It doesn't totally solve the problem, but one approach I sometimes try is to only move up the quality ladder (insofar as there actually is a linear quality scale, which is itself a bit of a simplification) when I can consistently tell the difference. It seems many people jump straight to the best they can afford, while I find it more enjoyable to slowly work my way up, so e.g. there's no point in jumping straight to world-class wines if you can't even tell much cheaper wines apart (it's surprisingly hard to get any good at blind taste testing).

With coffee I think the biggest low-hanging fruit is recently ground coffee: coffee that's brewed weeks after being ground is a lot different than freshly ground coffee, and it's fairly noticeable I think. You don't have to jump straight to hand-roasted small-batch coffees ground in a $1000 grinder minutes before you brew it in your high-end espresso machine.

Another more psychological issue is just separating different things for different purposes. I used to have trouble drinking "normal" beer after becoming something of a microbrew aficionado, but these days I'm a bit better at mentally distinguishing beer-for-beer-tasting from beer-for-drinking-with-a-burger. I just sort of consider them different beverages that happen to both be within the very broad class called "beer". I think I mentally class normal lagerish beer as a kind of soft drink that happens to have alcohol instead of a kind of beer--- I don't think "man this sucks, I could be drinking [fancy microbrew] instead", but "hmm do I want a lager or a coke today?".