The Cost of Playing Small: How to Trust Yourself & Take the Leap

Return

Send us a text

 "We settle in business. We settle in relationships. We settle in life. We tell ourselves it's fine, but deep down you know that you are meant for more." -Caitlan Siegenthaler

*This episode could be the thing that finally gets you unstuck...* Settling is Self-Betrayal*

Episode 65: The Cost of Playing Small: How to Trust Yourself & Take the Leap

Cue the confetti and grab your cowgirl boots—we’re celebrating TWO years of Return! 🪩✨

In this milestone episode, Caitlan is keeping it real about why settling (in love, business, or life) is low-key self-sabotage.

If you've ever convinced yourself that 'good enough' is fine—even when your gut says hell no—this one's for you.

We’re talking about:
💡 The sneaky fears that keep you stuck in “meh” situations
🔥 How to build self-trust and actually take the bold leap
🚀 Why waiting for ‘the perfect time’ is just an excuse

Caitlan’s spilling personal stories, hard-earned lessons, and giving you a loving (but firm) nudge out of your comfort zone.

Plus, she’s introducing the Messy Action Launch Pad—the group program designed to help you stop overthinking and start moving.

🚀 Ready to make a change? Tune in, take notes, and let’s stop settling for almost.

If you want more info on the Messy Action Launchpad + an exclusive discount on the program, sign up here.

🎧 Listen now & DM @caitlansiegenthaler“messy” on IG to learn more!

Episode Breakdown:

00:00 | Celebrating 2 Years of Return! 🎉
00:47 | Why Settling is Self-Betrayal (and why we do it)
01:46 | Caitlan gets personal—real stories, real talk
09:42 | The actual cost of playing small
15:17 | Steps to stop settling (yes, even if it’s scary)
20:22 | Your next move + how to work with Caitlan

🔗 Caitlan's website