Keep after that guy in front of you
For too many sailors, the upwind leg is a chance to get buried by failing to attack or by failing to defend. Think about this one:
A boat well to weather of you (and slightly back on your hip) experiences a favorable windshift. What do you do? Howie Hamlin, world champion in the 505 dinghy, 18-foot skiff, and, as of 2006, the International 14, says: “In that case you have to tack. I learned this from Jon Andron a long time ago, and I see the evidence around me all the time on the racecourse, but I’ve never heard anyone else talk about it.”
Here are two ways this can play out.
The boat above you (A) gets a lift, and you (B) carry on without tacking. Your opponent pulls farther ahead of you because he’s inside the lift.
The boat above you (A) gets a lift, and you (B) tack. Relative to your opponent’s hypothetical opposite-tack heading, you are now lifted and therefore sailing the best course available. And you’re sailing toward the new breeze. No, you’re not killing the other guy, but you were already behind. Think of this as a defensive move that positions you for whatever comes next. Perhaps he will get headed back down to his original course, but if he holds there or gets lifted further, you’ll be with him, and he won’t have a private breeze.
Based on these examples, in this situation tacking is a no-brainer. It’s key, however, to have your boathandling dialed in so that you can concentrate on playing the game and react instantly.