What can you learn from your greatest sporting moment?

Many people are asking*: What can the world learn from Race 3 of the 2001 Laser II Worlds in Pwllheli, Wales?

Thanks for reading Oscillations - a newsletter where I look for lessons in growth from all aspects of work & life, making them applicable to all areas of work & life. Why’s it called ‘oscillations’? I explain it here. 

🏆 In September 2001 - half a lifetime ago - a friend and I won race 3 in a 92-boat sailing world championship. We ended up finishing the event in 11th place. We were young and seen as upstart underdogs in the eyes of our peers, despite having notched some decent results as we trained. By the end of the event, we would be the only Irish crew to have won a race, even with some of Ireland’s top dinghy sailors among the fleet. It was small potatoes in the greater scheme of things, but that one race remains, to this day, my fondest sporting memory for many reasons. 

The race lasted all of 70 minutes, but is etched in my memory. We led from the first turn all the way to the finish. Turning around on the final leg to see a blaze of 91 fluttering, multicolored spinnakers fanned out in a slow chasing line behind us is something I’ll never forget.

⛵️ I had never mined this day for deeper meaning. In part because I’m a parent now, I am constantly searching for ways I might explain the world and how to navigate it, ways to give my children frameworks I never had to understand the world. I also like to use analogies and storytelling to make concepts more lucid in the workplace. So, what lessons could I extract from that one shining moment into my mediocre sporting life? How would I use big moments in my children’s lives to prepare them for even bigger moments down the road? What life lessons might that race have contained for a younger me, had I been present enough to see them?

The answer is: a lot. 

PLAN THE RACE, RACE THE PLAN

🌞 The day of the race was blisteringly hot - or at least as hot as Welsh summer gets – and incredibly still. Watercolor cloud reflections lay reversed on a mirror sea. The sailors in the fleet had sat ashore all day, boats rigged and ready, waiting for wind to fill in. Just when we thought the day was a write-off, a zephyr tickled the bay and we were sent out onto the water to get a quick race in.

We knew the organizers would hurry to anchor the turning marks to shape the racecourse and start the race before the breeze faded, so we wouldn’t have much time to do a practice sail up the first leg and still get back to the starting line before the start. We needed a smart but quick-and-dirty plan. We sailed a portion of the first leg, formed our opinions quickly, and prepared for the start.

⚓️ By the time the start countdown began, we had landed on a few things:

• We needed to break free and do our own thing immediately. The ability to sail our plan depended on it.

• We would live or die on our ability to gain and retain momentum on that first leg. Every decision would be made on that basis - did it improve or reduce our chances of sailing fast? 

• We reckoned that any gusts of slightly stronger breeze were all coming from the right side of the course - the side of the upwind leg closer to the land. So we wanted to get out there and find some of those to accelerate as much as possible.

• The pin end of the start line - the left side - was favored. What does that mean? In sailing, the fleet lines up to start along an imaginary start line between the mast of an anchored boat (the boat end) and an anchored buoy (the pin end). The line those points form is meant to be perfectly perpendicular to the wind, so that both ends are equidistant to the windward mark, your first objective, which lies directly upwind of the middle of the line – in theory (see the pic below). In reality, it’s rarely a perfect triangle. There’s always a favored, or ‘biased’ end that is further upwind and thus nearer to the windward mark, and that end of the line draws a crowd who are trying to get an early advantage. We were in luck, that crowd would be drawn away from where we wanted to be - we wanted to get to the right side of the course so we would start close to the boat end.

  

💥 When the starting gun went, we were nicely positioned at the boat end. Within the first 90 seconds, we had a clear lane to peel off towards the right-hand side of the course and sail in clear, undisturbed air, with not many boats around us. The crowd mostly went left. We were free.

🥵 We sailed fast, we stayed laser focused on momentum (I’ll talk about that in a later post), we didn’t make any unnecessary turns and found a few of those precious gusts off the land to keep us moving. We arrived at the first mark in first place - by a considerable margin. And we never lost first place after that. It was a dream race.

REAL-LIFE PARALLELS

🧐 Looking back on it, if I could take my younger self for a post-race walk and wax philosophical, what are the teachable moments from that first phase of the race? Let’s dig in.

🚦 In a big fleet – like in any competitive crowd or market - how well you position yourself at the start and during the first leg is (almost) everything. If you break out ahead of the pack early on, it’s easier to stay out. You gain first-mover advantage. Everyone else is playing catch-up, trying to get out from under you, sail around you, for the rest of the race. Assuming you’re heading the right direction, they’re likely to have to rely on outlier scenarios, luck or a big change in circumstances to overtake you.

What had we done to put ourselves in that position?

📝 We’d done just enough homework to come up with a quick-and-dirty plan. But it was a plan. In real-life terms, it was an MVP, if you like, a minimum viable plan. We had to be at the start line when the gun went off, so our research time was constrained. We did what we could to form a good first principles hypothesis with a few solid fundamentals to focus on, and then committed hard to executing on it. 

