I'm a sailor wannabe. Oh, I do sail, but I keep proving to myself that I haven't mastered sailing. I can raise the sails, tack the boat (turn it around), and in general, get the boat to take me to some place I wish to be. But I've done things like snap the mast in half because I forgot to attach the stabilizers before I started raising it. I yell at the boat for not listening to me when I'm frustrated. What I have learned in sailing is the need to plan—not just for the long-term events, but also for the things that will occur in the next few minutes.

Several years ago, I came up with a sail plan for an upcoming circumnavigation of the Chesapeake. It was to be my first extended sail, and I attacked it like a management project. I spent hours developing a very detailed plan as to exactly where I would be and when I would be there. I had latitudes and longitudes for each waypoint. I determined distances in miles and nautical miles. I knew not only to which ports I would sail, but also the "gunk holes" (small protected harbors) along the route that would provide shelter if the weather turned bad.

Once the sail plan was complete, I assembled all the things I figured I'd need on the trip: clothing, food, fuel, spare parts, reading material, and Jimmy Buffett CDs. This preparation took many hours and drove my wife (and a few friends) nuts while I went over every detail again and again. Finally, I announced I was ready for the "Big Sail."

The trip was to be a single-handed sail (one person per boat) with two boats participating. The other boat was manned by a sailor with 40 years of sailing experience. When I gave him a copy of the plan, he thanked me and walked away chuckling. I would soon understand why.

I believe it was General Eisenhower who, when asked about the plan for the D-Day invasion, said, "The plan is good until the first shot is fired." I found out what he meant an hour after we launched the boats in the Chesapeake. The wind had picked up, and as I was pulling into the slip for my first night on the water, the wind caught the bow, pushed it against the dock, and smashed my bow running lights. With all my planning, I did not have the spare parts needed to fix the lights. But I had determined where there were marine supply stores along the route and was able to replace the lights several days later.

The next morning, we set sail. I pulled out my sail plan, my GPS, and a chart and tried to sail to the first waypoint. Unfortunately, the wind was on the bow of the boat and sailboats do not sail into the wind. As a result, the plan would not work. The first shot had been fired. The planned sail was modified to meet the circumstances at hand.

For the next 22 days, we sailed about the Chesapeake following the spirit of the sail plan, which was now stored below, not used since the first day. We did stop at most of the ports of call I had planned to see, but wind direction and other factors forced me to rethink the plan I had made. When we finished the trip, we had sailed 350 nautical miles over 22 days and accomplished what we wanted to do.

Many people might think the hours spent developing the sail plan were wasted time. I don't. It's the planning that is critical, not the plan itself. Planning provides vast amounts of information that may never become part of the plan. That information yields alternatives once "the first shot is fired," functioning as a safety net when the plan fails. Although I didn't have to use them, I knew where to find gunk holes. Planning taught me in advance what to look for as I entered a harbor for the first time. I even learned the location of the only pay phone on Tangier Island. (Cell phones don't work out there, and I called my wife every night of the trip to tell her not to file a missing person report.)

I believe that planning, not the plan, is often the most important part of any adventure, project, or day-to-day management opportunity. Remember, it's usually too late to plan once the first shot is fired.