Reflections on an Endless Summer

A lifetime of sailing is a meaningful learning process. From "The Jobson Report" for our November/December 2009 issue

February 2, 2010

Gary Jobson 368

As I think about my sailing career, I now marvel how I was able to spend as many as 250 days on the water year after year. That routine stretched for nearly 30 years before it came to a grinding halt over the past few years as business and family commitments took a higher priority. With my children graduating from college and getting married, however, I decided to fill the summer of 2009 with sailing. And what a summer it was. Along the way, I took notes on the highs and lows I experienced on and off the water. From May through September,
there was a mountain of logistics, dozens of lessons learned (and re-learned), and plenty of laughter, jokes, and memories. Busy as it was, I wouldn’t have had it any other way.

Throughout the summer months, I regularly checked back into my logbooks to see what I was doing during a specific week years, and even decades, earlier. It made me realize that, when I was younger, I underappreciated the events surrounding me. But this year I was wide-eyed at everything. Perhaps age begets appreciation. For example, on the first morning of the 12 Metre World Championship in Newport, R.I., in September, onboard Freedom, I called for the entire crew to come back into the cockpit so we could pause and take a look around at 17 of these classic yachts tuning up for the first start. This was the largest fleet of 12s to ever sail on the same racecourse in the United States. To see such winning America’s Cup boats as Columbia, Weatherly, Intrepid, Courageous, and our own Freedom, sailing in perfect condition was heartwarming. There were Cup veterans on almost every boat, and I had to smile because winning races was still the priority for most of the competitors. There are few other sports in which a team averaging over 50 years of age can still be competitive at such a high level.

I have to admit that my skills at 59 are not as strong as they were at 25, or even 49. I suppose this is one of the twists of life with which all of us must come to terms. The difference for me today, however, is that losing is not the end of the world. In many ways, taking part is reward enough. Dr. Stuart Walker would most certainly consider this a rationalization for losing, but I don’t think so. Victory takes many forms. For example, I raced with a friend who had a hip replaced a few months earlier. We did not win the races, but he did a fine job steering, and we were energized by the experience. This in itself was a victory, as were our two second-place finishes.


In the Stamford Vineyard Race, an overnight distance race sailed in the Northeast over Labor Day weekend, my crew and I had an excellent seesaw battle with two identical boats in our class. Only 18 miles from the finish we were even with one and well ahead of the other. Then disaster struck, as the wind died for us. The two boats sailed right past us, about a mile away. It was a painful three hours waiting for new breeze to reach our windless sails. Years ago, I would’ve been going wild during the pass. This time, I simply laughed, thinking that I had been in their very spot many times over the years. It was a reminder that breaks eventually even out.

At our post-race crew meeting, I took full responsibility for the error of not getting into the new breeze. And then the next day, I sent an e-mail of congratulations to the rival skipper. He promptly forwarded my message to his crew. They appreciated the gesture, and deep down I felt good about the whole thing, which reinforced to me an important and often overlooked element of competitive sailing-basic sportsmanship. Besides, I bet we will have our own good fortune the next time the wind fades.

In August, during Nantucket Race Week, I recalled that, exactly 40 years earlier, I was planning to attend a rock concert in New York. That same weekend, the 420 Nationals were taking place on Barnegat Bay, my home waters. I clearly remember my father’s suggestion that I sail that weekend and not attend the concert. “Look, you can go to a concert any time,” he said, “but the 420 Nationals only come here once in a lifetime.” I took his advice, finished mid-fleet, and missed Woodstock.


In Nantucket, I accepted an offer to helm a classic wooden 12-Meter for a day of racing. A strong easterly breeze challenged these old boats. A leeward boat protested us for barging at the start. Yikes. It was the first protest for me in many years, and we went through the entire protest procedure. The other skipper said he’d taken a Dave Perry seminar the previous winter, during which Perry encouraged his attendees to always go through with protests because they are learning experiences. Be that as it may, fortunately for me, there were two video cameras recording the start, and the committee dismissed the protest. It reminded me to simply stay out of the protest room at all costs.

I raced my NYYC Swan 42 Mustang in eight events, and trust me, every regatta proved to be a learning experience in some form or another. I could fill a book with my observations, (see SW Sept. 2009 for a few). At the end of the season, however, I watched from the “sidelines” as I covered the New York Yacht Club Invitational Cup for ESPN. My view of this class went from the helm to 300 feet above the racecourse, hovering in a helicopter, filming the races. From this vantage point, I was able to see how the top boats used clear lanes to work their way into the top of the pack, something I will be sure to commit to memory next time I race.

I have to admit I got tired of sailing so many perfect, windward-leeward courses. It can be refreshing to race on courses that feature reaching legs and point-to-point legs, and I encourage race committees to experiment, listen to sailors, and mix in a few unexpected legs. This would most certainly keep the racing interesting for those of us who’ve been at it for a long time.


In my hometown of Annapolis, Md., Wednesday-night races are an important part of the summer. I steered a Farr 30 on a rare, blustery night. Two boats crossed us halfway up the four-mile beat. We continued on in the direction they’d been sailing, and presto! We were in the lead. Here, again, was a reminder that you can learn where to go during a race. I still wonder why the other boats let us off the hook.

I attended 15 Leukemia Cup fundraising regattas, which are going strong. On the weekend of Sept. 21, five events raised more than a million dollars. Even in these tough economic times, sailors continue to support a noble cause.

I presented at a number of regattas and spoke with many passionate sailors along the way-on both coasts and in between. The regatta that stands out most is the Lightning North American Championship in Sodus Bay, N.Y. Sailors from around the country, ranging in age from 10 to 85, participated. I had never been to Sodus Bay, on Lake Ontario, but it was a beautiful scene and the competition was first-rate. Olin Stephens, who designed the Lightning, would’ve been proud.


I made stops for speaking engagements in Chicago, Sheboygan, Wisc., San Francisco, Watch Hill and Newport, R.I., Cape Fear, N.C., Castine, Me., Marblehead and Nantucket, Mass., and even a Flying Dutchman regatta held in New York Harbor. I can report that sailing is vibrant in all these waterfront towns.

Throughout the summer, I endured many losses and a few wins. Out of 74 starts, I came away with only seven individual race wins and 16 top-three finishes. But I also finished last three times to balance the scorecard. And as I reflect on this summer of sailing, it dawns on me what little difference there is between winning and losing. It’s the process and the experience that count most.


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