Flying into the unknown

Flying Into the Unknown is a conversation about risk, identity and what it means to stay steady when life tilts. In this episode, I sit down with Josh De Maid, a pilot whose journey through aviation, redundancy and reinvention has shaped a powerful perspective on resilience and human performance.

We explore how flying teaches humility, why systems matter more than heroics and what happens when the identity you’ve built is suddenly taken away. Josh opens up about the psychology of risk, the cultural habits that weaken organisations and the behaviours that reveal whether a team is truly resilient.

Together, we dive into the world of unknown unknowns, cognitive traps under pressure and how organisations can prepare for events they cannot imagine. We also look ahead to the future, where AI becomes a cognitive co‑pilot and reshapes how humans make decisions, feel risk and navigate uncertainty.

Across the episode, we cover:

• The aviation mindset and what flying teaches about risk and decision making

• Redundancy, identity loss and the journey into resilience work•

The psychology of risk and why blame‑free cultures matter

• How resilient cultures behave in everyday moments• Preparing for the unexpected without overwhelming people

• The role of AI in future risk and real‑time situational awareness

• Resilience as identity, not just capability

This episode is for anyone interested in resilience, leadership, aviation, psychology, organisational culture or the future of risk. It’s a human story about breaking, rebuilding and learning to navigate uncertainty with clarity and courage.

🎧 Available now on Spotify, Apple, and all your favourite streaming platforms to watch and listen.

Until next time, keep on investing in your resilience.

Rina Singh