The HaltingWinter Podcast

177: Book of the Week: The Hard Thing About Hard Things


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Show Notes: Book of the Week – "The Hard Thing About Hard Things" Episode 177 of The HaltingWinter Podcast The Hard Things About Municipal Leadership (Part 1 of 5: "The Hard Thing About Hard Things" Series)

Episode Overview

This week inside the MLDC, Seth Winterhalter kicks off a new series exploring The Hard Thing About Hard Things by Ben Horowitz, reframed for the real-world realities of municipal leadership.

This first episode introduces the concept of “the struggle”—those moments in leadership when everything seems to be going wrong, and there’s no playbook to follow. Whether it’s a budget collapse, political turmoil, or community crisis, municipal leaders face these hard things more often than most. As Seth explains, the solution isn’t found in easy answers—it’s found in clarity, transparency, resilience, and the ability to lead decisively through uncertainty.

Key Takeaways
  • Why the hardest leadership moments offer no clear right answer

  • What “the struggle” feels like in city management and why it’s a normal part of the job

  • The power of transparency during difficult decisions

  • How to model “the right kind of ambition” focused on community, not ego

  • Peacetime vs. Wartime leadership: when to shift your style and how to know the difference

  • Leading with the truth even when the truth is unpopular or politically risky

This Week’s Journey in the MLDC

Monday: Introducing the struggle and the realities of leading without a script Tuesday–Thursday: Culture, communication, talent, and personal resilience Friday: Virtual Book Club – What’s your version of “the hard thing,” and how are you leading through it?

Special: Free 7-Day MLDC Trial

This week only, get full access to:

  • All five episodes in The Speed of Trust podcast series

  • Daily blog content and leadership tools

  • Live Friday Virtual Book Club discussion

  • A growing national network of municipal leaders inside the MLDC → Start your free trial today at HaltingWinter.com/MLDC

Resources Mentioned
  • Book: The Hard Thing About Hard Things by Ben Horowitz

  • MLDC: The Municipal Leadership Development Circle

Connect with Seth
  • LinkedIn: www.linkedin.com/in/sethwinterhalter

  • Website: www.HaltingWinter.com

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The HaltingWinter PodcastBy Seth Winterhalter

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