Episode 16: How to Have Hard Conversations Without Making Everything a Fight with Kyle Depiesse

28 Apr 2026 · 40 min
39:38

In this episode of the Scar Tissue podcast, host Melissa Dlugolecki interviews Kyle Depiesse, a former corporate executive turned high‑school teacher, grief‑focused entrepreneur, and creator of the Guy’s Trip retreat brand. The conversation opens with a discussion of men’s mental‑health crises, especially the high suicide rate among men, and identifies isolation as a primary driver. Kyle shares his personal story of burnout in retail e‑commerce, a career shift to teaching, and the accidental founding of Guy’s Trip – intimate, low‑key retreats that blend physical challenges, sobriety, and structured reflection. He explains the retreat’s core tools: a “personal balance sheet” questionnaire and a “ladder” visual that helps participants prioritize life domains. The dialogue explores the concept of sonder – recognizing that every person carries unseen stories – and stresses the importance of surrounding oneself with honest, truth‑telling friends to avoid echo chambers. Melissa and Kyle discuss the destructive loop of people‑pleasing, the need for non‑confrontational communication, and practical tactics such as frequent expectation‑checking checkpoints. Kyle uses the mangrove‑vs‑oak metaphor to illustrate why relational interdependence (horizontal growth) beats solitary vertical achievement. The episode concludes with concrete resources: a PDF guide for partners, the guystrip.co website, and Kyle’s preferred LinkedIn presence, encouraging listeners of any gender to engage with the retreats or apply the discussed frameworks in their own lives.

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