In Episode 4, we get real about the tension between freedom and structure, what it means to balance work and life when you’re your own boss, and how discipline often becomes the training ground for self-love.

We explore the habits that keep us grounded (like journaling, bullet calendars, and time blocking), but also open up about what happens when ego, doubt, and trauma creep in. There’s a deep convo around masculinity, fatherhood, and the weight men carry silently and how important it is to unlearn that “suck it up” mentality we were raised with.

This episode also touches on dating in your 30s, building trust, and why community feels harder to build in L.A. than anywhere else. It’s raw, thoughtful, and full of those moments that make you stop and check in with yourself.

Topics We Covered

• The illusion of “perfect” routines & how to stay present hour-by-hour
• Why freedom without structure can become a trap
• The tools we use to stay accountable (journals, calendars, phone blockers)
• How discipline builds the foundation for self-love
• Vulnerability, therapy, and the emotional weight men carry
• Parenting, love, and breaking generational habits
• Dating while sober & how trust really works
• The dream of building community—and why it’s so hard in L.A.
• Our hopes for barbershop culture and inspiring the next generation