Most men don’t “lose” purpose overnight. It fades through tiny compromises: safer choices, social pressure, and years of doing what’s expected. In this episode, Kevin and Joe revisit childhood ambitions—not as nostalgia, but as data. What you loved early can reveal what your current life is missing, and what your next chapter is asking from you.

Kevin Rogers and Joe DiRoma have spent decades leading teams, building communities, and doing the inner work that midlife demands. They speak from experience—career pivots, leadership pressure, family responsibility, recovery, and hard-earned perspective.

“The only regrets that come to mind… are the shots I didn’t take.”

“Don’t fight it. It doesn’t matter where it leads.”

“People can really feel the difference between when you’re talking to them or you’re talking at them.”

“No one finds this enlightening… they’re not going to keep listening.”

“All we really take in life comes down to experiences and relationships.”

“You have to seek counsel… from scars, not wounds.”

1. Childhood dreams as clues to adult purpose
2. Identity vs. true aptitude: when something “looks cool” but isn’t your lane
3. How early gifts evolve into leadership strengths
4. Humor: talent, tool, and defense mechanism
5. Regret as avoidance—and how to reclaim “missed shots” now
6. Recovery, integrity, and rebuilding a life without self-hatred
7. Retirement without purpose (and why it can accelerate decline)
8. Career uncertainty in midlife and how to adapt without panic
9. The role of community: why you can’t do this alone

1. Your childhood interests are not childish. They’re often the earliest evidence of what energizes you.
2. Regret is usually about fear, not failure. The cost of “playing it safe” compounds over decades.
3. Your gifts can change form without losing meaning. You may not become the “actor,” but you can become the leader who creates presence and connection.
4. Purpose must outlive your job title. If your identity depends on your role, retirement (or job loss) can become a crisis.
5. Healing requires honesty and relationships. Growth accelerates when you stop managing it alone.

If this episode inspired you to reconnect with joy and curiosity, please share it with someone who could use the encouragement. Leave a review on Apple Podcasts to help us reach more listeners navigating midlife...

You've built a successful life, climbed the ladder, and proven yourself. So why does the idea of starting over as a beginner feel both terrifying and necessary? In this season two premiere, Kevin and Joe tackle the uncomfortable truth about midlife: everything after "but" is usually an excuse, and staying comfortable is the most dangerous choice you can make. Through raw personal stories, Joe's transformation from bodybuilder to triathlete and Kevin's journey learning to dance alone at 55, they reveal why reclaiming the beginner's mindset might be the key to living fully again.

If you're a professional man who has achieved what you set out to accomplish but still feel something is missing, this episode offers a roadmap for renewal. Kevin and Joe don't just talk about change, they're living it. You'll discover why the discomfort you feel isn't a problem to solve but an invitation to grow, and how becoming a beginner again can unlock joy, purpose, and vitality you thought were behind you.

1. Listen for your "buts" - Every time you say "I'd love to, but..." you're likely feeding yourself an excuse disguised as logic. The moment you hear yourself say "but," pause and ask what fear is really driving that statement.
2. Start before you're ready - You don't need the perfect plan, equipment, or knowledge to begin. Those who do the most sweeping discover what makes a good broom through the doing. Start messy, start imperfect, just start.
3. Practice being uncomfortable - Find something that makes you the new guy again. The humility and growth that comes from beginner status is medicine for the stagnant soul. Whether it's a sport, skill, or social situation, put yourself in positions where you don't have all the answers.
4. Remove friction from new habits - If you're serious about a new pursuit, eliminate barriers. Joe shaved his head for swimming efficiency. What's your equivalent? Make it easier to do the thing than to avoid it.

1. "The Middle Passage: From Misery to Meaning in Midlife" by James Hollis - A guide to understanding that the task of midlife is not to look into the light, but to bring light into the darkness through self-realization and growth.

If this episode inspired you to reconnect with joy and curiosity, please share it with someone who could use the encouragement. Leave a review on Apple Podcasts to help us reach more listeners navigating midlife transitions. Every episode is complemented with a weekly newsletter so sign up for our SubStack at maninthemiddleshow.com

What if rediscovering joy and play could unlock a deeper connection with yourself and those around you? In this lively episode, Kevin and Joe discuss why midlife is the perfect time to let go of seriousness, embrace curiosity, and reclaim the playfulness of childhood.

Kevin Rogers and Joe DiRoma, known for their authentic and insightful takes on midlife challenges, explore how men can integrate joy and creativity into their lives. Their combined experiences in personal development and leadership provide a unique lens on why play is more than just fun—it’s essential for growth.

As men navigate midlife, the pressures of career, family, and societal expectations often leave little room for joy and spontaneity. This episode challenges the narrative that adulthood must be devoid of play, offering actionable ways to reignite curiosity and embrace creativity.

• The Importance of Play in Midlife: Rediscovering activities that bring joy, such as dancing, hiking, or creative hobbies, can provide mental clarity and emotional release.
• Letting Go of Judgment: Fear of how others perceive us often blocks joy. Kevin emphasizes the power of being the first to step on the dance floor or try something new, giving others permission to do the same.
• Curiosity as a Gateway to Joy: Cultivating curiosity can reignite a sense of wonder. Joe highlights how asking questions, exploring interests, and breaking from routines open pathways to creativity.
• The Productivity of Non-Productivity: Structured play or even intentional downtime allows for self-reflection, growth, and recharging.

• Book: Memories, Dreams, Reflections by Carl Jung
• Book: The Middle Passage by James Hollis
• Study: George Land’s NASA creativity study, revealing that 98% of five-year-olds demonstrate genius-level creativity
• Quote: Maya Angelou’s insight on how people remember how you make them feel

If this episode inspired you to reconnect with joy and curiosity, please share it with someone who could use the encouragement. Leave a review on Apple Podcasts to help us reach more listeners navigating midlife transitions. Every episode is complemented with a weekly newsletter so sign up for our SubStack at maninthemiddleshow.com

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