The most obvious way is to play Boomer at a high enough level that you usually lose. Similar to playing a person that is better than you, you are forced to raise your game (mentally and physically) to stand a chance of beating them. This might involve hitting the ball harder, hitting deeper or going for the lines, adopting new strategies, changing your grips; in general, getting out of your comfort zone. Anytime you do that, you are likely to make a lot more mistakes, otherwise you’d already be playing at that higher level. But if you don’t try, you won’t improve very fast. The great Ivan Lendl thought that there were benefits to playing people below, at and above your level. Playing people below your level lets you learn how to win (and also work on new strategies and improve weaknesses, like the chip and charge strategy to improve your volleys and overheads, for example). Playing people above your level lets you see how much harder (or more accurately, or consistently) you need to play to win a single point. And you can play people at your level to see how much out of your comfort zone is necessary to win. John McEnroe says that tennis is a cerebral sport and that you need to know yourself to play the best tennis. When you play a person you may have expectations of your level and their level and think that you may lose or win before you start. To give yourself the best chance of winning, you need to be able to adjust to your level THAT DAY and your opponents level THAT DAY. Against someone close to your level you probably don’t need to hit 4 winners to win a game. Many points are won on the opponents errors. You can only control your level, but since your opponent is usually another human that is also trying to control their level and each is trying to play their best tennis and win, it is no wonder there are so many ebbs and flows in a match. When one person is winning, the opponent is motivated to change their game otherwise they will predictably lose. The best mentally tough players know their abilities very well and don’t panic by trying to raise their game too much when they are losing. Each ball of each point of each game requires you to make a decision on how much risk you want to take. The right answer is very personal and depends on your abilities, the ball you’ve been given to hit, your opponent and a number of other factors. All these decisions have to be made very quickly and this requires putting yourself in these pressure situations to learn your best strategy. Part of winning is playing just good enough to beat the person, not necessarily strive to hit a winner every time. Boomer has no ego and will never choke. This gives you an excellent tool to judge your progress and set Boomer at whatever level you think will help you improve the most. You can track your progress as well by trying other grips, fitness training, strategies. Anytime you manage to beat Boomer at a higher level than you’ve done before; you know you’ve earned it. If you can consistently beat Boomer at this higher level, it is NOT luck; you have become a better player. This will translate into beating people you’re previously lost to. Incidentally, no one yet has beaten Boomer at its higher level, even in a tiebreaker. The closest was Ryler DeHeart, NCAA Division I indoor champion, who was up 6-4 in a tiebreaker, then ran out of gas and lost 6-8.