Forgive me if I ramble...
Yet I lie awake at night and worry about bills, retirement, and everything else that accompanies money.
Money is one of the "funny" things in life. It is not really important, but try living with not enough of it, even if the that "not enough" is only a matter of perception and not realiity. Like you Monkeyleg, my daily driver is a beater, a '91 Civic bought shortly after college, getting my first professional job and midst of the Crazy Years in my life (so far). Its not pretty, nor is it fast, but it gets the job done.
From first perspective, I can see two issue. The "Jones" issue, and doing what you can't understand or ID. The first is really just a trap IMAO, the sweet siren song of consumerism and status that we've been feed all our lives. Sure the toys are nice to have, but that "status" issue is a hollow reward. In the end it does not matter how many possesions you accumulate, or even the quality of those possesions. If they fit your needs, and make YOU happy, who gives a frell what the neighbors think?
On doing what you can't understand and ID, then I think its time to re-evaluate what you are doing and change course. Maybe I'm the odd man out, but I've known all along what I want to do next, and have worked in that direction. In High School/College, the goal was Biotechnology. So I did that. Course work and a work study helped me secure a position with a bright and shiny company full of potential to change the world. Then it got old, and I took a different track in another feild that captured my interest. Now after a few years there, I'm starting the assess where I want to go next. This field is fun in some respects, not so in others. The question now, for me, is do I chase the long held dream of chasing spiders in the roofs of the forests, or follow the lure of power via politics?
Retirement? Time enough to rest in the grave. Retirement IMAO is a vanishing phenomena of a by gone era. I fully expect to work at something until its time for my buddies to prop my corpse up against a tree in the woods where it can frighten hikers and small children. The key is working at something *I* find worthwhile. If I can feed myself and my pets, then I'm content. Possessions don't really matter, nor really does status.
Maybe you're trapped in nostalgia for when you were "young" and the world was full of promise and opportunity. Now that those years are past, you want to return to them, and miss the joys to the now. Dancing until dawn, spending the night on the town is fun, but then, so is sitting about the camp fire after spending the afternoon killing soda cans with ones rifle.
Back in the late 1980's, I was probably the highest-paid staff photographer in the state. If my wife or I wanted something, we just bought it (after some discussion, of course). Without bragging too much, I made more money than most professionals I knew--doctors, lawyers, pharmacists, engineers
So what happened to the money you made??
But we went out, we went out to eat, we went out for drinks, and we had the most fun I'll ever know.
You still can. It's simply a matter of adjusting your sights from Ritz-Carlton to Ritz Bits. I live in california, so wherever you are has got to be cheaper. I go to the farmer's market every weekend; right now they're almost giving away peaches and nectarines, and the heirloom tomatoes are showing up. It's a week's good eating for under $10. you can still have your "date nights". Here, it's taquerias or sushi; elsewhere, that little ethnic place or a millenium-old greasy spoon or hamburger stand. Or grab the burgers and the peaches and a good four-dollar bottle of wine (no longer a contradiction, happily), get an old blanket, and have a picnic. The State Fair is pricey, but there are going to be harvest festivals every weekend until Thanksgiving.
The thing about having money is, it does make everything easier; by easier, I mean that you have to invest less of yourself into it. A new movie, Disneyworld, etc-someone else's labor replaces your own. Remember what it was that made those times as much fun as it was-friends, the love you had for each other (And that overwhelming sense of smug superiority that comes with youth probably enhanced it!). You can still have your friends, or new ones, and you still have each other, so you're really doing well.
If you save twenty dollars by not going out, but you sit and simmer and stress about it, you're still paying-it just isn't coming out of your wallet. it's coming out of your hide, and hers, and out of your sleep. That's a lot to pay for a night out.