Man in the Middle Show w/ Kevin & Joe

Kevin Rogers & Joe DiRoma

Man in the Middle Show with Kevin & Joe Are you a middle-aged man feeling trapped in your life? Stuck in a relationship, career, health situation, or financial rut that leaves you unfulfilled? Do you find yourself asking, "Is this it? Is it me? Is there more?" You're not alone, and the Man in the Middle Show is here to prove it. Join Kevin and Joe, two regular guys living in the "middle", as they dive deep into the challenges, triumphs, and existential questions that plague men in midlife. This isn't your typical self-help podcast – it's a raw, honest conversation between friends who've been there, done that, and are still figuring it out. Meet Your Hosts: Kevin at 54, he's a bald, bionic entrepreneur with a metal heart valve and 20 years in the "bonus round" of life. A former stand-up comic turned business owner, Kevin's journey includes: - 25 years of marriage - Raising two newly adult children - A near-death experience and open-heart surgery at 35 - Navigating major career shifts and life transitions Joe is The 42-year-old "regular guy" with an extraordinary story: - 15 years sober after a 13-year battle with addiction - High school dropout turned successful restaurant industry leader and now COO in digital marketing - Father to a teenager and expecting a newborn (talk about a midlife shake-up!) - Proof that it's never too late to turn your life around Why Listen? Real Talk, No BS... Kevin and Joe aren't therapists or gurus – they're guys just like you, sharing their experiences and struggles without filters. You're Not Alone! Discover that those feelings of emptiness, confusion, and restlessness are normal and part of the midlife journey for many men. Diverse Perspectives are critical. With their vastly different backgrounds and life experiences, Kevin and Joe offer unique insights into common midlife challenges. Inspiration to Ask Bigger Questions. Instead of easy answers, you'll be motivated to dig deeper and rediscover what truly matters to you. A Safe Space for Men. Finally, a place where you can hear open, honest discussions about the topics men often feel they can't talk about. Practical Wisdom. Learn from the hosts' successes and failures as they navigate relationships, career transitions, health scares, and major life changes. Finally... some Humor and Heart. Expect laughs alongside the deep stuff – because sometimes, you've got to find the funny in life's challenges. The Man in the Middle Show isn't about having it all figured out. It's about embracing the messy middle, finding meaning in the struggle, and realizing that your best years might still be ahead of you. Whether you're feeling lost, looking for a change, or just want to hear from guys who get it, Kevin and Joe are here to bring you into the middle of the conversation. You're not above, you're not below – you're right there with them, part of a community of men facing midlife head-on. Tune in and discover: - Strategies for reigniting passion in your relationships and career - How to navigate major life transitions with grace (or at least a sense of humor) - Ways to redefine success and fulfillment on your own terms - The power of vulnerability and authentic male friendships - Tools for managing stress, health concerns, and the infamous midlife crisis Don't let society tell you how to age or what your life should look like. Join Kevin, Joe, and a growing tribe of men who are rewriting the rules of midlife, one honest conversation at a time. Subscribe to the Man in the Middle Show w/ Kevin & Joe because midlife doesn't have to be a crisis. It can be your awakening. New episodes drop weekly. Available wherever you get your podcasts. Remember... You're not stuck. You're not alone. And there's definitely more to life – let's find it together.

  1. 1D AGO

    Episode 15: Dr. James Hollis Joins Man in the Middle (Our Exclusive Interview)

    “Dr. James Hollis Joins Man in the Middle (Our Exclusive Interview)”Episode OverviewWhat 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 Why listenDr. 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 Key Quotes“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.” Main Topics CoveredThe psychology of midlife transitionFirst adulthood vs. second adulthoodWhy achievement can become a prisonDepression as a summons, not a disorderEnergy, meaning, and inner authorityShadow work and the unlived lifeDreams as guidance systemsPatience, endurance, and courage Masculinity, isolation, and authenticityLegacy beyond success Key TakeawaysMidlife unrest is not failure, it is initiation.Letting go of old identities is necessary before new meaning emerges.Feelings, energy levels, and dreams are diagnostic tools, not inconveniences.The second half of life asks for service, not status.This journey cannot be rushed but it can be honored. Recommended ResourceThe Middle Passage by James Hollis (a foundational text for men in midlife)Audiobook versions of Hollis’ work, read by the authorPrisms and other writings by James Hollis Next StepsIf 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...

