In this conversation, Shaun sits down with Damian Gomes — a father, technologist, and long-time Scout leader — to explore what it means to raise two sons who couldn’t be more different. From leading Boy Scouts and teaching leadership through failure to navigating remote schooling during the pandemic, Damian shares the lessons, struggles, and surprising gifts of modern fatherhood. One son thrived in self-paced learning and now builds AI systems with his dad; the other is still discovering his path through art and curiosity. Together, they reflect on letting kids fail safely, adapting parenting styles, and staying conscious and present even when patience runs thin.

Key Takeaways / Topics Covered

1. Leadership Is Learned Through Chaos: Scouting teaches “storming, norming, performing” — a real-world model for how boys (and adults) learn to lead, adapt, and collaborate through trial and error.
2. Independence Requires Letting Go: Damian’s older son thrived once school became self-paced. The hardest part was letting him fail, fall behind, and figure it out without rescuing him too early.
3. Parent Each Child Differently: What worked for one son — freedom and code — failed for the other. Fatherhood isn’t a formula; it’s an evolving experiment in empathy and adaptation.
4. Redefining Education and Failure: Damian learned that the goal of learning isn’t perfection but persistence. Retaking a failed quiz became a metaphor for life — you haven’t failed until you stop trying.
5. Conscious Fatherhood Is a Daily Practice: His guiding principle: staying self-aware enough to choose a new reaction rather than repeating old patterns. That pause — between emotion and response — is where growth happens.

Pull Quotes

00:35 Official Introduction

01:41 Involvement and Value in Boy Scouts

03:51 Cubmaster to Scout Leader: The Transition

05:37 "Storming, Norming, and Performing" in Leadership

09:52 Scouting's Offer to Modern Boys

14:44 Contrived Structure for Organic Skills

16:52 The Value of Inventing the Solution

17:47 Doubling Down on Scouting During Challenges

21:39 The Pandemic's Impact on Family Dynamics

24:33 The Shift to Self-Paced Virtual Learning

27:40 Rethinking Failure and Retaking Tests

30:13 Homeschooling vs. Virtual School Decisions

32:38 The Older Son's Success Story

37:03 The Hardest Part: Allowing for Failure

38:55 The Younger Son's Struggle for Structure

42:26 The Future of Learning

43:08 Hopes for Sons' Memories

45:08 One Principle for Raising Men

47:35 Closing Remarks

Supporting Content

Organizations & Concepts

• Boy Scouts of America – emphasizing youth leadership and structured independence.
• YPT (Youth Protection Training) – mandatory training for all Scout leaders.
• EDGE Method – Explain, Demonstrate, Guide, Enable — a Scouting framework for mentorship and teaching.

Education & Tech

• Florida Virtual School – one of the first large-scale online K–12 programs mentioned in the episode.
• Duval Virtual Instruction Academy – Damian’s local district’s virtual learning platform.
• Automation Watchdog – Damian and his son’s company, building systems that verify automation and AI performance.
• Mark Rober’s YouTube Channel – inspiration for Damian’s younger son’s curiosity in science and engineering.
• Open Source Software Movement – central to his son’s learning and development path.

Books & Ideas

• “Mindset: The New Psychology of Success” by Carol S. Dweck – on learning through growth and persistence.
• “The Conscious Parent” by Dr. Shefali Tsabary – echoes Damian’s principle of awareness and conscious parenting.
• “The Scoutmaster’s Other Handbook” by Mark A. Ray – practical modern guide to leadership and youth development through Scouting.

In this thoughtful and often funny conversation, Dr. Daniel Singley—founder of The Center for Men’s Excellence and creator of MenExcel—joins Shaun to unpack what it really means to raise emotionally healthy boys in a rapidly changing world. Together, they explore how traditional models of masculinity can evolve without abandoning strength, why fatherhood is the “tip of the spear” for redefining what it means to be a man, and how dads can model emotional resilience and connection in everyday life.

Dr. Singley shares evidence-based insights on the transition from “dude to dad,” the power of emotional flexibility, and the importance of community for fathers. This episode is a practical and deeply human look at how we can raise sons—and become men—of both heart and strength.

Key Takeaways / Topics Covered

1. Masculinity isn’t under attack—it’s under construction. Healthy masculinity requires flexibility, not rigidity; the ability to be strong in some contexts and empathetic in others.
2. Fatherhood is the frontline of modern manhood. Early involvement during pregnancy and infancy predicts stronger emotional connection, better outcomes for children, and greater well-being for fathers.
3. Emotional literacy is courage, not weakness. When fathers model emotional awareness—naming their feelings, owning their mistakes—they teach their sons that vulnerability is strength.
4. Community is critical for men’s mental health. Isolation is as damaging as smoking a pack a day; fathers need intentional friendships and spaces to be honest with other dads.
5. Kindness is strength. Dr. Singley’s parting message: “Have the strength to be kind”—because cruelty often stems from fear, and choosing compassion is an act of real courage.

