Episode 37

Feeling Regret? Here’s Your Permission Slip to Move Forward

Published on: 28th January, 2026

It's totally okay to regret a past version of yourself, and that's the big takeaway from our chat today. We’re often told to let go of regrets, but let’s keep it real—sometimes, those feelings can actually help us grow. I’ve had my fair share of moments where I wish I’d handled things differently, whether it was staying silent when I should’ve spoken up or choosing fear over authenticity. But here’s the kicker: regret isn’t the enemy; it’s just a sign of growth and reflection. So, if you’re feeling that weight today, give yourself some grace—embrace it, learn from it, and know that you can still love who you’re becoming while acknowledging who you were.

Takeaways:

  1. It's completely normal to look back and feel regret about past choices we made.
  2. Regret serves as a guide for our growth, helping us understand how we've evolved.
  3. Embracing regret doesn't mean we dwell on it; it’s about learning and moving forward.
  4. We can hold both regret for our past and love for our present self simultaneously.
Transcript
Speaker A:

Hey, this is.

Speaker A:

It's okay if bite sized permission slips.

Speaker A:

I'm Matt Gilhooley.

Speaker A:

And today's permission.

Speaker A:

It's okay if you regret a past version of yourself.

Speaker A:

We're told not to have regrets, that every past version of us was just doing their best.

Speaker A:

And sure, sometimes that's true.

Speaker A:

But if I'm honest, there are versions of me that I do regret.

Speaker A:

Times when I stay quiet, when I have spoken up.

Speaker A:

Times when I hurt people because I was hurting.

Speaker A:

Times when I chose fear over authenticity.

Speaker A:

Regret isn't comfortable, but it's also not the enemy.

Speaker A:

It shows us where we've grown, where we've learned, where we've become someone that we're proud of.

Speaker A:

It's okay to look back and think, I wish I had handled that differently.

Speaker A:

That's not self loathing.

Speaker A:

That's reflection.

Speaker A:

The key is not getting stuck there.

Speaker A:

Not defining yourself by who you used to be.

Speaker A:

The past versions of you, the ones you regret, they got you here.

Speaker A:

To this moment, to this awareness, to this growth, you can hold regret and still hold love for yourself.

Speaker A:

Both can be true.

Speaker A:

So if you're feeling that regret today, give yourself grace.

Speaker A:

You're allowed to feel it.

Speaker A:

You're also allowed to grow from it.

Speaker A:

So if you're up for it, tell yourself, I give myself permission to regret who I was and still love who I am becoming.

Speaker A:

That's your permission slip, friend.

Speaker A:

Tuck it in your pocket and I'll see you next time.

Next Episode All Episodes Previous Episode
Show artwork for It’s Okay If… Permission Slips for Mental Health, Self-Acceptance, and Growth

About the Podcast

It’s Okay If… Permission Slips for Mental Health, Self-Acceptance, and Growth
Bite-Sized Permission Slips for Real Life
What if you didn’t need to have it all figured out?

It’s Okay If… is your weekly permission slip to be human.

I created this short-form podcast as part of my own healing process — a way to slow down, process grief, and reconnect with what I was feeling.

Each bite-sized episode (just 3 minutes or less) offers a short, honest reflection to challenge perfectionism, embrace your real self, and remind you that you're not alone.

Hosted by Matt Gilhooly, creator of The Life Shift Podcast, this show delivers midday nudges of self-acceptance, insight, and calm – whether you're walking the dog, stuck in traffic, or just need a breath.

No fluff. No fixing. Just a moment of truth.

New episodes every Wednesday at noon. Follow wherever you get your podcasts.

About your host

Profile picture for Matt Gilhooly

Matt Gilhooly