Lessons from a Sailing Vacation Adventure
I just returned from sailing with friends for two weeks from St. Lucia and St. Vincent in the Caribbean. I am sharing our experience working together in the boat’s close quarters as an illustration of a team working together for a common goal and the essential requirements for team success and, yes, it was a wonderful vacation and adventure.
I race a J 130 sailboat from Marblehead, Massachusetts. Most of the six guys and gals on the boat had raced with me for regional regattas and long-distance races to Nova Scotia and Bermuda. When we are racing, I am the skipper. We are competing to win the race. We chartered a sailboat from St. Lucia to have a mid-winter vacation and adventure exploring a new part of the world. Having fun was our goal.
Delegate: Letting go was an essential first step for me. I had to let go of “work” and let go of controlling everything happening on the boat. A team member handled all the charter arrangements with Moorings, the boat charter company. Another team member made the onshore reservations. Others compiled the provisioning lists. Another member sketched out an island-hopping itinerary.
Let the Team Develop: If I am the skipper, team leader, or company CEO and have a rigid vision of where we are going and of each team member’s contribution, the team’s performance will be less than it could be. Each team member’s unique contribution enriched our experience far beyond what I could have planned by micromanaging the trip.
One member loved the boat and what was working and not working. Another became our scout, separating from the group to find the best bar or reprovisioning market. Cleanliness was the priority of another. I was often the one making arrangements for someone to cook us fish on the beach or get us into a resort’s beach-side restaurant.
Find Your Passion: Fishing from the boat while we were anchored was a team member’s passion. Another was our window to everything available online about each place we stopped and each super yacht and its owner that came into our anchorage. A team member’s passion for snorkeling and swimming with the colorful fish just below the surface of the water got us to the best snorkeling spots. I liked driving the boat even when we were in high wind and rough seas between St. Vincent and St. Lucia. I was thrilled and liberated as I drove the boat up and down the waves, letting go of everything else from my thinking.
Build Trust by Learning About Each Other: We already knew each other, but after one or two weeks together on a 40-foot sailboat you love or hate each other. We ate, drank, slept, swam, cooked, played cards, cleaned, and lived together. We shared our life stories and life plans. We came to care about each other as friends and partners we could trust. When we set the anchor to hold the boat for the night, we trusted the team members who set the anchor on the bottom to make sure it grabbed the bottom and did not let go overnight. The better I got to know each team member, the more I trusted them, and the more I trusted my understanding of where they would be during difficult times.
When you go on your next vacation, I am not suggesting that you prepare a written leadership and management plan. OK – a mom with kids has a plan for every day and vacation. Whether you are leading your company forward or going on vacation, I am encouraging you to find your passion, delegate, let your “team” develop, put down your cell phone, and learn about each other.
The ancestors of every resident we met had come to the islands as slaves. By listening to their stories, I learned about wonderful people living in a world very different from my own. And I am comfortable saying that our team came to love each other by the end of our adventure.
The Last Bar Before the Jungle
On Mayreau in the Tobago Keys, I met Richard Williams, owner of “The Last Bar Before the Jungle.” Drinks on the menu included a Pain Killer and Coconut Kiss. I hope he will promote my leadership guidebook, Create the Future, to his customers.