Timestamps / Chapter Markers

00:00 Introduction: Cultivating Strength and Sensitivity in Raising Boys

01:18 Dr. Singley's Journey: Why Study the Psychology of Men and Fatherhood?

03:08 The Consequence of Ignoring Cisgender Masculinity in Academia

05:33 The Rising Tide: Empowering Men and Boys Doesn't Harm Other Genders

06:55 Is Masculinity a Problem? Under Attack or Under Construction?

07:54 The Core Issue: Rigidity in Traditional Masculine Roles

09:11 The Benefits of Flexibility: Longevity, Relationships, and Mental Health

10:45 Addressing the Pushback: The "Pacification of the American Male"

13:43 Finding a Balanced Vision: Serving Yourself vs. Holding Yourself Back

16:39 Workplace Benefits of Balanced Masculinity (Strengths with Heart)

18:22 The "Fair Play" Card Exercise and Its Role in Domestic Roles

20:21 Early Fatherhood: Why It's the "Tip of the Spear" for Contemporary Masculinity

23:46 Fatherhood as an Opportunity to Cultivate Caregiving Muscles

25:40 Key Predictors for Father Involvement: Pregnancy and Co-Parent Support

27:48 The Vicious/Virtuous Cycle of Co-Parenting Support

29:04 Shaun's Story: The "No Divorce for a Year" Deal

31:17 Shaun's Story: Catching Inflexibility in Action (Kissing His Son)

32:22 Equating Physicality with Sexuality (and Its Impact on Parenting)

34:10 Parenting with Intention: Be Thoughtful, Not on Autopilot

36:24 Practical Tools: The 10-Year Vision and Modeling Behavior

38:20 The Greatest Gift: Owning Mistakes and Naming Underlying Emotions

41:30 Upgrading Your OS: Why Flexibility is Essential for Modern Men

42:59 Navigating the Extremes: The Paradox of Ideological Purity

47:10 Reflections on Fatherhood: What Dr. Singley Did Right

49:27 The One Step: Overcoming Isolation and Building Community

51:13 The Hidden Danger: Loneliness and the Anxiety of "Bro-Dating"

54:41 Closing Principle: Have the Strength to Be Kind

56:16 Outro and Conclusion

Supporting Content & References

Center for Men’s Excellence – Dr. Singley’s organization focused on men’s mental health and father-inclusive psychology  https://www.menexcel.com
American Psychological Association, Division 51: Society for the Psychological Study of Men and Masculinity** https://www.apa.org/about/division/div51
Fair Play by Eve Rodsky – referenced for practical tools in balancing domestic roles https://www.fairplaylife.com
Strengths with Heart by Tom Rath (referenced in discussion on leadership and empathy) https://www.strengthswithheart.com
US Surgeon General’s Report on Loneliness and Social Isolation (2023)** – cited in Dr. Singley’s point about community and health https://www.hhs.gov/surgeongeneral/priorities/loneliness/index.html

In Part Two, Sean reflects on losing his stepfather and guiding his sons through grief, legacy, and growth. He shares stories of finding laughter in pain, of writing a eulogy that helped him truly understand the man who raised him, and of passing those lessons forward. Together, Shaun and Sean unpack how fathers can model empathy, resilience, and strength through vulnerability—and why raising sons of character starts with being honest about our own humanity.

Key Takeaways / Topics Covered

1. Grief is a teacher — How fathers can lead their families through loss with honesty and calm strength.
2. Model before you teach — Kids copy what they see; your actions are the real lesson.
3. Empathy is legacy — Raising sons who choose kindness and courage in a noisy world.
4. Humor heals — Laughter and humility are part of resilience.
5. Love is conditional in effort, not worth — Sean reminds that love is deep, but accountability still matters.

Supporting Content

• The Kids Are Sleep podcast: https://thekidsaresleeppod.com/
• Instagram (Sean): https://www.instagram.com/therealseanharvey/

