One of the most difficult decisions for a captain and crew to make in the sport of sailing is when to call it quits. There are many reasons to pull out of a race: no wind, too much wind, illness, and damage to the boat among them. And yet in more than 35 years of racing I had never withdrawn from a distance race until the Chicago Yacht Club’s 109th Race to Mackinac in July.

During my flight to Chicago, I reviewed the forecast and attempted to derive from it a strategy for how best to route up Lake Michigan. It was a rather daunting forecast. If our predictors were correct, Mother Nature would dish up more than 360 degrees worth of wind shifts (worsening for our boat with each degree of change) and velocities ranging from 10 up to 30 and then back down to zero.

We embarked under Code Zero and full main in about 10 knots of wind – a great way to start a 333 mile race. During the next several hours we enjoyed champagne conditions and spirits were high. Our competition was in check and although we weren’t leading, we felt comfortable with our position and the prospect of more wind from a favorable direction for at least a while. As we hoped, the wind began to back around and allowed us to eventually get into our big A2 spinnaker in about 15 knots of wind. We were passing boats – lots of ‘em. Perfect.

Another first time experience for me came during the early evening hours. While I have been in my fair share of nasty squalls, each of them had given indicators that they were approaching. This one didn’t. We were treated to a spectacular lightning show on the distant horizon, but were gaining bearing on the cell that was producing it, so we felt pretty good about staying our course and avoiding major weather. Under clear skies the wind shifted nearly 180 degrees and increased to 38 knots nearly instantly, knocking us over for more than a minute as it built to 50. During that time we were able to snuff the spinnaker, drop it, and get back underway with a J3 and reefed mainsail. This unexpected blast (which we would later find out was a heat burst) signaled the change we were dreading, as the conditions were now dead upwind and in 25 knots of wind. In the next few hours, the sea state changed from calm to very choppy with short-period 3-, 4- and 5-footers – uncomfortable and slow for our boat, but certainly manageable. Two other boats were not so lucky. One of them – a trimaran – flipped over and turned turtle and another experienced a man overboard situation. In both cases, crews were recovered safe and unharmed.

Throughout the night we made adjustments to sails and tacked our way up the Michigan coast. The next morning, the sea state continued to build and the boat pounded away. Just before our watch change, we could hear one of our crewmembers getting seasick, a sound that no sailor ever wishes to hear. While our sick crewmember is a hardy chap and would have continued the race, it was an added situation we now had to closely monitor.

During an early afternoon watch change, the topic of retiring from the race came up. With the boat’s owner away on business, it was decided that for a trio of reasons it was prudent to call it quits. The first was, of course, our crewmate’s wellbeing; the second the health of the boat; and the third the questionable forecast. Turning the corner to sail fast downwind is usually a feeling of elation, although this time it felt a rather uneasy. While I enjoy surfing along at 18 knots, doing so away from the finish line left me with a sense of failure. My competitive spirit wouldn’t let it go.

It’s amazing, however, what a nice cigar, a flat deck and some downwind time for reflection will do for a certain sailor. As the sting of defeat wafted away with each puff of my Ashton White Label, I became more comfortable and accepting of our decision. We pushed the boat, we pushed ourselves and we pushed our timetable to a reasonable limit. I then thought of circumstances in the past when the decision sat with me to bail on a race and I didn’t, at times leading to a TLE or breakage. I’d failed to use those as learning experiences. I think that settling into the decision of retiring was ultimately what I needed in order to learn that it’s OK and — when it comes to crew wellbeing — the obvious choice.

At the end of the day nearly 90 boats retired from the race. What a roller coaster ride this event turned out to be (both literally and figuratively). On the last leg of my Chicago Mac journey, I thought of all of the modes of transportation I’d employed: car, plane, car, boat, car, plane, horse and carriage, plane, car, plane, car. On the final plane ride home, as I wrote this, I recalled a quote from Robert E. Lee I heard long ago; “We must expect reverses, even defeats. They are sent to teach us wisdom and prudence, to call forth greater energies, and to prevent our falling into greater disasters.”

Be safe out there, and remember sometimes your nearest exit may be behind you!

See you on the water.

Chris Gill

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