426: The Lie of the Alpha Male: Jason Wilson on Breaking Free from Emotional Incarceration and How Culture Distorts Masculinity

This week on Win Today, we’re peeling back the layers of masculinity, identity, and emotional resilience with Jason Wilson. If you’ve ever felt trapped in cycles of emotional suppression, struggled with the pressure to be strong at all costs, or wrestled with the tension between vulnerability and leadership, this conversation is for you.

Jason is here to expose the myth of the alpha male and reveal why true strength isn’t about dominance, but about wholeness. He’ll challenge us to stop running from the battles that make us feel weak—and instead, step into them with courage.

• Why emotional incarceration keeps so many men stuck
• How culture distorts masculinity—and what real manhood looks like
• Why avoiding pain makes us weak, and how to reclaim true resilience
• The foundation of comprehensive manhood and how it leads to freedom

If you’re tired of surface-level self-help and want real transformation, this episode will challenge you, stretch you, and equip you to pursue maturity in a way that lasts.

Guest Bio

Jason Wilson is a best-selling author and the founder of The Yunion, a Detroit-based nonprofit that has impacted over 17,000 youth through mentorship, leadership training, and emotional resilience programs. In 2008, he launched the Cave of Adullam Transformational Training Academy (CATTA) to equip boys with the tools to process emotions in a healthy way. His innovative Emotional Stability Training® has gained worldwide recognition, including a viral 2016 video with over 300 million views.

Jason’s journey was captured in the award-winning 2022 Tribeca Film Festival documentary, produced by Laurence Fishburne. With over 25 years in martial arts and a deep commitment to guiding men toward comprehensive manhood, Jason is a devoted husband, father, and man of faith, leading the next generation with wisdom and strength.

Dive Deeper

If you enjoy this episode, I’m sure you’ll also enjoy:

• 393: Tasha Cobbs Leonard on Unmasking a Root of Rejection, Freedom from Self-Hatred, What it Means to Live a Planted Life, and Grieving with Hope
• 358: Dr. Anita Phillips on What’s Missing in the Mental Health Conversation, Why Science and Faith Are Not in Conflict, Why We Must Stop Demonizing Emotions, and Healing the Nervous System

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Guest Links

Website | Instagram | Facebook

Resources Mentioned This Week

• Healing What You Can’t Erase: Transform Your Mental, Emotional, and Spiritual Health from the Inside Out
• The Man the Moment Demands: Master the 10 Characteristics of the Comprehensive Man
• Battle Cry: Waging and Winning the War Within
• Cry Like a Man: Fighting for Freedom from Emotional Incarceration

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