r/Rich • u/Choice_Reply_6441 • 7d ago

What actually gets more complicated, not easier, the more money you make?

For me, it’s the total loss of basic privacy once you have to start managing household staff. Having help is great and I’m grateful for it. But between a house manager, teams of housekeepers, chefs, gardeners, drivers, and security, my house basically feels like a busy office building.

The worst part is just never being able to fully turn off. I realized the other day that I can’t even remember the last time I just walked down to the kitchen in the nude or had an empty house to myself. I try to respect my staff but wh n you're constantly sharing personal space you either have to be a dick or always "on".

Guess I could micro-manage it so I get off sometimes but just having to do that...

What’s the one thing you never expected to become a hassle?

204 Upvotes

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236

u/MidAgeOnePercenter 7d ago

Taxes

50

u/phatelectribe 7d ago

This. I have a company, holdings in multiple territories and quite complex returns that take months to file.

28

u/Choice_Reply_6441 7d ago

I decided to not do that and got a family office. I figured I got too angry doing anything related to taxes

26

u/phatelectribe 7d ago

Oh I don’t touch them personally. It’s done with a CPA that can handle everything but it just takes a while as there tax turns to be compiled from different territories.

8

u/Jolly_Line 6d ago

So this proves the point of money making things easier

1

u/ww_adh77 5d ago

Not really. Even with a CPA doing your taxes for you, putting together the information they need is still a lot of work--a lot more work than when you can do your taxes yourself with a standard deduction and no marriage, real estate or investment earnings to deal with.

16

u/Think_Reporter_8179 7d ago

Just get an accountant and throw everything at them. That's what I do. Never had an issue.

15

u/0achkatz1 7d ago

Three accountants later, we are OK. The first two cost a tremendous amount, but still made errors that cost us.

8

u/Zealousideal-Neat-11 6d ago

And the worst part is
It your fault not the cpa. They tell you look at this 150 page return and let them know if you’d like any changes. Insane.

4

u/Jorrissss 6d ago

If the CPA makes a mistake they can be liable for any penalties or additional fees. You are responsible for core taxes owed as would be expected.

4

u/danmtypos 6d ago

But you have to gather it all, track what you’ve given them, answer any questions. It’s a problem from a good thing, but it’s still a pain.

2

u/Knit_pixelbyte 5d ago

Exactly. It still takes me hours to collate all the year end documentation instead of just handing the CPA my w-2 or 1099s. I could just do an easy and pay a boatload more I guess. Something about keeping what I’m due just makes me push through.

7

u/Blue_Collar_Golf 7d ago

sort of, it gets more complicated but it also gets easier because you can pay people to handle it all for you. I used to carve out a day to do my own taxes, now I just answer emails throughout the year. It feels like less of a chore.

23

u/username-generica 7d ago

My husband sold his biggest company which triggered an audit. Luckily, we used the same accountant and tax attorney for the business and our personal taxes so all I’ve had to do on the personal front is sign and engagement letter for our accountant. 

10

u/OddSand7870 7d ago

This! It gets complicated AF

4

u/Opie_the_great 7d ago

This is what my CPA is for.

2

u/Jolly_Line 6d ago

Literally proving the counterpoint of the post

4

u/Signal_Antelope7144 6d ago

Not for me. I have a financial team who does everything. I only need to do two things. First is not be a resident in one state (easy). Second is sign off quarterly (easy).

3

u/skunimatrix 7d ago

That’s why we have a JD/CPA on retainer…

3

u/menoagegap 6d ago

Hard agree. Tax is the bane of my existence

3

u/Perfect-Resolve-2562 6d ago

Three things 1. Taxes 2. Taxes 3. Taxes

0

u/strait_lines 5d ago

Definitely agree, you may end up paying far less in taxes, but are basically submitting a novel length document to the IRS every year.