Ben Lipps: When Leadership Gets Personal
Incivility, Threats, and Staying Steady in Local Government

Episode 290 of The HaltingWinter Podcast
Brought to you by Tyler Technologies

What happens when leadership stops being theoretical and starts showing up at your door?

In this episode of The HaltingWinter Podcast, Seth Winterhalter sits down with Ben Lipps, Town Manager of Cumberland, Indiana, to explore what it means to lead when public service becomes personal.

Ben's journey into local government didn't begin in city hall; it began on the front lines of public works. From mowing grass and fixing potholes to supervising infrastructure, managing emergencies, and ultimately stepping into the town manager's seat, Ben's story is one of earned credibility, steady growth, and leadership forged through experience rather than title.

But this conversation goes deeper.

Ben shares candidly about navigating community growth, zoning conflict, and the rising incivility many local government leaders now face, including personal threats that tested not just his role, but his resilience. Together, Seth and Ben unpack the emotional weight of the manager's chair, the hidden cost of public outrage, and what it takes to stay grounded when leadership stops at 5:00 pm for no one.

Sponsored by:

• Tyler Technologies – the nation's leading provider of software solutions designed specifically for the public sector and local government. Learn more at https://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 https://haltingwinter.com/MLDC

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

Becky Windt Pearson: Governing at the Edge of the World
What Alaska Teaches Us About Leadership, Resilience, and Responsibility

Episode 289 of The HaltingWinter Podcast
Brought to you by Tyler Technologies

What does leadership look like when your city is the end of the road...literally?

In this episode of The HaltingWinter Podcast, Seth Winterhalter sits down with Becky Windt Pearson, City Manager of Anchorage, Alaska, to explore what municipal leadership looks like in one of the most demanding contexts in North America.

Anchorage isn't just Alaska's largest city; it's a hub for healthcare, transportation, emergency response, and essential services for communities across the state. That reality creates pressures, responsibilities, and leadership challenges that most cities never face. And yet, the lessons Becky shares extend far beyond Alaska.

This conversation is about clarity under pressure, leadership without illusion, and the responsibility local government carries when no one else can step in.

Sponsored by:

• Tyler Technologies – the nation's leading provider of software solutions designed specifically for the public sector and local government. Learn more at https://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 https://haltingwinter.com/MLDC

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

Show Notes: MLDC Book of the Week – The Burnout Epidemic
Episode 288 of The HaltingWinter Podcast

Your wellness program isn't fixing burnout, and Jennifer Moss explains why. This week's MLDC book, "The Burnout Epidemic," reveals that burnout isn't a personal problem requiring more yoga and meditation apps. It's an organizational design flaw that local government leaders have the power to fix.

In this episode, Seth introduces the six root causes of burnout and why each one shows up uniquely in municipal and county government. Moss wrote this book during the pandemic while experiencing burnout herself, and her insights hit differently for leaders still navigating hybrid work, staffing shortages, and exhausted teams. This isn't another self-care prescription. It's a framework for diagnosing what's actually broken in your organization and taking specific steps to fix it.

Join the Municipal Leadership Development Circle (MLDC) to explore this book in depth with daily insights, practical applications, and a community of peers facing the same challenges. Learn more at HaltingWinter.com/MLDC.

Join the MLDC for the Complete 5-Part Series

The Municipal Leadership Development Circle (MLDC) is a network of local government leaders from across North America, including city/county managers, administrators, and department heads, giving you access to:

✔ A weekly podcast series breaking down one book for municipal applications
✔ Daily blog reflections and implementation tools
✔ Our live, weekly, virtual mastermind session
✔ Monthly webinars with relevant training from local gov leaders

➡ Learn more at www.HaltingWinter.com/MLDC

Resources Mentioned

• Book: The Burnout Epidemic by Jennifer Moss

Connect with Seth Winterhalter

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