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.

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.

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.

• 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.

• 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

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.

Watch on YouTube

Listen on Apple

Listen on Spotify

Sign up for the Newsletter

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.

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.

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.

"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

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.

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.

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 info@maninthemiddleshow.com. And of course, subscribe to the newsletter at maninthemiddleshow.com.

Watch on YouTube

Listen on Apple

Listen on Spotify

Sign up for the Newsletter

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.

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.

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.

• “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

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.

• 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.

Enjoyed this episode? Share it with someone navigating their own journey of self-discovery. Subscribe to the Man in the Middle Show for more powerful discussions, and if you’re finding value, leave us a review!

Watch on YouTube

Listen on Apple

Listen on Spotify

Sign up for the Newsletter

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.

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.

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.

"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

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.

"The Stoic Challenge" by William B. Irvine

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

Mindfulness meditation apps and resources

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 info@maninthemiddleshow.com. And of course, subscribe to the newsletter at maninthemiddleshow.com.

Watch on YouTube

Listen on Apple

Listen on Spotify

Sign up for the Newsletter

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.

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.

“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

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.

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.

Liked the episode? Subscribe for more insightful discussions and leave us a review. Have questions or stories to share? Reach out at info@maninthemiddleshow.com. And don’t forget to share this episode with someone who might need it—sometimes the right message can spark a life-changing conversation.

1. Watch on YouTube
2. Listen on Apple
3. Listen on Spotify
4. Sign up for the Newsletter

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.

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.

"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

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.

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.

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 info@maninthemiddleshow.com.

1. Watch on YouTube
2. Listen on Apple
3. Listen on Spotify
4. Sign up for the Newsletter

Are you feeling stuck in life—trapped in a career, relationship, or situation that no longer brings you joy? Do you catch yourself asking, "Is this it? Is it me? Is there more?" You’re not alone.

Welcome to The Man in the Middle Show, where hosts Kevin Rogers and Joe DiRoma invite you on a journey through the messy, exciting, and sometimes overwhelming landscape of midlife as a man.

In this kickoff trailer, Kevin and Joe introduce themselves, share their personal stories, and set the stage for what’s to come. It’s not a therapy session, and they don’t claim to have all the answers. They are just two regular guys—living different lives but sharing common midlife struggles—here to create a space where men can reflect, connect, and feel heard.

• Kevin Rogers: A 54-year-old entrepreneur and father of two adult children, Kevin's life reads like an adventure novel. From life on the road as a stand-up comic to surviving open-heart surgery with a new lease on life, Kevin’s journey is all about reinvention and living what he calls his “bonus round.”
• Joe DiRoma: At 42, Joe's life has been a tale of redemption—15 years sober after battling addiction and early run-ins with the law. Now a family man, Joe is balancing the chaos of having a teenage son and expecting a newborn daughter. Formerly in the restaurant industry, Joe now thrives as a COO in digital marketing, where he and Kevin crossed paths.

This episode sets the tone for the honest, relatable conversations that will unfold on this podcast. Kevin and Joe open up about their personal challenges with change, relationships, careers, and health—all common struggles for men in midlife. Their goal is simple:

This isn’t a self-help lecture. It’s a conversation designed to inspire you to ask yourself bigger questions, like:

• What does fulfillment really look like for me?
• How do I navigate relationships and fatherhood at this stage of life?
• How do I reinvent myself in a way that feels true?

Tune in to Episode 0 and get ready for candid stories, laughter, and insights that will leave you reflecting on your own journey—and knowing you don’t have to walk it alone.

In This Episode:

• Kevin’s life-changing journey from stand-up comic to entrepreneur
• Joe’s story of recovery and fatherhood
• The mission of The Man in the Middle Show: Creating space for men to connect and grow through open, honest conversations

Get ready to explore what it means to thrive in the middle of life—because there’s so much more to come.