Software tends towards more technical debt. Without the discipline to reverse this, we won’t succeed in a rewrite either. – Johannes Brodwall

The article that he linked to is the “The Big Redesign In The Sky” from Uncle Bob. If you understand Norwegian also check out Karianne Berg’s really good lightning talk on the subject.

I myself really have to fight the urge to start over on a green field application. I know it takes too much time, and the result will be much worse than what I hope for when I start out. But what it really comes down to is wether you have the mechanisms in place that lets you incrementally improve your application. Without confidence in the changes made developers will avoid doing them, and your application will continue to rot. So what can you do to encourage changes? Some of my personal favourites:

• Unit tests
• Functional tests
• Web tests
• Database tests and migrations

All of these can also resist change if done badly, but you need to start somewhere. It’s really hard, but finding a path for incremental improvement is the best way.