Hi First name / Friend,

 

When I was leading the FootJoy brand in Canada, we were moving into men's apparel beyond our initial outerwear offering. The product was solid. We were entering a crowded market, and if we launched like everyone else, we'd get lost. 

 

So I decided to do something nobody in golf apparel was doing: I put it on the runway. Actual runway. Fashion models. Music, lights, champagne. Like Paris, Milan, New York, except this was golf apparel in Montreal. We blocked off part of Sherbrooke Street for valet parking. Rented a spectacular venue, soaring ceilings, stunning architecture. Invited the voice of the Montreal Canadiens hockey team to be our emcee. My entire team was all hands-on deck, either backstage helping models change between collections or front-of-house greeting guests.

It was a labour of love. It was also absolutely terrifying.

 

Because here's what I haven't mentioned yet: I'd already put my neck on the line earlier that year, insisting that Canada be moved from a second-tier country to first-tier for the global launch. I'd fought for us to be in the initial phase, not waiting a year behind other markets.

 

If this runway event flopped, if people thought it was ridiculous, if it came across as golf trying too hard to be fashion, I wasn't just risking the launch. I was risking my reputation, my credibility. The night before the event, I barely slept. What if no one showed up? What if they showed up and laughed? What if this became the story of how I tanked a critical moment in the business? But I did it anyway.

 

The event was unforgettable. People talked about it for years. We didn't just launch a product line, we changed how the market saw the brand. We were the golf brand that did things differently. I learned that bold moves only work if you're willing to own the risk. I could have played it safe. Done a standard product launch. No one would have criticized that approach. It also wouldn't have mattered.

 

Leadership isn't about avoiding risk. It's about deciding which risks are worth taking, and then committing fully, even when you're terrified it might not work. The moments I regret in my career aren't the bold bets that didn't land perfectly. They're the times I talked myself out of something unconventional because I was protecting myself from potential failure.

 

If you only do things you're certain will succeed, you'll never do anything that actually moves the needle. Differentiation requires risk. Impact requires vulnerability. And sometimes, leadership means putting your reputation on the line for something you believe in, even when there's no guarantee it will work.

 

So let me ask you:

For this week, think of one idea you've been sitting on because it feels too unconventional, too risky, or too different from how things are normally done. You don’t have to commit to doing it yet, just explore it seriously. Talk to someone you trust about it. Sketch out what it would take. Ask yourself: what's the worst that could happen? And what's the cost if you don't try? Sometimes the riskiest thing you can do is play it safe.

 

 

Here's to the bold moves that scare us and doing them anyway.