Book by Alain de Botton published in 2005
For some reason, I haven't been able to get my hands on a Kindle edition (Amazon doesn't seem to have it), so I finally bought the physical book since a friend of mine has been raving about it for years. This book is an extremely sensible historical exploration into the question: How did we become so tied up in status? Why do we make decisions that undermine our long-term happiness to elevate our status? Happiness is something like success / pretentions, so either, you try to succeed more, or you fight against your community and values to lower your pretentions. This book is more about how society has increased the number of pretentions--it's not necessarily practical guidance on how to reduce them yourself, but to raise your awareness as to how they have elevated themselves to this point. It reminds me of this Emerson quote: "It is easy in the world to live after the world's opinion; it is easy in solitude to live after our own, but the great man is he who amid the crowd keeps with perfect sweetness the independence of solitude."
I find it difficult to summarize, either because I didn't absorb the book well enough, or because the answer is so complicated that there is no simple answer. If this is a question that interests you, you should pick it up. I'll most likely re-read this soon in an attempt to absorb it better.