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What does it feel like to be rich? I come from a family that I was brought up to think of as "comfortable". Everyone in my family worked, no one lived ostentatiously, and neither I nor my siblings were raised to be 'rich kids'. While my family was clearly respected by everyone, it was quite apparently because of the general integrity, intelligence and public-mindedness of the way everyone behaved. Our family name was known in some professional circles, but not in the society pages, or to people in the street.
Nevertheless, it was constantly drilled into our heads from the very beginning that we were extraordinarily lucky on every conceivable spectrum: living in the a free country, in the 21st century, with a strong nuclear and extended family, in good heath, with great educations (I went to a great public school for seven years, followed by private school), the ability to travel, a house full of books, and most every rational thing that a kid could want. Thanksgiving was a major holiday in our home, with heartfelt, self-aware toasts about our immense good fortune.
Because of this, we were told by my parents, we had an obligation to give back to society, to produce more than we consumed, to think of others even more than ourselves. We were taught that money is a tool, and a magnifier...that's all. It's a tool that can be used for good or for bad, and that it has no intrinsic virtue or vice. In fact, we were all brought up to completely disassociate "money" from anything having to do with the way we lived our life. We were not expected to be anything in particular, or make any particular amount of money...but we certainly were expected to do something, and to do it to the absolute best of our abilities. The explicit understanding for all of us was that when we grew up our lifestyles should be "appropriate", without regard to whether we were a poet or a Master of the Universe.
When I proposed to the woman who would become my wife, she had clearly come from a less economically privileged background, but with almost exactly the same philosophy from her parents. I had been supported completely by my parents all through college and graduate school, with an allowance that continued even after I had gotten my first job; she had not taken a penny from her parents after the age of seventeen, and had put herself through college and graduate school while supporting her siblings. She was hardworking and frugal, and had managed to save quite a bit of cash from her salary by the time we married; I was hardworking and "comfortable" thanks to my family. Despite different backgrounds, we both considered ourselves to be relatively comparably well-off, and our marriage as something of a union of equals. My wife paid for our lovely, intimate wedding completely out of her savings; my parents paid for a larger reception the following evening.
It was only a year or two later that I understood just how "comfortable" we were...when the first issue of Forbes magazine came out with a list of the 400 richest families in America. And guess who was on it? Soon thereafter, an event happened that triggered the revelation of some previously anonymous charitable contributions which now had the family name attached. Well, not just 'some'. A lot. And big. Well known and highly visible. If I told you the name, you'd likely recognize it.
How did this change in perception affect me and my siblings? The truth is, not much at all. We had been raised with such consistent values for so long, and with money being generally available but not overwhelming, that when things became more visible (and each of us received direct access as adults to something like nine figures of cash, with more to come) there was nothing to change. All of us lived, and continue to live, very well, with "very well" being defined as something just north of a highly compensated doctor or lawyer or banker; NOT like Paris Hilton or Larry Ellison or Donald Trump. All of us work full time, extremely hard, and are near the tops of our respective professions, which include academia, business and public service. None of us felt any particular need to change things.
So, what does it feel like to be rich? (because, I guess if you want to be sorta technical about it, I'm rich. Quite.) In our case it simply means that money isn't generally a factor that needs to be worried about, at all. If we want to take a vacation (anywhere), get tickets (to anything), purchase a gadget or a collectable (of any kind), support a worthy cause (in any area), we simply do it. We have access to a private jet, which is incredibly convenient when you really need it...but the vast majority of our travel is commercial. We have personal assistants and support staff for some of our activities...but no full time cook, butler or chauffeur, just a cleaning lady who comes in once a week. Some of us have nicer cars than others; I personally drive a 20 year old car with 150,000 miles on it. We are all involved with charitable causes, but consider our major contributions to them to be our 'wisdom and work', rather than our wealth.
Most importantly, for all of those in our family, our overriding goal is to do as good a job in raising our own children as our parents did with us, where money is simply a tool and a magnifier, no more and no less. I personally work 12-14 hours a day, six or seven days a week, and hope to set an example of hard work, conscientiousness and integrity that our children will follow. In addition to my day job, I spend nearly equal amounts of time (my most precious asset) giving back, through social and charitable service, teaching and mentoring, and, yes, frequently answering questions here on Quora in areas in which I am knowledgeable.
Having read all the other answers to this question, it seems to me that the bottom line is...my parents were right: money is simply a magnifier of who you are and how you have been raised.