Cleared Hot Podcast: Episode 414 Chad Wittman – What Do You Do When Life Falls Apart?

Date: November 3, 2025
Host: Andy Stumpf
Guest: Chad Wittman
Theme: Navigating life crisis, rebuilding identity, and lessons in letting go, connection, faith, vulnerability, and leadership.

Episode Overview

This episode is a raw, deeply personal exploration between Andy Stumpf and Chad Wittman. The two recount their shared history in the worlds of Reebok, CrossFit, and elite teams before diving into how Chad’s life unraveled after leaving the fast-paced corporate world and how he began to piece it back together. The conversation ranges from landmark business deals to profound existential reflection on suffering, faith, and self-discovery. Chad’s journey includes business success, family challenges, the struggle to find purpose, leaning on faith, contemplating suicide, and ultimately finding meaning—offering inspiration and wisdom for anyone facing life’s darkest chapters.

Key Discussion Points & Insights

1. The Reebok & CrossFit Partnership [00:31–29:48]

• Origin Story: Chad shares how Reebok, struggling with its North American strategy post-Adidas acquisition, formed a “task force” to pivot back into fitness. CrossFit, then underground, became the target (07:00).
  • "If we can get in with this community, game changer. Reebok that quick. Game changer immediately." – Chad [11:32]
• Cultural Clash: The negotiation and partnership between the established corporate Reebok and the anti-establishment CrossFit culture was turbulent, breaking traditional business rules (18:01).
  • "Never have I been a part of a negotiation like this before. Every rule in the book was broken." – Matt (relayed by Chad) [18:13]
• Deal Finalization Drama: Chad vividly recalls last-minute deal issues, a "no-deal" moment over ownership stakes, and the unique company events surrounding the announcement (21:19, 22:04).
  • "We wanted a portion of ownership. ...And I'm freaking devastated. [...] And the head of all of legal... [said] why do you want the ownership? ...It means nothing. [...] Call the CrossFit guys, we can do the deal." – Chad [23:18]
• Reflecting on Impact: Both discuss the cultural and commercial legacy of CrossFit-Reebok, the challenges in expanding beyond the core community, and the misalignment that ultimately led to the end of the partnership.
  • "We lit fire to this movement... CrossFit spread all over the globe." – Chad [33:02]

2. Rebuilding After Corporate Life: Family, Failures, and Facing the Abyss [41:24–88:00]

• Falling Apart: Leaving Reebok left Chad drifting; his marriage was strained, and he felt lost at home, lacking the structure and identity that his career had provided (77:56).
  • "I thought it was going to be great... I’m in the house now, not traveling... I could not relax." – Chad [76:49]
• Struggles at Home: He and his wife Gail, who later suffered undiagnosed Lyme disease, clashed; Chad felt unequipped for fatherhood or partnership now that the dynamics were so different.
• Spiritual Crisis & Suicidal Thoughts: At his lowest, Chad admits to contemplating suicide for the first time, recording himself as a record of that low point (83:02).
  • "I thought about how I’d do this... I filmed myself because it was such a profound moment." – Chad [83:02]
• Turning Point – The Power of Help and Serving Others: He describes how coaching a struggling business owner (Max in China) began to restore his sense of purpose, and how helping someone else allowed him to start healing himself (94:43).
  • "By helping somebody else, I started to understand what I was going through, and it started to heal me." – Chad [95:52]
• Receiving & Giving Love: A pivotal relationship with his brother-in-law Aaron gave Chad unconditional, practical support—teaching humility, allowing Chad to accept help, and reinforcing the importance of not being alone.
• Aiding Others While Healing: Chad describes taking in a struggling man, Scott, who was homeless, and the deep lessons both learned—underscoring the messy, demanding, and rewarding side of real-world compassion (103:33).

3. Letting Go, Faith, and Learning From Suffering [52:00–140:30]

• Embracing Uncertainty & Letting Go: The hosts reflect on how clinging to control feeds anxiety, and that opening up to life’s unpredictability often brings unexpected, positive opportunities (54:49).
  • "You let go. It's the art of letting go." – Chad [55:33]
• Faith and Paradox: Chad recounts how his relationship with faith shifted—from a rigid Christian orthodoxy to a more inclusive, paradoxical understanding (90:33).
  • "I believe Jesus showed us the path to enlightenment... Never do I recall Jesus saying, worship me and make me a religion." – Chad [110:03]
• On Suffering and Growth: Chad reframes suffering as an inescapable part of growth—a “workout” for the soul—and stresses the importance of controlling one’s reactions over external events, especially in parenting (58:37).
  • "Everything’s wired for growth... your job is to recognize that's part of what you signed up for here." – Chad [58:37]
• Openness & Vulnerability: Both reflect on being open about failures and dark moments as “life-saving medicine” for others—a rejection of curated, Instagram-perfect realities (74:16).
  • "I'm so tired of people talking about how awesome everything is.... The reality is we're all an absolute dumpster fire." – Andy [74:08]

