I did a LOT of road bike racing a while back. Out of a large starting group (often 60+), one person wins.* Being prepared helps -- you want your fitness dialed and your equipment in good shape. But then Shih Tzu happens, even if you have the equanimity of Lao Tzu. If you conserve energy at the right times and expend energy at the right times -- and luck goes your way -- and the right combination of people work collaboratively -- then you might win. Or flat. Or crash. (Or die, but that's pretty rare.)

In bike racing, winning feels really good, but I don't think people really do it for the winning, because if you dominate one category, _congratulations!_ now you get to compete against the next level, replete with additional helpings of pain, exertion, and whatever the opposite of mental acuity is.

* In contrast to many sports where one of the two participants is guaranteed to win.