Timestamps / Chapter Markers

00:00 Cultivating Understanding: Communicating Why We Push Our Kids (The Right-Hand Layup)
03:22 The Challenge of Independence: Figuring Out the "Redo" for the Second Child
05:46 The Genetics and The Goals: Tall Parents, Athletic Potential, and Non-Athletic Kids
09:22The Asset vs. Liability: Getting Young Girls into Sports
11:24 The Specialization Trap: Dealing with Pressure from Club Sports
14:34 Courage in Vulnerability: What Motivates Sharing the "Messy Life" of Parenting
17:07 The Identity Shift: From Political Satire/Rapper to Public Fatherhood
21:28 The Strength of Vulnerability: The Castle Metaphor and Letting People In
23:31 The True Measure of Success: How Well Kids Do Once They Leave
24:20 Values to Instill: Hard Work, Compassion, and Conditional Love
26:49 Managing the Tension: Unconditional Love vs. Raising Independent Adults
28:22 The "College Hair" Conversation: Comforting Kids vs. Facing Reality
30:10 Advice for Failing Dads: Keep Trying, Keep Failing (The Road to Excellence)
31:54 The Difficult Talk: Using Chess to Broach Uncomfortable Topics with His Son
34:00 The Most Important Example: Showing Sons How to Love and Respect Their Mother
35:51 Excellence is Failure: Why You Must Embrace Continuous Failure in Fatherhood
37:42 The Core Principle: How to Raise Powerful, Compassionate Men – "Don't Be a Dick"
40:03 The Power of Childhood Humiliation: A Puddle of Pee and the Iconoclastic Path
43:10 The Ripple Effect: Why Good Deeds and Positivity are the True Source of Empowerment
45:20 Breaking the Cycle: Not Raising Kids Who "Were Raised by a Dick"
47:35 The Small Act of Kindness: The Calculus of Holding a Door
49:26 Conclusion: The Value of a Mother's Love and Early Loss

In this first half of our conversation, The Kids Are Sleep co-host Sean Harvey joins Shaun to talk about the messy, meaningful side of marriage and modern fatherhood. From late-night talks with his wife Shannon to the daily rhythm of keeping love alive while raising two boys, Sean opens up about what real connection looks like when life gets chaotic. They explore how humor, honesty, and presence keep a family grounded—and how redefining masculinity starts at home.

Key Takeaways / Topics Covered

1. Connection is daily work — Sean and Shannon intentionally sit down together every night to talk and decompress.
2. Presence over perfection — Fatherhood is about showing up, not having it figured out.
3. Evolving masculinity — Redefining strength through gentleness, humor, and communication.
4. Raising sons means modeling love — Kids learn how to love and respect by what they witness between their parents.
5. Balance is the new success — True fatherhood integrates ambition, love, and emotional awareness.

Timelines

00:00 Introduction: Sean Harvey and The Kids Are Sleep Podcast

01:02 Inspiration: The Show Was Born from Post-COVID Couple Laughter

02:57 Marriage Dynamics: Having Each Other's Backs vs. Ribbing Each Other

04:22Marriage Seasons: Friendship vs. Transactional Partnership (Especially with Kids)

05:00 Parenting Strategy: Why You Can't Undermine Your Partner

06:08 The Kids are Ingenious: How Children Exploit Cracks in the Routine

07:05 Discussing the Joy and Planning of Children (Gender Preferences)

08:55 The Terror of a Teenage Girl vs. Early Troubles with Boys

10:13 Balancing Kids, Marriage, and Self: The Need for Late-Night Space

12:25 Risking It All: Why Constant Daily Connection is Crucial for Marriage

13:08 The WFH Dynamic: Learning How to Share Space and Not Kill Each Other

14:36 The Beard Principle: Optimizing for What Your Partner Wants

16:23 The Unorthodox Childhood: How a Dream-Chasing Father Shaped Sean

18:56 The Sacrifice of Excellence: Choosing Family Over Journeyman Fame

19:26 Parallel Story: A World-Class Sportscaster Father and the Cost of Excellence

23:04 The Moment of Realization: Seeing His Dad Through New Eyes in Portland

27:14 The Generational Divide: Confronting Fatherhood in the Modern Era

28:42 Finding Balance: The Next Generation of Parenting

29:38 New Threats: Why Fathers Must Be More Present Than Ever

30:51 Tech Gap: Kids' Savvy vs. The "Turn It Off and On Again" Rule

32:00 Dealing with Loss: Announcing a Close Family Death to Children

34:56 The Grieving Process: Observing Kids Looking for Emotional Cues

35:58 Coping with Loss: The Life Lesson of Normalcy After Death

37:42 A Story of Empathy and Normalcy: Going to Work After Losing a Parent

40:00 Coping Mechanisms: The Power of Humor and Levity in Trauma

41:05 The Tension: Joking About Seriousness to Retain Poignancy

42:17 The Final Interaction: A New Coming-of-Age Threshold

44:08 The Pressure Motivator: Writing the Eulogy the Day Before

46:15 Intergenerational Realization: The "Asshole" Dad Who Asked Too Many Questions

47:19 The Final Challenge: How to Cultivate Understanding in Our Kids Now

Supporting Content

• The Kids Are Sleep podcast: https://thekidsaresleeppod.com/
• Spotify: https://open.spotify.com/show/2BLqNnuXNGpzCioZOlzKsM
• Apple Podcasts: https://podcasts.apple.com/us/podcast/the-kids-are-sleep/id1678661363
• Instagram (Sean): https://www.instagram.com/therealseanharvey/
• Instagram (Shannon): https://www.instagram.com/therealshannonharvey

In this conversation, Eli Weinstein unpacks the emotional journey men go through as they shift from “just a guy” to a present, grounded, emotionally intelligent dad. Drawing from his work as a therapist, author, and host of The Dude Therapist, Eli breaks down the fears, expectations, and heart-level responsibilities that come with modern fatherhood — and how men can rise to them with honesty, humility, and strength. His new book, Dudes to Dads, gives fathers a roadmap to show up with clarity and connection in the moments that matter most.

