What changes when you stop performing for approval, and start living from a quieter, truer center?

In this episode, Kevin and Joe unpack a powerful Alan Watts passage that names what many men feel in midlife but struggle to explain: the usual way of connecting stops making sense. You don’t hate people. You’re not “better than.” You simply can’t keep participating in conversations built on status, gossip, and shared illusions.

They explore what happens when a man begins to see the hidden performance underneath everyday interaction, the need to be liked, to belong, to say the right thing, and how stepping back isn’t loneliness. It’s the space between who you used to be and who you’re becoming.

Along the way, Joe connects this inner shift to his triathlon journey: long hours of training alone, learning what’s real, what can’t be faked, and what it means to endure discomfort without needing an audience.

This is an episode for the man who feels himself pulling away and isn’t sure if it means something is wrong, or something is finally becoming honest.

Kevin and Joe give language to the internal transition from performance to presence, and remind you that this is a normal part of waking up. They also offer a grounded perspective: meaning deepens when you stop chasing approval, stop pretending, and start choosing relationships and rituals that are real.

If you’ve been feeling less interested in shallow connection, more protective of your time, and more aware of what’s false in yourself and your environment, this conversation will make you feel seen.

“Loneliness does not come from not having people around you, but being unable to communicate the things that seem important to you.”

“He didn’t cut ties. He didn’t burn bridges. He simply stopped pretending.”

“It’s not loneliness, just space between who he used to be and who he’s becoming.”

“People might still wave… but the connection is no longer there because it was never real to begin with.”

“Faith is what keeps you going through the unknown in the belief that there’s something better on the other side.”

1. Alan Watts on awakening and pulling away from the crowd
2. Why the “usual way of connecting” can stop making sense in midlife
3. Performance, approval-seeking, and the need to be liked
4. The difference between solitude and loneliness
5. Carl Jung’s view: loneliness as an inability to share what matters
6. Triathlon training as real solitude: no headphones, no distractions, no faking it
7. Why discipline earns respect in a world of curated images
8. Breaking consumer patterns and cultural “shared illusions”
9. Legacy, family values, and choosing experiences over stuff
10. The role of faith when you’re between identities and outcomes aren’t clear
11. Why men need deeper...

What do you do when you’re going through something difficult, and the people you expected to hear from stay silent?

In this episode, Kevin and Joe name a quiet midlife reality: many men feel isolated, not because they have no one, but because they’re waiting, resentfully, for someone else to make the first move. Kevin shares what he learned during a season of deep solitude and life transition: assumptions create suffering, and silence can easily become a story we use against others.

Joe offers a direct, practical alternative: stop waiting to be loved. Be the man who leads with love. When someone enters your consciousness, reach out immediately. A simple text, sent at the right time, can repair distance, reopen brotherhood, and change the emotional weather of a man’s life.

Kevin and Joe continue integrating insights from their recent conversation with Dr. James Hollis, especially the idea that real change requires insight, courage, and endurance. This episode focuses on what courage looks like in everyday life: choosing discomfort, initiating connection, and acting on the inner nudge to show up for someone.

If you’ve been feeling disconnected, disappointed in friendships, or quietly angry that “nobody checks on me,” this is a clean reset. Not with platitudes, with a specific practice you can start today.

“Don’t blame others for inaction when you need them, create the action that sparks what you needed.”

“Unstated unrealistic expectations are only premeditated resentments.”

“When somebody entered my consciousness, I would call or text them… ‘I was thinking about you.’ It radically transformed my relationships.”

“You’ve got to fight for peace… schedule your priorities.”

“When you’re at your lowest, do something. Do something for other people. Do something for yourself. And keep moving.”

1. Men, isolation, and the habit of waiting for others to initiate
2. How midlife transitions expose friendship gaps and unmet expectations
3. Why silence isn’t always betrayal, it’s often discomfort and avoidance
4. Choosing growth over comfort in relationships
5. Insight, courage, and endurance as everyday practices
6. How resentment builds when expectations are unspoken
7. A simple relationship rule: “If they enter your mind, reach out”
8. Scheduling peace, nature, and movement for mental stability
9. Fatherhood, legacy, and defining success beyond money
10. Small actions that rebuild meaning: journaling, walking, showing up

1. If you need support, initiate, silence is not proof of disloyalty.
2. The “nudge” to reach out is often worth following immediately.

What happens when the life you worked so hard to build suddenly feels too small?

In this rare and deeply reflective conversation, Kevin and Joe sit down with Dr. James Hollis to explore the inner crisis many men face in midlife, when achievement no longer satisfies, certainty dissolves, and the soul begins asking different question

Dr. James Hollis is a renowned Jungian analyst and the author of more than 19 books, including The Middle Passage, a foundational work that has given language to the psychological and spiritual transition of midlife. His writing has guided generations of men through the often unspoken inner reckoning of the second half of life

“The ego never knows enough to know enough.”

