Episode 105

May 11, 2026

Matt Ross

Feeling Stuck at 50: How to Find Your Magic and Start Again | Matt Ross

Feeling Stuck at 50: How to Find Your Magic and Start Again | Matt Ross

The moment everything starts falling apart might be the moment your life finally comes together.

In this episode, Chip Conley sits down with entrepreneur and author of Grow or Fold, Matt Ross, to explore a powerful story of midlife reinvention. From a high-pressure career in radio to building purpose-driven businesses, Matt shares how personal crisis, burnout, and uncertainty became the catalyst for real change.

Here’s what you’ll take away:

  • Why feeling “stuck” at 50 is often the start of something better
  • The simple mindset shift that turns breakdown into breakthrough
  • How to treat your life like a business—and actually redesign it
  • What it really means to “find your magic” (and how to do it)
  • Why growth, not comfort, is the key to a fulfilling second half of life

If you’re at a crossroads, questioning what’s next, or just know there’s more out there for you—this conversation will hit home.

Watch now and take the first step toward your next chapter.

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