Topics Covered

1. The emotional transition from “dude” to fully engaged father — what men often struggle with but rarely say out loud.
2. Modern masculinity and mental health — unlearning the silence of past generations and building new patterns of emotional strength.
3. Key insights from Dudes to Dads — identity shifts, communication, and redefining what support looks like.
4. The role of fathers in raising emotionally grounded sons — modeling vulnerability, presence, and healthy expression.
5. Practical, everyday habits for better connection — tools men can start using today to strengthen their relationships and parenting.

Timestamps

00:00 - Introduction: Ellie Weinstein & the Book

04:41 - Why the Book Was Written

07:45 - Relationship Strain After Kids

11:41 - Paternal Postpartum Anxiety

13:05 - Male Vulnerability & Societal Pressure

15:01 - Masculinity and True Strength

21:20 - Raising Sons with Emotional Honesty

27:19 - The Import/Export Home Culture Tool

33:52 - The Dude-to-Dad Transition

37:43 - Interdependence vs. Losing Self

41:33 - Sharing Hobbies with Kids

43:47 - How to Connect with Eli

44:54 - One Final Principle

47:10 - Closing Thoughts

Topics, Books & Ideas Linked

Dudes to Dads (Book): https://www.elivation.org/dudes-to-dads
The Dude Therapist Podcast: https://www.elivation.org/the-dude-therapist-podcast
Apple Podcast Link: https://podcasts.apple.com/us/podcast/the-dude-therapist/id1523217780
Spotify Podcast Link: https://open.spotify.com/show/0lQzVztPzPN8ZOcN0X2w1S
ELIvation Website: https://www.elivation.org
Emotional Fitness Concepts (Blog & Resources): https://www.elivation.org/blog
General Resources Page: https://www.elivation.org/resources

In this conversation, Dr. Michelle Watson Canfield shares her insights on the unique dynamics between fathers and daughters, emphasizing the importance of emotional connection and communication. She discusses practical tools for fathers to improve their relationships with their children, particularly daughters, and highlights the significant influence fathers have on their children's emotional health. The conversation also touches on the challenges fathers face in understanding and responding to their children's emotional needs, and the necessity of self-regulation in parenting.

Key Takeaways / Topics Covered

1. Never underestimate the power of your presence. Every area of a child’s life improves when they feel connected to their father. Presence — not perfection — is what transforms kids.
2. Connection > Correction. Heart-level connection opens the drawbridge. Correction without connection triggers defensiveness and shutdown. 
3. Regulate yourself first. If you’re at an 8, 9, or 10 internally, that’s your old story firing — not your child’s fault. Calm your nervous system before responding.
4. Ask questions that open the heart, not interrogate it. Use “I’m wondering…” + who/what/when/where/how + key/last-word questions to help kids talk and feel understood. 
5. Drop your anger. Dr. Michelle said dads must “drop anger” — not just control it — because anger closes the drawbridge and disconnects kids.

Principle #1:

“Never underestimate the power of your presence as a father.” Connection is what changes everything — not getting it perfect. 

Principle #2:

“Drop your anger.” Not just manage it — drop it. When anger leads, connection dies.

Practical tips

1. Use bilateral stimulation to calm down. Tap your legs left–right (“going on a bear hunt”) or go for a walk to get out of fight/flight/freeze. 

2. Use “I’m wondering…” to soften tough conversations. Example: “I’m wondering what was going on for you today?” This instantly opens your child's heart rather than triggering defensiveness. 

3. Use who/what/when/where/how (avoid “why”) Pair it with the key word or last word your child said to keep conversations flowing.

4. Write sticky notes or mirror notes. A simple “Have a great day” from dad becomes a lifelong identity seed. Women especially internalize written encouragement. 

5. If estranged: start a dated “time capsule journal”. Write entries to your child so they can one day see you never stopped showing up emotionally. 

6. Expand your “window of tolerance”. Especially for daughters who talk more — slow down, listen more, and tolerate messiness. 

