Playing Unsafe
When I was a teenager, I abseiled off the side of a building.
I still remember the guy before me, Ari Costi, half-smiling while one leg shook uncontrollably as he went over the edge.
As a guy scared of heights, terrified of roller coasters, and generally cautious about everything, this was a massive deal. It was the first time I'd done anything truly daring.
For a trust exercise, we had to go halfway down, let go of the line, and rely on our teammate on the ground to hold the rope tight as a brake.
The main thing I remember is the feeling when my feet touched the ground:
I want to do it again! Let's do it again!
It was exhilarating.
Abseiling off a school building in 1996 - a smile baked in anxiety! I haven't abseiled since, but looking back, I realise how much I gained from that single moment.
The years following that day threw up a strange paradox.
I mostly saw myself as shy, inward-looking, and a follower. Yet, bizarrely, I simultaneously found myself making daring, life-changing decisions, going against convention, and taking the lead.
This risk-taking streak may have come from my entrepreneurial parents, or simply the overwhelming survival instinct we all share.
Either way, taking calculated chances has provided me with opportunities, experiences, and relationships money can't buy. It turns out that taking a chance has created a level of safety and security I never could have imagined.
So, how can we improve our comfort and safety by taking on more risk?
Scarcity Mindset is The Enemy
When we are poor, losing, or under threat we lose IQ (The Boot Room, The Rhythm Effect).
We get so worried about hitting the car directly in front of us that we forget everything else about the journey. This shows up in how we think, act, speak, and make decisions:
Cafes with fewer customers cut staff, leading to poorer service and fewer returning patrons.
Salespeople facing rejections make fewer calls and set fewer meetings.
Executives under pressure call for more meetings, request more reports, and change everything including the processes that were working well.
It's easy to understand why we react this way: it's self-protection. But our instinctual need for immediate safety often leads to bad decisions, undermining the very stability we crave.
What's The Alternative?
We deal in extremes without realising it: if someone doesn't work themselves into the ground, they're lazy; if someone is shy, they are hopeless; if someone is late, they're unreliable.
Real life is more nuanced and acknowledging this is helpful.
It is the same with risk-taking. Entrepreneur pin-up boy, Gary Vaynerchuk points out that good entrepreneurs aren't reckless risk takers; they are exceptional at mitigating risk. They put effort into understanding their exposure so they don't fall on the wrong side of it.
Real risk-taking isn't about blind leaps of faith. It comes down to three habits:
1. Be Considered
Kerry Packer had spent years trying to partner with traditional administrators in cricket. After failing, he spent over a year working in secret to launch a breakaway cricket league (World Series Cricket, 1977). It shocked the sporting world, but the move had been coming for years.
Similarly, in 2006, Body Shop founder Dame Anita Roddick shocked everyone by 'selling out' to L'Oréal. On the surface, it appeared she had taken big money and abandoned her principles. In reality, this had been Roddick's plan for years - a deliberate strategy to scale her impact. The acquisition forced L'Oréal to raise standards around animal testing and sustainable supply chains across its global portfolio.
Take time to consider your moves - whether that takes hours, weeks, or months. Once you understand the terrain, pounce.
2. Keep Moving
Brad Pitt's character, Gerry Lane, in the movie World War Z uses the phrase "Movement is life" to convince a family to travel with him.
This quote always resonated with me. Staying still may feel safe, but moving or exposing ourselves to something new or different is fundamental to building up what is termed 'resilience'.
Just like building up a child's immune system or building strength and endurance when training for a marathon, incremental movement exposes us to insights, experiences, and knowledge we need to navigate uncertain times.
3. Talk It Out
The recently retired English Cricket Captain, Ben Stokes spoke about his decision to step away from the game. After a brutal tour to Australia he had six months off before the home series against New Zealand. He did a lot of thinking and writing in isolation, but rarely talked to others. He questioned his own reflections. In his own words, he was "cooked" before a ball was bowled because he was trapped in his own internal dialogue.
Voicing your doubts, observations, and ideas to trusted people is one of the best ways to connect dots and make sense of complex decisions.
Are You The Question Asker In Chief?
We are generally more conservative in our decision-making than we realise. We default to the devil we know; anything else requires convincing.
Recognising this bias unlocks huge opportunities.
When facilitating groups or coaching executives, my role is to act as the Chief Question Asker. It's structured, guided, and deliberate - and it's a habit every leader needs to develop.
Asking great questions delivers three critical benefits:
Powers Accountability: In 1980, Don Chipp coined the phrase "keep the bastards honest." Asking targeted questions of people in power helps you (and them) surface and address the destructive consequences of Scarcity Thinking.
Drives Autonomous Decisions: I've coached dozens of executives who felt an overwhelming urge to quit their job. In every single case, taking 90 minutes to explore the root causes transformed an emotional reaction into a clear strategy for progress.
Liberates and Empowers: Playing small becomes the norm when teams are micromanaged or undersell their own abilities. Regular, supportive questioning creates fresh perspective, fuels confidence, and empowers people to take initiative - breeding a genuine sense of security.
Big gambles and reckless leaps of faith are usually bad ideas. But sitting still, waiting, and hoping for change won't improve much either.
Between those two vast extremes lies a massive opportunity to gain exposure, build progress, and boost resilience. Like abseiling, stepping outside your comfort zone usually turns out to be far more exhilarating than terrifying.
