He Had Everything. Midlife Broke Him Anyway | Blake Mycoskie
He Had Everything. Midlife Broke Him Anyway | Blake Mycoskie  
Podcast: The Midlife Chrysalis
Published On: Fri Jan 16 2026
Description: What happens when success stops working and midlife hits hard?Blake Mycoskie, founder of TOMS Shoes, shares the story behind his most difficult chapter. After building a global brand and achieving massive success, Blake found himself facing a deep midlife reckoning marked by depression, loss of identity, and an urgent search for meaning beyond achievement.Blake opens up about:- How selling part of TOMS triggered an unexpected identity collapse- Why midlife depression often follows success, not failure- The treatments and inner work that helped him recover, including ketamine therapy and TMS- The simple but life-changing realization that shifted everything: “I am enough”- Why connection and community matter more than success or status👉 Watch now to hear Blake Mycoskie’s most vulnerable and meaningful story yet. Timestamps:01:11 Blake’s early entrepreneur journey02:49 Reality Central and first major failure04:59 The business lesson that shaped TOMS07:49 Creating the one for one model08:43 Selling TOMS and losing identity12:36 Depression behind the public image16:23 Searching for relief outside himself17:24 Medication fog and deep isolation19:30 Why telling others saved his life20:54 Moving beyond traditional medication21:12 Ketamine and TMS25:53 Discovering the core wound28:49 India and lasting inner freedom33:27 Launching the Enough initiative35:58 I’m Enough ritual poem37:57 How the nonprofit model works38:47 The growing mental health crisis43:13 Self compassion and flow state46:28 How to support someone in depression51:54 Living with fear of relapse54:17 Wisdom bumper sticker Learn more about MEA at ⁠https://www.meawisdom.com/#BlakeMycoskie #MidlifeCrisis #MentalHealthAwareness #EntrepreneurMentalHealth #SuccessAndDepression #TOMSFounder #MidlifeJourney #DepressionRecovery #FindingPurpose #SelfWorth #MentalHealthPodcast #MidlifeTransformation #HealingJourney #MenAndMentalHealth #IAmEnough