Pull Quotes

Timestamps / Chapter Markers

00:07 Intro & Meeting Dr. Michelle Watson Canfield
01:46 The Unique Dynamic of Dads and Daughters
03:00 Turning the Hearts of Fathers to Their Daughters
05:20 Similarities and Differences in Raising Sons vs. Daughters
06:20 How Daughter Relationships Benefit All Your Relationships
07:49 The Castle Metaphor: Strength vs. Enclosure
09:59 Why Men Freeze: Doing Nothing vs. Doing it Wrong
12:15 Action Figures: The Need for Dads to Take Action
13:00 Understanding the Freeze Response (Fight, Flight, Freeze, Fawn)
14:38 Calming Techniques: Getting Out of the Activated Nervous System
16:53 Conan the Barbarian Brain vs. Sherlock Holmes Brain
18:54 Identifying Your "Old Stuff" (Triggers)
23:45 Genetics and Gender: Why Daughters Need More Listening
25:36 Venusian Communication: Figuring Things Out by Talking
26:58 Example: Co-Regulating a Child's Meltdown
32:27 The Intentionality Trap: Why We Think Kids are Lying
35:20 Practical Tool: Using Who, What, When, Where, How
40:41 Practical Tool: The Power of "I'm Wondering..."
43:32 Practical Tool: Writing Notes on Mirrors
46:58 The Love Bank: 5 Deposits to 1 Withdrawal
48:42 The Guiding Principle for Fathers
49:20 Never Underestimate the Power of Your Presence
51:47 Don't Respond in Anger: Drop Your Anger
53:38 Closing & Where to Find Dr. Michelle

Supporting Content

1. Let’s Talk: Conversation Starters for Dads and Daughters https://www.bethanyhouse.com/9780764235689/lets-talk/
2. Dad, Here’s What I Really Need From You https://drmichellewatson.com/books/
3. The Dad Whisperer Podcast https://drmichellewatson.com/podcast/
4. The Abba Project https://drmichellewatson.com/the-abba-project/
5. Dr. Michelle Watson Canfield – Website https://drmichellewatson.com/
6. The Female Brain — Louann Brizendine https://www.penguinrandomhouse.com/books/19178/the-female-brain-by-louann-brizendine-md/

Connect with Dr. Michelle Watson-Canfield

1. Website: drmichellewatson.com
2. Facebook: facebook.com/drmichellewatson
3. Instagram: @michellejwatson + @thedadwhispererpodcast
4. X: @mwatsonphd
5. LinkedIn: Dr. Michelle Watson Canfield
6. YouTube: @thedadwhisperer

In this episode of Raising Men, host Shaun Dawson sits down with Christopher Veal — author of The Whole Man: Evolving Masculinity, Marine veteran, and host of The Vulnerable Man Podcast — to explore what it really means to be a “whole man.” Together, they unpack the myths of masculine strength, the courage behind vulnerability, and how fathers can model emotional integrity for their kids.

Key Takeaways

1. True strength isn’t in the walls we build.  Masculinity isn’t about armor or control — it’s about creating space where life and connection can thrive.
2. Healthy masculinity lives in the ‘both/and.’  Real manhood blends courage and compassion. It’s not dominance or softness — it’s the balance of both.
3. Vulnerability is leadership.  Showing emotion or admitting mistakes doesn’t weaken fathers — it builds trust and emotional safety for sons.
4. Fathers shape emotional literacy. Boys learn more from what we model than what we say. Our responses to fear, love, and failure teach manhood.
5. Legacy is wholeness, not perfection. The “whole man” integrates every side of himself — strong yet open, firm yet kind. That’s what our sons remember.

Pull Quotes

Timestamps / Chapter Markers
00:00 – 02:45 – Intro: male vulnerability & authentic friendships
02:45 – 05:30 – Masculinity & societal pressures
05:30 – 08:10 – Vulnerability and strength in high-pressure environments
08:10 – 11:05 – Fatherhood: teaching through action
11:05 – 14:00 – Self-awareness, ego, and confidence vs. arrogance
14:00 – 17:20 – Excellence vs. perfection
17:20 – 20:05 – Learning from failure & embracing mistakes
20:05 – 22:50 – Connecting emotionally with other men
22:50 – 25:00 – Going second: showing openness to build trust
25:01 – 28:15 – Father figures & cross-cultural influences
28:16 – 31:45 – Grace in parenting & male friendships
31:46 – 34:30 – Confronting flaws & modeling honesty
34:31 – 37:50 – Navigating polarized cultural narratives
37:51 – 41:00 – Fostering meaningful male connections
41:01 – 44:15 – Practical advice: self-awareness & intentionality
44:16 – 47:30 – Key takeaways & lessons learned
47:31 – End – Closing remarks & final encouragement

🔗 Supporting Content & Resources

Book: The Whole Man: Evolving Masculinity by Christopher Veal Explores how men can integrate vulnerability and emotional intelligence into leadership and fatherhood.
Podcast: The Vulnerable Man Podcast Christopher’s ongoing conversations with men about courage, leadership, and emotional truth.

