The titular question was posed on Quora, and one rich person, who claims to have made $15M after selling a tech startup offers a surprisingly nuanced and insightful answer :
“Being rich is better than not being rich, but it’s not nearly as good as you imagine it is.”
Other rich responders were less enthusiastic. Another writes:
“Made $20M on second start-up. Finally, real f’you money. I feel no better. Yes, I bought a better house. I didn’t even bother to buy nicer cars. Who cares. I just bought some more jeans. Look, I am intellectually proud and gratified to have this money. But it didn’t buy my freedom, which I had from before. It didn’t improve the quality of my life.”
Informally, I’ve also had the chance to meet rich people. My sense from those encounters is that being rich is nice, but it’s hardly the panacea people make it to be. I doubt many of those rich people are significantly happier than they would be with only a moderate income. Some may even be less happy.
The research also sides with this intuition. Kahneman shares in this talk  that the relationship between money and happiness flattens at around $60,000 per year.
However, when I ask people who aren’t earning a lot of money about this, the responses are nearly universal. They would be ecstatic to have such wealth, and can’t comprehend why those spoiled, ungrateful rich people aren’t living in utopia.
I imagine even now many of you are rolling your eyes at even the mention of rich people complaining about being rich. But that’s exactly my point. Why are our intuitions so different from reality? If being fabulously rich is only a moderate boost to happiness, why don’t we see it that way, in advance?
Location Independence, Freedom and Money
Being rich is just one fantasy. You could replace the entire preceding introduction with “location independence”, “fame” or “a relationship”. People who don’t have them feel they would change everything. People who do have them find they don’t change nearly as much as they had thought.
In that way, I suppose I too live a life which is only a fantasy to some. I’m a full-time blogger. I can live wherever I want, work on whatever I want and how much I want. While I’m not super rich, I’m earning much more than I had expected when I got started nearly seven years ago.
I say this not to brag, but to provide contrast. For the first eighteen years of my life I lived in an isolated tiny town in northern Manitoba. My parents are middle class, but I definitely had my poor moments in college. I washed my clothes in a bathtub for a year because the laundromat was too expensive.
I’ve been enormously lucky, and I’m both grateful and happy. Success has made me happier, but like the previous respondents, the change is less dramatic than you would think. I worry about money less, I travel more, and I certainly don’t have the entrepreneurial angst that came with starting an unproven business.
I feel my success may have even been buffered from the disillusionment of the previous examples. I never really strove for location independence, fame or money. All I wanted to do was to be able to run a business without needing a job. My dream was to do something, not to have something. This might explain why having a lot of money and nothing to do feels empty. Life is more about doing, than having.
I was fortunate enough to anticipate that money and location independence wouldn’t make me happy. So when they entered my life, I saw them as being nice perks, not disappointments because my day-to-day life remained mostly unchanged.
The one thing I didn’t predict in advance was the orienting power of my goal itself. Having devoted myself for seven years towards a goal that I not only achieved, but surpassed my expectations was wonderful. But it also led inevitably to ask what could possibly fill the gap?
The Hungers of Life
Imagine, for a moment, the last time you were extremely hungry. So hungry that all you could think about was food (if you can’t think of that, then imagine a time you were in another physical pain, such as exhaustion, heat or cold). In those moments, that pain constrains your life—it focuses your attention and defines how you see the world.
Now remember what it was like to eat food again after that moment of hunger. It probably felt good, for a few minutes, and then there was nothing. When you’re starving, food feels like it will fill you forever and make all your worries disappear. When you’re satiated, the pleasure lasts only for a moment before your mind orients itself to something different.
I argue being rich is like being full. It’s not a bad feeling, and certainly better than being hungry. But as long as you’re well fed, food just isn’t something you think much about.
Most of us have had enough experience with both hunger and fullness to realize that being well-fed doesn’t mean life becomes perfect. But few people have had the same sense of ‘fullness’ with money, to have had the same experience.
If you currently have some hunger in your life for something, be it money, fame, freedom or a relationship, realizing that these hungers are a lot like the physical hungers can help you avoid the disappointment you might feel when you realize that satiation didn’t fix all your problems.
Life Needs Constraints
Great designs always have constraints. In many ways, design is defined by constraints and using them elegantly. Often these constraints are from the environment, but good designers also self-impose constraints.
Life, in this sense, is like a process of design. Without constraints, you have a mess, not blissful freedom. People who live well either take constraints from the environment, or impose others on themselves to live in a more meaningful way.
Some constraints aren’t particularly inspiring of great works. The lowest possible budget hasn’t been the constraint that has produced the best architecture and art. But, it can also be argued, neither has having an unlimited budget with no other limiting scope.
Having more money, location independence, or success in any other dimension, often lifts environmental constraints from our lives. This is usually a positive thing, as I believe self-selected constraints probably result in better art than the random assortment of constraints given to us at birth.
But with more freedom, there is more discipline required to constrain your art.
Maybe you’ll never be rich or location independent. Maybe you even scoff at the idea that these represent real problems, and aren’t just narcissistic whining.
However we live in a rapidly changing world where many of the old constraints may no longer apply. Location independence becomes more common, as GDP rises, more people will live far above subsistence. As old constraints become less relevant, it will be up to us to decide what the new ones should be.