Each dwelling or retreat needs a manager who keeps tabs on the property and reports back to the mother ship. Last spring, the majordomo of my haunt in the desert reported to me that a pipe had burst under the floor of my pad there and half of the house was flooded. It is at those moments that you wonder why you bothered working like a madman all of those years: to buy a home on a golf course with plumbing that would make you insane? Was that it?

Then you have to worry about your cars. You have to have cars at every house and they have to be the right cars to express your status in life. These break too, and they have to be taken in to be fixed. If your wife’s best friend gets a better one than yours, you have to go shopping for a new car too.

This is not even counting worrying about insurance for all of these houses and cars and jewelry (oh, did I forget to mention jewelry?). Or insurance for your artwork. If you have money in the bank, you can’t just have posters anymore, the way you did in college. You need real art, real six-figure art, and it needs to be hung right—and if your wife’s friends say it isn’t clear to them that it’s a Lichtenstein, you have to have it hung again (and insured, or did I say that?). As I said, I am a homeless bum compared with the people in Greenwich, Connecticut, (many of whom’s hedge funds make way, way more than mine do—just so you know, not that I’m jealous) but even my lowly insurance file is a good six inches thick each year.

Yes, you’ll say, but at least you don’t have to live paycheck-to-paycheck, worrying about making your rent. That’s true. But if you have a good chunk of change in the market and it goes down 4 percent in a week, you have the sickening feeling that you have lost as much in that week as one of your houses cost. You also have the nauseating feeling that every quarter you are writing a check to the I.R.S. for 20 times what you earned when you first got out of school. Yup, every quarter.

And you have to worry about what happens if there’s a dollar crisis and the exchange rate becomes four to the euro, and a session with a Pilates instructor costs as much as a visit to a surgeon did just a few years ago, and the stock market loses 50 percent in a year. (The Nasdaq lost far more than that between 2000 and 2002.) You have to worry about what happens if some stock market banshee comes screaming out of hell to make you stop being rich. You can become a slave to that fear in a way you never imagined back when you were working your way up.

Then there is the endless parade of philanthropies that make their way into your life: your old schools, your wife’s old schools, your faith’s causes, your political party’s exigencies. Seals, school children, starving children, victims of disease, lovers of music—they all find you. And they are all deserving. Really. If they only want a check, you’re lucky. If they want to use your home for a fundraiser and want to bring in strangers to hear about some obscure problem in Botswana at excruciating length, you really start to long for the days when you were back in school with your dreams and your bong and not a dime in your pocket.

Don’t get me wrong. It’s nice to be able to buy pretty much anything you like. It’s nice to realize you have a little empire of homes stretching across the nation. But it sure ain’t like being a god, unless it’s a god of accounting and home maintenance and bookkeeping. Never mind. I’ll take it. I’m not complaining. Wait, yes I am.