E404 | The Hardest Conversation I've Ever Had with My Son - On Loneliness, Conviction and Doing Hard Things

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E404 | The Hardest Conversation I've Ever Had with My Son - On Loneliness, Conviction and Doing Hard Things

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This episode dives into one of the most personal and difficult conversations Brett’s ever had — not with a client, colleague, or friend, but with his son. It started when Bronson said he felt lonely — that the kids around him didn’t like to do hard things, didn’t stick with commitments, and quit when things got tough. What followed was a raw conversation about what it really means to live with conviction, pursue mastery, and stay committed even when it feels isolating. Brett unpacks how this moment with his son connects to leadership, resilience, and the reality that walking your own path often means walking it alone — at least for a while. This isn’t about parenting advice or some polished motivational talk. It’s about what happens when you realize that the same lessons we try to teach others are the ones we have to keep learning ourselves. ⸻ What You’ll Learn: •Why loneliness isn’t always a bad sign — it’s often proof you’re growing •How to reframe discomfort and isolation as signals of progress •The link between conviction, curiosity, and finding your real tribe •How to talk about hard truths with kids — or anyone — without sugarcoating •What it means to model lifelong learning instead of preaching it

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Related Resources: •Want help improving your communication, leadership, and decision-making under pressure? Apply for our 1-to-1 or small-group mentoring programs at www.artofcoaching.com/mentoring. •Join us for our next live Apprenticeship Workshop in Phoenix, AZ – May 2026, where we’ll dig into influence, power dynamics, and the practical side of human behavior. Details and registration: www.artofcoaching.com/events.

Website: ArtofCoaching.com

Instagram: @coach_brettb

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