Show Notes: Michael Herbert – Second Chances and Stronger Cities: From Addiction to Public Impact

Episode 190 of The HaltingWinter Podcast

Overview

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.

Episode Highlights:

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.

Connect with Michael Herbert

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

Connect with Seth Winterhalter:

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

About HaltingWinter Municipal Solutions

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. 

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Seth's Upcoming Keynotes:

2025 South Carolina APWA Chapter Annual Conference June 24 | Spartanburg, SC Details at SCAPWA

2025 Kentucky League of Cities Annual Conference & Expo September 24 | Owensboro, KY Details at KLC

2025 Kansas City/County Management Association Annual Conference December 4 | Manhattan, KS Details at KCMA

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