Money Can’t Buy You Happiness: The Biggest Problems Rich People Experience

My rich friend has no kids so he’s trying to figure out how to spend all his money before he dies so it doesn’t go to some cousins he doesn’t like. If I just mention something I like, he’ll buy it for me immediately. It’s ridiculous.

The owner of the company I once worked for often had IT people from the company do any techy work he needed done to his house. I was putting in some wifi access points for him when his secretary called and asked me if I would mind driving the Maybach to the office and then take the Porsche he had driven to work back to his house. He was having some back issues and didn't want to get in the Porsche. I say sure no problem, talk to the butler, get the keys, hop in the pristine white Maybach and drive the couple miles to the office. When I pulled up he was already outside and when I handed him the keys he said "Huh, thought I had the silver one at home...must have left it in (other city)"

Okay I'm actually going to answer the question seriously. For context, I was born in a wealthy family (not obscenely rich, but well off). I'm perfectly aware that these problems are frivolous compared to what others have to go through, and I don't feel sorry for myself at all, but you asked, so here it goes:

Never really being sure whether your partner actually loves you, or tolerates you because your money makes their life easier at times.

Having all your accomplishments invalidated by the fact that you have money. I'm the first to recognize that I haven't had to face most of the barriers that others had, that I'm benefiting from incredible privilege. I'm eternally grateful for that. That said, I still think I have at least a bit of merit for the things I've done. I've known other people born into wealth who haven't done sh*t with their lives because they take everything for granted and think success is owed to them.

Alternatively, having all your everyday life problems brushed away. For example, I understand than suffering from mental health issues is a lot easier when you can afford therapy, but it's still hard at times and money doesn't magically make those go away overnight.

As a woman, it can make it hard to navigate relationships because a lot of men still identify with the breadwinner role.

The general guilt that comes with recognizing your privilege. I see a lot of my friends struggle with crippling debt and financial issues. I know I'm not personally responsible for this and there isn't much I can do beyond helping out here and there. But it's very guilt inducing to see how much this system is rigged against them while simultaneously making it easier for me.

This is from a conversation I had with a guy I met on vacation, he had grown up fabulously rich. But he never really saw his parents that much, especially when he was a kid as they were both high achieving workaholics.

Instead he had a maid, that had been there for as long as he could remember, put him to bed at night, breakfast in the morning etc... So in his mind, he had two moms. The one that he met for dinner a few days a week, that demanded he brush his hair and put on presentable clothes, and his real mom, the one that was always there, actually taking care of him.

When he was 5 years old the maid quit. She had gotten a better job somewhere else, and was looking forward to spending more time with her ACTUAL kids. And everybody was happy for her. Everybody smiled and told him to be happy she was moving on to something better. As she hugged him goodbye and happily walked out forever. He lost his real mom, and he wasn't even allowed to feel bad about it. I met this guy when he was 27, and he was still struggling with it.

I heard that this is a problem in the Philippines when someone wins the lottery, relatives you have never met will suddenly be at your door, and culturally, families are supposed to take care of each other, so lottery winners will often end up handing out money to all their relatives, and once they are no longer rich, the relatives disappear, never to be heard of again.

My boss is a pretty significantly wealthy guy, and his family in general is very wealthy and looking in from the outside when he's in his venue drinking with people, there's definitely a problem of people taking advantage of being your friend for freebies and privilege over your staff. Cannot imagine going through life with that many fake people trying to get something.

The other day, a client of my dad’s wrote a 3k check for my medical bills. I’ve been sick for a while and it came up in some casual conversation, the client recommended a place for medical testing. We went, got a consultation, but the price was too high to justify without insurance coverage.

The client calls the place, sees we haven’t done the tests yet and he writes my dad a check for the full amount.

3k doesn’t sound like a lot compared to some of these stories, but this may change the course of my life. His justification - “I have more money than I can ever spend”.

A friend of mine married into a family that has old money. Was never my friend’s intention, just turned out that the awesome down-to-earth person friend married was from serious old money.

Two of the adult children in the family are currently trying to stop their parent from buying random houses for other rich families’ kids. They don’t even want the money - they want the parent to invest in philanthropy and the local community. Parent won’t do it and just wants the rich kids from other families to be grateful to them.

So somewhere out there, some people my age from a wealthy family are getting a free house from another wealthy family. Meanwhile my partner’s unemployment ran out, we have about 2 months runway before we have nothing, we’re picking groceries carefully to save a few dollars, houses in our area have gone up $50k in the past year and we may as well be renters forever… it’s surreal.

Not being able to understand what money means to people below their financial status. I’m well off compared to other people in my country but go to a school where most people are actually wealthy. Between both levels I see that people cannot relate to the people below them in that regard and it causes friction.

