It's not a question of if, really.
When you don't succeed on the first try (maybe not every first try, but I bet you won't succeed on a lot of them), what will you then do? Pack it in? Give up? Tell yourself it wasn't meant to be? Hang it up? Walk away?
Carolyn Davidson failed when she first pitched her logo ideas. And now? She's the creator of one of the most iconic symbols in the world.
That's right: the folks at Nike didn't like the swoosh when they first saw it. And Carolyn could have thrown in the towel, told herself she wasn't any good, stopped designing altogether, and found another line of work.
But she kept at it.
When at first you don't succeed, keep going. There is no other plan.