In this episode of Trying Not to Die, Jack Osbourne and Ryan Drexler sit down with comedian and longtime friend Jim Norton for one of the most brutally honest conversations yet. Jim opens up about getting sober at just 18 years old, why he still struggles with self-worth decades later, and how shame, addiction, and impulse control have shaped his life both on and off stage. From sex addiction and dopamine-driven habits to the reality of long-term recovery, this is a raw, unfiltered look at what it actually means to "work on yourself." The conversation dives deep into relationships, communication, and the damage that can come from saying things you can't take back, as well as the discipline it takes to stop yourself in the moment. Jim also shares his thoughts on confidence, comedy, and why he's never fully believed in his own success despite a massive career.

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In this episode of Trying Not To Die, hosts Jack Osbourne and Ryan Drexler sit down with actor and endurance athlete Dan MacPherson for a deep dive into discipline, identity, and what it really takes to push your limits.

Dan shares his journey from starring on Neighbours to competing at Ironman world championship level, and eventually transforming his body and mindset for intense Hollywood roles alongside Russell Crowe. The conversation explores the brutal reality of training for MMA film roles, the mental and physical demands of high-performance acting, and the lessons learned from years of endurance sports.

They also get into the deeper side of life, including why your late 30s and early 40s can feel like the hardest years, the shift from boyhood to manhood, and the struggle of maintaining purpose and identity through major life transitions. Dan opens up about balancing fatherhood, career, and health, while emphasizing the importance of discipline, routine, and staying grounded.

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Music by Ryan Hahn.

In this episode of Trying Not to Die, Jack Osbourne and Ryan Drexler dive deep into motorcycle and tattoo culture with brothers Brian Vaillancourt and Mark Vaillancourt. Brian and Mark Vaillancourt are brothers deeply rooted in motorcycle and tattoo culture, known for their passion for Harleys, club rides, and the lifestyle that comes with being fully immersed in ink and biker communities. Together they represent a blend of brotherhood, identity, and subculture perspective that bridges tattoo art with the open-road ethos of modern motorcycle life. The brothers break down how they got heavily tattooed starting at 18, the decision to go fully covered, the crossover between biker culture and tattooes, and how society reacts when you're tattooed from head to toe. There's also honest discussion about club life, perception vs reality, stereotypes about prison ink, and how the culture has shifted over the decades.

Thank you to our sponsors:

- Need Delicious Coffee? Go to https://www.drinkcaveman.com and use code trying15 for 15% off your first order.

-Get up to 39% off your Mitopure Gummies at Timeline.com/TRYING

Music by Ryan Hahn.