Like when my friend and I organize holiday together she doesn’t understand why I get annoyed when she wants to wait until the last minute to book tickets because she genuinely doesn’t care whether they’re 50 or 500 euros. Or when my partner’s family’s car got stolen they didn’t bother getting a reimbursement from the insurance because it was too annoying to set up. This means people also sometimes don’t reimburse you when you pay for lunch because they already forgot about this, and for them 30 bucks is nothing so why would it be for you. And they don’t notice when you get them a really nice gift because all the gifts they get are really nice. This isn’t malicious at all just a genuinely different perception of reality.

Not rich myself, but I have a family member who earns low seven figures annually. Biggest problem they've struggled with is that our whole family comes from being poor and they're the one that "made it". They've had to cut off entire parts of the family, including siblings and parents, because everyone just wants stuff from them. One of their parents demanded they buy them a home because, "You owe me for raising you". It's even worse from their siblings.

They have kept their social media feed on a week long delay so if they travel anywhere that other family members are they won't hit them up with a new scheme or asking for a loan. It's terrible to watch.

I grew up wealthy, but not obscenely rich. Here’s a few: Personally I find it hard to accept the fact that it’s very unlikely that I’ll make the same amount my parents did.

It’s sometimes awkward when people realize that my family is wealthy. Especially in college with a lot of left-wing people. It was hard for my parents growing up to not spoil me though personally, I think they did a very good job. Saying no to your kid when you easily have the means to say yes with little cost to yourself is hard.

It feels like a lot of your issues get downplayed because you’re wealthy. I’ve been struggling with mental health for the past few years and a lot of the times people’s attitude is that when you’re wealthy you don’t have problems. It can feel very dismissive. I don’t want this to sound like complaining, as I’m grateful for how I was raised, just observations.

know a few people from extremely rich families. I see a terrible outcome with third-generation wealth. When dad is super successful, the kid doesn't have to do much but at least sees someone working.

When that kid, who doesn't do st, then has kids, his kids are completely unmoored from reality. It's a lonely dark existence when you are completely incompatible with society.

From my experience of working a day with a billionaire: Just not being able to live a normal life, having a beer in an ordinary bar, having normal conversations not revolving about work, having time for a simple walk and so on.

My husband has a rich acquaintance who was just agonizing about buying a $5-million yacht (which will probably be used a handful of times a year), so he decided to buy only a $3-million yacht instead. I can’t wrap my mind around it.

Long story short: A family friend tried to buy a house (something like 5 mil), signed the papers and everything, the owners sold it to someone else out from under him, and instead of going to court they paid him to walk away. So he tried to buy a house and EARNED a million dollars.

I grew up poor (father worked in flea market), and I make mid-$300’s now, and household income is around $450k. Wouldn’t say I’m filthy rich or anything, but I have seen both sides of the coin. The main thing I noticed is this: you compare yourself to your peers, and when you’re wealthy, your peers are wealthy, and you often feel like you’re falling behind your friends, even when you’re at 5-10x median income.

I went to a top MBA, and many of my close friends are fking killing it….millions of dollars in start up equity, consulting partners, directors at FAANG. I compare myself to these people, not the people I knew growing up ( I remember wanting to impress my high school friends and peers when I started this journey but honestly I haven’t even thought about them in a decade). I’m actually leaving a job I enjoy that paid $235-250k for a new job because I felt like I needed more money and more senior title. I often feel just average.

I remember growing up and thinking if I made $60k by 40 I’d be rich (I guess that’s be around $90k now inflation adjusted). And I’m only 34…

Second thing I noticed is this: rich people live in rich neighborhoods, which tend to eat up a lot of income. If I stay in Manhattan, or if I move to Westchester, minimum I can spend on a house and live near my friends and peers is like $1.4M…I can’t really move to a lcol area because my job mostly only exists in NYC. Then with day care costs, and private schools (nyc public school system is sh*t), not that much left over, even with moderate spending habits else-wise.

But look, compared to being poor, having money is great. I have outsourced everything I hate doing. I can afford healthy food and fitness. I walk to work for a 12 minute commute. I take taxis everywhere and don’t need to take mass transit. My apartment is huge. I go on multiple international vacations a year. I have a high degree autonomy at work. I’ll retire early. I enjoy the status that comes with all this (I still remember being a low status poor kids and having people at the front desk follow me around because they thought I’d steal…). I have much better friendships and relationships than I had growing up. Have a kick a wife. So I guess no real complaints.

I've seen cases where your private life eventually becomes a full time job for someone else. You often have 'people' or 'a team' who do things like arrange repairs to your home, line-manage your household cleaners and gardeners, get your shopping, book your holidays, sort your car, look after your PR if you do something dumb and the media come knocking, even book music lessons for your kids. You are doing nothing for yourself except accruing wealth.

