Stop Taking Yourself So Seriously: Reclaiming Joy and Curiosity in MidlifeEpisode Summary

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.

Why You Should Listen

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.

Why This Episode Matters

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.

Key Quotes“The ego’s need for control often masquerades as maturity.” – Joe, quoting James Hollis“Playfulness isn’t just for children—it’s a way to access the deepest parts of ourselves.” – Kevin“When your work becomes play, there’s no difference between them.” – JoeKey Takeaways

• 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.

Resources Mentioned

• 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

Call-to-Action

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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Operation Separation: Finding Freedom and Identity After a Major Life ShiftEpisode Summary

What happens when you’re faced with the reality of redefining your life after a long-term relationship ends? In this deeply personal episode, Kevin and Joe discuss the challenges, lessons, and unexpected growth that come from navigating separation. With honesty and insight, they explore what it takes to find freedom, redefine identity, and embrace a new chapter of life.

Why You Should Listen

Kevin Rogers and Joe DiRoma bring years of wisdom and life experience to their conversations about midlife transitions. Kevin’s candid storytelling and Joe’s grounded philosophical perspectives create a unique dialogue that resonates with men grappling with major life changes.

Why This Episode Matters

Separation in midlife can feel like a seismic shift, especially for men who’ve built their lives around stability, routine, and family. Whether it’s divorce, career pivots, or personal reinvention, this episode offers actionable insights and emotional depth for anyone questioning their path forward.

Key Quotes“The hardest part wasn’t knowing what I wanted—it was creating the space to figure it out.” – Kevin“Growth always requires stepping into the unknown.” – Joe, quoting James Hollis“Sadness is a station we stop at, not a station we stay at.” – JoeKey Takeaways

• The Process of Separation: Kevin shares his journey of moving out after a 24-year marriage and the profound shifts in identity, routine, and emotions that followed.
• Grief as Growth: Both hosts emphasize the importance of allowing oneself to grieve the end of a relationship—not as failure, but as part of personal evolution.
• Finding Flow Beyond Fight, Flight, or Freeze: Joe introduces the concept of “flow” as a fourth response to trauma, offering a perspective that helps navigate life’s inevitable disruptions.
• Redefining Space: Kevin highlights how creating a personal space that reflects your identity—whether through art, music, or routine—can help foster healing and self-discovery.
• The Importance of Community: Both Kevin and Joe stress the need for authentic male friendships and mentorship, urging men to reach out to their “Joe” or “Kevin” when life gets overwhelming.

Resources Mentioned

• Books:
• The Middle Passage by James Hollis
• Memories, Dreams, Reflections by Carl Jung
• Music:
• Tom Petty’s Wildflowers
• Leonard Cohen’s Live in London
• Quote: “Our wounds become our wisdom.” – James Hollis

Call-to-Action

If this episode resonated with you, take a moment to share it with someone who might be navigating their own transition. Subscribe to the podcast and leave a review on Apple Podcasts to help us reach more men in need of meaningful conversations. Every episode is complemented with a weekly newsletter so sign up for our SubStack at maninthemiddleshow.com

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Choosing To LeadEpisode Summary

What does it mean to truly lead, and how do you step into that role intentionally? In this episode, Kevin and Joe tackle the journey of choosing to lead—whether in business, family, or within yourself. They discuss what authentic leadership looks like and share personal stories of how stepping up as leaders has reshaped their lives and relationships.

Why You Should Listen

Kevin Rogers and Joe DiRoma are leaders with extensive backgrounds in business and personal growth. Known for their honest, relatable discussions, they explore the realities of leadership beyond titles, focusing on character, integrity, and the impact of leading by example.

Why This Episode Matters

For men navigating midlife, the call to lead can come in many forms. As career paths, family dynamics, and personal goals evolve, there’s a growing awareness that leadership is less about authority and more about guiding with purpose and empathy. This episode explores the steps to embody meaningful leadership and the challenges of balancing self-accountability with empathy for others.

