Would you rather be poor and discontent with the chance of being rich, or rich and miserable yet no chance of ever being glad?
Concerning your question, I’d say yes. It would be better to be poor and unhappy with the possibility of being rich instead of being rich and unhappy with no possibility of ever being happy. Why?
What if I say, I found the way to be happy by being rich enough. Well, I would be discussing that, before I conclude my answer. For now, let’s discuss the points that would support my version, as stated at the beginning of the answer.
As I hail from a modest background, despite that, in my childhood days, I had friends from influential families. I have grown up seeing the lifestyle of rich people closely. Rich people or I’d say, rich kids, literally have no dreams unfulfilled when they are young. As they become mature, they take hold of that and repeat the same for their kids. That’s how wealth passes among generations in the case of rich people.
However, my fate wasn’t that lucky. As I was talking about my childhood days, the rich kids’ parents seldom had an outing with them, but the kids used to have outings frequently. Their companions for most of the outings were their nannies or babysitters. On the contrary, we seldom had outings, but those were family outings.
Anyhow, I could not observe the granularity of such behaviors of rich people at that time, what I wanted at that time was just to be rich. After completing college, I landed on a nine to five job. That paid me well. For jobs, I’d say, any person who works for someone would probably never sleep on an empty stomach, but in turn would never have a chance to enjoy a month-long vacation on a deserted island. That’s reality. Tit for tat.
To do the latter, either you need to be rich or very smart with money and lifestyle planning. Eventually, I realized that the job I had been doing would not let me attain financial freedom, and working harder at it would not net me any equivalent rewards. Then the idea of being an entrepreneur appeared in my mind, and I started working on that. Presently I have enough to never work a standard job, and sooner or later I will attain complete financial freedom, which to me is the ability to work very little and easily afford whatever you desire. I am working on that.
Coming back to your question, while I was in the process of growing my income, I had a chance to meet and learn about the lives of rich people. I always had an affinity for a rich lifestyle that increased my curiosity. Without naming those rich personalities, I would say that after closely being a part of their life, my point of view changed. Now, it’s a big NO. I don’t want to be rich, not like most rich people are. You would be surprised to know that now I think being a millionaire means nothing. It is the emptiest goal any person could chase.
At times, even I feel shocked about how my childhood dream suddenly changed. If it’s not the case with all rich people, then it’s with most of them. While chasing money, rich people either forget, or they are bound to ignore their family, health, friends, etc., and that makes them unhappy. Everyone wishes to have money. Getting more money, and by not being content with that, is a sort of intoxication which gets more severe as you get richer. I believe in making as much money as possible in a way that leaves you better off. Instead of sacrificing your health, social life, time, passions, etc. you find income methods that are effective enough to still let you focus on these other sides of life.
Getting a million dollars, getting promoted to a certain wage level, these things are just numbers, ignorant of the context, the deeper cost, to getting them. Do not chase numbers. Would you work 20 hours a day, every day, for 10 straight years for a million dollars? I wouldn’t, even for a billion dollars. My time is more powerful and valuable than that, and so is everyone else’s, if they grow their skills and assets intelligently.
Anyways, I am aware of my answer getting long, and I have more to discuss. I would recommend you read my post which covers a context similar to your question, that would give you more reasons to support it, it would be better to be poor instead of being rich and unhappy. My post: The Homeless Millionaire: How Making Money Is Only Half the Battle, discusses the secret to being happy before you get what you want. That post also has a link to the way that I have found to be rich enough by being happy and maintaining the right perspective, which I have mentioned at the beginning of my answer.
In the end, I would say: Live a life that makes you happy. Do not chase numbers.
Please feel free to reply to me in case you need more information on that post or the points discussed in this answer.