In this powerful and deeply honest episode, Will welcomes Josh O’Bear to the show for a conversation that unpacks the real, often unspoken experiences of men in relationships—and the societal misconceptions that follow them.
Josh opens up about his upbringing on a farm in Delaware, growing up with strong family values and a father whose career in law enforcement shaped much of his worldview. At just 17, Josh’s life took a dramatic turn after a severe back injury left him in unmanaged pain for months. With no medical guidance and caught in the height of the pill epidemic, he slipped into opioid addiction, relying on pills from friends just to function.
Despite multiple attempts at recovery—including a stay at Teen Challenge—Josh continued to struggle until age 19, when a pain management specialist finally diagnosed the true cause of his suffering. Through targeted treatment and a refusal to undergo surgery, Josh found a path to stability with regulated prescriptions and long-term pain management.
But the end of addiction was only the beginning of another set of challenges.
Josh married his wife in 2017, and the couple soon found themselves battling communication breakdowns, lingering guilt from Josh’s past, and a relationship dynamic where he felt stripped of confidence and placed his wife on a pedestal. Frequent conflicts and threats of divorce left the marriage teetering on the edge.
With Will’s help in therapy, Josh began rebuilding his confidence, reshaping communication patterns, and reclaiming balance in the relationship. The transformation was dramatic—a significant drop in conflicts and a shift toward genuine partnership.
Throughout the episode, Josh challenges harmful stereotypes that paint men as narcissists by default and speaks to the importance of prioritizing relationships, personal growth, and emotional honesty. His journey from pain and addiction to stability and healthier connection offers valuable insight for men, couples, and anyone seeking hope through adversity.
This is an inspiring story of resilience, accountability, and the power of doing the work. Tune in for a conversation that’s raw, real, and ultimately redemptive.
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