Have you ever known anyone who was a multi-millionaire (or had a large amount of money) who lived modestly? In other words, sort of like a Howard Hughes type, as I’ve read he drove an old car, yet he was extremely wealthy. Also, do you think very wealthy people get used to the finer things in life, and that after a while it seems ordinary to them? For example, if a wealthy person buys a new Mercedes, does it still seem special if you’ve been driving a Mercedes for the past 20 years?
Human beings have the tendency go get used to pretty much anything, good or bad. So it’s hard to appreciate something nice when you’ve had it for a while. Happiness also largely returns to a personal set point.
Not exactly a millionaire, but there’s one thing that certainly continues to make me happy: that I have all the music I’ve ever liked in my pocket in very high quality. If I find something I don’t have yet I can either pirate it or just buy it. Back when I was a kid the former meant making copies on cassette tape, which was a hassle, and the latter involved vinyl records, also a hassle, and way too expensive relative to my income to do regularly.
But I’m not walking around in an overjoyed state 24/7.
The owner of the largest institutional coffee brand was worth hundreds of millions. He drove a 25 year old car and spent his days training and caring for his racing pigeons. He showed up each morning in a suit and tie. Sampled and wrote the recipes for each days coffee blends and then retired to the back lot with his birds. In the afternoon he would dress back up and have a 1 hour meeting with his excecs and then go home. Never took a single vacation in over 50 years.
My grandfather’s second cousin was Henrietta “Hetty” Robinson Green. I grew up with tales of her miserliness.
When I was in college, for a while I lived in a rooming house that was one of many owned by a very elderly man. He lived in the basement of one of his rooming houses, and slept on a cot in a small windowless room. To see him, you’d think he was a homeless person. When he finally died, it turned out he had many millions of dollars hidden away in cash in his room.
In his case at least, I think he crossed the line into the pathological.
Many people with a LOT of money spend a lot of time trying to hide it from other people. They would rather not stand out as being “rich”. Other people like you a whole lot more if they think you are poor.
As for getting used to things like buying a new Mercedes, etc., yes people with money are used to buying quality things - buying things which do what they want / need /prefer.
With that said, they are QUITE unhappy these days with all the crappy products on the market. Quality seems to be a thing of the past!
I’m a multi millionaire. I live modestly. My neighbors are hair stylists and teachers (its a nice middle class neighborhood). I drive a used Volvo - my kids drive a fifteen year old Honda Pilot that has definitely seen better days - and they have to share it (much to their chagrin). Its going to be 90 degrees today - I turned on the air. It was only 83 yesterday - that’s fan weather. In the Winter in my house, you wear a sweater - I’m not turning up the heat so you can sit around in a t-shirt. I really need to get new carpet - but with two teenagers, a cat, a dog, and a puppy - yeah, another few years of it looking like crap.
I don’t consider myself extremely wealthy - a million dollars doesn’t go very far when you are talking two college educations on the horizon (my son is doing tech school so that will be less expensive), retirement not too far down the line (I’m already semi-retired - I run our businesses out of the house about 10 hours a week or so). And I’m barely a multimillionaire - I won’t be after the kids finish college - a net worth of $60 Million is way different than a net worth of just around $2M.
You do get used to some of the nicer things - I couldn’t go back to being an Applebee’s regular - good dining experiences are a worthwhile expense in our house. But it does still seem special. And we don’t eat at Applebee’s often, but we eat cheap delivery pizza and McDonalds and go to Noodles and Company. My husband doesn’t let me buy wine in a box anymore - and the bottles are at least $12 instead of $6. And the liquor in the house tends to be pretty good - no big bottles of Jim Beam.
But honestly, how do you become a multimillionaire other than by being frugal? You could make millions every year as a investment banker or Taylor Swift, or inherit it, but most multimillionaires saved it. And the first million is the hard part (that took 15 years, the second million took five).
As to its relationship to happiness - I suffer from anxiety and depression. Since one of my anxiety triggers is money - it helps (and also explains why you wear a sweater in my house in the winter). But one of the most content people I know lives in her van and does migrant labor six months a year and then comes back and crashes with friends. It would drive me over the bend - but she is happy.
I had an uncle (my father’s mother’s brother – I guess he was my uncle) who had a large potato farm. In the late 1950s they took part of his farm to build an exchange on an Interstate highway and paid him $1.6 million – a ton of money in those days.
He bought a new rowboat for his farm pond and three new pairs of white cotton socks. He drove his 1949 Pontiac until he died around 1980. He continued to farm potatoes on his remaining land, selling them to the local potato chip plant and living off that money … never touched the money in the bank from the land sale – left it all to his son.
I forgot to mention that some car salesmen, who judge people by the way they dress, have lost out on some BIG sales. A guy may walk in looking like a bum, then order 6 new pick-up trucks! (In construction or farming - tons of money!)
What to see a bunch of cheap people, go to a Mercedes repair forum. 
Or the Bogelheads board. Or a Berkshire Hathaway annual meeting.