Key Quotes“We’re all leaders, whether by default or design. It’s about knowing your role and leading from there.” – Kevin“Real leadership is creating breaks in the current reality for people to see new possibilities.” – Joe“In order to lead, you have to connect. And that starts with knowing your own intentions and being willing to listen.” – KevinKey Takeaways

• Intention-Driven Leadership: Real leadership starts with clear, purposeful intentions. Kevin and Joe discuss how knowing your intent is essential to guiding others and setting the foundation for authentic leadership.
• Empathy and Connection: Leaders connect through empathy, understanding, and the courage to have difficult conversations. Building trust and fostering a genuine connection can turn challenges into growth opportunities.
• The Power of Presence: Leadership is not only about big decisions; it’s also about small, everyday actions. From engaging a cashier meaningfully to being the person who steps up in times of need, leadership is built through presence and integrity in each moment.
• Understanding Expectations: Unmet expectations often lead to conflict. Joe highlights the importance of setting clear expectations in both personal and professional settings, noting that holding yourself accountable to those standards is a powerful form of leadership.

Resources Mentioned

• Book: 
• Supercommunicator by Charles Dewey (for insights on types of conversations)
• The Middle Passage by James Hollis
• Quotes: Carl Jung and other notable thinkers on leadership and personal growth

Call-to-Action

If this episode sparked new insights on leadership, please share it with others and consider leaving a review on Apple Podcasts. Your feedback helps us reach more men looking to step into their leadership roles meaningfully. Every episode is complemented with a weekly newsletter so sign up for our SubStack at maninthemiddleshow.com

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All The Decisions You've Made Along The WayEpisode Summary

How do the decisions you've made, big or small, shape your journey? In this episode, Kevin and Joe dig into the lasting impact of pivotal life decisions. From personal breakthroughs to career shifts and spiritual awakenings, they discuss how the choices we make define who we are and who we strive to become.

Why You Should Listen

Kevin Rogers and Joe DiRoma, known for their deep insights and straight talk, bring life experience and a wealth of knowledge on topics that matter to men navigating the complexities of midlife. In this episode, they explore the importance of self-reflection, taking responsibility, and embracing uncertainty.

Why This Episode Matters

For men in midlife, career transitions, health concerns, and family responsibilities often require tough decisions. These moments can lead to a powerful reassessment of life, helping men align their actions with their core values. Drawing from personal stories and timeless philosophy, Kevin and Joe guide listeners through the decision-making process, exploring how each choice—whether in relationships, careers, or personal growth—can pave the way to a more meaningful life.

Key Quotes“Meaning is not given to us. It must be discovered. It is a hard and lonely work, but it is the work that we are meant to do.” – Joe, quoting James Hollis“Your only job is to accept that it will be different, and then use your instincts along the way to form what it becomes next.” – Kevin“The privilege of a lifetime is to become who you truly are.” – Joe, quoting Carl JungKey Takeaways

• Making Decisions with Impact: Big decisions often require the courage to leave comfort behind and pursue meaning. True fulfillment lies in aligning choices with who we are and who we want to become.
• Embracing Vulnerability: Both Kevin and Joe share moments of struggle, from overcoming addiction to career changes. They discuss how these experiences can be transformative when embraced honestly.
• Clarity through Writing: Kevin advises taking the time to write out difficult choices to gain clarity and peace of mind. By defining the decision, asking "Then what?" at each step, you can often ease your fear and discover potential outcomes.
• Service as a Path to Self-Discovery: Joe discusses the profound sense of fulfillment that comes from helping others, highlighting the importance of community and service in the journey toward personal growth.

Resources Mentioned

• Books:
• The Middle Passage by James Hollis
• Modern Man in Search of a Soul by Carl Jung
• Film: 1917 (Referenced for its line on faith in tough situations)

Call-to-Action

If you’re finding value in these discussions, help us grow by sharing this episode and leaving a review on Apple Podcasts. Each review supports our mission to connect with more men facing similar challenges. Every comment, rating, and share makes a difference. Every episode is complemented with a weekly newsletter so sign up for our SubStack at maninthemiddleshow.com

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Relationship w/ Our Fathers & Being Fathers In MidlifeEpisode Summary

As fathers and sons, we inherit and carry powerful stories, unspoken expectations, and lasting lessons. In this thought-provoking episode, hosts Kevin Rogers and Joe DiRoma dive into the complex, often untold realities of fatherhood – both as sons reflecting on their fathers and as fathers guiding their own sons through life's biggest transitions.

