This is so exciting! I’m curious as to how to handle tax resistance as a freelancer/small business owner. I have the advantage of taxes not coming directly out of my check, but when I pay my quarterly/yearly, how can I make sure it isn’t going to harmful places?
Thanks for this question, Anabelle! Lots of similar q's over on IG. I think I'm going to need to publish an article specifically for small biz owners, for sure.
I would love to understand the shape of outcomes that this could potentially create. Without considering the risk of "targeted" audits and penalties for folks (The IRS is part of the executive branch...) it seems worthwhile to quantify the cost of additional complexity may introduce.
Taxes are explicitly not my department for good reason, but here are some questions that come to mind:
If we imagine a hypothetical household with 100k in income that's currently filling taxes through turbotax or similar, what additional costs are introduced from seeking counsel or otherwise? What potential penalties come on the scene if one deliberately underpays? How good are individuals at managing large piles of cash meant for tax liabilities, and how often do they mess it up?
The example that comes to mind for me is freelancers, who often have to manage their own withholdings... and often f*** it up....
This is so exciting! I’m curious as to how to handle tax resistance as a freelancer/small business owner. I have the advantage of taxes not coming directly out of my check, but when I pay my quarterly/yearly, how can I make sure it isn’t going to harmful places?
Thanks for this question, Anabelle! Lots of similar q's over on IG. I think I'm going to need to publish an article specifically for small biz owners, for sure.
Cheers Leo, thanks for this great initiative!
I would love to understand the shape of outcomes that this could potentially create. Without considering the risk of "targeted" audits and penalties for folks (The IRS is part of the executive branch...) it seems worthwhile to quantify the cost of additional complexity may introduce.
Taxes are explicitly not my department for good reason, but here are some questions that come to mind:
If we imagine a hypothetical household with 100k in income that's currently filling taxes through turbotax or similar, what additional costs are introduced from seeking counsel or otherwise? What potential penalties come on the scene if one deliberately underpays? How good are individuals at managing large piles of cash meant for tax liabilities, and how often do they mess it up?
The example that comes to mind for me is freelancers, who often have to manage their own withholdings... and often f*** it up....
Sending good vibes your way --
Sloane
thanks for this question, Sloane! I'll add it to my list of q's for the live convo on Tuesday.