Gay Men Going Deeper

You know the type — ambitious, perfectionistic, and always striving to do more and be more… yet secretly fuelled by pressure, anxiety, and fear.   In this episode, Michael is joined by special guest Scott Stirrett as they share their own stories of hustling for achievement and how they’ve learned to stay ambitious without destroying themselves in the process. Together, they unpack how perfectionism, internalized shame, and the need for external validation can be ways we attempt to outrun our insecurities — and pivot toward ambition that’s healthy, sustainable, and soul-driven.  Topics covered in this episode: Why gay men are uniquely wired for overachievement How perfectionism shows up in covert and overt ways  How adversity can build anti-fragility and real confidence The difference between healthy ambition vs shame-fuelled hustle Learning to slow down without feeling lazy, guilty, or like you’re falling behind  Rewiring your motivation so it feeds you instead of drains you  By the end of this episode, you’ll be inspired to pursue success in a way that keeps you driven and impactful — without burning yourself out — and to start measuring your worth from the inside out. Today's Guest: Scott Stirrett LinkedIn Instagram Today's Host: Michael DiIorio Instagram Men's Group Support the Show - viewer and listener support helps us to continue making episodes - CONNECT WITH US - Watch podcast episodes on YouTube Join the Gay Men's Brotherhood Facebook community Get on our email list to get access to our monthly Zoom calls Follow us on Instagram | TikTok Learn more about our community at GayMenGoingDeeper.com - LEARN WITH US - Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others. Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame. Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series. Take the Attachment Style Quiz to determine your attachment style and get a free report.

In this final installment of our 4-part series on grief, we explore the powerful practice of Radical Acceptance—what it means, why it’s so difficult, and how it becomes the turning point in your healing journey. Whether you're grieving the person you used to be, mourning a friendship that faded, or facing the slow heartbreak of watching your parents age, grief often leaves us wrestling with reality. Radical acceptance is what allows us to stop fighting what is, and start living again with peace, presence, and purpose. Topics we explore in this episode include: What radical acceptance really means (and why it’s radical) How it differs from giving up, resignation, or bypassing Why acceptance is often the hardest part of grief The role of faith and inner trust when you’re still hurting Personal stories of surrender, softness, and finding peace How to move forward when closure isn’t coming This episode offers a hopeful, grounded perspective for anyone still sitting with loss, longing, or unanswered questions. Today's Hosts: Michael DiIorio Matt Landsiedel Support the Show - viewer and listener support helps us to continue making episodes - CONNECT WITH US - Watch podcast episodes on YouTube Join the Gay Men's Brotherhood Facebook community Get on our email list to get access to our monthly Zoom calls Follow us on Instagram | TikTok Learn more about our community at GayMenGoingDeeper.com - LEARN WITH US - Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others. Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame. Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series. Take the Attachment Style Quiz to determine your attachment style and get a free report.

As our parents get older, many of us are faced with a new kind of grief- the quiet, ongoing loss that comes not from death, but from watching the people who once raised us begin to slow down and need us in ways they never did before. In this deeply personal episode, we open up about the emotional complexity of witnessing our parents age. From role reversals and unresolved wounds, to meaningful moments and surprising lessons, we reflect on how our relationships with our parents evolve, and how it stirs up questions of our own mortality.   We explore: The quiet grief of losing parts of who they were The guilt, tenderness, and sometimes resentment of becoming the caretaker How aging parents trigger our own fears about time, mortality, and purpose Ways to heal, connect, and make meaningful memories before it’s too late This is an episode for anyone navigating that in-between space—where love, loss, and legacy all live at once. Today's Hosts: Michael DiIorio Matt Landsiedel Support the Show - viewer and listener support helps us to continue making episodes - CONNECT WITH US - Watch podcast episodes on YouTube Join the Gay Men's Brotherhood Facebook community Get on our email list to get access to our monthly Zoom calls Follow us on Instagram | TikTok Learn more about our community at GayMenGoingDeeper.com - LEARN WITH US - Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others. Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame. Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series. Take the Attachment Style Quiz to determine your attachment style and get a free report.

Grief isn't just about death; it can stem from lost relationships, including breakups and friendships. The hosts explore the emotional spectrum of grief, discussing the stages and the unique pain of letting go. They share personal stories about processing sadness after losing loved ones, whether human or pet, and highlight the healing power of acknowledging one's feelings. There's a focus on self-love, introspection, and the importance of navigating solitude as a path to personal growth after heartbreak.

Grief isn’t just about death—it’s also about the quiet losses we carry as we grow and evolve. In this episode, we’re kicking off a 4-part series on grief by exploring what it means to grieve your past. Whether it’s a version of yourself that felt more confident, more desirable, or more socially “relevant,” we often feel a deep emotional pull toward who we used to be. From aging and identity shifts to the grief of letting go of our dreams, we’re diving into the invisible grief that comes with change. We discuss: What grieving your past looks like How grief can show up as you grow and evolve  Letting go of your youth, body, or social capital as a gay man The bittersweet nostalgia of past chapters—even ones you chose to leave behind How to know when it’s time to move on, and how to do it with self-compassion This conversation is about honoring who you were while embracing who you’re becoming. Related Episode: Grappling with Grief: Addison Brasil Today's Hosts: Michael DiIorio Matt Landsiedel Support the Show - viewer and listener support helps us to continue making episodes - CONNECT WITH US - Watch podcast episodes on YouTube Join the Gay Men's Brotherhood Facebook community Get on our email list to get access to our monthly Zoom calls Follow us on Instagram | TikTok Learn more about our community at GayMenGoingDeeper.com - LEARN WITH US - Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others. Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame. Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series. Take the Attachment Style Quiz to determine your attachment style and get a free report.

