What happens when you outgrow the life you worked so hard to build? In this episode, Meghan explores the unexpected grief that comes with positive change—the mourning that happens when you release a successful career, comfortable identity, or accomplished version of yourself that no longer fits who you’re becoming.

This isn’t about traditional loss. It’s about the complex emotions of saying goodbye to dreams you’ve achieved, identities that served you well, and the version of yourself that others could easily understand and categorize.

If you’ve ever felt guilty for being sad about letting go of something you chose to release, or you’re navigating the tender space between who you were and who you’re becoming, this episode offers validation and wisdom for honoring both your growth and your grief.

Essential listening for anyone in transition who needs permission to mourn their former selves with grace.

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Covered In This Episode

• Growth often begins with grief—the quiet mourning of what you once built.

• Letting go of a life that looks “successful” can feel scarier than starting from scratch.

• The sunk cost fallacy keeps us clinging to paths that no longer serve us.

• True alignment asks you to release even the things you worked hardest for.

• Fear of disappointing others can trap you in a version of life you’ve outgrown.

• Change isn’t always about adding more—it’s about creating space by letting go.

• Your next chapter demands trust in yourself, not just a well-planned strategy.

• Emotional pain is often proof that you’re breaking old patterns.

• Freedom lives on the other side of surrender, not control.

• Grieving the past is how you honor it—and finally move forward.

Chapters

00:00 Welcome to the Courageous Pivot Podcast
02:55 Personal Updates and Reflections
06:02 The Silent Grief of Growth
12:42 Navigating Professional Identity Crisis
16:00 Honoring the Past and Embracing the Future
20:15 Final 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:

Purpose: To help you honor the version of yourself you’re releasing, process the grief of growth, and gently create space for who you are becoming.

Step 1: Name Your Former Self

• Think of a chapter, role, or identity you’ve recently outgrown—or feel yourself beginning to outgrow.

• Write down a short “name” for this version of you (e.g., The Hustler, The Perfectionist, The Always-Available Friend).

Step 2: Offer Tender Acknowledgment

• Write a brief letter to this past self.

• Thank them for what they helped you learn, create, or survive.

• Keep it compassionate—this isn’t about judgment.

Step 3: Identify What You’re Carrying 

• List any expectations, habits, or beliefs from this former self that you’re still holding onto.

• Notice which ones feel heavy or outdated.

Step 4: Create a Gentle Goodbye 

• Choose one small ritual to honor this transition:

  • Light a candle while reading your letter aloud.

  • Fold the letter and place it in a keepsake box.

  • Shred or recycle it as a symbolic release.

• Allow any emotions—grief, relief, nostalgia—to arise without rushing them.