4. Reassembling Purpose: Love, Relationships, and New Directions [147:22–159:20]

• Rebuilding Identity: Through supporting others and introspection, Chad began to reconstruct his identity, now rooted in guiding others, love, and real connection.
  • "I believe that we are all here to learn how to love and to be loved... to coach and guide based on my experience." – Chad [63:48]
• Practical Mysticism & Newfound Openness: The episode veers into the metaphysical—past lives, mystical experiences, and the importance (and humor) of not taking oneself too seriously.
  • [On dancing, crying, and authenticity]: Chad: "There's nothing better than watching a man's heart open who has been closed for decades. It's beautiful." [129:40]
• Ballet and Masculinity: Chad openly discusses embracing traditionally “feminine” expressions (dancing, crying), challenging cultural norms, and advocating for men to reconnect with suppressed emotions as a source of healing and wholeness (127:07–133:21).
• Launching “Activate”: Chad discusses his new venture, Activate, executive coaching and business alignment, born from the synthesis of his corporate acumen and personal transformation (154:10).

Notable Quotes & Memorable Moments

• On Meeting CrossFit's Founder:
  "He introduced me as the Reebok guy... Greg kind of, you know, brushed me off a little bit, but he was like, walk with me, kid. And so we were walking, and here I am walking with this guy, and he’s signing people’s boobs... He's like this demigod." – Chad [13:35]

• On Letting Go:
  "It's the art of letting go... I don't know how to teach that to people, though. [...] You can't short circuit experience." – Andy [55:36–61:27]

• On Suffering and Perspective:
  "Suffering is not suffering any longer. Suffering is just an opportunity to grow." – Chad [139:12]

• On Comparing Struggles:
  "We’re all an absolute dumpster fire, and anything you see on social media is completely optional. It’s curated at best." – Andy [74:08]

• On Suicidal Thoughts:
  "I thought about how I'd do this... I filmed myself because it was such a profound moment." – Chad [83:02]

• On Coming Out the Other Side:
  "By helping somebody else, I started to understand what I was going through, and it started to heal me." – Chad [95:52]

• On Faith and Paradox:
  "To stand in that place between two opposing truths is the only place I think there’s some absolute, maybe some absolute truth because you have to accept both and that is freaking hard." – Chad [90:06]

• On Vulnerability as Strength:
  "I was so terrified, dude... I got a lot of people saying, thank you so much because I was there. I thought about taking my life. I lost. I didn't know who I was. I had a lack of identity." – Chad [136:36–137:52]

Timestamps for Key Segments

• [00:31–29:48] – Reebok & CrossFit: meeting, negotiations, deal drama, cultural learning
• [41:24–88:00] – Life post-corporate: marital struggles, parental challenges, mental health, finding help by helping others
• [52:00–61:27] – Letting go, openness, how to teach resilience, parenting tough lessons
• [83:02–95:52] – Suicidal ideation, the shift from being helped to helping; the redemptive power of service
• [90:06–111:00] – Wrestling with faith, paradoxical truth, inclusivity, and spiritual skepticism
• [127:07–133:21] – Ballet, masculinity, emotion, safe expressions for men
• [147:22–159:20] – Packaging lessons, new venture Activate, bringing workplace and spiritual insights together

Episode Takeaways

• Transformation is a messy, non-linear process. Things can—and often do—fall apart before coming back together in unexpectedly beautiful ways.
• Helping others is a powerful pathway to self-healing. Service is not a distraction, but often the very medicine required.
• Letting go of control is the gateway to peace. Plans are useful, but openness to disruption and responding in the moment is essential.
• Faith, purpose, and suffering can coexist in paradox. Accepting the unknown, and living authentically, are recurring themes.
• Vulnerability inspires connection. Sharing your truth—especially the messy bits—gives permission for others to do the same.
• Leadership and culture require alignment, not just strategy. Alignment in purpose, people, and process can create magnetic, world-changing organizations.

Find Chad Wittman and his work:
ActivateMyIdentity.com

“Life is about just being in the trenches and maybe getting an inch at a time.” – Andy Stumpf [138:41]

This episode is a must-listen for anyone navigating transitions, seeking meaning after success, or simply wondering how we keep going when life falls apart.