The eighth of Dave Dellenbaugh's Top Ten Tactical Tips was "Evaluate Risk".
If you're considering making a move that you know to be high risk for high gain -- such as pulling off that perfect port tack pin end start or banging the corner -- then you need to evaluate whether the risk is worth it or not. If you are happy with your position in the race (or series) now, then it is probably not worth taking a big risk. Now is the time to sail conservatively and to consolidate your position. On the other hand if you have nothing to lose, why not roll the dice?
Do you follow this advice? What is the biggest risk you have taken in a sailboat race -- and was it worth it?
And here is the next tip.