You will also have accountants, lawyers, and whatnot at your beck and call. The primary function of the accountant and the lawyer is to let you fiddle your taxes and pay as little as possible.

This may not necessarily be a “problem”, but something I didn’t realize until later in life is that wealth is ALWAYS relative. I live in NYC, and upper middle class here is wealthy anywhere else. I know someone with a $3.4m apartment and a 900k/year income and they don’t even register as wealthy here, and sometimes are quietly wistful about what they don’t have (while understanding how ridiculous that sounds). I know someone else worth $60m+ and they are definitely wealthy, but then there’s a whole other social level above that, which are the multi-$100m people.

And everyone knows who is who - the $60m-er has a few houses and charters a private jet a few times a year, while the $200m-er has estates and a netjets card for use on a whim (or owns a plane, though honestly netjets can be more convenient). The $60m-er said to me once after a few drinks and without a trace of irony, “you know, if I had just gotten to $100m, maybe $120m, then I could have really done something”

To be clear, all of these people are as happy as anyone else, and yes, money solves a lot of inconveniences (if you need to go to the ER, for example, you call from your car on the way over and an “ambassador” will meet you at the entrance to rush you up directly to see a dr). But from inside, it’s impossible to not see that there are people who are levels above you, and there are a surprising number of levels.

Ok, I’m a first-generation wealthy individual - NW north of 20M+. Came to the US some 20+ years ago as an immigrant on work visa. Made good money in job, stocks, consulting, real estate, etc...

The problems I have are mostly stemming from the financial insecurities I grew up with. I have passive income sources that get me some 30k+ every month on top of a 350k+ a year job - yet I wear 14$ Costco jeans and t-shirts and live a very frugal life - I have the constant fear of losing everything and feeling the sense of poverty to save money - knowing very well that there isn’t a way for me to outlive my money at the pace I spend.

Having the awkwardness of going out with family/friends or partying and paying. like I'm not trying to flex, just doing the right thing. when you go out with me, I pay, it's nothing and I just want to hang out with you.

One of the unexpected problems was vacationing with friends. I work long, hard hours, so when I can take time off, I don't care the resort costs $1k/night and I'm not flying 5 hours in coach.

But with that attitude, it's going to price it way out of budget of most of my friends. So it becomes this odd decision between do I want a really nice vacation or to hang out with old friends.

I'm working middle class and for awhile dated this girl from a rich family. She had been bought a clothing boutique store to run, she basically used it as her personal wardrobe. What I found weird was we never paid for anything, when we went out, entry was free, drinks were free, food was free. However we never had any alone time, everything for free meant the owner and colleagues sat with us. Go for a quiet drink, nope, owner was with us and every other extremely wealthy person joined in.

Though it sounds all good, i think never getting your own time wore her down, she was always exhausted as she felt she had to represent her family at all times. She also could not comprehend why I would not go out some nights because I had work. Everything was free for her so money was not an issue.

Kinda rich guy here (upper middle) After getting a high rise apartment where all my walls are windows I wanted to get a nice, big a TV. I wanted an OLED but my apartment is too bright because, again, all my walls are windows. So I had to make due with a QLED instead. I'm aware.

I had a really rich friend when I was younger, and she usually hosted our outings because I was too embarrassed to have her see my house and not be able to reciprocate (her mom would drop us off at the mall and hand me a $50 bill, wouldn't take no for an answer). My mom talked to hers and agreed that the next hangout would be hosted by us. I was humiliated by how poor we were and terrified of the judgment I was sure I would get. I did my best to try to make it as entertaining as possible with the little we had, so since it was in October I decided we should carve pumpkins when she was over. She was absolutely elated. Her parents would never let her carve a pumpkin because "it didn't mesh" with their mansions "aesthetics" and "the neighbors might see". And that it'd make the maids job hard. I guess Jack'olantern carving is a poor person activity. She loved it and lamented over the fact she wouldn't be able to do it at her home.

I used to be a struggling single mom. Now, I run a semi-successful business with my husband. We have worked hard for what we have. But people act differently around us now than they used to. My husband’s family is always calling with sob stories and asking for money but they never call to ask how we are. On my side, I’ve been called a gold digger and a stay at home mom, but I work just as hard as he does.

My mom has even told me not to post pictures of our new home build on Facebook because of people’s jealousy, but come to find out her jealousy and judgment was the problem. My husband and I have pretty much isolated ourselves and have only recently tried to remedy that by making new friends who never knew us when we were poor. The fact that we successfully brought ourselves up out of the ditches and into a leisurely life, is too much for some people to bear. The envy is too much. We’ve lost friends and family because of it. That was something I never anticipated.

They'll want you to do good, but never better than them. This is just one case of people turning on each other due to one's success.

I'm not super rich, but I guess by many people's standards where I live we appear to be (nice house, car etc). We're comfortable. Now I understand why money doesn't buy happiness.

