Plan Your Sail and Sail Your Plan!

I’ve been sailing since 1969. Sailing has taught me much about leadership and life. An old sailing adage states, “Plan your sail and sail your plan.” Simplistically speaking, this means identify your goal(s), strategically determine how to accomplish same, then follow your planned strategy (or multiple contingency strategies) until you safely complete your mission. 

As a young man one of my favorite adventures was sailing Lake Michigan from Muskegon, Michigan to Chicago, Illinois aboard my seaworthy 27-foot sailboat. The adventure was always thrilling—and on some occasions harrowing. The 118 nautical mile trek could take more than 25 hours depending upon the Big Lake’s everchanging winds and waves. I typically hugged the Michigan-Indiana shoreline. Once weather forecasts ensured safety, I’d cross Southern Lake Michigan somewhere between Michigan City, Indiana and Chicago’s Burnham Harbor. Hugging the shoreline allowed me to head into any one of many safe ports should Lake Michigan kick up a raging tempest. However, sooner or later, I had to sail across 30 nautical miles of Southern Lake Michigan’s open water with no sight of land. It always was an eerie feeling when only water was visible on the horizon in all directions. In the middle of Lake Michigan there were no familiar landmarks or safe ports to easily access. Losing sight of land didn’t mean Michigan or Indiana had suddenly vaporized. The states never shifted or left their geographic boundaries. Instead, I simply was sailing beyond the sight of landfall for a couple hours and relied on my compass and sailing strategy until I saw my goal--the Chicago Skyline. Once I saw Chicago on the horizon, my sailing and navigation strategies were confirmed and I continued my heading toward my desired goal--Downtown Chicago’s Burnham Harbor smack dab between Soldier Stadium and Shedd’s Aquarium. And, that meant I was just a short rickshaw or cab ride to Navy Pier and Rush Street’s famous Tavern on Rush for prime rib.

Leaders, like wise sailors, are always seeking new goals that better their organizations. They ensure the vessels they pilot are seaworthy before embarking toward new goals. And, they do not abandon ship simply, because they enter uncharted and unfamiliar waters. Instead they know it is imperative to hold course and follow the strategic plans they and their teams created to attain the new goals. They do not panic when familiar sights disappear. Leaders fight the urge to return to the familiar when their teams fear the unknown. Instead, good leaders instill confidence in their crews and they keep their eyes on the horizon while continually compensating for changing wind and wave conditions. They know if lake conditions truly threaten the safety of their vessels or crews they can always turn back—they have clear “B”, “C”, and “D” plans. Leaders know they always have options. They thoroughly and wisely plan their sail with multiple contingency options and then they sail their plans. 

Will there be unexpected challenges? Almost certainly there will! Every sailing adventure has them. However WHEN challenges happen, the wisest leaders don’t waste valuable time and energy worrying if they made the “right decisions”. Instead, they know they made the best decisions based upon available data at the time, and they simply move on! That is what wise leadership is about. Successfully trimming your sails to address everchanging conditions and following course to a safe and successful completion.

Happy Sailing!

Jerry