Joy isn’t just fireworks and big milestones; it’s in the ordinary, everyday moments we often overlook. Yet for many of us, joy feels slippery and hard to find.
In this episode of Gay Men Going Deeper, we’re diving into what joy really feels like, how it shifts as we evolve and age, and why it’s less about chasing highs and more about cultivating presence.
We’ll explore:
The difference between joy and pleasure (and why we confuse them)
Joy-givers vs. joy-suckers (and how to spot yours)
The role of play, laughter, and lightheartedness in a joyful life
How to deepen your relationship with joy in your next chapter
Why joy is a skill you can practice, not just a mood you stumble into
If you’re ready to move beyond quick fixes and start building a life that feels nourishing, playful, and deeply fulfilling, this conversation is for you.
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
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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.
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Perfectionism, Pressure, and the Gay Overachiever
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
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Today's Host: Michael DiIorio
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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.
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1:05:48
Radical Acceptance: Grief’s Final Lesson
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.
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Aging Parents and Pre-Grief
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.
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Grieving Relationships
Not all grief is about death. Sometimes, the hardest losses are the people (or pets) who are still alive—but no longer in our lives.
In this episode, we’re talking about the heartbreak of losing relationships: romantic breakups, friendship fallouts, and the deep sadness that comes with saying goodbye to a beloved pet. We explore how grief shows up emotionally, mentally, and even physically—and the unique challenges of letting go of someone who once meant everything to you.
Together, we share personal experiences of:
The stages of grief
Grieving people who are still alive
Letting go of “what could’ve been”
Healing after a breakup
Losing chosen family or long-time friends
Learning how to let go without lingering
This conversation shines a light on the many ways we experience loss and how to move through the grief with compassion, courage, and clarity.
Related Episodes:
Grieving Your Past
When It's Time to Say Goodbye
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.
Gay Men Going Deeper is a weekly podcast that showcases raw and real conversations about personal development, mental health, and sexuality - from an unapologetically gay perspective.
Hosted by Matt Landsiedel and Michael DiIorio, and featuring a wide range of special guests, you can expect to be inspired, entertained, and even a little triggered from time to time.
This provocative podcast is for anyone who craves deeper conversations on topics ranging from spirituality to sexuality - and everything in between.
Visit us at www.GayMenGoingDeeper.com
Support the show: https://www.paypal.com/donate/?hosted_button_id=LT55M79CMH5FN