Municipal Leaders: Develop Faster, Lead Stronger, Build Better

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

Municipal leadership has a way of creeping into every corner of life.

The meetings don’t end when the workday does.
The pressure doesn’t pause on weekends.
And over time, it becomes easy to confuse dedication with depletion.

In Episode 278 of The HaltingWinter Podcast, Seth Winterhalter sits down with Jamie Gwynn, Township Manager of New Hanover Township, Pennsylvania, for a candid conversation about the hidden cost of municipal leadership and what it takes to lead without losing yourself along the way.

Jamie’s journey into city management wasn’t polished or predictable. It was shaped by early responsibility, nonlinear choices, mentorship, hard lessons, and moments of reckoning that forced him to confront not just how he was leading, but who he was becoming.

This episode goes beyond leadership tactics. It explores identity, family, mental health, and the quiet tradeoffs leaders make when the job starts to consume more than it should.

It’s a reminder that:

  • You can care deeply about your community without sacrificing your humanity
  • Leadership sustainability matters just as much as leadership success
  • And the people who feel the cost of your overwork aren’t usually the ones in the room

If you’re a city manager, administrator, department head, or public servant who feels the weight of the role, and wants to carry it more intentionally, this conversation will resonate.

Listen to Episode 278: Jamie Gwynn – Leading Without Losing Yourself
Because strong leadership shouldn’t come at the expense of your life, your family, or your sense of self.


Tyler Technologies

This episode is sponsored by Tyler Technologies, the leader in empowering the public sector with software solutions that connect data, streamline operations, and improve service delivery. From civic services to public safety, Tyler helps local governments build stronger, more resilient communities. 
Learn more at tylertech.com/winter →

The Municipal Leadership Development Circle (MLDC)

The MLDC is where local government leaders go to grow, together. It’s the fastest-growing leadership development community designed specifically for the public sector, now paired with a comprehensive 9-month Leadership & Culture Program for those ready to elevate their organization.

Members receive weekly leadership content, access to our daily podcast, monthly virtual trainings, and a clear roadmap for building a culture that reduces burnout, strengthens retention, and drives meaningful impact in every department.
Learn more at haltingwinter.com/mldc →


The HaltingWinter Podcast celebrates and elevates the people who power local government. Through in-depth conversations with leaders from cities, counties, and communities of all sizes, host Seth Winterhalter explores the journeys, challenges, and innovations happening in municipal leadership across America.