For most people of a materialistic nature, “better” is always superior to great. This is a problem because there’s always something better. If there isn’t now, it’ll be out in six months. So if you ever want to be happy, focus on what you have that’s “great”, and forget about what could be an improvement over it.
Another way to look at it is to view happiness as being about relative changes, i.e. becoming more or less content with your situation. If you accept that view, it becomes important to maintain relatively modest and static expectations if you want to be happy. Then, as your material situation improves it will continue to pull away from your expectations, and you’ll become more happy. But if you let your expectations follow you as you progress, you’ll always be in search of the elusive duo — better and more.
Tom The Cool Guy
A good example of this is Tom the cool guy who has a beautiful wife, a nice C-Class Mercedes, and a 3-bedroom house in a good neighborhood. He’s quite happy with this situation because he’s never had these things before. But now he’s getting a promotion and a whole lot more money. He decides to move to the “really” nice neighborhood.
Suddenly, all the wives are better looking — so he’s not as happy with his anymore. His C-Class Mercedes is now being laughed at by people as he drives by, and all the houses in this area are at least 4-bedrooms. Now his baseline has shifted; what he was happy with just two weeks ago is now sub-standard. That would have been fine if he wanted it to happen, but the odds are that it was completely subconscious.
As a result, Tom won’t be ever be happy again until he “upgrades” somehow, and that is the never-ending road to an empty, shallow existence. He’ll always be looking at the houses up the hill — pining for them. He’ll get a 5-Series BMW and hate it within a month because some guy up the street (with a prettier wife) has a 7-Series.
I think the trick to capturing “enough” is to not let it change without your permission. Enough should be relatively static, and should only change after a long, hard internal debate. This is important because if enough is less than your reality then you tend to be happy, but as soon as it creeps up above reality you have problems. Don’t let it creep.