I think there's also a strong element where things we've learned from experience are often hard to articulate in a way that adequately counters "But this time it's different!".
I know I didn't really learn the value of experience until a few years into my first full-time job, where I had a boss who was extremely smart, but not the best of communicators. There were quite a few conversations that ended with comments like "you know, in the time you've spent arguing with me about this, you could have implemented it the way I told you to".
However, despite that, I eventually came to really respect his judgement, because I worked for him long enough that there were multiple occasions where he turned out to be right and I turned out to be wrong (independent of whether I'd listened or not in the first place).