My twenty seconds of Google research was unable to uncover the origin of the 100 Rejection Letters idea, but I will say that I don't take credit for it.
Here's what it is: Writing and submitting work for publication is incredibly stressful. You're putting yourself out there to potentially be pooped on (in the form of rejection letters and not real poo-poo, hopefully), and that can create a pretty significant psychological hurdle. It does for me, anyway.
See, if I get one or two rejection letters for a piece, that can sometimes be enough to take all the wind out of my sails. I stop submitting, sometimes I even stop writing altogether for a time. I know, I'm a big baby. Even thinking about all the world famous authors who have dealt with much more rejection than I've faced doesn't help in those moments.
So instead of letting a rejection flatten me, I'm gonna gamify the sumbitch.
My goal is to acquire 100 rejections within a year. That means I have to keep writing and sending. And each rejection becomes a point in my favor, one more notch on the bedpost that is this unfortunate metaphor I've chosen.
And along the way, conceivably, I'll "fail" and accidentally get some acceptances, too. Whoops!
Anybody out there tried this? If so, has it been effective for you? Genuinely curious, since this is a new thing for me. Let me know in the comments.