Krista O'Reilly-Davi-Digui: Embracing Midlife with Joy and Freedom

“It is time to search out your uniqueness, applaud and acknowledge yourself, and let your own light shine.” ~ Debbie Ford

Guest Introduction: 

Welcome to Exploring the Seasons of Life: Travel Edition! I’m Cindy MacMillan, and it’s an absolute joy to share this adventure with you.

Travel isn’t just about where you go—it’s about who you become along the way. And I’m so glad you’re here, ready to explore, dream, and discover.

After today’s conversation with Joyful Living Educator, Krista O'Reilly-Davi-Digui, I’ll be taking a break from recording new episodes as I reimagine and rebrand the podcast. This pause is intentional—because just like travel, growth happens when we give ourselves space to reflect, refine, and create something even more meaningful.

Thank you for being part of this journey. I can’t wait to share what’s next!

So, grab your coffee, get comfy, and let’s dive into the incredible possibilities that await.

It’s my pleasure to formally introduce my guest.

Krista O'Reilly-Davi-Digui offers her work as a writer, mind-body coach, and Joyful Living Educator. Through story, grief and trauma-informed education, and brave community, Krista’s words and work empower midlife women to befriend their True Selves and (re)claim freedom, wholeness, and joy. Connect with her at alifeinprogress.ca.

Here’s a glimpse of our conversation: 

2:30 My background is in education. I chose to stay home and homeschool my children, but as I approached 40 and faced my own midlife crossroads, I had a very clear knowing that it was time for me to go back to school and step into that dream number two.

4:17 I had to remind myself that I wasn’t claiming to have it all figured out—I was simply acknowledging what I needed.

5:37 If I’m honest, I never approach things head-on, like saying, “We’re going to learn about joy.” Many people admit they don’t know how to access joy or where to begin. But to me, that feels too big and elusive.

Instead, I start with something more foundational—building a friendship with ourselves first.

16:40 Joy is one of the most vulnerable emotions. Like happiness, many people keep it at arm’s length because allowing themselves to feel too good can be scary. There’s often a fear—what happens when the next bad thing comes?

18:42 Some seasons feel rockier, while others are more intimate and comfortable. But like any relationship, it requires attention—an investment of energy and a choice to show up and practice. It’s not like signing a marriage certificate and assuming no more effort is needed. It takes ongoing work, which makes it vulnerable.

29:12 Inner child work isn’t a primary focus of my approach, but it naturally emerges along the way.

35:50 One of the root stories I grew up with was that being good and compassionate meant giving everything away. Over time, I had to learn to hold onto some of my money—not giving away every moment or every penny—for my own well-being and the stability of my children.

41:44 I primarily work with people in two ways: one-on-one coaching and my Brave and Beautiful community, which is designed for midlife women—mainly in their 40s, 50s, 60s, and early 70s, though there are some outliers. I let people decide for themselves if it’s the right fit, as long as they know my work is centered on the needs and experiences of midlife women.

You can find Krista O'Reilly-Davi-Digui at:

Website | Instagram | Podcast

Thank you so much for joining me on Exploring the Seasons of Life: Travel Edition. I’m Cindy MacMillan, and you can find me at PangeaWorldTravelAgency.com. If you enjoyed this episode—and I truly hope you did—be sure to hit the subscribe button so you never miss an episode.

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Until next time, keep exploring, stay curious, and take care!