Whenever a newcomer comes to town I usher him or her to our priceless waterfront and we talk sailing. If I see even a flicker of curiosity, I suggest sailing lessons. Our town benefits greatly from one of sailing’s best schools; a community sailing center offering inexpensive lessons to all ages, and if you pass a skills test, shared boats for graduates to sail on at their leisure.

The classes (and the certificates earned in them) are organized logically by weather condition. Newbies earn a “light air rating” that enables them to skipper a boat in wind from 1 to 10 knots, and then, can advance with more coursework to sail in “medium air” (11 to 15 knots), and so on.

One such newcomer—a kid named Kendri from Kansas who came here for work and has signed up for lessons this summer after our shoreside chat—is also crewing on our sailboat during beer can racing. Kendri’s sensory overload is palpable. He’s standing in a firehose trying to figure out sailing’s basics, like getting around on a crowded deck while heeled, while learning an ancient lingo, while teaming with crewmates on a spinnaker takedown, all at once. And he wonders where his investment in sailing education might take him. Might he sail forever?

Kendri recently asked if there is a weather condition that would prevent us from racing. The sailing center had raised its “black flag,” which announces winds or a wind forecast over 21 knots, keeping even “heavy air” graduates off the water until more benign breeze returns. Kendri wondered, logically, if all sailors only sail in calm conditions.

It’s complicated. Experienced sailors generally know to stay ashore during a gale. But one of the benefits of experience is to have experienced a gale, that is, to have found oneself in a gale (perhaps more than one) and to deal with it; to emerge with all one’s limbs and with the crew and boat intact and ready for another adventure.

Most sailing schools, which understandably must ensure the well-being of their students first, are forced to put a box around the activity based on weather. The easiest way to keep people safe is to keep them away from danger. So student time on the water is limited by the whims of Mother Nature. This leaves a gap in heavy-weather sailing experience that can be hard to fill.

So Kendri and I called up YouTube footage of the 2021 Fastnet Race, which started upwind despite 25 to 30 knots of wind, an opposing tide creating chaotic waves, and had all the competitors reefed and in foulies as they pounded out of the Solent. This led to clips of Sydney-Hobart, Golden Globe and Volvo races. Kendri reflected aloud that through racing, he might learn to sail in many conditions.

There is a strong case to be made that sailing skills are learned in order to adapt to weather, not to avoid it. In a time when most humans seek comfort, many sailors seek connection. They want to learn to be in their world. An effective curriculum includes two vital elements: (1) In-depth preplanning—the study of proven techniques from old salts or mentors—and (2) boatloads of hands-on experience.

The best heavy weather sailors read a lot about it (you’ll find a tattered copy of the standout book “Heavy Weather Sailing” by K. Adlard Coles in every library), and then put themselves in a position to have to face the unexpected. They go racing; on whatever boat they have and wherever they are, over and over and over. (This experience can also be gained by committing to long cruises and passages; but for working stiffs like Kendri and me, evening and weekend racing is what is possible.)

My wife and lifelong crewmate likes to explain to newcomers like Kendri that a key reason to race a sailboat is that the race schedule is fixed long before forecasters can forecast conditions. “You get the weather you get,” she says.  Since you commit, you go, and as a result, you’ll inevitably sail both when the conditions are idyllic, and when they are not. You will experience rain and wind and waves and fog and darkness, because over time, these things are impossible to avoid. Within a few years, and through this panoply of experiences in the natural world, you become part of the rain and wind and waves and fog and darkness. And that makes life worth living.