    1h 12m
  2. FEB 2

    Episode 14: Facing Our Dark Side - Dealing with the Parts of Ourselves We Don’t Like to Admit Exist

    “Facing Our Dark Side: Dealing with the Parts of Ourselves We Don’t Like to Admit Exist”Episode OverviewWhat 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. Why listenKevin 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. Key Quotes“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.” Main Topics CoveredJung’s shadow: what it is and why it matters.Cultural conditioning vs personal morality.Guilt vs shame.Triggers, judgments, projections, and patterns.Emotional suppression in families (especially men).Humor as avoidance vs connection.Midlife awakening and identity transformation.Accountability, integrity, and conscious living. Key TakeawaysYour shadow isn’t evil, it’s exiledThe “dark parts” are often natural emotions or desires that were punished, shamed, or rejected.Your triggers are your trailIf someone annoys you irrationally, there’s usually something in you asking to be acknowledged.Midlife forces truthThis is why men in midlife start asking: “Is this really my life? Is this really me?”Bring the unconscious into the lightThe shadow has power when it’s hidden.Once seen clearly, it becomes something you can integrate instead of fear. Recommended Resourcespan class="ql-ui"...

    51 min
  3. JAN 26

    Episode 13: Career Change Without Burning Your Life Down

    “Career Change Without Burning Your Life Down”Episode OverviewWhat 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. Why listenKevin 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. Key Quotes“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.” Main Topics CoveredMidlife career changes after 45: why they’re rising.Provider pressure + identity crisis in men.Fear of incompetence and sunk-cost fallacy.Family expectations and lifestyle resistance.How layoffs can become a “calling”.Finding alignment vs forcing discipline.Transferable skills and resume reframing.Blue-collar opportunities and buying businesses.Why communication with your spouse is crucial. Key TakeawaysMidlife career change isn’t only professional, it’s personal identity.Don’t ignore the inner restlessness—explore before you’re forced.Look for the through-line: what wants to come to life in you now?You’re more qualified than you think—your experience contains transferable skills.Discipline without alignment becomes misery. Alignment creates discipline naturally.If your marriage can’t handle these conversations, fix that first. Recommended ResourceJames Hollis - The Middle Passage.Carl Jung (unlived life concept). Next StepsIf this episode inspired you to reconnect with joy and curiosity, please...

    58 min
  4. JAN 19

    Episode12: The Dreams You Abandoned: Why Your Childhood Ambitions Hold the Key to Midlife Purpose

    “The Dreams You Abandoned: Why Your Childhood Ambitions Hold the Key to Midlife Purpose”Episode OverviewMost 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. Why listenKevin 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. Key Quotes“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.” Main Topics CoveredChildhood dreams as clues to adult purposeIdentity vs. true aptitude: when something “looks cool” but isn’t your laneHow early gifts evolve into leadership strengthsHumor: talent, tool, and defense mechanismRegret as avoidance—and how to reclaim “missed shots” nowRecovery, integrity, and rebuilding a life without self-hatredRetirement without purpose (and why it can accelerate decline)Career uncertainty in midlife and how to adapt without panicThe role of community: why you can’t do this alone Key TakeawaysYour childhood interests are not childish. They’re often the earliest evidence of what energizes you.Regret is usually about fear, not failure. The cost of “playing it safe” compounds over decades.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.Purpose must outlive your job title. If your identity depends on your role, retirement (or job loss) can become a crisis.Healing requires honesty and relationships. Growth accelerates when you stop managing it alone. Call-to-ActionIf 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...

    52 min
  5. JAN 12

    Episode 11: Everything After 'But' is Bulls**t: How to Cut Through Your Own Excuses and Live Again

    "Everything After 'But' is Bulls**t: How to Cut Through Your Own Excuses and Live Again"Episode SummaryYou'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. Why You Should ListenIf 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. Key Quotes"Everything after 'but' is usually b******t." - Joe's mentor"The privilege of a lifetime is to become who you truly are." - Carl Jung"Shit's coming, everybody. That's the one promise. Appreciate the blessing of every day that goes your way. And be ready for when it doesn't." - Kevin Rogers"The task of midlife is not to look into the light, but to bring light into the darkness." - James HollisKey TakeawaysListen 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.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.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.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. Resources Mentioned"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. Call-to-ActionIf 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 Connect with Usa...

