Happy New Year, everyone!
In the past few months I've been thinking several thoughts that all seem to point in the same direction:
1) People who live in developed Western countries usually make and spend much more money than people in poorer countries, but aren't that much happier. It feels like we're overpaying for happiness, spending too much money to get a single bit of enjoyment.
2) When you get enjoyment from something, the association between "that thing" and "pleasure" in your mind gets stronger, but at the same time it becomes less sensitive and requires more stimulus. For example if you like sweet food, you can get into a cycle of eating more and more food that's sweeter and sweeter. But the guy next door, who's eating much less and periodically fasting to keep the association fresh, is actually getting more pleasure from food than you are! The same thing happens when you learn to deeply appreciate certain kinds of art, and then notice that the folks who enjoy "low" art are visibly having more fun.
3) People sometimes get unrealistic dreams and endlessly chase them, like trying to "make it big" in writing or sports, because they randomly got rewarded for it at an early age. I wrote a post about that.
I'm not offering any easy answers here. But it seems like too many people get locked in loops where they spend more and more effort to get less and less happiness. The most obvious examples are drug addiction and video gaming, but also "one-itis" in dating, overeating, being a connoisseur of anything, striving for popular success, all these things follow the same pattern. You're just chasing after some Skinner-box thing that you think you "love", but it doesn't love you back.
Sooo... if you like eating, give yourself a break every once in a while? If you like comfort, maybe get a cold shower sometimes? Might be a good idea to make yourself the kind of person that can get happiness cheaply.
Sorry if this post is not up to LW standards, I typed it really quickly as it came to my mind.
I feel like that is a really short-term version of what the OP is talking about, but yes, it applies. Same in other areas: playing any given video game for too long at a time, sometimes even reading a good book for too long, even spending too much time doing the same exotic/unusual thing. The amount of time it takes to get adapted and the level your happiness adapts to may differ from scenario to scenario, but it does happen. I try to remember to switch activities every few hours even when I'm still enjoying myself, unless I'm enjoying myself at least as much as I was earlier.