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Lessons in Leadership, Tech, and Letting Go with Damian Gomes

Lessons in Leadership, Tech, and Letting Go with Damian Gomes

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 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 CoveredLeadership 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.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.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.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.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“You’re not just building automation systems — you’re helping two young men find their own operating systems for life.” — Shaun Dawson“If you give them the plan, what are they learning? Let them carry on tradition by word of mouth — that’s where the leadership happens.” — Damian Gomes“I’d rather my sons fail at home, with us around to help them, than discover they don’t have the skills later when it really matters.” — Damian Gomes00:35 Official Introduction01:41 Involvement and Value in Boy Scouts03:51 Cubmaster to Scout Leader: The Transition05:37 "Storming, Norming, and Performing" in Leadership09:52 Scouting's Offer to Modern Boys14:44 Contrived Structure for Organic Skills16:52 The Value of Inventing the Solution17:47 Doubling Down on Scouting During Challenges21:39 The Pandemic's Impact on Family Dynamics24:33 The Shift to Self-Paced Virtual Learning27:40 Rethinking Failure and Retaking Tests30:13 Homeschooling vs. Virtual School Decisions32:38 The Older Son's Success Story37:03 The Hardest Part: Allowing for Failure38:55 The Younger Son's Struggle for Structure42:26 The Future of Learning43:08 Hopes for Sons' Memories45:08 One Principle for Raising Men47:35 Closing RemarksSupporting ContentOrganizations & ConceptsBoy 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 & TechFlorida 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.
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