In this episode of The Future With Friends, Simon Waller sits down with long-time colleague and leadership expert Leanne Williams to explore a provocative and timely topic: The Future of Doing Risky Things.

Leanne shares a future scenario set in 2049 — a world so consumed by policies, procedures, and the pursuit of safety that risk itself has become taboo. But instead of creating a safer society, this hyper-regulated world gives rise to something unexpected: an underground leadership experiment where people go to remember what it feels like to not be safe.

What follows is a direct and honest conversation about our shifting relationship with risk. Simon and Leanne reflect on their own experiences with discomfort, and how risk has often been the catalyst for growth. They explore how risk aversion is showing up in leadership, workplaces, and culture — and what it might cost us if we keep trying to safety-proof life.

They also examine how technology, insurance, and a culture of compliance are reshaping our sense of what’s acceptable — and where the line sits between smart safeguards and stifling control.