Reluctant Leader, Relentless Impact: The Leadership Journey of Rebecca Houseman

Some people chase leadership. Others step up because the job simply needs doing.
Rebecca Houseman is the latter and the kind of leader every community deserves.

In this week’s episode of The HaltingWinter Podcast, I sit down with Rebecca Houseman, City Manager of Fort Atkinson, Wisconsin, whose journey into municipal leadership is anything but traditional. She didn’t plan to become a planner. She wasn’t trained to be a clerk. And yet—through grit, humility, and an unwavering commitment to service—she mastered both, ultimately stepping into the top role.

From navigating fire and EMS reform to spearheading a major housing development (and surviving a two-year deal that fell apart), Rebecca walks us through the real work of local government: the slow, often invisible, always essential kind.

This is one of the most grounded and insightful conversations we’ve had—especially for those leading small to mid-sized cities with limited resources and unlimited expectations.

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In This Episode:

• How a college internship changed Rebecca’s life—and why every city needs a structured, intentional program to shape the next generation.
• What it’s like to break a public safety contract before the funding is secured—and lead through the political firestorm that follows.
• Why wearing “all the hats” in smaller communities builds unmatched leadership depth.
• What to do when a development deal collapses after years of work and how to keep moving forward.
• Why Fort Atkinson’s transformation is rooted in quiet courage, collaboration, and relentless follow-through.

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Why You Should Listen

If you’ve ever had to justify your budget, fight for a referendum, or watch your best-laid plans unravel—you’ll see yourself in Rebecca’s story.

More importantly, you’ll be reminded of why this work matters.

As Rebecca puts it:

“Most people won’t see what we do until it’s on a council agenda. But the invisible work is often the most important.”

If you’re leading in local government—this one’s for you.

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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.