Most of us want to be seen, heard, and understood, but the fear of judgment can stop us from doing so. Whether it’s being more social, speaking your feelings, or sharing creative work, putting yourself out there can feel risky, especially when we’ve been conditioned to play it safe due to past hurt or rejection.  In this episode, we’re sharing: 👉 Our personal journeys from shy and self-conscious to being more visible 👉 The fears that held us back, and sometimes still do 👉 How we want to be perceived vs. showing up authentically  👉 What helps us keep showing up, even when it’s uncomfortable If you’ve ever held back because you’re scared of what people might think, this episode is for you. Today's Hosts: Michael DiIorio Matt Landsiedel Reno Johnston Support the Show - viewer and listener support helps us to continue making episodes - CONNECT WITH US - Watch podcast episodes on YouTube Join the Gay Men's Brotherhood Facebook community Get on our email list to get access to our monthly Zoom calls Follow us on Instagram | TikTok Learn more about our community at GayMenGoingDeeper.com - LEARN WITH US - Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others. Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame. Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series. Take the Attachment Style Quiz to determine your attachment style and get a free report.

We all know self-love is important, but what happens when it goes too far in the wrong direction? In this episode, Michael DiIorio is joined by therapist Michael Pezzullo for an honest conversation about the shadow side of self-love. Together, they explore: The difference between self-comforting and self-coddling How emotional sensitivity can become emotional fragility Why self-bulldozing is just as harmful as avoidance The four zones of the Self-Love Spectrum How trauma impacts the way we “love” ourselves How to tell if you're truly healing…or just hiding. You’ll learn about the Self-Love Spectrum, the signs of self-coddling and self-bulldozing, and how to practice a more empowering, growth-oriented version of self-love- without abandoning your need for care and compassion. Join us for an episode that will help you get honest about how you love yourself, and what real self-love actually looks like. Today's Guest: Michael Pezzullo Website Instagram Today's Host: Michael DiIorio Website Instagram Support the Show - viewer and listener support helps us to continue making episodes - CONNECT WITH US - Watch podcast episodes on YouTube Join the Gay Men's Brotherhood Facebook community Get on our email list to get access to our monthly Zoom calls Follow us on Instagram | TikTok Learn more about our community at GayMenGoingDeeper.com - LEARN WITH US - Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others. Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame. Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series. Take the Attachment Style Quiz to determine your attachment style and get a free report.

Some of us didn’t choose to become lone wolves—we were shaped into them. Many gay men have learned to rely only on themselves, and while that self-sufficiency can feel empowering, it often comes at the cost of connection and intimacy. In this personal and vulnerable episode, Michael and Matt open up about their own lone wolf energy—where it comes from, how it’s served them, and the moments when it became more isolating than empowering. Together, we’re unpacking: The origin stories of our lone wolf instincts The protective thoughts that sound strong but hide deeper wounds What makes us want to cut people off—and what’s really underneath that urge How this energy shows up in dating and relationships And how to honour your need for space without shutting people out Whether you identify as a lone wolf or love someone who does, this episode will help you navigate the delicate balance between fierce independence and meaningful connection. Today's Hosts: Michael DiIorio Matt Landsiedel Support the Show - viewer and listener support helps us to continue making episodes - CONNECT WITH US - Watch podcast episodes on YouTube Join the Gay Men's Brotherhood Facebook community Get on our email list to get access to our monthly Zoom calls Follow us on Instagram | TikTok Learn more about our community at GayMenGoingDeeper.com - LEARN WITH US - Building Better Relationships online course: Learn how to nurture more meaningful and authentic connections with yourself and others. Healing Your Shame online course: Begin the journey toward greater confidence and self-worth by learning how to recognize and deal with toxic shame. Gay Men Going Deeper Coaching Collection: Lifetime access to BOTH courses + 45 coaching videos and 2 workshop series. Take the Attachment Style Quiz to determine your attachment style and get a free report.

Lonay Halloum, a queer relationship coach and rapid transformational therapy practitioner, joins Matt to delve into the compelling reasons behind attracting unavailable partners. They candidly share personal experiences and discuss the role of attachment styles in relationship patterns. The conversation highlights the impact of childhood experiences on emotional availability and self-worth. Lonay offers insights into healing self-abandonment wounds and emphasizes the importance of self-awareness and kindness in breaking the cycle to find fulfilling relationships.

Dive into the heart of rejection sensitivity, exploring its roots from childhood experiences. Discover how societal norms and internalized shame shape feelings of inadequacy. Personal stories highlight the impact of dating culture and the struggle for self-acceptance. Learn practical ways to build resilience and embrace vulnerability. The conversation emphasizes the importance of community support in overcoming emotional challenges and finding authenticity. If you've ever felt overwhelmed by rejection, this discussion offers insight and hope.