Leading Through the Wilderness
McKinsey estimates that roughly 70% of large-scale transformation programmes fail to achieve their objectives. That figure has barely moved in a decade — despite every advance in project methodology, change management and technology. We've become remarkably good at describing transformation. We remain stubbornly bad at doing it.
Part of the problem is the leaders themselves. Not their intelligence or their intent — but the relentless pace at which they are expected to operate. The gap between the transformations organisations must make and the leadership capability to execute them has never been wider.
And now that gap has a new name: artificial intelligence. Every senior leader is being asked to lead transformations they don't yet fully understand, at a speed their organisation cannot yet match, while their own role is being quietly redefined from below. The case for stepping back to see the wider picture has never been stronger.
My proposition is simple. Leaders need to renew their skills and perspective faster — and to do that, they need to know where they're going and why. They need time and space to think. They need to look hard in the mirror.
Get lost!
Spend some time in the wilderness. Wander around with nothing on the agenda, the chance to go anywhere, and the uncomfortable opportunity to take a long, hard look at yourself.
In early 2012, I was three years into a role at Arup — a firm I enjoyed — when I made a deliberate decision to take six months away. Not because things were going badly. Because I knew that if I didn't create the space to think, the next chapter would simply be a continuation of the current one. I told my boss in January. He didn't flinch. Within a few months, Kerry and I had sold the car and the motorbike, stored everything else with family, and I had handed over my work. We were heading to France.
You’ve got mail
The timing produced an unexpected bonus. As I cleared my desk, an email arrived from my colleague Tim Jarvis, inviting people to join the support team for his Shackleton Epic — a re-enactment of Sir Ernest Shackleton's legendary 1916 survival journey across the Southern Ocean and South Georgia. Nobody else seemed interested. I figured: why not? I tossed my name in the ring and headed for the airport.
We started on the Camino de Santiago in Le Puy-en-Velay, walking 735 kilometres across France to Saint-Jean-Pied-de-Port. Then, in January 2013, I joined Tim and his crew in Antarctica — nine days aboard Australis, moving through the channels and bays of the Peninsula, preparing for what lay ahead. The work was the Shackleton's Way programme — a leadership model built on Shackleton's extraordinary record of keeping his men alive, sane and functioning through conditions that should have broken them entirely.
The words of expedition photographer Frank Hurley have stayed with me: "I always found him rising to his best and inspiring confidence when things were at their blackest." That is still, twelve years later, the most useful sentence I know about what real leadership looks like under pressure.
Shackleton’s journey recreated
On 22 January, Tim and his crew set out from Elephant Island in an open boat. They battled eight-metre swells, 50-knot gales, frostbite and constant cold across 800 miles of the world's most hostile ocean. When they finally reached Stromness on South Georgia — nineteen days later, in the same footsteps as Shackleton himself — the word that came to mind wasn't heroic. It was earned.
Before returning to work, I found a week of quiet in Rio de Janeiro and Sydney. Early in the trip, at a maritime museum in Punta Arenas, I had come across a plaque bearing Shackleton's own words:
"We were the fools who could not rest in the dull earth we left behind, but burnt with passion for the South and drank strange frenzy from its wind. The world where wise men sit at ease fades from our unregretful eyes, and thus across uncharted seas we stagger on our enterprise."
I wouldn't have understood those words before. I found I did now.
How long do you spend in front of the mirror each day? And what are you looking for?
The wilderness — whatever form it takes for you — acts as a mirror on your thoughts, feelings and assumptions. Disconnected from the daily noise, you can make time for the kind of honest self-examination that a crowded diary never allows.
Leading through the wilderness means stepping deliberately out of your established way of doing things, into a wide space of not knowing — of uncertainty and possibility both. In that space, you have the chance to write a new story. One you can come back and tell others with real conviction, because you have lived it.
I'll leave the last word to the Boss himself, from South — his account of the Endurance expedition:
"In memories we were rich. We had pierced the veneer of outside things. We had reached the naked soul of man."
Not a bad return on six months away.
