Say there are two possible solutions to a problem: the first is quick but hacky; the second is preferable but would take longer to implement. You need to solve the problem fast, so you decide to get the hack in place as quickly as you can, planning to start work on the better solution afterwards. The trouble is, as soon as the problem is alleviated, it plummets down the to-do list. You're still planning to put in the better solution at some point, but it's hard to justify implementing it right now. Suddenly you find you've spent five years using the less-than-perfect solution, cursing it the while.
Does this sound familiar? I know it's happened more than once where I work. One colleague describes deliberately making a bad GUI so that it wouldn't be accidentally adopted long-term. Do you have a better strategy?