> A decade later you find that you don't just have one half-assed solution to rewrite, you have a decade's worth.
Whereas if you don't have a good sense of priorities, and you don't get your product out the door, a decade later your company's been dead for nine years.
Of course, but these are ends on the spectrum, it's important to find the happy medium.
One of the biggest downsides of taking on a lot of technical debt is that the cost tends to be indirect and diffuse. And that's the sort of thing that organizations find it easiest to ignore. It's only when the pain becomes acute and obvious that it tends to be addressed, but by then the cost of addressing it is often several orders of magnitude higher than it would have been if it was addressed at a more appropriate time. This can cause a severe stoppage of development velocity and has doomed a sizable number of major projects and products over the years.
Whereas if you don't have a good sense of priorities, and you don't get your product out the door, a decade later your company's been dead for nine years.