    43 min
  6. 12/16/2024

    Episode 10: Stop Taking Yourself So Seriously Reclaiming Joy and Curiosity in Midlife

    Stop Taking Yourself So Seriously: Reclaiming Joy and Curiosity in MidlifeEpisode SummaryWhat 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 ListenKevin 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 MattersAs 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 TakeawaysThe 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 MentionedBook: Memories, Dreams, Reflections by Carl JungBook: The Middle Passage by James HollisStudy: George Land’s NASA creativity study, revealing that 98% of five-year-olds demonstrate genius-level creativityQuote: Maya Angelou’s insight on how people remember how you make them feel Call-to-ActionIf 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 Connect with UsWatch on YouTube Listen on Apple Listen on Spotify Sign up for the Newsletter

    53 min
  7. 12/09/2024

    Episode 9: Operation Separation Finding Freedom and Identity After a Major Life Shift

    Operation Separation: Finding Freedom and Identity After a Major Life ShiftEpisode SummaryWhat 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 ListenKevin 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 MattersSeparation 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 TakeawaysThe 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 MentionedBooks:The Middle Passage by James HollisMemories, Dreams, Reflections by Carl JungMusic:Tom Petty’s WildflowersLeonard Cohen’s Live in LondonQuote: “Our wounds become our wisdom.” – James Hollis Call-to-ActionIf 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 Connect with UsWatch on YouTube Listen on Apple Listen on Spotify Sign up for the Newsletter

    48 min
  8. 12/02/2024

    Episode 8: Choosing To Lead

    Choosing To LeadEpisode SummaryWhat 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 ListenKevin 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 MattersFor 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 TakeawaysIntention-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 MentionedBook: Supercommunicator by Charles Dewey (for insights on types of conversations)The Middle Passage by James HollisQuotes: Carl Jung and other notable thinkers on leadership and personal growth Call-to-ActionIf 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 Connect with UsWatch on YouTube Listen on Apple Listen on Spotify a href="https://maninthemiddleshow.com/" rel="noopener...

    54 min
4.4
out of 5
29 Ratings

About

Man in the Middle Show with Kevin & Joe Are you a middle-aged man feeling trapped in your life? Stuck in a relationship, career, health situation, or financial rut that leaves you unfulfilled? Do you find yourself asking, "Is this it? Is it me? Is there more?" You're not alone, and the Man in the Middle Show is here to prove it. Join Kevin and Joe, two regular guys living in the "middle", as they dive deep into the challenges, triumphs, and existential questions that plague men in midlife. This isn't your typical self-help podcast – it's a raw, honest conversation between friends who've been there, done that, and are still figuring it out. Meet Your Hosts: Kevin at 54, he's a bald, bionic entrepreneur with a metal heart valve and 20 years in the "bonus round" of life. A former stand-up comic turned business owner, Kevin's journey includes: - 25 years of marriage - Raising two newly adult children - A near-death experience and open-heart surgery at 35 - Navigating major career shifts and life transitions Joe is The 42-year-old "regular guy" with an extraordinary story: - 15 years sober after a 13-year battle with addiction - High school dropout turned successful restaurant industry leader and now COO in digital marketing - Father to a teenager and expecting a newborn (talk about a midlife shake-up!) - Proof that it's never too late to turn your life around Why Listen? Real Talk, No BS... Kevin and Joe aren't therapists or gurus – they're guys just like you, sharing their experiences and struggles without filters. You're Not Alone! Discover that those feelings of emptiness, confusion, and restlessness are normal and part of the midlife journey for many men. Diverse Perspectives are critical. With their vastly different backgrounds and life experiences, Kevin and Joe offer unique insights into common midlife challenges. Inspiration to Ask Bigger Questions. Instead of easy answers, you'll be motivated to dig deeper and rediscover what truly matters to you. A Safe Space for Men. Finally, a place where you can hear open, honest discussions about the topics men often feel they can't talk about. Practical Wisdom. Learn from the hosts' successes and failures as they navigate relationships, career transitions, health scares, and major life changes. Finally... some Humor and Heart. Expect laughs alongside the deep stuff – because sometimes, you've got to find the funny in life's challenges. The Man in the Middle Show isn't about having it all figured out. It's about embracing the messy middle, finding meaning in the struggle, and realizing that your best years might still be ahead of you. Whether you're feeling lost, looking for a change, or just want to hear from guys who get it, Kevin and Joe are here to bring you into the middle of the conversation. You're not above, you're not below – you're right there with them, part of a community of men facing midlife head-on. Tune in and discover: - Strategies for reigniting passion in your relationships and career - How to navigate major life transitions with grace (or at least a sense of humor) - Ways to redefine success and fulfillment on your own terms - The power of vulnerability and authentic male friendships - Tools for managing stress, health concerns, and the infamous midlife crisis Don't let society tell you how to age or what your life should look like. Join Kevin, Joe, and a growing tribe of men who are rewriting the rules of midlife, one honest conversation at a time. Subscribe to the Man in the Middle Show w/ Kevin & Joe because midlife doesn't have to be a crisis. It can be your awakening. New episodes drop weekly. Available wherever you get your podcasts. Remember... You're not stuck. You're not alone. And there's definitely more to life – let's find it together.