This is painful for me as a Rails dev because the real technical debt is always a lack of test coverage. Cleaning up cruft is great, except without tests I'm just going to break my application in the process (and probably not know it.) Without first defining the behavior of the application, there's a reduced incentive to refactor anything. In this way, there's effectively two layers to the technical debt.

This becomes a compounding problem, where the technical debt gets so great that it becomes more appealing to just keep pushing out features and dealing with the fallout. Everywhere I've worked, the code has ended up exactly this yucky. And yes I've contributed to it too. I just don't think that the idea of paying for someone to go back and make the code nicer with no tangible changes to the application's external behavior doesn't seem to resonate with my CTOs. Maybe I just need to find better places to work.