@Hypocrisy_Central Thank you for clarifying; you were really coming across as a total asshole for a moment there. Now let me give you my take.
Many people face The Pretender Problem; maybe you know that song and remember the line, “Caught between the longing for love and the struggle for the legal tender…”. One way or another, their life will suck, whether it be from losing their soul or struggling their entire lives. There really is no way for such a person to ever have a decent life.
I consider myself to be lucky in that I am in the minority in that what I love to do is something that will also earn me a living, so I don’t have that problem. The only real complaint I have about my job is that the pay, while enough to avoid struggling, is only ~60% of what most people in my position earn.
However, that is merely the dollars. The reason I put up with it is because of the non-dollar things about my job that more than balance things out. If I were all about the paycheck then I would have left long ago, but when I factor in the total compensation package (placing some value on happiness) I wind up ahead of where I would be at other jobs that paid more.
Now let us look at the people I know that have money. All of the ones I know fall into one of the following types:
1) Those so concerned with accumulating/retaining wealth that they cannot actually enjoy it – Maybe they work 80+ hours a week, maybe they are under a lot of stress, or maybe they just hate wearing “Golden handcuffs”, but their lives suck. They may seem happy, but I’ve seen them behind the scenes and that is just an act.
2) Those that have their money without effort – Inheritance, trust fund, sugar daddy/mama… these people never had to make such a choice because the money has always been there.
3) Those that got sick of the rat race and regret chasing cheese to the exclusion of all else for so long – Nice house(s), nice car(s), and a crushing feeling that they wasted at least a couple of decades of their lives.
I have seen people who had relatively little achieve a great degree of happiness in their later years, and a lot of rich people totally dissatisfied and/or full of regret. And I consider the happier people to be more successful regardless of financial considerations.
To sum up, this question is basically a different way of asking, “How do you define Success in life?”