In the wide ranging conversation of S2E3, Billy Riggs and longtime colleague and friend Bruce Appleyard unpack the concept of “wicked opportunities” — a framework for understanding the messy, uncertain, and deeply interconnected challenges surrounding autonomous vehicles, AI, and emerging technologies.

Drawing from decades of research in urban planning, transportation, and policy, the conversation explores why AVs are not simply a technology problem, but a systems problem rooted in governance, infrastructure, human behavior, public trust, and social complexity.The discussion spans everything from California AV regulation and the ambiguity of the dynamic driving task to the geopolitics of automation, public transit integration, induced demand, deadheading myths, and the tension between safety, sustainability, and innovation.

Riggs and Appleyard argue that autonomous vehicles represent neither utopia nor apocalypse — but rather a “wicked opportunity” requiring ongoing adaptation, ethical judgment, and public engagement.

Takeaways and Key Themes

• AV adoption is fundamentally tied to governance, infrastructure, and social systems.
• Autonomous vehicles may ultimately improve both safety and sustainability outcomes.
• California’s AV regulatory framework is messy — but intentionally public and iterative.
• Many fears about runaway VMT and “deadheading” misunderstand shared fleet economics.
• The future of automation is likely to be multimodal and integrated with public transit.
• Cities that fail to plan for automation risk losing influence over how systems evolve.
• AI and AVs should be understood as adaptive societal transitions, not isolated technologies.

Soundbites

• “A wicked problem doesn’t mean evil. It means stubbornly resistant to being solved.” — Bruce Appleyard
• “We now have the safest driver on the road — and yet we want to make it more human-like, even though humans are the worst drivers on the road.” — Billy Riggs
• “Transit agencies need to stop complaining agency and take agency.” — Billy Riggs
• “Complexity grows over time. Wicked opportunities tend to get more complex, not simpler.” — Bruce Appleyard
• “Planning under uncertainty is not a weakness. It’s an opportunity.” — Billy Riggs

Additional Resources

• Livable Streets 2.0 — Bruce Appleyard, https://www.amazon.com/Livable-Streets-2-0-Bruce-Appleyard/dp/0128160284 
• “Street Livability in the Era of Driverless Cars” — Appleyard & Riggs, https://www.sciencedirect.com/science/article/pii/S259019822300115X
• “Wicked Opportunities: The Trials of Innovation in the Age of Complexity” — Appleyard & Riggs, (forthcoming)
• Autonomous Vehicles and the City, 10th Anniversary Symposium, April 17, 2026, https://www.youtube.com/watch?v=7aBKQgtt_wE

Chapters

00:00 - Introduction to Wicked Opportunities and Autonomous Vehicles

04:54 - Defining Wicked Problems in Urban Planning

08:20 - Policy Evolution and The Complexity of Regulations

11:28 - Safety as a Major Opportunity in AVs

14:10 - Market Dynamics, Pricing Systems and Fleet Economics

18:20 - The Rules of Wicked Opportunities

27:31 - The Meme Generation: Media Influence and Social Media Impact

28:45  - Historical Context and Automobility

31:00 - Infrastructure and Street-Level Design
35:00 - AV Companies Pursing Safety Alongside Sustainability 

39:22 - Conclusion: Planning in Uncertainty and Future Directions