Mike Lewis

Author, former professional athlete, San Francisco, California

The former professional squash player and founder of When to Jump talks big dreams and how to make them a reality.

By: Michael Small + Taylor McKinnon | Photos: Daniel Dent

Lewis is wearing the Unrestricted Blazer

A leap of faith. On paper, it’s a simple concept – believing in something without any evidence that it’s true. In reality, taking that jump, without the benefit of a safety net, is often a bewildering experience packed with doubt, confusion and anxiety. But when successful, these ambitious bids can be transformative. No one knows this better than Mike Lewis.

Growing up in Santa Barbara, California, Lewis fantasized about travelling the globe as a professional squash player. The dream persisted into adulthood – Lewis was recruited to play at Dartmouth, so the racquet remained firmly in hand. But with the conclusion of his collegiate career and the acceptance of a position at a venture capitalist investment firm, the prospects of joining the pro-tour were hazy at best.

But after stumbling upon an inspiring story of a woman who left Wall Street to become an Olympic cyclist, Lewis knew it was now or never. He joined the pro tour part-time and dedicated himself to training. “I would take a sick day or fly out in the late afternoon and go to Chicago or New York to play a tournament match, then come back for work the next morning,” he explains.

It wasn’t long before Lewis left his job to fully take on the game of squash. In no time, his bags were packed for New Zealand and life as a pro-tournament player. His professional squash career saw Lewis travelling 200-plus thousand miles, visiting nearly 50 countries and meeting countless people along the way. It was these human interactions, in fact, that led him to his latest venture.

“What I learned along the way was that everyone has something that they're thinking about doing,” he explains. “Whether it was other bus passengers, bartenders, or people at the gym, someone would say to me, ‘I really want to leave consulting’ or, ‘I'm thinking of leaving my electrician job. I want to open a bookstore.’" These personal stories of people wanting to chase their dreams struck a chord.

Today, Lewis is focused on starting a global conversation about the “jump,” including a When to Jump site and upcoming book featuring stories of people from around the world. “Ultimately, it was these conversations with others who had told me their experience – knowing when to jump – that encouraged me and supported me to take my own risk,” he explains. “It's a different type of adventure, and in a lot of ways, it's much scarier than the last one,” he laughs when talking about his latest project – but if there’s anyone who knows how to embrace the unknown, it's him.

Meet Mike Lewis.

“What I learned was there's never a good time to jump. There's always going to be a reason to push it back.”

Lewis is wearing the Time Out Brushed V Neck Tee

“Everything I set out to achieve in squash – and more – was accomplished. I feel like I have a different dream now.”


“On an average day, I could be going to a meeting, taking a hike, waking up early for cross-training and writing at my desk. All of these things require clothing that is high quality, versatile, and that I can feel really comfortable in.”

Lewis is wearing the Bidwell Pant
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“I’m building a curated community of storied people and ideas related to leaving something comfortable and chasing a passion.”

Lewis is wearing the Hero Blazer

For more of Lewis’s and other inspirational stories, visit When to Jump.