Usopp waking hours were often a walking nightmare. The Grand Line—nay, the world!—was a terrifying place. If something wasn't trying to eat you it was trying to kill you just for the fun of it. There were sea monsters. There were pirates. The seas themselves seemed to want you dead.
And it was a dream come true.
For the self-aware coward, the Grand Line was a place to avoid like the plague, and not just because you might just catch the plague while visiting. But for the self-aware coward who wanted to someday be brave…the Grand Line was the place to be.
Usopp fought against evil fishmen and corrupt kings. He faced Warlords and gods and lived to tell the tale. Somewhere along the line, he got a little bit stronger, a little bit more sure in his abilities, until he began to delude himself into believing that the Straw Hats could take on the world.
Then Aokiji happened, and those delusions were torn away leaving behind the stark, naked truth. The Straw Hats were small fries. Weak. Lucky to be alive. And Usopp, poor, pathetic Usopp, was the weakest of them all.
For the first time since his mother died, Usopp's fears crept into his dreams unbidden. His visions of heroism and greatness crumbled into dust, leaving a bleak and grey picture of his future. Crippling self-doubt and negativity—usually buried so deep—bubbled to the surface, and Usopp realized that he could never, ever fulfill the expectations he had set for himself. He could never be like his dad.
This realization was devastating, but Usopp didn't have much time to dwell on it. Robin had tried to sacrifice herself for their sakes, and the Straw Hats were attempting to heroically save her. Usopp was no hero, never could be, but he couldn't let her die.
What Usopp didn't know at the time, what he wouldn't understand for several years, was that if he was to be a brave warrior of the sea, the lies he had built up for himself had to be destroyed. It was necessary for him to face his nightmares to overcome them and rebuild his dreams on what was real. Then, and only then, would he understand what courage truly was.