Further Reading Mentioned:

• Daring Greatly by Brené Brown — Understanding vulnerability as the birthplace of courage and connection.
• The Mask of Masculinity by Lewis Howes — On breaking emotional armor and redefining male strength.
• The Way of the Superior Man by David Deida — Classic work on balancing masculine energy with openness.

Simon shares how mindfulness transformed his life after years of mental-health struggle and burnout — helping him become a more present father, husband, and therapist. Together, Shaun and Simon explore how mindfulness, emotional awareness, and healthy masculinity shape the next generation of men.

Key Takeaways

1. Mindfulness begins with awareness. Bringing the subconscious to the conscious allows fathers to be truly present with their children.
2. Healing starts with connection. Therapy, lived-experience storytelling, and vulnerability create powerful pathways for men to recover and grow.
3. Redefining masculinity is generational work. By modeling emotional awareness and imperfection, fathers teach sons that strength and softness can coexist.

Pull Quotes 

Timestamps / Chapter Markers

• 00:00 — Welcome back + who is Simon Rinne
• 00:36 — Mindfulness defined: “conscious awareness” for parents
• 01:15 — Simon’s backstory: OCD at 8, anxiety, depression
• 02:21 — Coping with alcohol and delaying help
• 03:14 — 2020 burnout: work, study, two kids, lockdown
• 03:43 — Discovering mindfulness and “lived-experience” therapy
• 04:39 — Feeling seen and heard for the first time
• 05:12 — Why men delay getting help
• 06:04 — Growing up in Adelaide; 80s/90s “suck it up” culture
• 07:26 — Bottling emotions, anger as the only “allowed” feeling
• 08:26 — Parents split at 13; “man of the house” pressure
• 09:18 — Alcohol at 15; clinic calls for positive male role models
• 10:15 — Social constructions of masculinity across eras
• 11:37 — Reframing masculinity: healthy vs “toxic” labels
• 12:50 — Past, present, future reflection for dads and sons
• 14:30 — Biggest misconception: “men can’t seek help”
• 15:26 — Lived experience builds trust; team problem-solving
• 16:39 — Finding the right “fit” in therapy, like fitness modalities
• 17:50 — Beyond therapy: sleep, food, movement, addictions
• 18:36 — Dopamine loops and sustainable change
• 19:44 — Mindful parenting: patience, presence, emotions
• 21:08 — The playbook is changing; imperfect parenting and repair
• 23:24 — Modeling apologies and rebuilding bridges
• 24:49 — Negative vs virtuous feedback loops
• 26:15 — “Always working” anxiety and learning to unplug
• 27:22 — Provider tension in a 24/7 world
• 29:00 — Connection is what kids want most
• 30:23 — Regaining control by letting go of control
• 31:17 — Live by values; kids learn from what we model
• 32:50 — Start mindfulness “day one” by modeling, not lectures
• 34:01 — Nature slows time; fewer screens, more real life
• 35:23 — Tactical first step: “tune-up” your mind like a car
• 36:53 — Pitfalls: old pain surfaces; that is part of healing
• 38:09 — Wabi-sabi: the beauty of imperfection
• 38:46 — How to engage with Mindful Men: podcast, therapy, group
• 40:36 — One principle: identify 5–6 core values and live them
• 41:53 — Close

Supporting Content & Mentions

• Mindful Men Website: https://mindfulmen.com.au
• Mindful Men Podcast: https://mindfulmen.com.au/podcast
• Mindful Men Community (Facebook Group): https://www.facebook.com/groups/mindfulmencommunity
• Mental Health Awareness Month (Australia): https://www.mentalhealthmonth.org.au/
• Concept Mentioned — Wabi-Sabi (Japanese philosophy of beauty in imperfection)

In this conversation, Shaun Dawson and Luke Entrup explore what it really means to guide boys into manhood in a culture that has lost its rites of passage. Luke shares how fathers can reclaim the ancient practice of initiation to raise sons of character, courage, and conviction. Together, they discuss how emotional intelligence, mentorship, and time in nature can help boys develop “heart-connected power” — strength balanced with compassion.

Key Takeaways

1. Rites of passage matter. When boys lack meaningful thresholds into adulthood, they seek belonging in unhealthy or toxic ways.
2. Healthy masculinity is heart-connected power. Strength and sensitivity can coexist; empowerment means “power with,” not “power over.”
3. Mentorship is missing. Fathers and communities must step up to guide boys intentionally into manhood.
4. Growth requires discomfort. Modern initiations should challenge boys safely but meaningfully.
5. Connection before correction. Daily “special time” strengthens the bond that supports discipline and trust.
6. Digital disconnection. Real growth happens offline — in nature, in silence, and through shared experiences.

