Diving in the deep end: how to be truly fearless in business

Swimming has always been a huge part of my life. As a teenager, I competed in butterfly at a high level, representing the British youth squad and the South African national team. Butterfly is not just physically tough; it is also one of the most mentally demanding strokes.

Training 800-metre butterfly sets pushed me beyond what I thought possible. At the start of those sessions, I was convinced I would never reach the full distance without stopping. Yet after the first 200 metres, something would shift. My brain and body would click into rhythm, and suddenly I could carry on almost endlessly.

That experience taught me lessons that have stayed with me long after I left competitive swimming. Rhythm, resilience, and the ability to keep going when you feel completely out of breath are as relevant in the pool as they are in the boardroom. In fact, many of the qualities that help swimmers succeed are exactly those that help founders thrive in business.

Calculated courage

Fearlessness in business is often misunderstood. It is not about recklessness or throwing yourself into situations blindly. It is about informed risk-taking backed by preparation.

When I stood on the starting block before a race, I wasn’t fearless. I was prepared. Hours of training, discipline, and conditioning gave me the confidence to dive in knowing I had built the foundations to perform. The same principle applies in business. Founders need to take leaps into the unknown, but those leaps are not blind if the groundwork has been done.

That is the role I often play for clients. I help them build the solid ground beneath the jump. We put structures in place so that if something doesn’t go to plan, there is a way to recover, reset, and try again. True fearlessness is not about never failing. It is about having the courage to act because you know you can handle the outcome, whatever it may be.

The confidence gap

One of the greatest risks in business is hesitation. Mistakes can usually be corrected, but missed opportunities are gone for good. I have worked with founders who sat on an idea too long, waiting for the perfect moment, only to see competitors seize the initiative.

The cost of not trying is rarely talked about, yet it is often higher than the cost of a misstep. Getting something moving is far more valuable than holding out for perfection. The best businesses are those that learn to refine and improve while already in motion.

Just as in swimming, the start matters. If you hesitate on the blocks, the race is lost before it begins. Business is no different. Decisive action secures first-mover advantage and sends a powerful signal to investors, clients, and competitors alike. Perfection is not the goal. Momentum is.

Resilience in the unknown

Perhaps the hardest lesson swimming taught me is how to stay calm in discomfort. Butterfly is not a gentle stroke. It tests every muscle, every breath, every ounce of stamina. The first few lengths always felt unbearable, but I knew that if I leaned into the rhythm and pushed through, the struggle would ease, and strength would carry me forward.

Business has the same rhythm. The first time you submit a funding bid, the nerves can feel overwhelming. The first time you pitch to investors, the uncertainty can feel unbearable. Yet the second time is easier. By the third, you are confident. By the fifth, you are flying.

Resilience comes from repetition and from accepting discomfort as the price of progress. The most successful leaders are not those who avoid the unknown, but those who learn to find energy within it. Growth never happens in the safety of the shallow end. It lives in the deep water where you must trust yourself to keep swimming.

Final thoughts

Swimming butterfly taught me that rhythm, preparation, and resilience are the real foundations of fearlessness. In business, as in the pool, success is not about being reckless. It is about building the discipline and structure that make bold action possible.

The founders who thrive are those who recognise that hesitation costs more than mistakes, that perfection is not required to begin, and that resilience is forged in the moments of greatest discomfort.

Fearlessness is not the absence of fear. It is the decision to dive in anyway, knowing you are prepared, supported, and strong enough to keep going until you find your rhythm. That is how champions are made in sport, and it is how great businesses are built in the real world.