I think this concept extends even farther, to applications of all kinds: big, small, web, GUIs, console applications, you name it. I've often said that a well-designed system makes it easy to do the right things and annoying (but not impossible) to do the wrong things.
If we design our applications properly, our users should be inexorably drawn into the pit of success. Some may take longer than others, but they should all get there eventually.
If users aren't finding success on their own – or if they're not finding it within a reasonable amount of time – it's not their fault. It's our fault. We didn't make it easy enough for them to fall into the pit of success. Consider your project a Big Dig: your job is to constantly rearchitect your language, your API, or your application to make that pit of success ever deeper and wider.
