the plight of the american HENRY

Welcome to the upper middle class where you can't decide if you're tastefully well off or if you're broke. You know that you're not rich though. You're certainly not rich because you don't feel rich and you still have stress eczema on the inside of your elbows every time you look at your monthly credit card bill. You seem to have just enough pre-tax income to secretly think of it every once in a while with pride. You make the kind of money that your younger self would have thought was impressive, and yet you can never breathe easy. You can never take the vacations you want. You can't afford the private school that you worry you ought to be sending your kids to. You rent because you live in a big city in order to have that super high paying job. You're not super satisfied with the schools. Your whole family is squeezed into a two bedroom. Your problem is not that you want FU money. You just want breathe easy money. Okay? You just want berries at the farmers market money. Is this character and all their foils and sympathies with their $550,000 combined household income deserving of sympathy? I would argue they are. Consider the trap. To make the big income you need to live in the expensive city. To live in an expensive city you need to live in a tiny apartment. To live in a tiny apartment you need to buy tasteful minimalist furniture. You know, to survive. You work all the time. All the time. You're hyper available, yet you also intend to be the most present, the most active, the most patient, the most emotionally attuned parent. So you bundle up all your stress and where does that go? You're too virtuous to have any real outlets. Honey, I can't make it to Susan's piano recital. I need to stay late so I can get promoted and keep grinding on this PE deal. So we can afford private school for Susan, so that she too may one day go to Yale and work on PE deals. You pay absolutely the highest tax rate in the nation. It is undeniable that high earning W2s are like, propping up the tax system. But you're so busy and you're so stressed that you've had to accumulate a very expensive lifestyle. Nannies, takeout, home cleaners, and so now you can never quite make the numbers work. To take that big, terrifying, risky jump into your entrepreneurial dream that you think might bust you out of this upper middle income trap. It's a trap. It's a squeeze. It's a treadmill. No, it's a Peloton bike ride. Worse. You do absolutely everything the hardest possible way. You want a creative career, but also a profitable one. And to make both of those things happen, you have to be really, really excellent. You have to work really, really hard. You wanna be at work all the time, climbing the ladder, maybe even doing your own thing. But you also wanna be the most hyper present parent, which just means you never sleep. But you have to sleep because your Oura ring says you have to sleep. Otherwise you're going to die young. With all these excellences, your excellent taste, your excellent analytical ability, your excellent SAT score, you would have thought that you would have won for yourself by now a life of leisure. Yet you have not. It's the opposite. The whole world feels like a judgment. Your whole life is composed of judgmental numbers staring you down. And every moment feels like you're just hoping for the lottery win, that drawing down, that refresh. Once a month you turn to your spouse and you say, should we just move back to the Midwest? And if you're not saying that, you're saying, should we move to the Netherlands? You tell yourself you're too smart for the rat race. But yet that also means you're too smart to quit. Because you're good at this. You're good at all of it. So why haven't the rewards been greater? Why haven't your (you feel) comparably modest asks of the universe been answered? Come on, you're not asking for anything crazy. You just want a three bedroom townhouse. You just wanna be able to drive your beat up Volvo to a rundown farmhouse in Connecticut. The problem is, there's really only two ways out of the great upper middle class trap. The first is to radically not care. Genuinely not care. I mean, you give up on the violin lessons and the soccer lessons and the chess lessons and the Mandarin lessons. You send your kid to free local public school the system is going to give them. Or you don't care so hard that you don't have kids. Or to achieve genuine, transcendental excellence, to transcend the entire trap. But that is exactly what is so torturous. It is very, very torturous to be so proximate to transcendental well, transcendental good fortune. Was it virtue that made that 26 year old found that startup? And now you work for him. Or luck? Doesn't matter.