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Thoughts on the LessWrong "don't pay taxes" post?

lesswrong.com

There was a recent post on lesswrong, which also got highlighted on AC10, that struck my interest. It claimed that he had been avoiding taxes for 20 years through "one simple trick:" filing, but not actually paying them. The idea is that the IRS is so small and incompetent that they basically won't do anything against this sort of passive resistance.

Is this too good to be true? I'm not any sort of "effective altruist," I just don't want to pay taxes. And as it happens, I have a lot of capital gains income this year. According to the rules, I'm supposed to write the IRS a big check by Jan 15 for "estimated taxes." I can afford it, but it would make my life better to keep that money for myself. Can I just... not...? This feels like a real Matrix, red pill moment-

"You're telling me that I can dodge taxes?" "No. I'm telling you that when the time comes- you won't have to."

Then again... I really, really don't want to go to prison. even just getting my passport suspended would be a major hassle. And the guy who wrote that post seems like a real hippy... no bank account and no salary income??? how does he live?

Perhaps it would be better to set up a shady small business and claim all sorts of vague tax deductions. Thoughts on this?

btw: long time lurker, first time poster. I'm asking here because you seem like people who are smart, outside-the-box, and not simps for the government.

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Setting up a shady small business and taking deductions can indeed reduce your apparent tax burden, but it also exponentially increases your chances of an audit (and the penalties you will incur in the process).

This also sharply increases the chances your behavior will be seen as criminal. Simply failing to pay appropriately will almost certainly result in nothing more than payment plus fines and interest, even if no one really believes that your mistake was honest. Going out of your way to set up an illegal tax evasion scheme would likely result in the same treatment, but must be an order of magnitude more likely to be treated as a criminal offense, and you'd really have no plausible defense if you had an obvious sham business.