Looking back, I’d point this out to my young self: that there will be plenty of times where you have limited information with which to make a big decision or form a plan, just like on this upwind leg. You’ll have to decide quickly which bits of what you know you’re confident enough about to act on, then go do it. It might work out, it might not. But you’ll have tried and you’ll be able to defend your reasoning for doing so. Remember this moment. Don’t let yourself get paralyzed by analysis. Go with what you know. Act fast, but be ready to revise your thinking if things change.

💨 We knew we had one trait in common with the top tier - great straight-line speed. But we didn’t want to compete in a straight-line drag race in a crowded space, where our moves would be constrained by the positioning of the bulk of the competition, putting our straight-line speed and our ability to capitalize on it at greater risk and a lower premium. 

We wanted a monopoly on some aspect. 

🤌 Looking back, I’d point out to young me how PayPal founder Peter Thiel famously talks a lot about how competition is for losers, and how you really want to establish a monopoly, and seal off an advantage that others don’t have or can’t see. If you apply that at a micro level, why not seek to monopolize a series of smaller factors? It doesn’t have to be an entire market. Monopolize a channel. Monopolize a small network. Monopolize a discount arrangement. But do find SOMETHING that you can exploit to a greater advantage than anyone else, and use it to tilt the scales in your favor, even if only for a time. Press that advantage while you have it.

🔀 We reckoned that being among the faster boats in the fleet, we should monopolize that right side of the course and whatever gains lay there, at least until others realized and headed across to join us. 

The conservative, tried-and-tested play off the start line was to start at the empirically advantageous end - the end of the line closer to the windward mark. It was the no-brainer. It’s what everyone almost always does. On this day, it meant less distance to sail in what would already be a short race. The gain was immediate. But it was over-subscribed. Only a small few would actually eke out the benefit. 

🎲 Our option was riskier but the gains compounded if it paid off. We sacrificed the shorter-distance up-front advantage at the pin end in favor of giving ourselves freedom to manouever. We would be seeking less certain gains but in a much less crowded part of the racecourse. If the gains materialized, we’d be one of the few there to capitalize on them. We’d have a little more distance to sail but a much higher likelihood that we’d be able to sail faster the whole time - if we’d judged the conditions correctly (we had). With fewer competitors to dodge, we were masters of our own destiny. Nobody was there to force us to correct course, robbing us of momentum. We retained full focus. It’s as if we were sailing a completely different set of circumstances, and yet, the same options were available to everyone. Most just went after the obvious thing first. 

🐶 We had one more thing going for us. We were disruptors, underdogs. Nobody was watching us as a signal of where to go, they had all written us off as a major competitive force. The group that all went left early were likely to focus on each other, benchmark against each other. We could operate with minimal scrutiny, which gave us even more freedom. If you’re familiar with disruption theory, this is almost a perfect analogy. Challenger brand goes after opportunities that incumbents see as lesser, incumbents don’t recognize challenger as a threat and don’t defend against it, challenger finds traction, and sails past incumbents who end up chasing the challenger who’s now in an enviable position. In sailing we call that gap ‘gaining separation’. You are sailing in clear, undisturbed air. 

We now had a win under our belt, but it felt like many still dismissed it as a fluke, which can often happen on light days. So while the fleet may have been a little warier of us, we retained our underdog nature even after the win. Fine by us. We’d finished second at the Irish nationals earlier in the year, trained hard on all the basics and knew we made the smart calls. 

🤓 Looking back, I’d point out to young me how nervous I had been in my teens about not following the herd, how I felt that you always had to be doing the same thing as everyone else. I was terrified of standing out, not fitting in. But it turns out that while breaking free and doing your own thing seems riskier, as long as you know why you’re doing it, and you believe it’s of value, you have a better shot of coming out ahead, and enjoying yourself in the process. And if you do hit your goals without the herd around you, nobody can claim any part of that. The confidence it gives you has a compounding effect. Maybe some people write your behavior off as anomalous, but screw them. You’ll know that you did something that felt right and turned out right. And over time, people will recognize it.

Another point is that if you choose to be part of the herd, there’s no personal space in there, no room to manouever or deviate from the direction of movement. Once you’re in the middle, it’s harder and harder to break away. You either elbow your way to the front, or fall out the back. If you make conscious call to zag away from the herd at the start, the eyes aren’t on you. You are free. Win or lose, you’re doing things on your own terms.

Why did so few of the top tier follow our plan? Why did we have the freedom to end up so far ahead that afternoon? I honestly can’t say, with complete certainty. I know we set ourselves up well, and made very few mistakes. I know we sailed with absolute focus and concentration. And I know it changed the way I sailed forever.

*Many people are not asking