Andrew Osenga is a singer-songwriter, a guitarist, a record producer, a podcaster, a writer, and a friend and mentor to countless artists. For twenty years and more, he has been right in the middle of things in Nashville’s creative community. In this episode, recorded live at The Habit 2025 Winter Writers’ Weekend, Andy speaks with Jonathan Rogers about being a jack of all trades, the importance of community, and Andy's journey from bitterness to joy and purpose in his work.