What does 48 years in local government teach you about leadership, reinvention, and staying authentically yourself? In this episode, we sit down with Craig Rapp, consultant, mentor, and creator of Compass Peer Groups, for a conversation that spans from his first job as a 25-year-old city administrator to his current work supporting the next generation of local government leaders.

Craig takes us through two remarkable halves of his career: the first 22 years as a striver in city management, and the last 25 years as a seeker navigating consulting, face plants, learning curves, and ultimately building something meaningful. Along the way, we explore the unexpected connections between Canadian tuxedos, Gordon Lightfoot, Arnold Schwarzenegger, Jesse Ventura, bow ties, and the leadership frameworks that shaped Craig's journey.

We dig into the messy middle of career transitions, the courage it takes to reinvent yourself at any age, the power of peer support, and why putting the ladder back down matters more than pulling it up. Craig shares wisdom about navigating failure, staying curious, and being a person of your time while still pushing forward into new territory (yes, even AI artifacts).

This is a conversation about authenticity, longevity, and what it means to build a career that serves not just yourself, but the profession and the people coming up behind you.

#LocalGovernment #Leadership #CareerReinvention #CityManagement #AuthenticityFM

01:34 Craig Rapp's Journey into Local Government

04:13 Career Transitions and Reinvention

09:48 The Importance of Support Systems

15:33 Authenticity in Professional Life

22:36 The Connection to Ore Boats and Personal History

25:54 Early Influences and Upbringing

29:03 Navigating Political Challenges

37:42 Lessons from Jesse Ventura's Tenure

42:59 Courage in Leadership

48:27 The Importance of Peer Support

58:50 Compass Peer Groups and Their Impact

01:01:06 The Power of Optimism in Leadership

01:04:28 Peer Support: The Backbone of Resilience

01:08:31 Real Stories of Peer Group Impact

01:10:58 Improv and Leadership: A Unique Connection

01:15:39 Imagining Life Beyond City Management

01:21:17 Advice for the Next Generation of Leaders