What really gives people meaning and happiness is a combination of four things: Control over what they're doing, progress in what they're pursuing, being connected with others, and being part of something they enjoy that's bigger than themselves.

At a party given by a billionaire on Shelter Island, Kurt Vonnegut informs his pal, Joseph Heller, that their host, a hedge fund manager, had made more money in a single day than Heller had earned from his wildly popular novel Catch-22 over its whole history. Heller responds, “Yes, but I have something he will never have … enough.” Enough. I was stunned by the simple eloquence of that word — stunned for two reasons: first, because I have been given so much in my own life and, second, because Joseph Heller couldn’t have been more accurate. For a critical element of our society, including many of the wealthiest and most powerful among us, there seems to be no limit today on what enough entails.

Someone driving a $100,000 car might be wealthy. But the only data point you have about their wealth is that they have $100,000 less than they did before they bought the car (or $100,000 more in debt). That's all you know about them.

We tend to judge wealth by what we see, because that's the (self-edit: only) information we have in front of us.

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Modern capitalism is a pro at two things: generating wealth and generating envy. Perhaps they go hand in hand; wanting to surpass your peers can be the fuel of hard work. But life isn’t any fun without a sense of enough. Happiness, as it’s said, is just results minus expectations.

The letter I wrote after my son was born said, “You might think you want an expensive car, a fancy watch, and a huge house. But I’m telling you, you don’t. What you want is respect and admiration from other people, and you think having expensive stuff will bring it. It almost never does — especially from the people you want to respect and admire you.” I learned that as a valet, when I began thinking about all the people driving up to the hotel in their Ferraris, watching me gawk. People must gawk everywhere they went, and I’m sure they loved it. I’m sure they felt admired. But did they know I did not care about them, or even notice them? Did they know I was only gawking at the car, and imagining myself in the driver’s seat? Did they buy a Ferrari thinking it would bring them admiration without realizing that I — and likely most others — who are impressed with the car didn’t actually give them, the driver, a moment’s thought? Does this same idea apply to those living in big homes? Almost certainly. Jewelry and clothes? Yep. My point here is not to abandon the pursuit of wealth. Or even fancy cars. I like both. It’s a subtle recognition that people generally aspire to be respected and admired by others, and using money to buy fancy things may bring less of it than you imagine. If respect and admiration are your goal, be careful how you seek it. Humility, kindness, and empathy will bring you more respect than horsepower ever will. We’re not done talking about Ferraris.

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Being swayed by people playing a different game can also throw off how you think you’re supposed to spend your money. So much consumer spending, particularly in developed countries, is socially driven: subtly influenced by people you admire, and done because you subtly want people to admire you. But while we can see how much money other people spend on cars, homes, clothes, and vacations, we don’t get to see their goals, worries, and aspirations. A young lawyer aiming to be a partner at a prestigious law firm might need to maintain an appearance that I, a writer who can work in sweatpants, have no need for. But when his purchases set my own expectations, I’m wandering down a path of potential disappointment because I’m spending the money without the career boost he’s getting. We might not even have different styles. We’re just playing a different game. It took me years to figure this out. A takeaway here is that few things matter more with money than understanding your own time horizon and not being persuaded by the actions and behaviors of people playing different games than you are.

It’s not whether you’re right or wrong that’s important,” George Soros once said, “but how much money you make when you’re right and how much you lose when you’re wrong.” You can be wrong half the time and still make a fortune.

Having a gap between what you can technically endure versus what’s emotionally possible is an overlooked version of room for error.