What if your greatest success has become your most beautiful prison? In this powerful episode, Meghan Telpner tackles the hardest part of any pivot: letting go of what you've built, invested in, and poured your heart into—especially when it still looks successful from the outside.

Drawing from the liberating concept of the sunk cost fallacy, Meghan reveals why we often choose the certainty of familiar unhappiness over the uncertain possibility of fulfillment.

If you've ever felt like an employee in a life you wouldn't have applied for, or wondered why you feel trapped despite your apparent success, this episode offers both permission and a pathway. Meghan transforms the narrative around "letting go" from loss to liberation, showing how releasing what no longer serves you becomes a sacred act of trust.

Essential listening for anyone feeling the quiet rebellion of their own heart.

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Covered In This Episode

• Letting go of something you’ve built can be the most courageous step forward.

• Success isn’t just about holding on—it’s knowing when to release.

• Your identity isn’t tied to what you’ve created.

• Endings often open the door to your next big beginning.

• Growth sometimes requires dismantling the thing that got you here.

• Attachment can quietly limit your future potential.

• True leadership is modeling change, even when it’s uncomfortable.

• Trusting yourself matters more than defending past decisions.

• Saying goodbye to “what was” makes space for “what’s next.”

• Freedom often arrives disguised as loss.

Chapters

00:00 Introduction to the Courageous Pivot Podcast
00:27 Welcome Back and Podcast Evolution
02:12 The Challenge of Letting Go
07:01 Understanding the Sunk Cost Fallacy
14:10 Navigating the Unknown
18:49 Personal Reflections and Invitations
20:46 Closing Thoughts and Encouragement

Special Offers

• Free Heart Coherence Masterclass – A complimentary session with Meghan Telpner exploring how to create alignment between your heart and mind, access inner calm, and live from your most authentic self.

• Click here to get 30% off Rise & Shine: A Guided Approach To Heart-led Living and Leadership. (Click here if you reside in Canada)

This Week’s Exercise: The Letting Go Lab

Purpose:

To help you explore your relationship with what you’ve built, see where attachment might be holding you back, and practice releasing in a way that creates space for new opportunities.

Step 1: Identify What You’re Holding Onto 

• What’s the project, role, habit, or identity you’ve been clinging to?

• Write it down. Name it clearly—no sugarcoating. 

 Step 2: Ask “What’s Still True?”

• List what’s still meaningful and relevant about it today.

• Now, list what no longer feels aligned.

Seeing the split can help you discern whether it’s time to stay, shift, or release.

 Step 3: Examine the Fear Behind Letting Go

If you were to step away or release this, what’s the fear that bubbles up?

• Is it about disappointing others?

• Losing credibility?

• Feeling like a failure?

Get it on paper.

Step 4: Flip the Narrative

Ask yourself:

• What could I gain by letting go?

• What energy, time, or resources could be freed?

• What new opportunities could open up?

 Step 5: Design a Mini Release Experiment

Choose one low-stakes, small-scale way to practice letting go:

• Delegate a task you’ve always kept for yourself.

• Pause a commitment for two weeks.

• Archive a project file you’ve been holding “just in case.”

The goal is to feel the lightness and notice what shifts—not to overhaul your life overnight.

Step 6: Reflect on the Experience

After your mini experiment:

• What felt freeing?

• What surprised you?

• Did any of your fears prove untrue?

Your insights here will guide whether to take a bigger step—or simply keep practicing small releases until it feels natural.