For the second time in my life this past summer, as part of a corporate schmoozing exercise, I was lured aboard one of the many 12 Meter yachts that sail out of Newport, Rhode Island. For the second time, I also made the mistake of raising my hand when the skipper asked if anyone aboard had any sailing experience.

These old 12s are beautiful vessels, and I’d be very happy to sail on one again. But next time I’d like to be one of those people chatting gaily in the cockpit while someone else does all the work.

In this case, aboard American Eagle, I was asked to manage the mainsheet. Having received numerous picayune instructions on how to handle said sheet and the winch that managed it—as though I had never before seen or touched such things—I then spent several hours enduring a withering critique of my performance.

My biggest sin was not constantly treating the sheet and winch as if they were always carrying tremendous loads. Instead, I foolishly relied on my four decades of experience and when asked to ease it would quickly flip off a wrap or two before doing so—only to receive my umpteenth lecture on how to properly take line wraps off a highly loaded winch.

Even worse, when sailing closehauled I had a tendency to want to crouch in a comfortable position facing the winch so I could easily manage it, with the sail in view, with one foot braced against the rail. Instead I was ordered to assume a very uncomfortable position with both feet braced to leeward, lying flat on deck where I could neither see the winch or sail, nor easily manage the sheet without twisting myself into knots.

Of course, I realized what was going on here. Our skipper likely deals with hundreds of guests every year and has no idea whether they are idiots or not, so to keep them safe he must assume they are. Hence the mortal fear of heavy winch loads. I also assume my absurd working position was calculated to both keep me from slipping overboard and to keep my head well away from the boom.

This was at least better than my previous outing on a 12, aboard Courageous, where no one seemed at all concerned about my head not getting hit by the boom. In this case, having foolishly raised my hand when the fatal question was asked, I was assigned to pick up the running backstays. An attractive high-school girl was assigned the job of casting off, so she and I had to trade positions each time we tacked or gybed.

This was an actual race in which a “Famous Male Sailing Celebrity” was steering our boat. The skipper, who was directly responsible for the boat, stressed to me beforehand that it was very important not to let the runners touch the mainsail.

“Keep them away from the sail!” he urged.

Assuming he was concerned about chafe, I duly swore to do this. Except, of course, this made it impossible to quickly bring the runner taut, as it had so much slack in it. Even worse, if you rose up over the winch while grinding to get the runner on faster, you usually got hit in the head with the boom, which on Courageous is extremely low.

So I got hit in the head many times and was consistently late getting the runner on. Meanwhile, Mr. Sailing Celebrity was shamelessly hitting on the high-school girl while steering, and all he had to say to me each time we tacked or gybed was, “Backstay’s late.”

Looking up, I finally realized this was very important, because the boat had no fixed backstay, so I decided I better ignore the rule about the runner not touching the sail, and everything went fine from then on.

As we were getting off the boat, the skipper shook my hand and remarked, “Glad to see you finally got the hang of the runners. The trick is to keep them as close to sail as possible.”

I swear I wanted to punch him. But I just smiled and said, “So, now you tell me.”

Charles J. Doane is SAIL’s Cruising Editor. He lives and sails (mostly) in New England

October 2015