When customers start to leave because they hate the way things work, that's when the business bow downs to a refactor.
And if you've never clashed with your boss over ideological or philosophical issues (either productively or destructively), then I dare say you may not care very much about your work. (Or maybe, not far enough along in a career to have enough to say about it yet. I've been doing this for 18 years. I think that if you get to the point I got, where you care more about your work than your next paycheck... that that is a good thing.)
There were actually MANY times when I clashed productively with this guy. I respected him and he respected me. In fact I know that in the final battle we were both simply acting rationally. The directions were just completely at odds. And that is why I harbor no grudge or ill will towards that guy. Hell I'd probably have a beer with him still. I bet you that guy still respects me. It was just time to go.
I quit my last job because I could tell my boss had perverse incentives that he wouldn't admit to. I knew the codebase needed a refactor desperately and he insisted I work on something else (because he was leaving and didn't want to rock the boat). I can't work under those conditions. Turns out I was right... After I left, he announced he was leaving... right after his RSU's vested.