Why You Should Listen

Kevin Rogers and Joe DiRoma, known for their depth and authenticity, use this platform to address real, unfiltered issues faced by men navigating midlife. Drawing from personal experience and inspiration from thought leaders like Dr. James Hollis, they explore relationships, legacy, and personal growth.

Why This Episode Matters

Midlife can bring a re-evaluation of what it means to be a father, son, and man. Through reflections on relationships with their own fathers, Kevin and Joe uncover insights that challenge men to rethink fatherhood, face their fears, and connect with their own sons in ways that truly matter. The discussion finds grounding in "The Middle Passage" by Dr. James Hollis, which explores the "first" and "second" adulthood and their impacts on our identity and family dynamics.

Key Quotes“Men just don't give themselves permission to feel weak or vulnerable.” – Kevin“The greatest burden a child must bear is the unlived life of its parents.” – Joe, quoting Carl Jung“Our real job as fathers is to love, listen, and just be there.” – KevinKey Takeaways

• Facing Mortality & Legacy: Men often wrestle with their legacy and self-worth in midlife, especially as they contemplate what they’ll leave behind for their children.
• Healing Through Vulnerability: The strength of father-son relationships often lies in vulnerability. As sons, we may crave acknowledgment, but as fathers, opening up creates powerful bonds and fosters healing.
• Reimagining Fatherhood: The role of a father evolves. At its core, being a good father means letting children learn, guiding them with love and patience, and knowing when to let them find their own way.
• Supporting Generational Growth: By breaking cycles of inattentive parenting, men can create lasting, positive impacts on future generations, fostering a legacy of love, support, and responsibility.

Resources Mentioned

• Book: The Middle Passage by Dr. James Hollis
• Book: Swamplands of the Soul by James Hollis
• Book: Modern Man in Search of a Soul by Carl Jung

Call-to-Action

If this conversation resonates, support Man in the Middle by sharing this episode and leaving a review on Apple Podcasts. Every rating helps reach more men who can benefit from real discussions on life’s challenges and transitions. Every episode is complemented with a weekly newsletter so sign up for our SubStack at maninthemiddleshow.com.

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Choosing Authenticity Over ComfortEpisode Summary

In this compelling episode, Kevin Rogers and Joe DiRoma explore the journey of stepping out of comfort zones to embrace a more meaningful life. Aimed at men navigating midlife, the episode dives into the tension between comfort and authenticity, the role of solitude in self-discovery, and the courage needed to embark on new adventures. Kevin and Joe’s candid reflections provide insights into rediscovering passion, redefining success, and nurturing resilience amid life’s inevitable transitions.

Why You Should Listen

Kevin Rogers is a former comedian turned successful entrepreneur, and Joe DiRoma is an experienced leadership coach. Together, they bring unique perspectives to tackling midlife's complex challenges with humor, wisdom, and practical advice.

Why This Episode Matters

For many men in midlife, life can feel routine, even stagnant. Kevin and Joe share personal stories of navigating “the middle passage” – that pivotal time when career, relationships, and health demand reevaluation. This episode speaks to those seeking change, reigniting curiosity, and choosing paths that align with their core values, rather than simply staying comfortable.

Key Quotes

"Sometimes, to find what you want, you have to start with what you don’t want." – Kevin

"We must abandon our first adulthood... and pursue a new adventure, one of deeper meaning and authenticity." – Joe quoting James Hollis

"Depression will be your penance for not challenging yourself." – Kevin

Key Takeaways

Prioritize Self-Investment: Invest in growth, whether through coaching, new hobbies, or skill development.

Embrace the Beginner Mindset: Starting over can feel intimidating, but it’s essential for long-term growth and fulfillment.

Recognize the Power of Solitude: Time alone helps clarify priorities, encouraging decisions that align with one’s core values.

Challenge Comfort: Comfort can lead to stagnation. Seeking new experiences keeps life vibrant and fulfilling.