Timestamps / Chapter Markers

• 00:00 — Welcome + who is Luke Entrup
• 02:14 — What a rite of passage actually is
• 03:48 — Why thresholds matter (and what we lost)
• 05:41 — Two key transitions: childhood→adolescence, adolescence→manhood
• 08:56 — Belonging first, then independence
• 10:59 — Emotional intelligence as real power
• 13:56 — Adapting ancient rites for modern life
• 15:29 — Discomfort over danger: designing challenge well
• 16:29 — When boys miss initiation (mentorship gap)
• 18:39 — Screens hijack belonging
• 20:22 — Two ails: phone culture + loss of free-range mobility
• 22:02 — What healthy masculinity looks like
• 25:52 — Reframing “toxic” vs healthy masculinity
• 27:01 — How to build thresholds at home
• 27:43 — Father-Son Connection Experience (Luke’s program)
• 28:59 — Annual “hard thing together” in nature
• 31:17 — Daily “special time” (15-minute ritual)
• 32:43 — Closing the gap between the parent you are and hoped to be
• 34:50 — The power of repair: “I’m sorry”
• 37:13 — What Luke thinks he’s done well (awe + the natural world)
• 39:15 — What he’d change (rigidity → flexibility)
• 41:07 — Anti-fragility over brittleness
• 42:08 — One principle: “Silence is noble”
• 45:58 — The 3-step challenge for parents
• 47:20 — The 4th step: “What do you need from me this year?”
• 49:38 — Closing + credits

Supporting Content

• The Anxious Generation by Jonathan Haidt – on technology’s impact on youth.
• Bill Plotkin – Nature and the Human Soul – developmental stages and human initiation.
• Father–Son Connection Experience – Luke Entrup’s program for fathers and sons.
• Hand in Hand Parenting – source of the “special time” practice.
• Buddhist concept: “One eye in, one eye out” — awareness of both inner and outer landscapes.

The Father’s Challenge by Luke Entrup

Simple but powerful four-step challenge for fathers:

1. Daily Special Time – 15 minutes of uninterrupted, child-led play.
2. Join a Community – find or create a group of fathers committed to rites of passage.
3. An Annual Adventure – one outdoor challenge shared with your son each year.
4. Ask the Question – “What’s one thing you need from me this year to feel connected to me?”

In this conversation, Shaun sits down with Ken Mossman, leadership coach and host of Mojo for the Modern Man, to dismantle one of the most enduring myths in manhood — the “lone wolf” and “self-made man.” Together, they explore what it truly means for men to live with courage, connection, and curiosity in an age of isolation.

Key Takeaways / Topics Covered

1. The Lone Wolf is a Lie - Both Ken and Shaun dismantle the myth of the “self-made man” and the “lone cowboy.”
2. Connection Requires Courage - Men often equate vulnerability with weakness, but the real courage is in showing the cards.
3. Modeling Connection for Sons - Fathers teach by example. When they hide struggle, children inherit shame and perfectionism. When they model honesty, curiosity, and openness, they teach resilience and belonging.
4. Loneliness vs. Junk Connection - Social media feels like community but isn’t. Shaun calls it “junk connection — like potato chips: fine in small doses, but if that’s all you eat, you starve.” Real nourishment comes from face-to-face relationships and shared vulnerability.
5. Practical Starting Points
   1. Reach out to a friend you haven’t talked to in a while.
   2. Ask (and answer) “How are you really?”
   3. Join or start a men’s group — church-based, local, or Mankind Project-style.
   4. Give and receive help with grace; both are acts of generosity.

Timestamps / Chapter Markers

• 00:02 – Welcome and guest intro
• 00:40 – Where Ken is joining from
• 00:51 – The “lone wolf” myth
• 01:12 – Why fierce independence persists
• 02:37 – The not-so “self-made” man
• 03:56 – We stand on shoulders of giants
• 04:29 – Dreams still need a team
• 04:45 – Humility and asking for help
• 05:14 – Burnout from doing everything
• 05:24 – Shaun’s early fatherhood disconnect
• 07:41 – Naming shame without drowning in it
• 08:09 – What made Shaun open up
• 08:19 – A friend’s hidden decade of struggle
• 10:39 – Authority vs curiosity in men
• 12:12 – Why men avoid “I don’t know”
• 14:08 – Loneliness stats and concern
• 14:30 – Few close friends for many men
• 16:08 – Let others help you
• 17:08 – The give and receive “math”
• 18:12 – Generosity in receiving well
• 19:46 – Candle and campfire metaphor
• 20:23 – Info overload vs isolation
• 21:03 – Social media is not connection
• 21:53 – Performative feeds and algorithms
• 24:58 – Admitting “I am lonely”
• 25:42 – Belonging in echo chambers
• 26:10 – Modeling for our kids
• 27:26 – What example are we setting
• 29:48 – “You’re acting like a four-year-old”
• 31:00 – Meeting kids at their level
• 32:27 – Catching your own anger spiral
• 35:02 – Perfectionism shows up early
• 37:02 – Checklists beat memory
• 39:29 – Schooling, grades, and identity
• 41:30 – Authority with fallibility
• 43:02 – Permission to fail with grace
• 45:02 – When kids do not mirror you
• 46:33 – Tactical steps to reconnect
• 47:15 – Reach out first
• 48:20 – “How are you” vs “How are you really”
• 51:35 – Do the handshake then go deep
• 53:31 – Find a men’s group
• 55:29 – Rebuilding lost institutions
• 55:57 – Online groups need curation
• 56:24 – Nothing beats face to face
• 57:44 – One principle request
• 58:32 – “Wild curiosity” as a discipline
• 58:41 – Thanks and wrap-up
• 59:05 – Off-mic close

