Lessons from Sailing

I’ve been sailing for most of my life. I started out sailing sunfish on Lake Wequaquet on Cape Cod, later graduating to faster, more tender boats like the Sidewinder 16 that Melissa not-so-affectionately named Miss Manners. Eventually we bought our first keelboat – a 1974 O’Day 23 Sorcerer’s Apprentice – named for the many buckets of water we had to bail out of her. She was on the hard and had 2’ of water inside, so we knew that at the very least the hull was watertight. Eventually, in 2014 I graduated to my first cruising boat – our beloved 2002 Catalina 36 mkii Silent Sky, and finally our current rocket ship – our J/46 Windara.

Through all those boats and the different experiences I’ve had sailing them, working on them, reminiscing about the time spent with them as I’m doing now while a cold New Hampshire winter gives way to spring and soon another sailing season, there has been one constant. Every boat and every new challenge has taught me lessons that carry through to the non-sailing portion of my life.

Recently Melissa and I were discussing sailing as we drove to our nephews’ birthday party. As our conversations tend to go, we started out with a discussion of log keeping, veered off to how happy we were that we are installing a bilge alarm this offseason (hey, we’re sailors, odd things please us, ok?) and ended up with a discussion of our habits aboard.

A couple of months before, we had been aboard a friend’s catamaran, helping them sail it around Cape Hatteras late in the season. As is our habit when aboard someone else’s boat we learned the skipper’s preferences and followed them exactly rather than imposing our own. Aboard this boat the practice, as it is on many boats, is to write down position, speed, heading and in this case battery state of charge every hour. Some skippers add in true wind direction and barometric pressure (handy when trying to understand approaching weather), some add bilge checks, and some plot on a paper chart rather than just writing it down.

All these habits are intended to make for a safer, more enjoyable passage. We know that. We know that they matter, and yet we don’t do it as carefully as we should. Worse, the times we don’t do it as carefully as we should are those times when it matters the most – when the conditions are truly awful – because of course that is when things are the most likely to go wrong.

In our first season with Windara we had what has been hands down our worst passage to date. We left Beaufort, North Carolina on a Friday evening after work, bound for Charleston, South Carolina. A nasty low pressure system had been passing through the area and it was beginning to move on. With the wind out of the north and the conditions settling we figured we’d depart and by the time we were very far offshore, where the fetch was longer, it would be fine. The models we looked at (GFS, ECMWF, HRRR) all called for the wind to settle back to 20 out of the north in the next few hours and then slowly back down to 15 by the following morning. For us, on Windara, we consider that a fast, comfortable sail given that we would be broad reaching the whole way to Charleston.

Those were NOT the conditions we saw. Instead, the wind came back up and we saw 25 with frequent gusts to 35, steep 5-7 foot seas, and a 3-5 foot ground swell from another direction entirely. In short, it was awful. Melissa got thrown from her bunk at one point when we got hit by a particularly nasty wave from the wrong direction that crashed into the cockpit and soaked me at the helm. I couldn’t keep up with the habits we believe in following – log position, conditions etc. Why? I was OK on deck, but I knew that if I went below and tried to put pen to paper, I’d be done. Seasickness would get me before I got a line of information written out, so I didn’t do it. I stayed on deck and steered, where I knew I would be cold and wet, but also not seasick.

Fortunately, it was fine. Toward dawn the wind and seas did settle, nothing broke, and by morning we were comfortably reaching along in 3-5’ seas and 15-20 knots of breeze – some of our favorite conditions.

If something HAD broken though – say our GPS – we could have been in trouble quickly. We would have been 30 miles off the North Carolina coast, without a position, in ugly conditions. Somewhere to our west was Frying Pan shoal, and somewhere to our south was the Gulf Stream – neither one was something we’d want to encounter that night.

The problem that night was that I’d made a good habit hard to follow. I had gotten cocky and not taken my seasickness pill before we left. I rarely need one, so I didn’t take it. That night I did need it though, and that one bad decision had a cascade effect. We got lucky and nothing else went wrong so we didn’t pay a price for my mistake.

Contrast that to our first ever overnight passage – the night we left NYC headed south to Cape May, New Jersey. There was little wind and a large, long period swell rolling in from a tropical storm that had passed 36 hours before. We had been motoring all day due to the lack of wind, but Melissa did the battery check – and despite motoring all day the battery was showing 12.5 volts. We shut down non-essential electronics, including our navigation system and switched to traditional coastal pilotage with paper charts and a hand bearing compass. We recorded our positions and estimated speed – and it was fine.

We arrived at the Cape May breakwater the following morning exactly when we expected to and enjoyed a nice week in our first cruising destination. In that case the good habit – checking systems – was easy. Because of that a far worse potential outcome – losing electricity in the middle of the night and not having a position was avoided and working around the problem was no big deal.

I find this lesson – if you want a behavior to stick, make it a habit, and make it easy – holds in every other aspect of my life. I’ve used it professionally when leading software teams, personally to maintain fitness, and of course at sea.