I was watching the Indian Wells semifinals today between Novak Djokovic (the number 3 male tennis player in the world, all of 20 years old) and the veteran, Rafa Nadal (the number 2 male tennis player in world, all of 21 years old). And the commentators were talking about how to deal with the pressure of being in the semifinals of a major tournament.

On the one hand, the sports psychologists always say that you should “play your game”. In other words, don’t worry so much about your opponent. Whether you win or lose is all in your hands. Under this approach, you should “go for your shots”, meaning that you shouldn’t be afraid to take calculated risks. If you play it safe, you’re always going to be in the defensive position, and you have to wait for your opponent to lose rather that playing to win. Be the master of your own destiny!

On the other hand, players like the Williams sisters always get criticized for playing too aggressively. They’re always going for their shots. So sometimes, when the stars are all aligned, they play absolutely brilliant tennis and no one can beat them. The opponent becomes irrelevant as they hit winner after winner after winner. But if their games are a little bit off, or if their competitors are a little bit better prepared to deal with their go-for-broke approach, then they commit a lot of errors, frustrated that their winners are largely ineffective. In other words, their attempts to be the masters of their own destiny become largely ineffectual, whether because of the circumstances or because of their opponents.

Sometimes as CEO of nuroa, our property search engine, I wonder which approach is better. Probably a combination of the two. But as in tennis, you only know if the approach was the correct one after the fact, once you see the instant replay. If the ball goes in, your brilliant! If the ball goes out too many times, even by a few millimeters, you’re a reckless loser. And this applies not only to overall strategy, but to employee decisions, to partnership proposals, to deciding which investors to take in your company.

But isn’t part of being in a start-up the joy of being in a high-risk, high-reward venture? What do calculated risks mean in such a context? Can a start-up really afford to play it safe? That being said, can it afford to be too aggressive?

Is there a happy medium, or is it just a matter of the post-mortem evaluation of your start-up after it’s hit the dead pool, or the IPO prospectus as you prepare for your IPO?

What do YOU think?