Absolutely, and first is easy to go check out. On the sub fora about ‘personal financial’ or ‘personal consumer’, you’ll eventually run into remarkable bragging about extreme cheap skatism by people claiming to be wealthy. Relative to the cheap skate champions there, very few really rich people live really modestly. But with a more reasonable definition of living below means IME lots of wealthy people do that, it’s very common.
https://www.bogleheads.org/forum/index.php
Anyway I didn’t think the thread title and OP lined up exactly. A lot of people (again you can easily see it on BH forum) derive happiness, in part, from having money not necessarily spending money. Just because a rich person doesn’t spend lavishly doesn’t mean the wealth they’ve accumulated isn’t pretty central to their sense of life achievement and well being. And I don’t see anything wrong with that. Less benignly, money to some people is a way toward ‘happiness’ by manipulating other people. Mainly manipulation of family members is what I’m thinking about here, by ‘normally’ rich people, not conspiracies for global domination from the Koch brothers, Soros, Dr. Evil or whoever else is your political bette noir among famous rich people. 
I grew up very poor and now we make more than enough. In a lot of ways I enjoyed my childhood more than I do now. I think beyond a certain amount of money you miss what you cannot buy for any amount.
Years ago, my brother in laws girl friend had a nice sparkly bracelet that I complimented. She mentioned she had TONS of then and we should go shopping together. I said shopping would be nice, but I’m not much of a buyer. She said “what do you buy” I said “stocks.”
I have some jewelry, a few nice handbags, a couple pair of not terribly practical shoes (how often do you need purple high heels - although a LOT of my wardrobe is purple - so they actually get used pretty often). But compared to a lot of women, I don’t buy that sort of stuff. My last pair of jeans was $12 at Marshalls. I do buy stock - which gives me as more satisfaction as my nice Coach handbag.
I’d argue all rich people leave beneath their means - or they don’t stay rich. And people who got rich through something other than five years of extreme athletic ability or some other shot in the dark incredible income for a few years thing, inheritance, or winning the lottery, tend to understand that.
I have known many people who fit the “Millionaire Next Door” stereotype.
Millions in investments, living in a modest home, driving a 10-year-old car, wearing sweatshirts and jeans. Often times, the only extravagant thing they would do is travel, and even then, they would tend to stay in budget accommodations.
Also switch it around. I’ve known a LOT of people who can’t make their monthly bill payments, yet must purchase brand-name only products at the store (generic will not do).
They purchase very expensive stuff, then run out of money. Whereas they could be frugal and have money left over.
This is a common debate on the forum I mentioned. People who want to stay rich can’t live above their means (unless they reach the point of knowing they’re not long for this world). But they don’t have to live below, or far below. Common expressions on that forum are people living far below. This raises the question why do they bother accumulating the money? To give to heirs or charity could be a reason, OTOH depending on the case a person might be able to give money to adult heirs, or certainly charities, right now.
Part of the answer is degree of conservatism in how far the money will go, in supporting the person who earned it. Some people are very conservative about that. But IMO that tends to meld into the other answer I gave: some people enjoy having wealth as an end in itself, not necessarily for what it can buy, even in the future. Accumulating that wealth is an important achievement in their life, which most people haven’t to the same degree, and it’s painful to go on a trajectory of even partly gradually dissipating it by spending more, even later in life. I would admit that this psychology might be part of the explanation for the low level of my spending relative to assets, though I don’t hold a candle to some of the rich extreme cheapo’s at BH forum (or at least what they claim, it is the internet after all).
Yes, I have a friend just as you describe. I know he has lots of money and could easily be living large. But he lives very modestly, doesn’t even have a car, rents a low rent apartment etc. He’s never worked, inherited his wealth and has chosen to pursue painting and playing guitar. He’s made a few CDs, all self financed.
He’s definitely a very odd fellow. Socially awkward, never married, no partner, etc. But he’s definitely had a very different life from most people. He seems happy enough, in a tortured artist sort of fashion.
I’d bet the money, especially the never having to work, have helped to separate him from a more normal life. Without it I suspect he’d have been forced into circumstances that would have forced him beyond his awkwardness. But he never really had to, and his money allowed him to withdraw in a way that probably contributed to his being all alone now.
I think the rich and extreme cheapos (I know the type) tend to have some “issues” on security and spending that go beyond healthy. As someone with anxiety (and probably some OCD on the issue), I can relate - and need to watch it myself. On a forum like that (Mr. Money Mustache is another one that goes overboard), they find their kind and it becomes “normal.”
You have to earn more before you can save.
By my calculations, assuming around a 5% return on investments, you would need to stash away around $45k for 15 years. For most people that’s their entire income. Outside of investment banking and top tier law or management consulting firms (that require a JD or MBA), they won’t be making much more than that for the first 15 years of their career anyway.
5 years would be $180k a year.
So right there you start getting into the crux of the happiness issue. To make enough money to save the sort of money you are talking about, you really are restricted to a relatively small number of professions in finance, big law, tech, and management consulting. And those aren’t professions known to think about the happiness of their employees.