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I currently pay no income taxes, because I'm intentionally donating just enough to charity each year that after itemizing I have no taxable income. Even with that I have a decent nest egg to invest, currently it's a bit more then 250K, but it will be much lower once I get around to doing my end of the year donations, I haven't yet calculated how much I need to donate this year. My hopes are that this nest egg will continue to grow over the years even after my 'I refuse to pay taxes' end of year charitable donations*. I intend for this nest egg to also be donated to charity eventually, I just figured if I'm not getting any tax savings by donating this year I might as well save the rest to invest for now and donate it at some later date, plus it's nice to have a large emergency fund just in case.

I'm not asking how to invest this money most efferently, that's already covered here and I don't think my eventual plan to donate all the money significantly changes that information. For the record it's currently invested in index funds with the potential of eventually buying some real estate to rent once those prices come down to a more reasonable level. This is partially a compromise of laziness, I don't want to put in the effort it takes to do more targeted investments. It may make sense to look into starting to donate securities instead of money at the end of the year, but I have a separate question for that.

My question is how to maximize the amount of money I can keep away from the government so I can donate more of it. I'm already not paying income taxes each year, can I manage to keep even more money from the government?

I'm already putting as much into the 401K provided by my company as I'm allowed. I should probably also be maxing out the other kind of 401K, but I never seem to get around to setting that up. For what it's worth I'm planning to work as long as possible without retirement, and the way I live I'll probably manage to die at 40 anyways :P

I have wondered if I could somehow give money to, for example, my parents with the understanding they would donate more to charity and claim the corresponding tax savings. This idea would be great if not for the tiny problem that I'm pretty sure it's completely illegal. Though on the off chance there is somehow a legal variant of this scheme I could manage that would be great.

Failing that I suspect the real question comes down to what happens when I die. I already have a will that basically says "give it all to Givewell.com". But is there a better way to arrange things to avoid taxes on my estate?

Basically this question boils down to how do I steal as much money from the government I can to give to charity, regardless of when the money is given. I'm trying to be the worlds most boring Robin Hood here ;) Is it possible to manage anything more then I already save by not paying income taxes? Ignoring my potential profits from investing are there any tax saving advantages, or disadvantages, to delaying charitable donations to some undefined future date?

*If you're wondering how I think I can manage this it's because I live off of little more then minimum wage, which is ironically much easier to do when you have allot of money in the bank already and are actually making far more then minimum wage. Yes this makes me crazy, I, and the voices in my head, have long since accepted that.

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    This reads more as a rant than an answerable question. Can you narrow it down a bit? What do you mean "keep it from the government"? You say you're not paying any taxes, so what exactly are you keeping from the government?
    – littleadv
    Nov 22, 2022 at 17:38

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I agree that this reads like a rant rather than a question, but assuming you are in the US the answer is simple:

When you donate to tax-exempt charities they don't pay tax so you're already most of the way there.

If you want to go still farther, you can donate appreciated securities. You avoid paying tax on the gains, and the charity doesn't pay tax when they sell the securities. Most folks view this as a way to justify donating more, but if you insist on thinking of it as Sticking It To The Man we won't stop you.

That's about as tax-efficient as you are going to get here. Other countries, of course, have other tax laws.

All your other schemes really don't buy you much, if anything. Keep it simple.

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