Municipal Leaders: Develop Faster, Lead Stronger, Build Better
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Some leaders rise through the ranks.
Michael Herbert had to claw his way up from rock bottom.
In this week’s episode of The HaltingWinter Podcast, the Town Manager of Ashland, Massachusetts shares a story rarely heard in public sector leadership—a story of addiction, homelessness, and ultimately, redemption through service.
It’s not just a story of survival.
It’s a story of purpose.
And it’s a masterclass in the kind of quiet, resilient leadership that sustains local government through its hardest seasons.
Michael doesn’t hide from the past.
He talks about failing out of Berklee College of Music, being jobless and addicted, with no money, no plan, and a growing certainty that if something didn’t change he wouldn’t survive.
“I was very fortunate one day to have one of those spiritual experience that you hear about. It wasn’t like a flash of light type of thing. But I ended up deciding, “Hey, I’m ready for a new life.”
That moment led him to help, then back to school, then into a career in local government, and eventually into the role of Town Manager in a New England community he now helps shape every day.
Ashland operates under an open town meeting form of government. Every resident has a vote on budgets, bylaws, and big decisions.
There’s no political cover. No rubber-stamping. And certainly no easy path forward.
Michael shares what it’s like to lead in a system that demands constant transparency and buy-in—not just from elected officials, but from the community at large.
“You’re not just managing a city. You’re educating, engaging, and building trust every step of the way.”
One of the most impactful parts of the conversation is Michael’s honesty about the emotional weight of leadership.
He talks about the toll of making hard calls. About the risk of being transparent when people don’t want to hear the hard truths. About trying to balance stewardship with self-care.
“People say they want transparency. But when you show them how the sausage is made… it’s not always well received.”
Every city manager knows that tension. Michael gives it a name—and a voice.
From securing funding for sewer expansion to navigating ARPA dollars, Michael walks through the kind of long-haul, often invisible work that defines city leadership at its best.
He reminds us that many of the biggest wins in local government happen in slow motion and that patience, not popularity, is often the better measure of success.
“You have to be willing to do work today that won’t be appreciated for years. But that doesn’t mean it’s not worth doing.”
This conversation goes beyond policies and projects.
It’s a conversation about the cost of leadership, the gift of second chances, and the power of showing up every day—even when it’s hard.
Michael Herbert doesn’t pretend to have it all figured out.
He just shows what it looks like to lead with purpose after surviving the fire.
Listen to Episode 190 of The HaltingWinter Podcast
“Second Chances and Stronger Cities: From Addiction to Public Impact”
Available on Apple, Spotify, and all major podcast platforms: www.haltingwinter.com/resources
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.
