69. I was invited to Necker Island in the British Virgin Islands to meet with a group of super-sharp, bootstrapping entrepreneurs. This island had lemurs and pink flamingos and a gift shop where I bought every one of Richard Branson’s memoirs. We swapped business stories, discussed how to save the coral reefs, and had fun too. Like the costume party where we dressed like something you would find at the bottom of the sea (I wore seaweed-green eye shadow on my lips).
One clear night, we split up into small groups for a midnight catamaran race under the stars. These were type-A personalities who took performance seriously. A race to this group meant only one thing: victory.
I was fumbling with my life jacket while my team dashed to the boat; our rivals were already flying along the rippled surface, leaving us in their wake. It was mayhem.
We found ourselves trying every angle to catch the wind while our competition was already at the bar drinking margaritas. We were alone out there. We stopped hustling. We looked up. There were a million stars piercing the sky, and one bright moon reflecting light off the dark sea and onto our faces, where the weight of defeat started to transform into something else. A stillness. The boat rocked gently with the waves, and everyone grew quiet. The only sound was the flapping of the sail against the mast. And then it hit us.
Not the mast. An idea: Maybe we were looking at winning all wrong.
Competition is one of the most powerful drivers, but sometimes you may need to chart a different course.
Sail your own race.