In WordPress: How It Came To Be And Where It’s Heading Alex Moss interviews Matt Mullenweg and Mike Little, the two cofounders of WordPress. The whole interview is interesting, but their approach to technical debt caught my eye in particular:

We rewrite or refactor about 10 to 15% of WordPress in most releases, so that we can keep users getting updates and new features quickly, while doing the “ground up rebuild” incrementally in the background, fixing bugs and getting feedback as we go.

This is, in my experience, the best way to handle technical debt: pay down a little bit of it in every release. To steal a slide from my Product Management course, here’s my general rule of thumb (and of course there will be exceptions) for balancing a product roadmap: