Challenger Cities

Challenges Cities EP14: Exploring Joyful Cities with Paul Kalbfleisch


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Iain Montgomery of Now or Never Ventures speaks with Paul Kalbfleisch, author of The Joy Experiments: Reimagining Mid-Sized Cities to Heal Our Divided Society.

Paul shares his unique journey from marketing executive to accidental urbanist and his mission to reimagine cities as spaces for connection, joy, and belonging. Drawing from his experiences in Ontario’s Waterloo Region and beyond, Paul offers fresh perspectives on the transformative power of public spaces and why cities that prioritize play are the key to building stronger, more resilient communities.

What You'll Learn in This Episode

  • How Paul’s background in branding led to his work in urbanism.
  • Why mid-sized cities are uniquely positioned to become "challenger cities" and lead innovation.
  • The power of “play, live, work” as a new framework for designing cities.
  • Real-world examples of public art and play fostering community, like Meander in Cambridge, Ontario.
  • Why joy is not just an emotion but a practical tool for city building and social resilience.
  • How everyday people can influence their cities and advocate for joyful, engaging spaces.

Key Quotes from Paul

  • “Cities that know how to play, that's where we start this healing. We will change the world by how we change cities.”
  • “Play is the most complex social activity humans do. It’s where we learn to collaborate, see differences as assets, and celebrate together.”
  • “We will not solve the problems of the world by using grim determination to tackle grim problems. If we double down on grim, people will feel society is failing.”
  • “A city should make you happy. It should make you feel like you belong to something.”

Links and Resources

  • Paul’s Book: The Joy Experiments: Reimagining Mid-Sized Cities to Heal Our Divided Society
  • Connect with Paul: [LinkedIn/Profile Link]
  • Mentioned Projects:
    • Meander installation in Cambridge, Ontario
    • The Bentway in Toronto

Actionable Takeaways

  1. Engage with your city: Attend events, visit public spaces, and participate in community-driven activities.
  2. Advocate for joy: Let your city officials know you value joyful, engaging public spaces—and celebrate them when they’re created.
  3. Think differently about public spaces: Consider how parks, benches, and plazas can foster connection and play, not just quiet retreat.
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Challenger CitiesBy Iain Montgomery