ITT, Roger kicks the Planning Fallacy in the nads.
Now, if only I could get Filthy Assistant on board.

But that actually applies to just about anything, if you change the words around a little.
Joe wants to try doing stand up comedy.
He's inexperienced, and is reasonably sure he'll bomb, at least the first time out.
Joe psychs himself up to go out and make it happen, no matter what the audience does. Plans to do something exciting immediately afterward, to get rid of that awful feeling, so that he'll have the guts to try again.
Joe tries doing stand up comedy.