Let’s face it – most of us will never be lucky enough to have rich people problems. We have first world problems, which we recognize are privileged and not real problems, but privilege and wealth don’t always (or even often) go hand-in-hand.

It can be fun to muse on – or share our experience with – what rich folks consider problems, and these 17 people are happy to do just that.

17. Everything was free.

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.

16. Unmoored from reality.

I’m late, but have a specific one. I know a few people from extremely rich families. I see a terrible outcomes 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 s*%t, then has kids, his kids are completely unmoored from reality.

It’s a lonely dark existence when you are completely incompatible with society.

15. It’s hard to trust.


Is anyone doing things because they actually care for you or because of your money?

It is a real problem for rich guys I know looking for marriage. Sex is one thing, actually have someone love you is another.

14. Easy access to money.

Best friend’s family growing up won $4.5mil on the lottery, while previously already owning 6 coffee franchises and doing decently.

I remember his father making me and his son constantly sift through the mail. His mailbox was crammed to capacity almost everyday with offers and donation requests. He actually did donate frequently but that only prompted more requests.

Unfortunately both of his sons became heroin addicts which was enabled by easy access to money.

13. More than they can spend.

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”.

12. It messes with your self image.

I have two friends who were born into the $100M+ club and the main things I’ve seen are:

guilt that they were born into a situation by random dumb luck that other people would dream of. And then the weight of obligation to use the gift they were given to do things that don’t satisfy them (prioritizing the happiness of others over themselves)

a paranoia around friendships/relationships, not knowing whether people even a little bit love them for their money.

a feeling of inadequacy that no matter how successful or brilliant you are, you’ll never be as successful as your parents

feeling that your problems are not as important as “real” problems, even though to you they are of maximum importance and emotional weight

Generally it messes with your self image; it’s hard to find out who you are without money being a part of it

11. What a pain.

My boss was complaining the other day about having to clear all the junk out of his hangar to make room for his new plane so… I guess that?

10. This definitely qualifies.

Pablo Escobar’s problem with rats eating his stacks of money faster than he could deposit them would be a good poster child for this.

9. Sooooo many houses.

I used to work in fine art shipping and rich people constantly call and ask if we could remind them which house we’d shipped their expensive artwork too..

they would have trouble remembering

8. His “real” mom.

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, specially 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 brushed 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.

7. The silver one.

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)”

6. Everyone wants something.

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 keep 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.

5. Not enough airfields.

When I was in rehab, we were in an outside area doing a group session, when we were interrupted by a helicopter landing in the parking lot.

The guy ended up being in my primary group as well, and he told me that he had to take his helicopter from Philly, as it had been a last minute decision to check himself in, and the airports local to the rehab was too small for his private plane to land there.

So, I’d have to say: “Your town’s airport is too small for my plane,” is a problem I doubt I’ll ever have.

4. Luxury or friends?

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.

3. A different perception of reality.

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 a 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

2. That can’t be healthy.

When my great grandmother died, they found out she owned 2 vacant lots in the Bay Area that were now worth over $2 mil. It’s been 7 years and all these distant relatives are still suing each other over every penny of that money.

My great grandmother was a manipulative psychopath and intentionally made her will as vague as possible, and also changed it about once every three months for the last two decades of her life.

1. Remembering the poor exist.

I ran into an old friend who was doing extremely well a few years back and who grew up wealthy as well. He mentioned to me how he and his fiancé wanted to buy their own apartment in New York because he was sick of both of the, “throwing out 3 k each for rent each month” and how it was draining their ability to travel. Did not occur to him that as a teacher I made significantly less than 3k a month and when I told him he thought I was lying because he genuinely could not fathom living on less than 10k a month. It was eye opening for both of us for different reasons.

(Before anyone asks yes he knew and knows that the poor exist but he didn’t understand that his own friends were poor (by his standard or otherwise) and just how many of us were and are struggling to make ends meet. He thought most of us were living below our means on purpose and it took this conversation for it to click for him why he didn’t see any of his old friends traveling the world or getting professional portraits done or buying fancy cars. He thought were were just living lives and not doing those things just because and not because we couldn’t.)

Man, I wish I had problems like these, don’t you? I know it’s all about perspective, but dang.

If you have first (or second) hand knowledge of rich people problems, drop some more knowledge on us in the comments!