This wide-ranging conversation traces Mike Chapman’s unlikely path from doubting community-college student to one of orthopedics’ most influential trauma surgeons and textbook authors. He reflects on serendipity as a driving force—missed opportunities, regulatory barriers, and chance encounters continuously steering his career toward trauma and academic leadership. The discussion explores the origins and philosophy of Chapman’s Orthopaedic Surgery, built on global expertise, practical surgeon insight, and continuous updating. The dialogue also highlights a new partnership with JBJS to evolve the textbook for digital learning while honoring its comprehensive scope. Ultimately, the episode underscores how nonlinear careers, setbacks, and unexpected openings shape orthopedic innovation and mentorship.