone around you is asking: Are you sure about this?

This is the moment when most people retreat. Not because they made the wrong choice. But because the void is unbearable. Because freedom without form feels like chaos. Because transformation is supposed to feel good, and this feels like falling apart.

What You Actually Need

You need people who can hold you without trying to save you. People who trust that you can survive the free fall even when you’re not sure you can. People who reflect back your courage when you can’t feel it yourself. You need to grieve what you’re losing — even the parts that were hurting you — because loss is loss, and your body doesn’t care if you made the “right” choice.

You need to let yourself not know. Not have it figured out. Not land gracefully.

You need to stop performing certainty for everyone else and admit: I’m terrified. I don’t know who I am. And I’m doing it anyway. And you need to practice — every single day — trusting yourself even when there’s no applause.

The Truth About Freedom

Freedom doesn’t feel like liberation at first. It feels like vertigo. It feels like you’ve lost your footing and you’re reaching for something solid and finding only air. It feels like regret, like loneliness, like maybe you’ve made a terrible mistake.

And then, slowly — if you can stay with it, if you can let yourself fall without grabbing for the old life — it starts to feel like space. Room to breathe. Room to discover. Room to become.

But you have to weather the void first. You have to learn to hold yourself when no one else can. You have to trust that the free fall is not failure. It’s transformation. And transformation always feels like dying before it feels like living.

The Invitation

If you’re in the void right now — if you made the brave choice and it doesn’t feel brave, if you’re untethered and terrified and wondering if you made a mistake — I want you to know: You didn’t make a mistake. This is your right timing.

This is what it looks like to choose yourself. This disorientation. This grief. This free fall.

Stay with it.

Find the people who can witness you without trying to fix you. Let yourself grieve what you’ve lost, even if what you lost was hurting you. And practice — every day — becoming your own cheerleader. Not because it feels good. Because it’s what keeps you going when nothing else does.

The applause might never come. Your family might never understand. The world might never validate your choice. And you’ll do it anyway.

Because you’re learning something they can’t teach in any workshop or book:

How to trust yourself when there’s no one else to trust.
How to hold yourself when you’re falling.
How to choose freedom even when it feels like regret.
That’s the real work.
And you’re already doing it.

You Don’t Have to Do This Alone

This is the heart of The Art of Self-Approval™ — the work I guide women through, the space I hold, the witnessing I offer.

Not how to make the decision — you already know what you need to do.

But how to hold yourself after the decision. How to become your own witness when the applause doesn’t come. How to trust yourself in the void when everything feels like regret.

Because the bravest thing you’ll ever do isn’t leaving. It’s staying with yourself after you leave.

If you’re in the free fall right now and you need someone to hold you steady while you find your footing, I’m here.

With love,

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