The Self-Led Life
Notes from the Messy Middle
Getting Comfortable Being Uncomfortable
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Getting Comfortable Being Uncomfortable

The power of showing up when it would be easier to walk away.

Hey friends. I hope you’re doing well and soaking in the start of fall… even if it doesn’t exactly feel like it yet.

It’s still about 85 degrees here in Ohio, but I’ve fully embraced the season anyway. Pumpkins are out around the house, Halloween costumes are ordered (we’re going as Super Mario characters this year!), and thanks to my girls, our home has been decked out with ghosts and pumpkin spice candles since September 1st. No complaints here, it keeps me present and I do love fall.

Right now, we’re in the final stretch of softball season. With three kids playing, that means eight or nine games a week. Playoffs are around the corner, which will provide a little breathing room soon… before basketball season begins, of course.

Speaking of basketball, my oldest daughter recently started a new clinic. She was so excited. Last year was her first season playing and she absolutely fell in love with the game. This clinic is meant to help prepare her for middle school tryouts, and she couldn’t wait to get started.

But when we arrived for her first session, we realized she was the only girl who had signed up. I watched her clutching her ball, eyes scanning the gym, trying to decide whether to stay or walk back out.

And oh, do I know that feeling. Standing in a room full of people and feeling completely out of place. I’ve been there more times than I can count.

She was nervous. I could see it. But she stayed.

Not without a little encouragement, but she stayed. She played. She kept up. The boys treated her like one of their own, and the coach was kind and intentional. When it was time for week two, she didn’t hesitate nearly as much. She showed up again.

I’m so proud of her, and even better, she’s proud of herself.

Watching her reminded me how important it is to get comfortable being uncomfortable. We all step into spaces that feel unfamiliar or intimidating. It’s never easy, but that’s where growth lives, in that tension, in that uncertainty. The other side of discomfort is strength, confidence, and purpose.

And that’s really what Living on Purpose is about: showing up with intention, remembering who we are and what matters most, and trusting ourselves even when it feels hard.

You determine your life’s direction. The question is: how uncomfortable are you willing to get in order to grow into it?

🎧 In this week’s episode of the Living on Purpose podcast, I’m reading the first chapter of my book, Living on Purpose.

As you listen, think about your own version of that basketball court, the place that’s inviting you to step in, stay present, and grow. How willing are you to put yourself out there for the sake of growth?

Let’s get started.

💛 Catch up on past episodes of Living on Purpose here → https://eringregorycreative.substack.com/publish/posts/detail/173189448?referrer=%2Fpublish%2Fposts%2Fpublished

This show is produced by Mike Gregory at https://www.undergroundfunkmonk.com.


Erin Gregory Creative is the studio of Erin Gregory, a writer, marketing strategist, and full-time communications and branding consultant for mission-driven organizations.

She’s also the host of Notes from the Messy Middle, a podcast on Substack exploring creativity, communication, and intentional living. Her work connects personal growth with strategic storytelling, helping people and brands speak with more clarity and purpose.

Read more at www.eringregorycreative.com or connect on LinkedIn.

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