What is it to fail? I don't think "not succeeding" counts - all that means is that the positive outcome, the goal, has not yet been realized. True failure comes only when giving up, cutting off the hope of success.
Youthful perspective on that is somewhat different, however. The expectation of grandiose potential reward, of scoring big, sets up an unrealistic high. If it's actually achieved, man is it a sweet experience and the surge is intoxicating. If, however, the expectation is met with something else, anything else, that massive tension ruptures into abysmal misery. A lot of this is neurochemical - the development of the social-emotional areas of the brain are in overdrive, and wreak havoc on the nearby motivational center (which is responsible for providing that expectation, the highs and lows that give drive).
That misery is something we quickly learn to avoid, even so far as to shy away from those opportunities which could lead to such pits of despair - even though they're the same ones that could provide that high.
I tried big. Early on I had written off the disapproval of my peers as meaningless, either a jealousy toward the audacious, lack of real understanding, or outright desire to do me harm. This is a hard thing to do - that social-emotional development defines its rules for societal conduct based on the collective reflection of those around us, but it also does this under the evolutionary expectation that the mirror-neurons of others are firing in our favor. That all too often isn't true, but the motivational urgency persists regardless.
I'll break here for a moment and say that almost without exception there are no places after high-school where people are out to get you. Usually they're simply in it for themselves, and ignorant of any destruction they may cause for others, and almost never openly malicious. For some reason, elementary through secondary education (and attendant ages) are the only places and times where animosity is elevated to outright capricious sabotage. It gets a lot better, honest.
Having dismissed the derision of others thus, I tried. I put myself on the line, seized at various moments, and often took the bold course. Did I succeed? Sometimes. Sometimes I pulled off amazing physical feats, sometimes I scored a dance with the hot chick (and not all of them were pity dances), and sometimes I face-planted in front of the crowd and fortified a reputation as an inept glory-hog; but I wasn't doing it for them.
Bottom line, a lack of success simply leaves you where you are before trying (minus whatever time and resources are invested in the attempt, maybe some bruises [physical and otherwise] - this is the calculable risk). Nothing is stopping you from trying again except that petty fear. Aim high - you cannot succeed spectacularly unless you're also willing to fail spectacularly (simple conservation of energy and momentum, so say physics).
The notches of experience are worth it. And besides, I can barely remember most of their names anymore.