Seamanship Strategy: Planning for Uncertainty

September 16 was supposed to be the closing date on the sale of Icebear, our Swan 59. We’d had a contract in place since May with the buyer, a nonprofit that was set to purchase the boat along with the $40,000 entry fee in the retro round-the-world Ocean Globe Race (OGR), which we’d signed up for. Two weeks earlier I’d gotten wind that the deal might not close—raising money for a round-the-world race campaign is no easy feat—but until the 11th hour, I thought there was a chance it would happen. It didn’t.

I was in the U.K. then, and Icebear was in a marina only a few hundred yards from the shed where our new flagship Farr 65, Falken, is being refit. The sale of Icebear was to be symbolic and practical—a move from one era of 59 North to the next, and a way to help fund the increasingly expensive refit on the new boat. Instead, we were caught off guard and left with a major funding gap on Falken and a 59-foot boat that we now had to figure out what to do with.

In the big picture, living with uncertainty and learning how to mitigate against it is really the essence of good seamanship. The Icebear non-sale is a lesson in acknowledging the uncertain and a reminder to always be prepared for it.

Yet, uncertainty is weirdly counter to the notion of anticipation that I preach when it comes to offshore sailing. Anticipating the weather is probably the single most important aspect of sailing offshore; if you’re always ready for what’s to come over a 24-hour time window, then rarely will the unexpected happen. With anticipation as a foundational planning tool, you’ll be more likely to reef early, more likely to lash things down ahead of a forecast blow, more likely to be ready for a whole host of things over the horizon.

Uncertainty derails that anticipation. After all, there’s only so much planning and prep you can do to anticipate the future, which by nature is, of course, unpredictable.

The lesson is to plan for the uncertain. Think about the what-ifs. What if the forecast isn’t accurate? What if someone gets injured? What if, despite our preparation, we have a gear or systems failure? What if we miss a deadline or a weather window and are up against a time constraint?

In my confidence in always being prepared for a certain future, I fell prey to the reality of a decidedly uncertain future in the Icebear deal. I had planned and anticipated. We had a written contract in place since May. I had long email chains with the buyers about managing the OGR campaign and helping them spec a new mast and rigging ahead of the race. We had made marina reservations in the U.K. and blocked off calendar dates with the riggers. We had everything covered.

Icebear was set to sail her last passage from Sweden to the U.K. with our first-ever all-women’s crew, led by skipper Nikki Henderson and mates Emma Garschagen and my wife, Mia Karlsson. I had flights booked to meet them on arrival in the U.K., and four days later the deal was set to close.

Except I had forgotten that the future isn’t guaranteed. I didn’t plan for the uncertainty and broke a cardinal rule of seamanship—not having a backup plan.

We scrambled. I put together a skeleton crew for the delivery south. We’d leave the U.K. while the forecast was stable and sprint across Biscay and south to Portugal where we’d have options. We’d obviously continue to list the boat for sale, but we could also keep sailing her ourselves if we wanted to. Once south of Biscay the season extends considerably, and we’d be able to set off across the Atlantic any time. But once the U.K. fall sets in, it’s very difficult to escape it unscathed. Less than 48 hours after this new plan came together, we set sail from Gosport and headed south.

My friend and business partner, Nikki Henderson, likes to say that at sea, risk is “inversely proportional to flexibility”—meaning the more inflexible your plan becomes, the higher the risk you run in executing that plan.

Good seamanship requires that you learn how to anticipate the future and remove the uncertainty. Great seamanship requires you to admit that a certain future is impossible and to remain flexible.

Postscript: Icebear did sell in the end, very quickly. While we were at sea en route to Lisbon, a friend of a friend reached out and made us a lowball offer on the boat. With Falken in need of our full focus, we took it, and Icebear, as of September 26, is now in the hands of her new owner.

January/February 2023