I’m all about start-ups, business, cutting-edge technology, constant connectedness, etc., but every once in a while I need to get away from that. People get so caught up in their fast-paced lifestyles that they forget to sit back and appreciate the world in front of them. As Ferris Bueller so accurately put it, “Life moves pretty fast; if you don’t stop and look around once in a while, you could miss it!”

There are plenty of ways to get away from the chaos and you should never feel bound to one activity. I love to travel, write, explore, chat, think, but above all else, I love to sail. I come from a family of yachtsmen. My brother is a yacht designer and boatbuilder. My dad is a marine electrician and boatbuilder. His grandfather was a boatbuilder.

I was told to never lose sight of my heritage. And although my current path doesn’t strictly relate to yachting, I never want to lose those roots.

I love being able to leave all electronics and modern technology ashore and get out onto the water for an afternoon or evening of sailing. Nineteenth century seamen would have surely gotten a kick out of travelling in a car powered by a combustion engine, but I get an enormous kick out of travelling by wind power. It’s absolutely magical. In a world where it seems everything must have a battery or fuel of some sort, a sailboat’s only fuel is the wind (many sailboats larger than 20 feet have backup motors). There’s nothing like it, and it’s taught me so much more than I had ever expected.

Growing up I was hardly ever in a team setting. It’s my own fault; I didn’t put myself there. I didn’t want to be in those positions because I didn’t understand their value. I would always much rather stay in and take things apart or make stuff than “waste” my time on the soccer pitch or lacrosse field. I played on teams in middle school, but only because I had to. I also didn’t sail as much in those years. It was a tough time for a number of reasons.

When I got to high school, I was presented with a few options to meet the school’s athletic requirements. Among them was sailing. There was no choice. In the fall we sailed recreationally, but the spring marked the start of competitive sailing.

I was learning the intricacies of working with and sailing as a team rather than as an individual.

If you don’t know about team racing, it can be a bit confusing. I’ll try my best to explain it simply.

First, I’ll explain the opposite, “fleet racing,” so you have a base for comparison. Fleet racing is what you probably think of when you think of sailboats racing. Every sailboat is its own team, trying to be the fastest boat out there and the first one across the finish line. First across the finish line, and you win. Simple enough, right? OK.

Team racing is different. In the case of my high school sailing, each team sailed three boats at a time, and any given race contained two teams, thus one winner and one loser. In a race, you didn’t just want to be the fastest boat out there and leave everyone in your wake. If you’re the first across the finish line, but two boats from the opposing team and directly behind, you lose. Team racing relies heavily on the “gestalt” principle that an organized whole is perceived as greater than the sum of its parts. It’s not enough to be the fastest boat out there. You need to help the other two boats on your team to ensure you have a winning combination. “What in the hell is a winning combination?” You ask? It’s when the sum of the finishing positions of your team’s three boats is less than that of the other team’s boats. For example, if my team’s three boats finish in first, third, and fourth place, our sum is eight. The other team’s boats would then have finished in second, fifth, and sixth (last) place, so their sum is thirteen. Our sum is lower than theirs, and so we won that race. Make sense? Great! If not, read more.


So this was new to me. I had almost no idea what I was doing, and so I would just try to beat the other guys. However, because I’ve never really sailed for speed but rather for fun, it didn’t often work out. Over the next few years, I realized I didn’t have to be the fastest boat out there. I just had to outsmart the other guys! (I’m still not a stellar sailor by any means, but I did progress a lot over my high school career.) So I decided to learn the shit out of the racing rules of sailing (and also bluffing by calling a fake rule now and again).

Knowing these rules helped with communications on the water. My teammates and I had to work together, so we would tell each other where to go, where next to tack, so that we could trap the other team (without being protested) while we let our other boats get ahead. This teamwork experience has proven invaluable in my first job (sailing instructor) and is beginning to translate well in my current design and development job.

So sailing taught me to work with a team, but it taught me something else, much more crucial.

It taught me to pay attention and take risks.

Meets with other schools did not comprise just one match. We would always do best of three, five, or seven. This meant there was room for error in at least one of the races. I.e. you don’t have to win ‘em all.

There are so many variables on the water. You have to consistently be attuned to things like wind speed, direction, your current heading, the tides, currents, your and others’ crew weights, etc. If you’re paying attention, you know when things change, and that’s when you have a chance to get ahead. (Just like the stock market!)

Perhaps the most important to look out for in a race are wind shifts. Wind speed and direction are not constants, but after the start, your course is constant. Most races start upwind, meaning the start line is perpendicular to the direction of the wind, and the first leg is completed tacking back and forth to get to the windward mark. Upwind sailing is all about getting the most ideal angle to the wind so your sail (airfoil) is most efficient. It’s like a balancing act. Because you can’t sail directly upwind, you have to zig zag, which makes the distance longer as it’s not a straight line from where you are to where you need to be. You want the shortest course but you don’t want to sail to close to the wind because the sail as airfoil will be less efficient. Sailing farther from the wind (closer to a perpendicular angle) will be much faster, but the course will be much longer. So you have to find that sweet spot, which is not easy.

If you can tell that the wind direction shifted and the line from start to windward mark is no longer directly perpendicular to the wind direction, you can tell which tack (which of two zig zag directions) is favored. That way you will shorten your course and also have to change tacks (which slows you down) less frequently.

The example above is one of many ways to beat the other boats by understanding your environment. But as you might expect, the wind could shift back to where it was (or even continue past that point) while you think you’re getting ahead. And you’d be left in the dust.

So like the real world, it’s a game of risk and educated decision-making. I don’t make a decision or change, “just because.” I do so because I have an educated guess of the outcome that decision will most likely yield.

But sometimes, even your best guess could be completely wrong. Even the most experience sailors, with the best intuition, get it wrong. That’s inevitable. Like I mentioned earlier, you don’t have to (and you won’t) win ‘em all.

Try your hardest. Understand the game. Work with your peers. Pay attention to your surroundings. Think through decisions. But more important than any of that: have fun.