https://www.youtube.com/watch?v=XakfJ2spb3w
tl;dw: Technical debt is equivalent to the interest you are paying on it, where interest == pain. Some debt is planned and low interest, like a mortgage. Other debt is unplanned and high interest, like a credit card or payday loan. Sometimes that interest allows you to get larger returns. For example, if you could take out a loan at 3% in order to invest at 8% over the life of the loan, that's a pretty good deal, as long as you can pay it down. but, if you let that interest get out of control, if you don't pay down the principal, then it becomes more painful.