Rory Sutherland sits down with Lewis Oakley on Generation Uncharted to unpack why housing has become a generational trap, why innovation stalled in the physical world, and how AI could reshape work in ways no one is prepared for.
Lewis flips the script and asks Rory what he would do if he were 20 years old today — where he’d live, what skills he’d build, and how he’d define success in 2025.
Chapters
00:00 Aspirational culture & redefining success
01:15 If Rory were 20 again
03:09 Housing as a generational tax
08:46 You’re not buying a house — you’re buying planning permission
12:19 Why driving expands your life radius
17:53 The tech that improved everything except housing
21:03 Liberty ships & how to build homes like cars
37:34 Flying cars, blocked innovation & regulation
45:52 AI: huge potential, huge downsides
56:00 Missed opportunities: pubs, co-working, smart glasses
1:02:44 Rory’s product recommendation
