Decisions, decisions
I have been thinking a lot about decision-making. Ultimately, this newsletter is mostly about frameworks for making decisions – looking back on how I could & should have learned more about decision-making from sailing and wondering why I didn’t make better decisions in life when all the analogies that should have guided me were right under my nose. So let’s go!
I spent time last summer sailing J80s with a great team in Dun Laoghaire. The racing was super tight, we were always near the top of the fleet and the vibe on board was highly competitive but calm - exactly how I like it.
A few people asked me about it and while I really loved it, I kept thinking about bad decisions I’d made, and the speed of decision-making.
Often in a sailboat race, you have a very slim window to make a decision and take your opportunity. You have to move fast before the moment passes, otherwise you miss the chance to slot into a lane, or gain an advantage on a windshift, or whatever. It requires the fast-twitch reactivity that probably makes a good day trader – the ability to be constantly synthesizing all the information that’s coming at you until a signal alerts you to an opportunity, at which point you pounce.
Initial margins from these decisions in a race are small but positive, and those small gains add up to allow you reap the important rewards, whereas failing to act compounds quickly.
In a J80 you have a crew of 4-5 people. In heavy airs, everyone but the helm might be sitting boots-out on the rail upwind. Every decision takes around five seconds to execute from the moment the decision is made. Helm makes the call, it’s communicated up the rail, crew swing legs in & quickly prepare for the tack, and you tack. Even with the quickest team, you lack a certain amount of agency to act immediately (unless you’re an absolutely reckless/merciless skipper), so the super-valuable hair-trigger moves you might want to make on instinct are slowed & dulled. Unless you’re way ahead of decision-making - which you can’t always be - you can miss lanes or opportunities and lose boatlengths.
The window for a lot of these decisions may be only ten seconds in total. If it takes you five seconds to execute on a decision then that narrows the de facto decision window down to five seconds. Take two seconds of that for pure reaction time and you’re talking about three seconds of available time to make the call. If you’re fully alert & fully informed 100% of the time - good for you. But if you’re a normal human and/or have to have a conversation about a decision - well, tough cheese.
Worse, missed decisions can often compound and force you into less and less advantageous positions that become increasingly to get out of. A two-boatlength loss compounds to become twenty boatlengths, and all of a sudden the race is lost.
I’ve spent most of my life sailing boats where you have two, maybe three people at most on board. The fewer crew, the quicker you can change course or react. I’ve always enjoyed that.
With sailing anything bigger, I naturally set it against that small-boat reactivity. And when I go deeper in that framework, I got to introspection, asking myself where that puts me in terms of being a decision-maker on land? Do I over-index toward reactive, seat-of-the-pants decision-making in life as well as in sailing, rather than considered, planned maneuvering? Where does that put me in terms of Daniel Kahneman’s System 1 vs System 2 thinker framework? Seems likely that I’m naturally more of a System 1 thinker – instinctive and emotional – rather than being an instinctive System 2 thinker – deliberate and logical. Am I a good System 1 thinker? Well, ask my shrink. Should it translate into how I select the organisations I work in? The groups I’m part of?
Sailing small boats is, obviously, a short-course, highly reactive thing. You have to get out front early, and react fast to stay there. There’s no real long game, the slate is wiped clean, to a certain extent, after every 90-minute race. That’s not to say there’s no room for System 2 thinking in small boat racing. Planning a race, having a strategy, that’s System 2 (For proof I can actually be that kind of thinker, see this earlier post). Being a good System 2 thinker gives you a lot more freedom to act in a System-1 way, which is good, because once the starting gun goes, it’s fast-twitch that wins races.
Offshore, however, slower, more deliberate decision-making is rewarded.
I have done a sum total of one offshore race in my time, but recently interviewed solo ocean racer Tom Dolan for The Currency. Offshore racing takes place in longer arcs - you’re making decisions based on entire weather systems, or entire stretches of ocean, not just an hour in your little patch. Decision-making is at a vastly more macro scale, and more System 2 as a result.
For Tom, when he’s racing three-day legs of the Solitaire du Figaro, he only ever sleeps in 20-minute bursts, and that has an additional impact on how he makes decisions. Because of extreme sleep deprivation, Tom has a process for how to approach decision-making, that often results in him simply shutting down decision-making entirely.
Everything comes down to making smarter decisions than the competition, so sleep becomes part of a process. Sailors have to manage their exhaustion diligently. Dolan sets two alarms to 20 minutes: one on a wristwatch, and a ‘wake the dead’ alarm inside the boat.
“If I wake up before the 20-minute alarm, I know all things are good and I’m managing my sleep well. I'll wake up, I have a checklist process so I’ll check for seaweed, check the competitors, check the sail settings. And then you’d go straight back into another nap if you could. Ideally, you do like three or four in a row, then you get really good rest.
“If it's the watch that wakes me up, I know I'm starting to get a little bit tired. And if it's the thing that wakes the dead that wakes me, then I know, okay, I'm very, very tired. And then that goes into my decision-making process, which means I'm doing no big strategic decisions.”
In life we don’t often think about shutting down all decision-making, except for in the chaotic aftermath of major life events. When you’ve been bereaved, or gone through a major break-up, or had a major illness or injury, people will often tell you ‘Don’t make any big decisions’, which is exceedingly good advice that’s often hard to hear at the time. You’re not in the frame of mind for considered System 2 thinking. Even most good System 1 thinking will elude you, you’re reduced to the instinctual reactive things you can do without thinking, until you can actually think clearly again.
Some of the same principles from short-course racing also apply in life - good decisions made at the right time position you well, so your subsequent decisions are likely to require you select from a far better set of options. Delayed or bad decisions compound.
As always, I’m trying to pull apart my own processes to improve them, and prepare to pass on better advice to my kids. When I learned sailing, I was taught how to think about the thing I was doing - how to think about the tactics, how to think about the reactions.
But I was never encouraged to reflect on how and why I thought about things, or how and why I made the decisions that I made and how it might apply out of the boat. Now that I have more to look back on, I guess that’s what I’m doing. I’m thinking about the thinking, and what that says about how I think.
My first race after more than a decade off the water was with a good friend in a two-man boat. I was rusty when it came to many of the practical things. What came back fluently were the tactical things. And we won, so some of those decisions were obviously good ones. The best decision I made this summer was the simplest -getting back on the water.