I write sloppy code because, as Ward says, I become reluctant to improve it once it works. And if I never do that I will by definition rarely write truely expressive and elegant code. So by spending my time almost exclusively producing first draft code, I nurture the habit of writing crappy code.
Ward seems to have a lot of interesting (and inspiring) things to say about the philosophy of programming. I wish I worked at microsoft so he could be my mentor. Perhaps more videos from him might console me?