Lessons on Leadership and Life from My 600-Mile Caribbean Yacht Race with Skipper Nikki Henderson

Guest: Nikki Henderson, a world-class professional sailor. In 2018, Nikki became the youngest skipper to lead a team in the Clipper Round the World Yacht Race. At the age of 25, over the course of more than 40,000 miles of ocean racing, Nikki led a diverse team of mostly amateur sailors from 16 countries to an extraordinary second place finish. She's also skippered numerous transatlantic races and won the Race to Alaska.

In a Nutshell: How do you define your job as a leader?

Nikki Henderson says that what she does as a skipper is pull together disparate individuals, build them into high-performing amateur teams, and then compete in the most extreme sailing races in the world.

I experienced Nikki's leadership first hand a few weeks ago when I sailed with her in the Caribbean 600 as part of her amateur crew. This was a grueling 600-mile race around 11 Caribbean islands. Despite long odds, we ended up finishing third and celebrated on stage with our prize: a big bottle of rum.

On today's show, Nikki Henderson and I discuss making life transitions, paradoxes and polarities in leadership, and decision-making under pressure and uncertainty.