In both life and in extreme pursuits, we always have two options when weighing decisions. We can look at what we lose, the possible negative affects of our actions, or we can look at that which we can gain.
On a fundamental level, when we look at the negative aspects of decisions, we box ourselves in. Every action has a negative consequence, or at least a possible negative outcome. If there isn't, it is not really a decision, it is just an action. People trap themselves by only considering the negative aspects of decisions. People will stay with partners because they don't want to hurt them, or they don't want to be lonely. People will stay in jobs because they have financial obligations, don't want to rustle the coop, or can't take a risk on the unknown.
We can't live like that.
Making decisions that involve risk do turn out poorly sometimes, it is not that things will always turn out in the best way, but the risks that we take typically teach us, and define the goals that we are going to be able to achieve. Applying to jobs is risky, applying to schools is risky, asking someone on a date is risky, running a waterfall, hitting a jump, presenting in front of colleagues, entering a race; the list is endless. Our fear of vulnerability cannot be the determining factor in what shapes us, otherwise we will be sheltered and possibly unhappy.