Happiness comes from the satisfaction of the journey. For example if you save and save for something, once you have enough to purchase it, you are so happy. But if you have the money sitting there and just buy it because you want it, there isn't the same level of satisfaction.

Also mental health isn't taken as seriously by friends and peers. If you have 'the lifestyle' that people think would make them happy, then how could you possibly be suffering from depression/bipolar? How ungrateful of you!

Growing up rich, you depend on wait staff. If you make your own bed, they remake it anyway. So you just stop. You don't learn to cook, pay your taxes, clean, take care of your house's maintenance. Do yard work.

But then you leave home and you don't have money anymore, and all that stuff needs doing and you're unprepared. I know we make fun of it, but it feels awful. It's humiliating to try to hang a pair of pants, mop the floor, fix your car, overpay for everything, and this lasts long into your 20s and even 30s, and other people regard your efforts to adapt with amusement or bafflement. It sucks thinking Saturday is for fun, but now its spent cleaning your house because there wasnt really time during the week.

You can either learn humility and that privilege can be bad, or you start to hate being asked to do things you don't know how to because you hate drawing notice from people. And when you try to tell this to others all they hear is "Boo hoo, I was a lazy rich brat growing up" and you get zero empathy. It's lonely, embarrassing, and discouraging.

My parents were upper middle class before my father got sick. We went bankrupt and by the time I was in high school we were barely scraping by. I went to college on student loans that ran into the six figures. I married a woman who grew up middle class and had six figures of student loan debt herself. When we married we were making 50k between us. Now our household income is around $450k. My wife is a year or two from partner at a big four, and I own a multimillion dollar business. My wife worked her a off and continues to do so. I very much lucked into my success and am well aware that very little of it is due to my own skill and merit. As for problems, while prefacing this with the fact that I would much rather have these problems than living hand to mouth, and that I’m eternally grateful for all I have, I’ll echo what a lot of people here have already said:

With higher income comes more obligations. Many of these either allow us to continue to be high earners by outsourcing household obligations (childcare, house cleaners) and others set us up for the future (retirement funds, kid’s college funds). Our kids will never qualify for financial aid, so we need to be prepared to spend half a million to send two of them to college in 12-16 years. I understand that them not having to take out loans is extreme privilege, but what’s the point of making a lot of money if you don’t use it to make your kid’s lives easier/better. So right off the bat, nearly 100k goes into retirement and college every year.

We don’t live in a mansion, but we live in a 5/4.5 3600sqft house in a very nice neighborhood close to a major city, where we have to be for my wife’s job. Bigger houses cost more to maintain.

Beyond that it does become harder to relate to your friends and family who aren’t making as much. There’s extreme guilt when complaining of any problem that isn’t life or death because they feel small by comparison to most people’s problems.

How to raise two future white men who grew up wanting for nothing not to be entitled spoiled pieces of st keeps me and my wife up and night. We don’t want to deny them anything but we don’t want them to be spoiled. It’s a very tough line to walk and we are constantly worried we’re going too far in one direction or another.

As difficult as it was to get people to sympathize with mental health issues like acute anxiety or chronic depression, it’s not even worth mentioning them now. No one feels bad for someone who suffers from those things when they have money. Most people have anxiety about making next month’s rent. What could I possibly be depressed or have anxiety about?

We are extremely liberal and frequently shunned by the people who used to march side by side with us. We’d be happy to pay higher taxes to fund Medicare for all, paid leave, universal childcare etc. But now we’re seen as shills for evil capitalists because we aren’t living a life people think good liberals should lead.

We are extremely fortunate and grateful for all we have. We try to donate money to worthwhile causes, and are more than happy to help out friends when they need it, but as others have said, friends/family either start to see you a money spigot, or the dynamic shifts to one of patronage versus equality. Eventually you end up self-sorting into strata with people of similar means for all those reasons, plus geography, the parents of your kids in the high end public schools or private schools you send them to, etc. It can be very easy to lose touch with what it’s like to live wanting. I really hope this doesn’t come off as petty or ungrateful. But I wanted to answer the question as best I could.

Having to tune 2 Steinway concert grand pianos (worth $195,000 each) in the spacious living room every year, even though no one in the house knows how to play them.

Note: They have the pianos tuned at least once per year to keep them in shape. Once or twice per year they hire a professional pianist to play them for social events.

Everybody has issues. Being rich may make life more comfortable as far as possessions go but look at how many are completely bat st crazy or have substance or mental health problems.

I've known a few very wealthy people and none of them had fabulous lives like we are led to believe, they just have more stuff and fancier houses to be miserable in while being expected to act as if they are on top of the world.

We forget every single person on this Earth is human, with their own needs and problems. It's nice for such a thought to cross us every now and then.