Alex,

I've used this strategy before too. My way of dealing with it was to use the StickK.com website, and my brother as a referree.

I research procrastination and have tried this myself and I can offer a few thoughts.

1) Whatever time period you set with an incentive like that, it is almost certain that you will do all of your work in the last quarter of it. This is true whether you set the time period for a week or a year, and it is true for almost all people. I'm serious about that last part; I research procastination and one of the better moments of my life, and a great relief to me personally, was when I realized that the difference between procrastinators and non-procrastinators in a class of 150+ studenst was that the procrastinators did their essay on the day it was due, while the non-procrastinators did it the night before. Forgive yourself because you're not alone; people who try to finish their work weeks in advance are the exception, not the norm.

2) Incidentally, you can definitely refine your system to do a piece weekly by changing the enforcement period. If you risk $100 for not completing a story in a given week, you will write a story a week. I can vouch for this because I've done the same and it works like a charm.

3) Bad news: with enforced commitments like the one you're describing, people often take the easy way out by doing the bare minimum required in order to not lose the money. This doesn't happen all the time, but it happens often enough. You can use the $100 to trap yourself into doing a piece by being more specific about your commitment.

4) There are other, kinder ways to make yourself a disciplined writer that bolster your intrinsic motivation to write and also leave room for you to work on things like long pieces at your leisure.

Thing is, I've looked at your output and I'm not really sure you need any advice on these other ways. You're clearly writing a lot, so whatever you're doing probably works for getting writing done (although maybe not so much for avoiding deadline stress).

Also you care about writing enough to trap yourself into it using $100, which puts you in a rare crowd.

Happy to compare notes on productivity, though, if you're interested. Just message or send an email.