Supporting Content

• Mojo for the Modern Man — Ken Mossman’s podcast on manhood and connection
• Mankind Project & Everyman — structured men’s groups fostering community
• Raising Boys by Design by Gregory L. Jantz and Michael Gurian
• The Mask of Masculinity by Lewis Howes
• Of Boys and Men by Richard Reeves
• Everyman - men's community and platform helping men build connection, vulnerability and brotherhood

In this conversation, Caleb Scott shares his journey into fatherhood, discussing the unexpected challenges and emotional experiences that come with becoming a dad. He emphasizes the importance of community support, grace, and accountability in parenting. The discussion also touches on conflict management, resilience in children, and the significance of being present in their lives. Caleb reflects on the balance needed in parenting, learning from mistakes, and the invaluable gift of time spent with children. Ultimately, the conversation highlights the complexities of fatherhood and the growth that comes from navigating its challenges together.

Key Takeaways / Topics Covered

1. Navigating challenges in parenting requires support and community.
2. Grace is essential for parents and children alike.
3. Conflict management is crucial for emotional intelligence in parenting.
4. Accountability is a form of love in relationships.
5. Children learn resilience through their parents' actions.
6. Presence and attention are vital in a child's development.
7. Finding balance in parenting is key to success.
8. Mistakes in parenting can lead to growth and learning.
9. Time spent with children is the greatest gift a parent can give.

Pull Quotes

Timestamps / Chapter Markers

• 00:00 – Introduction
• 02:05 – Navigating Parenthood During a Pandemic
• 04:27 – Overcoming Overwhelm and Embracing Change
• 07:26 – The Importance of Community and Support
• 09:37 – Grace: A Key to Successful Parenting
• 12:38 – Understanding Emotions and Reactions
• 15:22 – The Role of Preparation in Fatherhood
• 17:49 – Conflict Management and Accountability in Parenting
• 29:40 – Navigating Parental Tensions
• 35:06 – The Balance of Accountability and Love
• 43:26 – Vulnerability vs. Resilience in Parenting
• 49:01 – The Resilience of Children and Parental Responsibility
• 50:28 – Learning from Mistakes: The Power of Apology
• 53:41 – Navigating Co-Parenting and Identity as a Father
• 55:58 – The Importance of Presence in Parenting
• 58:27 – Building Community Among Fathers
• 01:00:44 – The Journey of Fatherhood: Connection and Growth
• 01:02:55 – Normalizing the Struggles of Fatherhood
• 01:04:11 – Principles of Influence: Leading by Example

Supporting Content:

1. Two-Brain Theory (Conan the Barbarian vs. Sherlock Holmes Brain) — a metaphor discussed by Shaun for emotional regulation, based on neuroscience concepts around the amygdala and prefrontal cortex.
   • Daniel Kahneman – “Thinking, Fast and Slow” (System 1 and System 2 parallels)
   • Daniel Goleman – “Emotional Intelligence”
   • Robert Sapolsky – “Behave”

2. Parenting & Emotional Regulation: Discussion around emotional control and grace aligns with research in developmental psychology. 

• John Gottman – “Raising an Emotionally Intelligent Child
• Harvard Center on the Developing Child – Studies on father involvement

3. The Better Dad Podcast
4. Caleb Scott on Linkedin
5. Caleb Scott on Facebook
6. Soapbox Studios

Shaun Dawson opens Raising Men with a simple truth: our sons aren’t just watching us—they’re becoming us. This is where the journey begins to raise men of purpose, strength, and heart. 

Join Shaun Dawson in the important conversations shaping the next generation of men. Raising Men is a space for parents, mentors, and leaders committed to building character, courage, and conviction in today’s boys. Each episode dives deep into real stories and practical wisdom from thinkers, leaders, and fellow parents — all sharing tools for becoming more intentional guides in a world that often confuses masculinity with noise. Because raising men isn’t just about them — it’s about who we’re becoming, too.

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