Yes doing shit on top of shit will be paid later, but sometimes, maybe that's fine to pay later while you are scrambling to make money in the first place ?
It takes time for well maintained project to detoriate bad end enough for debt to impact business.
Even when it does , both the biz and new tech leaders are likely to refuse to acknowledge debt is important factor or blame it on you or start a rewrite without understanding what is going wrong to build on top of some shiny new tech everyone wants on their resume.
It's also possible to be both meticulous and flexible. Sometimes when I've gotten that "can we worry about it later" question, I'll tell them yes. If we have a big external deadline or something, I'm happy to treat tech debt like a high-interest credit card. We run up the bill in an emergency, and then as soon as the emergency's over, we pay off the credit card.
My experience has been that, once in a while, even this is not enough. You might just get accused of being a perfectionist or being overly meticulous about things that don't matter, and why can't we just do it the easy way and worry about it later?
Of course, if that does happen, it means that you are in a toxic work environment and you need to leave as soon as you can. But it does happen, and I have experienced it firsthand.