The Long Game of Leadership

In September 2026, I am looking forward to reuniting with a group of friends with whom I completed the Swim for Life event on Cape Cod for ten consecutive years. Although our lives have taken us in different directions, we are coming together again to swim the Wellfleet Lake course.

As I prepare for the event, I’ve found myself reflecting on a question that leaders face as well: What does success look like over the long term?

Learning to Play the Long Game
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Last year brought both new adventures and unexpected challenges. I completed the Marseille swim and the Brissago swims and prepared for the Clipper Round the World Yacht Race, spending several weeks learning the skills needed for offshore sailing.

The Clipper experience reminded me how energizing it is to be a beginner again. Whether learning to sail, training for a swim, writing a book, or taking on a new leadership role, growth doesn’t stop simply because we become more experienced.

Then, a sailing accident forced me to rethink my training and recovery. Rather than trying to return immediately to where I had been, I gradually rebuilt my routine: swimming several times a week, adding strength training, and occasionally going for a short run.

Today, what strikes me is not how much I can do, but how sustainable the routine feels.
I feel strong in the water. I have the energy to train, work, write, coach clients, and pursue new projects. While I may not be swimming as far or as fast as I was a year ago, I feel confident that I can continue doing the things I love.

Beyond Peak Performance

As I reflected on that change, I was reminded of Olivier Hamant’s concept of robustesse – the idea that living systems thrive not because they are perfectly optimized, but because they are resilient enough to adapt and continue to function over time.

The same is true for leaders

Much of our culture celebrates optimization, efficiency, and doing more. Those qualities certainly have value. But over the course of a career, another question becomes equally important: How do we sustain the energy, health, relationships, and capabilities that allow us to continue contributing over the long term?

Leadership is not simply about reaching the next milestone. It is about maintaining the capacity to continue learning, adapting, and showing up for others.

What Happens Between the Milestones

I still enjoy preparing for an event, challenging myself, and crossing a finish line. There is something deeply satisfying about setting a goal, putting in the work, and discovering what is possible.
What has changed is my appreciation for what happens between those milestones.

The greatest benefit of training is not the race itself. It is the way a sustainable routine supports every other part of life.  Swimming, strength training, and occasional runs give me energy. They help me think more clearly, manage stress, stay focused, and bring more presence to my work and relationships.

Perhaps that is where sport and leadership intersect. Ambitious goals inspire us to grow, but the habits we build along the way are what sustain us. They give us the capacity to continue learning, contributing, and enjoying the journey over the long term.

As I look ahead to September, I am grateful not only for the opportunity to swim but also for the chance to reconnect with old friends. Both remind me that some of the most important things in life are not achieved once and for all. They are maintained, renewed, and strengthened over time.
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This year, I will once again be participating in Swim for Life on Cape Cod, an event that has supported local organizations and community initiatives for decades. If you’d like to learn more about the event (https://swim4life.org/) or support my fundraising efforts (https://charity.pledgeit.org/f/e9fed2o03l), I would be grateful.

If you would like to explore your own career evolution or think intentionally about sustaining your leadership over the long term, I’d be happy to have that conversation. [email protected]