Ollie’s reflections offer a grounded view of resilience, leadership and mental health in high‑pressure environments.
Life’s all about the stories you tell yourself
For Ollie, resilience starts long before the crisis point. It begins with the internal narrative that determines whether you even step forward.
“Life’s all about the stories you tell yourself before you even begin,” he says. “There are definitely scenarios where I could have talked myself out of doing them.”
Ollie is open that he was not a natural candidate for many of his adventures, freely admitting he is not a rower – he had never rowed before – and nor is he a sailor, having never sailed in his life. What carried him through was curiosity, courage and a willingness to take risks and make mistakes, rather than any pre existing expertise.
The Atlantic: his toughest mental test
Despite a career in elite sport and an expedition to the North Pole, Ollie describes the Atlantic row as “the hardest thing I’ve ever done, mental health wise.”
The challenge was not just physical. The confinement of the boat, the inability to move freely and the constant heat and discomfort took a heavy toll.
“I’m an active individual. I can’t just sit still,” he explains. “Being confined to basically moving a metre every day was very difficult.”
He never considered quitting, drawing on a deep stubbornness to keep going, but he did have to find ways to cope. The most effective was breaking each day into small segments and filling them with simple tasks: preparing food, doing minor repairs, organising kit and grabbing short bursts of sleep.
“Breaking the days into specific segments and filling them with tasks was a welcome distraction from facing the reality of how I was feeling emotionally,” he says. It is a practical approach that translates directly into pressured professional environments: when the big picture feels overwhelming, shrink the timeframe and focus on the next 30 minutes.
Teams, tension and accountability: leadership lessons in resilience and performance
Whether in the England changing room, a PwC team or a 4 person ocean rowing crew, Ollie sees community as central to resilience.
“You don’t want to let people down,” he says. “That community, however big or small, creates an amazing sense of belonging and, as a result, responsibility. It helps create commitment and accountability.”
Yet he is honest that this cuts both ways: “The team dynamic was the best thing about the boat, but also the hardest thing about the boat.”
Teammates can regulate your emotions, but when you are fragile, their own stress can tip you over. A simple example was the crew’s agreement to be an “8 out of 10” boat in effort and commitment but they never defined what that meant for each person. “An 8 out of 10 for one person could mean something very different to an 8 out of 10 for someone else. That caused challenge and confusion.”
For leaders, the message is simple: shared words are not enough. You need shared understanding of what effort, support and wellbeing look like in practice.
The team dynamic was the best thing about the boat, but also the hardest thing about the boat.
From the top 1% in rugby to the Executive MBA
When Ollie arrived at Cambridge Judge to begin the Executive MBA, he was in the middle of a difficult transition. In rugby, he had been in the top 1% of his profession – at one point voted the best player in the world. In business, he was starting again.
“The Executive MBA gave me a huge amount of confidence,” he says. “It taught me the importance of asking great questions, of being present and that you don’t need to have all the answers.”
The programme helped him translate his sporting experience into the language of strategy, finance and leadership, and reinforced the importance of building teams and delegating effectively. What surprised him most, though, was the enduring value of the Cambridge Judge community – a network he still draws on today.
The Executive MBA gave me a huge amount of confidence […] It taught me the importance of asking great questions, of being present and that you don’t need to have all the answers
Resilience, leadership and mental health
Asked what he wishes more leaders understood about resilience and mental health, Ollie highlights one core idea: it is OK not to be OK, and it is OK not to have all the answers.
“If you think you’re king of the jungle, you’re about to get eaten,” he says. For him, real resilience lies in being courageous enough to make decisions without certainty, to operate outside your comfort zone, and to remain open and vulnerable even when others expect perfection.
As for what comes next, one ambition sits quietly on the horizon: “I’d like to do the South Pole at some point,” he says. “That’s on the horizon somewhere, but not yet.”
Executive MBA programmes
The Cambridge Executive MBA and Global Executive MBA are 20-month programmes for senior executives who want to apply their knowledge and skills as they learn.
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