Becoming A Man In Your 20's | S5E51

In this episode of the Exploring More podcast, Michael Thompson, SJ Jennings, and Caleb Richwine continue their series on the challenges men face by looking specifically at a defining decade in the masculine journey: a man's 20s. Your 20s can feel like the moment life suddenly starts asking bigger questions. Who are you? What are you going to do with your life? Are you capable? Are you strong enough? Who will you become? Career, money, relationships, marriage, independence, and responsibility all begin carrying greater weight—often while a man is still trying to answer fundamental questions about his identity. Caleb shares pieces of his own story, including how early experiences of conditional approval contributed to people-pleasing and a desire to earn affirmation. He describes how God began exposing those patterns and inviting him into healing, helping him move from an identity built on performance toward one rooted in what God says is true. Together, Michael, SJ, and Caleb explore the cultural pressures facing men in their 20s. Social media constantly presents images of success, wealth, status, comfort, power, and relationships, quietly shaping what men believe their lives should look like. Without intentionality, it's easy to spend this decade pursuing someone else's definition of success rather than discovering the man God is forming you to become. The conversation also highlights the importance of brotherhood and mentorship. Young men need older men whose lives demonstrate the fruit they're looking for—men who can offer wisdom, encouragement, perspective, and a hand back up when they fall. Your challenges aren't necessarily evidence that something is wrong with you. They may be revealing the places where God wants to bring healing, maturity, and freedom. Your 20s aren't simply about building a career or creating a life. They're about becoming a man.