I remember a little bit my grandpa used to tell me, which was (replacing the s-word with "crud");
Classic stuff, and I remember that to this day. But I definitely don't think that money is a defining factor in having a successful life. For instance, a drug dealer could have as much money as a doctor and if the same thing is asked, I wonder if the drug dealer would consider his/her life as successful compared to the other. But that's the rub though, isn't it? There are relative positions of what makes a person's life seem successful. Money is something I think is a byproduct of different successes though, not of a successful life. Gauging a successful life seems more abstract than business practice and so on. A successful life has to be something that, if you were stripped of everything you had in the manner of possessions and so on, you would still have a claim to a successful life.
To a point, I also think that a successful life is a liberal life
. Liberal in the sense that in every aspect of a person life, or even just in a specific area of their choosing, they choose to enrich themselves to the highest degree. For example, you could be a waiter for the worst restaurant in town, but if you devote yourself to your particular craft in such a way where you personally excel at it, that is a successful life. Everybody has their own calling and everyone is also entitled to owning to the fact that they had a successful life. If you compare a common soldier to the grandest general of an army, the fact that the general has higher station, higher privileges, higher pay, etc. does not negate the fact that the contribution of the soldier and the potential sacrifice that soldier makes to his craft less important or his service (and subsequently his life) unsuccessful. Simply, the top of the chain and the bottom both have reason to claim they had a successful life. But there has to be a line drawn somewhere. People that waste away their lives may not have so successful a life as others that try to make the most of it. Whatever people do in order make their lives as enriching as possible (as long as it is positive) have a successful life. That is a huge factor in modern philosophy, that is, having an active compared to a passive life. A liberal life is an active life.
But on the matter of social status, that is one of those things that is still a matter of contention. At least for most of us, we all probably subscribe to the notion of a meritocracy. Simply, if you work hard for it, you are entitled to it. This to me seems like the "American dream" and the fundamental basis for a free society (yay for democracy!). But this in turn also creates what some refer to as a "natural aristocracy."
It essentially states that unlike a normal aristocratic system in which your station was inherited without qualification, the "natural aristocrat" is one who assumes a higher station within society based off of education and so on for the benefit of that society. A medical doctor, an internet technology person, a lawyer, librarian, or anyone whose knowledge exceeds the norm for the benefit of others would be considered a natural aristocrat. I think many people operate under this notion of natural aristocracy. We consider (and compare to others) the levels of the schools we went to, the profession we have, how much money we make, and how we rank in the working world (and social) without much notice because we consider it normal. Natural aristocracy exists, and we consider it a good thing to boot. I do not want to believe that a natural aristocrat has as much a successful life as someone else, but I would think on some levels that they have managed to obtain some level of enrichment other may not have. They have managed to obtain a level of success other have or cannot based on their own liberal merits. But on the whole, I have mixed feelings about natural aristocracy. Certainly, someone would prefer the most qualified over the less qualified, the best and the brightest over the slightly dimmer. But when this translates into the social sphere, it makes these awful hierarchical structures that are difficult to look at without sneering at the disparities it creates.
So basically, money does not make a persons life successful because a successful life is an intrinsic quality that, stripped of everything, you would still possess. A liberal life which expounds and enriches you own life is what lends to the notion of a successful, active life. The status of a person should not translate into a successful life, however, natural aristocracy essentially underlines the goals of a successful life (although it in turn creates a framework of its own that may be just as bad).