Her Comeback: Transforming Your Life After 50 - hercomebackpodcast.com

Season 2, Episode 1

Guest: Cheryl Dillon

Founder of Funderful Experiences & Connected Hearts Community

Summary

In this powerful season premiere, host Michelle Thompson welcomes Cheryl Dillon, who transformed her life in her 50s by deliberately designing her next chapter instead of waiting for change to happen. Cheryl shares honest, vulnerable insights about making the shift from "doing the right things" to "doing YOUR thing"—and why midlife is the perfect time to start.

🔑 Key Takeaways

The Wake-Up Call Cheryl's pivotal realization: "If I want my life to be different, now's the time to do it, because if not now, then when?" She stopped waiting for life to feel different and started designing it herself—using the self-awareness and emotional intelligence that come with age.

Breaking Free from External Validation For decades, you've been the "good girl, good wife, good daughter." Cheryl asks: "Whose beliefs were those? Whose expectations were those?" You deserve to do things YOU love and be happy. This isn't selfish; it's essential.

The Pattern-Breaking Principle "If you keep doing what you're doing, you're gonna keep getting what you're getting." Cheryl saw patterns in older relatives she didn't want to repeat and made bold moves to change course. What patterns are you unconsciously following?

Connection Over Therapy Many midlife women crave deep conversations but don't need clinical help—they need authentic community. What's missing: emotional safety, vulnerability without judgment, and conversations beyond surface-level topics.

The Resilience Secret Be your own best friend. During transitions, practice self-trust, self-love, and self-care. Treat yourself the way you expect others to treat you. When you do this, you'll attract people and situations that mirror that care back. Resilience comes from within.

Identity Loss Is Real Whether you're an empty nester, divorcing, widowed, retiring, or looking in the mirror wondering "what happened?"—these transitions are like "little deaths" requiring grief. But after grief comes opportunity to design what's next.

From Complacency to Action Post-pandemic, Cheryl lost motivation—preferring sweatpants at home. She pushed through by getting certified in event planning and launching her business. Sometimes you need new skills to build your new life. Connection and transformation require bold moves and conscious decisions.

Overcoming Past Hurts Cheryl admits she was "scared of groups of women" due to competition, gossip, and exclusion. But she intentionally built the supportive community she always wanted. You can create something different now.

Connect with Cheryl

The Uplift Newsletter: Weekly inspiration and practical tips Subscribe: funderfulexperiences.com/get-the-uplift

Connected Hearts Community: Face-to-face membership for women 50s-60s Location: Coastal North County San Diego Learn more: funderfulexperiences.com

Also offering: Private coaching and mediation for divorce transitions

Bottom Line:

You have wisdom now you didn't have before. Use it. Your next chapter won't design itself—but you absolutely can design it.