#037 - Sex, Mystery, and the Modern Masculine Dilemma | Justin Ross

Justin Ross is a writer, musician, and thoughtful observer of modern masculinity. He authors the Substack newsletter "Square Man Round World," where he explores the complexities of being a man in today's world with refreshing honesty and depth. Justin brings a unique perspective shaped by his journey through sobriety and his willingness to examine the uncomfortable truths about male relationships, sexuality, and identity.In this episode, we discuss:The Father Paradox: How most men learn masculinity by doing the opposite of what their fathers did, and why this rejection might actually be a necessary part of development - plus the challenging question of whether fathers should be "hard" on their kids to force them to become strongerFrom Consumption to Creation: Why modern culture has shifted from creative sexual expression to passive consumption, how porn has rewired men's relationship with intimacy, and the importance of mystery and patience in building genuine romantic connectionsThe Death of Local Connection: How capitalism and technology have stripped men of hands-on skills, community bonds, and real-world mentorship, leaving them isolated and disconnected from the tangible world around themLearning by Running Away: Justin's philosophy that sometimes you have to do things wrong before you can do them right, and how trying different things (even failing) helps refine your sense of direction and identity as a manResources:Justin's Substack: "Square Man Round World"