As stated in the book, the First Penguin award went to students who went out on a limb and failed! This came "from the notion that when penguins are about to jump into water that might contain predators, well, somebody's got to be the first penguin." So, even if there are failures, it brings experience. Experience is what you get when you didn't get what you wanted. And experience is often the most valuable thing you have to offer.

Chapter 39: Be the First Penguin, p. 149 - The Last Lecture (2008)