How does one become rich enough to be unhappy, not miserable?
I would start my answer with a famous proverb: “Health is wealth.” If you are rich, but you spend most of your time seeking appointments with doctors for your illnesses, then that wealth could get you the costly treatments, but inside you would be unhappy. On the other hand, if you are rich enough and healthy, then even if, you don’t own the topmost luxury cars, you could still be happy. How?

Well, your question seems a complex one, rich enough to be unhappy? It’s everyone’s wish to be rich, but while becoming rich, most people forget that the path they are following might lead to misery. Achievement needs compromise.
In the context of our discussion, that compromise could be happiness. If seen at a broader level, then being unhappy and miserable might look the same. But it is not always possible to be in benefit from all directions. Then comes the role of contentment. If you feel contented to be unhappy, then it does not mean you are living in misery.
It is strange to know that the definition of happiness is not the same as it used to be. It used to be based on the preservation of normality, i.e., happy as long as nothing bad happens. Nowadays for most, it’s conditional, i.e. happy only if something good happens. The classic story is that anyone who does not make enough money becomes unhappy and thinks that to be happy, he needs money. On the contrary, the one who gets rich or is already rich, sooner or later realizes that despite living a lifestyle that is a dream for many, on the inner side, he is unhappy. To be clear, this is an oversimplification we are often taught to keep us in line. I have seen rich people who are plenty happy. I’ve also seen rich people who aren’t happy, and the correlation doesn’t have to do with money, not really.
Before I give you my exact answer to this question, let’s sum up the above discussion by concluding that, there are four main feelings attached directly or indirectly with richness. They are happiness, unhappiness, contentment, and misery.
For your question, to tell anyone how to be unhappy might seem odd, I would take that in another way as I think it’s a personal trait for anyone to be happy or unhappy. As many gurus have said, happiness is something you do, not something you have. However, anyone’s situation will have a hold over that.
Yes, I can suggest a way to be rich. I am an online entrepreneur, and that’s the way I make enough to fulfill my dreams. Calling myself rich would be boasting, and it also invites a lot of perspectives. Am I rich compared to Rupert Murdoch? Not even close. But am I rich compared to most people my age with my education level, and who work the number of hours that I do? Yes. I am happy with what I have, and I am fit and healthy too. I spend time with family and friends. I pursue hobbies passionately in between my entrepreneurial pursuits. After living an unhappy life with a nine to five job by being a programmable machine for routine tasks, now I realize that had I not been challenged myself, certainly I would have been living in misery.
I am at that point where, if I chase more money for its own sake, I could become unhappy, which is what I don’t want. And that’s the answer to your question: how could one become just rich enough to be unhappy.
To simplify that from another perspective, all things have diminishing returns, even wealth. When we keep on chasing money, we forget that we are also chasing the point where the money will no longer satisfy us or offer novelty. In other words, we are chasing the threshold where we go from happy to unhappy. At that time it’s hard to see that boundary, to know where to stop and be content. That’s the point where you become just rich enough to be unhappy.
In my post: The Homeless Millionaire: How Making Money Is Only Half the Battle, I have discussed how being a millionaire means nothing. You would understand better, how while chasing money, the feeling of having it changes over time. Initially being rich makes you happy, but over time anyone could become unhappy, and if you don’t learn from that, life could soon be miserable. That post covers all of those.
In the end, I would say that: chase happiness, not materialistic comforts.
Please feel free to leave me a reply as I would be pleased to have more discussion after you read that post.
Good Luck!
Thanks,
Cleo