Resources Mentioned

Ontological Coaching – Joe's transformative coaching program that redefined his approach to personal and professional life.

Books – Referenced works by Carl Jung and James Hollis on midlife transformation.

Health and Wellness Tools – Blood pressure monitoring as part of Joe's journey to better health.

Call to Action

If today’s episode resonated, please share it with others navigating similar midlife challenges. For thoughts, questions, or topics you’d like us to cover, email us at [email protected]. And of course, subscribe to the newsletter at maninthemiddleshow.com.

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Surrounded but Alone: Why Midlife Men Need True Connection, Not Just Company
Episode Summary

Are you navigating the crossroads of midlife and questioning the path you're on? In a world more connected yet lonelier than ever, Kevin and Joe delve into the profound difference between solitude and loneliness, and how embracing solitude can be the key to self-discovery and fulfillment in midlife.

Why You Should Listen

Kevin Rogers, a former stand-up comedian turned copywriter, and Joe DiRoma, an entrepreneur and life strategist, bring years of wisdom, humor, and insight to the Man in the Middle Show. Together, they tackle the deep, unspoken challenges of midlife with authenticity and practical guidance.

Why This Episode Matters

In an era where constant connectivity can lead to a void of meaningful connection, Kevin and Joe explore why loneliness often persists despite social media, and how solitude offers a path toward personal fulfillment. They address the fears, challenges, and desires men face in their middle years, including career reassessment, marriage dynamics, and the need for a lasting legacy.

Key Quotes

• “Loneliness isn’t about having no one around. It’s about being unable to communicate the things that matter most to you.” – Joe
• “Solitude isn’t just being alone; it’s a choice to be with yourself without distraction. It’s the space where self-discovery happens.” – Kevin

Key Takeaways

1. Difference Between Loneliness and Solitude: Loneliness is often a byproduct of unmet emotional needs, while solitude is a conscious, fulfilling choice that allows for introspection and growth.
2. The Impact of Social Media on Genuine Connection: The illusion of connection on social platforms can amplify loneliness. Real connections happen through meaningful face-to-face interactions.
3. The Value of Quieting the Mind: Practicing solitude means confronting the mind’s constant need for stimulation, leading to more inner peace and mental clarity.
4. Benefits of Solitude in Midlife: Solitude can foster self-discovery, enabling men to reassess life goals, redefine purpose, and build resilience.

Resources Mentioned

• James Hollis – referenced for his work on midlife transitions and the deeper significance of human existence.
• Carl Jung – quoted on the importance of facing life's questions to expand one's spiritual horizon.

Call-to-Action

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Loneliness vs. Solitude: A Midlife TransitionEpisode Summary

In a world where solitude can often slide into loneliness, how do midlife men navigate this delicate balance? Join Kevin Rogers and Joe DiRoma as they delve into the transformative period of midlife, exploring the nuanced journey from isolation to introspective solitude.

Why You Should Listen

Host Kevin Rogers, a seasoned communicator with a knack for deep dives into life's intricate topics, joins forces with Joe DiRoma, a thought leader in navigating midlife transitions. Together, they unpack the complexities of this significant life stage.

Episode Context and Relevance

This episode explores a pivotal transition for men in midlife—distinguishing between loneliness and solitude. It’s designed for those who are reevaluating their life's journey, seeking deeper meaning, and embracing the changes that come with this season.

Key Quotes

"Solitude is the richness of self that often gets drowned out by the noise of daily life." - Kevin

"Loneliness can be a signal, not just a symptom—it's telling us about what needs to change." - Joe

Key Takeaways

Understanding loneliness vs. solitude is crucial for mental health in midlife.

Engaging with personal growth tools can transform periods of loneliness into fruitful solitude.

Reflecting on personal experiences and stories helps normalize midlife transitions and fosters community.

Resources Mentioned

"The Stoic Challenge" by William B. Irvine

"Man’s Search for Meaning" by Viktor E. Frankl

Mindfulness meditation apps and resources

Call-to-Action

If today’s discussion resonated with you, consider diving deeper into the themes of solitude and personal growth with the books and resources mentioned. Share your thoughts and experiences with us via our social channels or email us at [email protected]. And of course, subscribe to the newsletter at maninthemiddleshow.com. 