“The question of the second half of life is not what the world wants from me—but what the soul wants of me.”

“You are not crazy. There is a purpose to what is breaking down.”

“The smallest thing with meaning is greater than the largest thing without it.”

1. The psychology of midlife transition
2. First adulthood vs. second adulthood
3. Why achievement can become a prison
4. Depression as a summons, not a disorder
5. Energy, meaning, and inner authority
6. Shadow work and the unlived life
7. Dreams as guidance systems
8. Patience, endurance, and courage
9. Masculinity, isolation, and authenticity
10. Legacy beyond success

1. Midlife unrest is not failure, it is initiation.
2. Letting go of old identities is necessary before new meaning emerges.
3. Feelings, energy levels, and dreams are diagnostic tools, not inconveniences.
4. The second half of life asks for service, not status.
5. This journey cannot be rushed but it can be honored.

1. The Middle Passage by James Hollis (a foundational text for men in midlife)
2. Audiobook versions of Hollis’ work, read by the author
3. Prisms and other writings by James Hollis

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...

What if the parts of you that you hide, your anger, cravings, judgments, shame, or “unacceptable” emotions, are actually the exact keys to your freedom?

In this episode, Kevin and Joe go deep into the shadow self (a.k.a. your dark side), not as something “bad,” but as the parts of you that were labeled unacceptable by family, culture, or society… and quietly shaped your life from behind the scenes.

Kevin and Joe don’t talk theory, they talk reality.

Joe brings structured insight from ontological coaching (including emotional deconstruction work), plus lived experience around recovery, identity shifts, and behavioral patterns. Kevin brings the midlife lens: self-awareness, morality, identity, and personal accountability in a way that’s honest and deeply relatable.

“Dark side doesn’t mean bad… it means unacceptable.”

“Guilt is breaking your own moral code. Shame is breaking society’s.”

“Your strongest emotional reactions show you where your shadow lives.”

“You’re one decision away from a different life.”

“Shadow work brings you back to your authentic self.”

1. Jung’s shadow: what it is and why it matters.
2. Cultural conditioning vs personal morality.
3. Guilt vs shame.
4. Triggers, judgments, projections, and patterns.
5. Emotional suppression in families (especially men).
6. Humor as avoidance vs connection.
7. Midlife awakening and identity transformation.
8. Accountability, integrity, and conscious living.

1. Your shadow isn’t evil, it’s exiled
2. The “dark parts” are often natural emotions or desires that were punished, shamed, or rejected.
3. Your triggers are your trail
4. If someone annoys you irrationally, there’s usually something in you asking to be acknowledged.
5. Midlife forces truth
6. This is why men in midlife start asking: “Is this really my life? Is this really me?”
7. Bring the unconscious into the light
8. The shadow has power when it’s hidden.
9. Once seen clearly, it becomes something you can integrate instead of fear.

What happens when you’re 45, 55, or even 65… and career change isn’t a choice—it’s forced?

In this episode, Kevin and Joe break down the real psychology behind midlife career transitions, especially when other people depend on you. If you’ve been feeling restless, drained, boxed in, or secretly craving a second chapter… this conversation will hit home.

Kevin and Joe bring a grounded mix of midlife coaching insight + real lived experience, including firsthand experience with layoffs, career pivots, and rebuilding identity after a major professional reset.

“It’s not something somebody could flippantly advise… you got a lot more concerns than just, ‘I look dumb here.’”

“The task of midlife is not to look outside for answers, but to look within…”

“The most important person in the world is watching everything that you do—and that’s yourself.”

“You don’t need to be stuck in this thing of something that you said you didn’t want in the first place.”

“We are not here to fit in… We are here to become ourselves.”

1. Midlife career changes after 45: why they’re rising.
2. Provider pressure + identity crisis in men.
3. Fear of incompetence and sunk-cost fallacy.
4. Family expectations and lifestyle resistance.
5. How layoffs can become a “calling”.
6. Finding alignment vs forcing discipline.
7. Transferable skills and resume reframing.
8. Blue-collar opportunities and buying businesses.
9. Why communication with your spouse is crucial.

1. Midlife career change isn’t only professional, it’s personal identity.
2. Don’t ignore the inner restlessness—explore before you’re forced.
3. Look for the through-line: what wants to come to life in you now?
4. You’re more qualified than you think—your experience contains transferable skills.
5. Discipline without alignment becomes misery. Alignment creates discipline naturally.
6. If your marriage can’t handle these conversations, fix that first.

1. James Hollis - The Middle Passage.
2. Carl Jung (unlived life concept).

If this episode inspired you to reconnect with joy and curiosity, please...

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

Watch on YouTube

Listen on Apple

Listen on Spotify

Sign up for the Newsletter