91³ÉÈË

Some days when I’m running around like a maniac juggling work, life and my dog leave me exhausted — but then I remember this week’s guest and realize I have no idea what tired actually means.

is the first American woman to race a sailboat solo, nonstop, and unassisted around the globe. In 2023, she set off in a 40-foot boat named First Light against 15 male competitors, and 130 days later she came home having broken the class speed record. She’s now co-skipper of , one of the biggest teams in ocean racing, and she just released her memoir, , which landed her a blurb from Billie Jean King calling it “a must-read for every young woman with a dream.” Cole joined me on the show to talk about her journey — and we broke down five highlights from our conversation to help fuel your own success.

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You Don’t Need a Lightning-Bolt Moment to Change Your Life 

Cole had a full ride toward medical school lined up when she chose professional sailing instead — but she says it wasn’t really a choice at all. “I did not really make the ‘decision’ to become the person that I am right now — I really spiraled into it,” she told me. Looking back, she says her advice to readers isn’t to “dream big” in some abstract way — it’s simpler than that. “I was saying pick something that you love and run with it.”
Takeaway: Stop waiting for a dramatic sign to change course — commit to what pulls you and let the decision reveal itself through action.

Turn “You Can’t” Into Rocket Fuel 

Cole was the only woman among 16 competitors in her race, and she says she was used to being underestimated. She traces it back to being a stubborn kid who snuck out her bedroom window when told no. “It didn’t really feel that much different when someone in my line of work would tell me, ‘No, you’re too small or you’re too that,'” she said. “And I’m like, okay, watch me. Let’s see.” That defiance carried her through years of being counted out in a male-dominated sport.
Takeaway: Treat people’s doubts as a dare, not a verdict.

Rip Open the Scar Tissue Instead of Letting It Fester 

Cole has been insulted to her face, in front of dozens of people, mid-race. When she asked one critic if there was something she could do differently, he simply said, “No.” Rather than avoid the sting of moments like that, she leans into it. “I try to never forget it,” she said. “I kind of take that type of wound and I just break it open… we’re just gonna keep ripping it apart until it stops hurting.”
Takeaway: Don’t bury your worst criticism — revisit it deliberately until it loses its power over you.

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Toughness Is a Choice You Make in the Worst Moment 

One month into her four-month race, Cole was flung across her boat and cracked ribs. Her instinct wasn’t to call for help or post about it — it was to protect her competitive position. “No matter what, I was like, we are racing,” she said. “I’m not here just to play around.” Her team waited days before sharing what happened, choosing timing over transparency.
Takeaway: When something goes wrong in your business, give yourself permission to stabilize privately before you decide what — and when — to share publicly.

Boredom Is a Choice — Choose Presence Instead 

With no team, no distractions, and months of solitude, Cole says the mental game mattered more than any physical training. “There’s really only two options that can really happen here,” she said of the isolation. “You journal a lot, and you kind of let your mind wander in this really beautiful presentness, or it makes you go mentally insane…And I chose the peaceful side.” She started calling the open ocean “my television” — watching clouds and birds instead of scrolling a screen.
Takeaway: Build a small daily ritual — journaling, a walk, simply noticing your surroundings — to keep your mind steady during the long grinds.

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Learn More

Follow Cole’s journey and her new team on Instagram, and track her races with. Her memoir, First Light: Sailing Solo but Not Alone, is out now — or wherever books are sold.

Want more on the themes from this episode? Check out these popular 91³ÉÈË.com reads:

• 5 Strategies for Overcoming Naysayers in Business
• Treat Your Career Like an Elite Athlete Treats Training
• 5 Steps to Stop Spinning Your Wheels and Start Following Your Passion

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About How Success Happens

Each episode of shares the inspiring, entertaining, and unexpected journeys that influential leaders in business, the arts, and sports traveled on their way to becoming household names. It’s a reminder that behind every big-time career, there is a person who persisted in the face of self-doubt, failure, and anything else that got thrown in their way.