One of the minor upsides of having to devote any brain-space to the Trump family is how vividly they demonstrate that an ultra-luxury lifestyle doesn’t lead to happiness. We’re all at least a little susceptible, I take it, to society’s message that celebrities’ lives are to be envied, leaving us feeling vaguely dissatisfied with our own. But I can state confidently there isn’t a shred of me that wants to swap existences with Donald, Ivanka, Don Jr or the others. In showing how easily the extremes of wealth, fame and power can coexist with the bored and angry restlessness they exude, they’re doing us a huge favour. There’s nothing like contemplating Trump in his bathrobe, distractedly watching Fox in a gold-encrusted Mar-a-Lago bedroom suite, to make you appreciate your cramped flat and non-celebrity life.

Then again, as the philosopher Todd May explained in a recent New York Times essay, this notion of wanting someone else’s life – even the life of some truly admirable, non-famous person – is exceedingly odd, once you think about it carefully. Taken literally, it would mean not only acquiring that person’s circumstances, but also surrendering your own. “My relationships with everyone – children, spouse, friends – and my whole history” would all need to be jettisoned, May writes. “I wouldn’t have undergone it. My loss would be that of the whole of my own experience.” Perhaps a few people have had lives so terrible they’d make that trade. But most of us don’t feel that way, even about the bad times – perhaps least of all about the bad times, which we tend to conclude are what made us who we are: “We want to have been there ourselves, even though it was not a joyous experience for us.” This, deep down, is the strangely self-hating implication of our culture of celebrity envy: not only that their gleaming lives would be fun, but that they’d be worth completely relinquishing our own for.

You might object that only a philosopher would take the idea of life-swapping literally. Obviously, when the rest of us say we’d like someone else’s life, we simply mean we’d like various things we don’t have, whether that’s things like money and fame, or things like stronger relationships and more fulfilling work. Yes, but even this poses a problem. Because where do those desires come from? From our unique personal histories, which have made us who we are. The very fact of your daydreaming about a radically different life is a product of your own.

The whole thing threatens to collapse into paradox: your view of someone else’s circumstances as more appealing arises from a perspective shaped entirely by your own interests and values. If you actually did have that person’s possessions, relationships and status, you’d be someone else. And who’s to say you’d share those interests and values? You’d probably just be envious of someone else. The grass is always greener at a distance. Which, come to think of it, is maybe why Trump seems to be spending his presidency on a never-ending tour of golf courses.

oliver.burkeman@theguardian.com