Episode 190 of The HaltingWinter Podcast

In this episode, Seth Winterhalter sits down with Michael Herbert, Town Manager of Ashland, Massachusetts, for one of the most powerful conversations we’ve had on the podcast to date.

Michael’s story isn’t just about policy or public administration—it’s about personal transformation. From struggling with addiction and homelessness to becoming a respected municipal leader, Michael shares how hitting rock bottom gave him the perspective, resilience, and purpose he now brings to his role every day.

We talk about the long arc of recovery, the slow work of rebuilding a town’s identity, and the courage it takes to lead with transparency even when it’s unpopular.

If you’ve ever wondered how someone’s past can shape their impact or how small towns can create big change, this episode is a must-listen.

From Rock Bottom to Town Hall:
Michael opens up about the lowest point in his life and the decision that helped him climb out and into a career of public service.

The Long Game of Leadership:
Why real change in local government requires patience, persistence, and a willingness to plant trees you may never sit under.

The Price and Power of Transparency:
An honest look at the emotional cost of being open with residents and why Michael believes it’s still worth it.

A New England Perspective:
What it means to lead in a “Open-Town-Meeting” form of government, and how tradition shapes leadership expectations in Massachusetts.

LinkedIn: www.linkedin.com/in/michael-herbert

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

At HaltingWinter, we help local government leaders build thriving teams and resilient workplace cultures through keynotes, workshops, and leadership development programs rooted in the ABCs of Impactful Leadership.

Learn more at HaltingWinter.com

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