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Relationships in Transition: Redefining Connections
Episode Overview

In this raw and insightful episode of Man in the Middle Show, hosts Kevin Rogers and Joe DiRoma dive deep into the complexities of relationships during midlife transitions. They explore the emotional layers and nuanced choices that arise when long-term relationships evolve, particularly in midlife. This episode is a compelling listen for any man navigating shifts in personal connections, seeking a balanced approach to self-discovery, and finding purpose beyond traditional roles.

Why You Should Listen

Kevin and Joe bring both personal experience and philosophical insight to help men facing relationship struggles, professional crossroads, or personal growth challenges. With humor and wisdom, they unpack how to manage internal conflicts, engage in healthy self-assessment, and navigate new paths with resilience and clarity.

Key Quotes

“The only way out of the darkness is through self-acceptance. Without it, there is no psychological healing.” – Kevin

“In life, you’re constantly challenged to find balance – between self-responsibility and understanding, between connection and independence.” – Joe

“Accepting that life could be radically different from what you expected is the first step toward true growth.” – Kevin

Key Takeaways

Self-Acceptance: Embracing your true self is crucial for both psychological healing and meaningful personal growth.

Mentorship: Trusted mentors can provide much-needed guidance, support, and perspective during challenging life phases.

Self-Reflection: Regular self-assessment and open dialogue with others help in navigating midlife transitions.

Empathy vs. Accountability: Knowing when to offer understanding and when to encourage responsibility is key to strong leadership and personal relationships.

Resources Mentioned

The Middle Passage: From Misery to Meaning in Midlife by James Hollis – An influential book for those navigating midlife crises.

Enneagram Types: A reference to Kevin and Joe's Enneagram discussion on personality types, useful for self-reflection and understanding interpersonal dynamics.

Call to Action

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Crossing the Threshold: The Call of Midlife
Episode Overview

In this premiere episode of Man in the Middle Show, hosts Kevin Rogers and Joe DiRoma challenge the conventional notion of the "midlife crisis," reframing it as a natural transition and call to deeper meaning. Through personal stories and candid discussion, they explore what happens when men begin questioning their achievements, relationships, and life direction. This episode offers valuable insights for any man feeling the pull toward authenticity and meaningful change in midlife.

Why You Should Listen

Kevin and Joe bring raw honesty and diverse perspectives to help men understand that feeling detached or questioning your path isn't a crisis—it's a natural transition. With vulnerability and humor, they discuss the challenges of creating space for self-reflection, managing relationship dynamics during personal transformation, and finding meaning beyond achievement. Their conversation validates the experience of men facing similar transitions while offering hope and practical wisdom.

Key Quotes

"Crisis creates change. Crisis creates questioning... This isn't actually a crisis. This is a natural, necessary part of our development through the human experience." -- Joe

"I found myself always trying to impress somebody I was impressed with... Then I got to a point somewhere around 50 where I thought, I don't think there's ever gonna be another person that I care that much to impress again." -- Kevin

"Midlife isn't a crisis; it's a call to return to who you were before life got so busy." -- Kevin

Key Takeaways

Transition vs Crisis: Understanding that midlife changes are a natural evolution rather than a breakdown.

Self-Reflection Space: The importance of creating time for introspection without guilt or external pressure.

Male Connection: Acknowledging the loneliness epidemic among men (63% of men 45-65 report feeling lonely) and the importance of authentic male friendships.

Identity Evolution: Shifting from external validation to self-guided purpose and meaning.

Resources Mentioned

The Middle Passage by James Hollis -- A foundational text for understanding and navigating midlife transitions from a Jungian perspective.

CDC Statistics on male suicide rates in the 45-54 age group -- Highlighting the critical need for support and connection during this life phase.

Call to Action

If this episode resonated with you, subscribe to Man in the Middle Show newsletter and join our community of men redefining midlife. Share your thoughts and experiences—your story might be exactly what another man needs to hear. Connect with us at [email protected].

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