278: Jamie Gwynn: Leading Without Losing Yourself

Jamie Gwynn: Leading Without Losing Yourself
Work, Family, and the Hidden Cost of Municipal Leadership

Episode 278 of The HaltingWinter Podcast
Brought to you by Tyler Technologies

Municipal leadership doesn't just test your competence; it tests your identity.

In this episode of The HaltingWinter Podcast, Seth sits down with Jamie Gwynn, Township Manager of New Hanover Township, Pennsylvania, for a deeply honest conversation about what it really takes to lead over the long haul without losing yourself in the process.

Jamie's path into city management wasn't linear or polished. From being raised in a pizza shop that doubled as a political crossroads, to struggling academically, to teaching in Baltimore through Teach for America, to stepping into the manager's chair at just 29 years old, his story mirrors the reality many local government leaders live but rarely articulate.

Together, Seth and Jamie unpack the hidden costs of municipal leadership: the pressure to always be on, the temptation to define yourself by the job, and the quiet toll leadership can take on health, relationships, and presence at home.

This is not a conversation about "balance" as a buzzword. It's about intention, sustainability, and staying human in a profession that constantly asks for more.

Sponsored by:

• Tyler Technologies – the nation's leading provider of software designed specifically for the public sector. Learn more at tylertech.com/winter

• The Municipal Leadership Development Circle (MLDC) is a global community for local government leaders who want ongoing support, practical insights, and a trusted peer network to help them lead with clarity and conviction. Learn more at haltingwinter.com/MLDC

Connect with Seth Winterhalter

• LinkedIn: www.linkedin.com/in/sethwinterhalter
• Website: www.HaltingWinter.com