When you left Yale, did you ever imagine how sailing would change, from Pyewacket to PlayStation to Groupama? Can you talk about the evolution? What’s surprised you?
Out of Yale, in those days we were still navigating with celestial. I remember doing my first Admiral’s Cup in 1981, aboard Bill Martin’s Stars & Stripes—Bruce Nelson and Dave Ullman and a bunch of us were doing our first Admirals’ Cup, and it was a great experience because we all had something to prove—and a huge part of the navigator’s job was figuring out where the hell you were, and how do you find the mark. And doing the Fastnet in the fog with celestial and RDF…it was frightening.

Then, of course, with time, electronics became legal to use for position determination, and later, computers became legal. And since then, it’s just been a continuous trend to more and more technology. For me, I just got lucky in that I was working in technology anyway, and then I had this other interest in navigation, but it was more in the art and the lore of it. You know, the dead reckoning and the celestial, but then as sailing evolved and navigation changed, it grew into an area where I was already pretty strong on the technical side.

In the early phases, I was actually writing my own software to do the routing and to learn the polars and to compare performance, but as time has gone on Graham Wynn and Nick White and so forth have done a better job than I had. So now I only occasionally use the programs I originally wrote. I almost entirely use the off-the-shelf tools from Expedition or Tactiq or Deckman for Windows.

So much has happened in a relatively brief time.
Yeah. So much is different. But it’s interesting in that I think a lot of people misuse the tools, because they don’t insist on tinkering with them. A lot of people sort of buy the software, get the grib files, download it, get a route, and say, okay, we just follow that path. And you’re exactly halfway across the creek.

You have to understand questions like, “Okay, that’s the optimum route, but how much less optimum is this other route?” Here’s an example. It’s a little contrived, but let’s say you’re crossing an ocean, and it’s a dead beat. Now of course it doesn’t matter where you go. Now let’s imagine there’s a 1-degree shift in the grib file. So now the router is going to take you all the way to the corner to take advantage of that 1-degree shift. Now if you didn’t understand what was going on, you’d say, “Okay, I’ve loaded the grib file, I’ve paid all this money for these great programs, and this is the optimum route, so we’ll follow it. But if you understand what’s going on, you’d say, “There’s very steady wind here, the router’s going all the way to the corner for a 1-degree shift, we know that there are 15-degree oscillations in the ocean, there always are, so we know that we’re much better off to hit the shifts up the middle. This is nuts to get yourself hung all the way out there for a 1-degree shift.” So no sensible sailor would do that. But unless you knew why it went out there, you wouldn’t realize that that’s crazy.

In your approach to navigation, how much is art and how much is science?
You know, it’s probably like a lot of crafts. You know, you get really good tools, and you know how to use them right. What goes wrong a lot in navigation is that people don’t understand the tool well enough to know what it’s good at and what it’s not good at and where the pitfalls are. You’ve got to ask common-sense sailing questions: What’s it doing, why is it doing it, how important is it? Okay, I understand that. Now how much slower is it if I go up the middle? Ten minutes. Suddenly you’re looking at it a different way.

There’s some Transpacs that work that way. Where for some boats there’s quite a big trade-off in the middle, where you can be further north, you have fewer miles, there’s lighter air…or further south, with more miles, but heavier air. Okay, where are the competitors, what are the risks? But you have to look at it from an uncertainly standpoint. It’s kind of like economics. What are the costs? What are the probabilities? It’s a really fun problem.

And the cool thing about a Volvo or a Jules Vern is that there’s a lot to do. Every forecast you’re trying to figure out: What’s important here? What do I know? What do I not know? What are the risks? That’s what’s really fun about navigating—you’re constantly tangling with interesting problems.