Welcome to this week’s edition of Simon Sees!
This edition was sparked by our latest Future With Friends episode with the brilliant Leanne Williams, where we explored The Future of Doing Risky Things. Together, we discussed 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.
We begin with a piece from Psychology Today that highlights how embracing risk in the corporate world is essential to creativity—and what we might lose when we prioritise control over experimentation.
Next, we look to the insurance industry, where John Hancock’s decision to offer Apple Watches to life insurance customers reveals a quieter, more calculated approach to managing personal risk—where wearable tech becomes a tool of behavioural nudging in the name of longevity.
And finally, we turn to our children’s playgrounds. The once-ordinary act of climbing too high or falling too hard is increasingly engineered out of existence. But are we raising safer kids—or just less resilient ones?
In a world designed to minimise risk, perhaps the real risk is never being tested at all. Because if we’re not willing to be uncomfortable, to get it wrong, or to fall (and get back up), how will we ever discover what we’re truly capable of?
PSYCHOLOGY TODAY
Risk-Taking and the Creative Workplace
“The more risks we’re willing to take at work, the more creative we become.”
CNBC
You can get an Apple Watch for only $25 … with one small catch
“Apple is exploring partnerships with insurance companies as a sales channel for its health and fitness-tracking Apple Watch. Apple recently held a series of meetings in August with health insurer Aetna to discuss giving out Apple Watches to its 23 million members.”
THE SYDNEY MORNING HERALD
Cotton wool club: are we right to remove risk from playgrounds?
“In the workplace we have zero tolerance to accidents. When kids are at play it is not a workplace so it is not a zero-tolerance affair,” says Eager. “What we want is for the kids to be able to make mistakes. Because they learn by making mistakes.”
THE FUTURE WITH FRIENDS PODCAST
Ep 10: The Future of doing Risky Things
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.
Also available on Apple Podcasts and Spotify.
Simon
