From City Management to Entrepreneurship

From City Management to Entrepreneurship

December 1, 2025 · 40 min · Episode 27

About this episode

Kellye and Charisse discuss the challenges and opportunities for city management professionals transitioning into entrepreneurship.

Kellye and Charisse discuss the potential challenges and opportunities faced by city management professionals as they transition into entrepreneurship. They explore the identity shifts that occur when leaving traditional roles, the transferable skills gained from city management, and the importance of coaching in supporting leaders. The conversation emphasizes the need for clarity, sustainability, and the creation of supportive environments for city managers and executives. Ultimately, they encourage listeners to embrace new possibilities and stay true to their passions while navigating their careers. Takeaways City management leaders are feeling overwhelmed and uncertain about their future. Many are considering leaving the profession not due to failure, but due to lack of support. Building our own tables means creating spaces that add value to city management. Identity shifts occur when transitioning from city management to entrepreneurship. The skills gained in city management are highly transferable to coaching and consulting. Coaching helps city leaders feel grounded and less fragmented. Sustainable leadership is about using existing skills in new ways. Clarity and capacity…

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