Reducing taxable income in US in December
Assuming that what you want to do is to counter the capital gains tax on the short term and long term gains, and that doing so will avoid any underpayment penalties, it is relatively simple to do so. Figure out the tax on the capital gains by determining your tax bracket. Lets say 25% short term and 15% long term or (0.25x7K) + (0.15*8K) or $2950.  If you donate to charities an additional amount of items or money to cover that tax. So taking the numbers in step 1 divide by the marginal tax rate $2950/0.25 or $11,800.  Money is easier to donate because you will be contributing enough value that the IRS may ask for proof of the value, and that proof needs to be gathered either before the donation is given or at the time the donation is given. Also don't wait until December 31st, if you miss the deadline and the donation is counted for next year, the purpose will have been missed. Now if the goal is just to avoid the underpayment penalty, you have two other options.  The safe harbor is the easiest of the two to determine. Look at last years tax form. Look for the amount of tax you paid last year. Not what was withheld, but what you actually paid. If all your withholding this year, is greater than 110% of the total tax from last year, you have reached the safe harbor. There are a few more twists depending on AGI Special rules for farmers, fishermen, and higher income taxpayers.   If at least two-thirds of your gross income for tax year 2014 or 2015   is from farming or fishing, substitute 662/3% for 90% in (2a) under   the General rule, earlier. If your AGI for 2014 was more than $150,000   ($75,000 if your filing status for 2015 is married filing a separate   return), substitute 110% for 100% in (2b) under General rule ,   earlier. See Figure 4-A and Publication 505, chapter 2 for more   information. My first question to you is if you itemize?  If not the charitable contributions will not do any good.  Along these lines, donating unused items to Goodwill or similar can help boost your charitable giving.   The bottom line is that the 401K is one of the few real deductions high earners have.  If you anticipate earning similarly next year, you could both contribute the max.  You still have some time before the end of the year, can you get more in your wife's account? Does your state have income tax?  You might be able to deduct sales tax for larger purchases if you made any.  However, I would not justify a large purchase just to write off the sales tax.  Conventional wisdom will tell you that you should have a large mortgage in order to deduct the interests.  However, it does not make sense to pay the bank 10K so you can get 3K back from the government.  That seems pretty dumb. If you did not do additional withholding, you probably will have to pay a significant amount plus penalty if you owe more than $1000.  You still have time to make one more quarterly payment, so you may want to do so by January 15th. For next year I would recommend the following: The funny thing about giving is that it rarely helps the recipient, it does so much more for the giver.  It helps you build wealth. For myself I like to give to charities that have a bent to helping people out of poverty or homelessness.  We have two excellent ones here in Orlando, FL:  Orlando Rescue Mission and Christian Help.  Both have significant job training and budgeting programs. Depending on the size of the donation, you may be able to reduce taxes further by donating appreciated assets, such as stock or fund shares that have gone up a lot. That lets you dodge the capital gains tax on redeeming the shares, and if you're donating to a tax-exempt organization they don't have to pay that tax either.  And as @JoeTaxpayer has confirmed, you still get to deduct the current value of the donation, not just the basis value of those shares. So if you're donating anyway, this comes close to being Free Money in exchange for some slightly annoying paperwork. (Yet another benefit of long-term investing!) Of course folks in the top brackets sometimes set up their own tax-exempt foundations so they can decouple taking the tax break from deciding what to do with the donation.
"The fair tax is a proposal to replace the US income tax with a sales tax. Pros of Fair Tax:  It's a large change to the way the United States currently does things. The ""Fair Tax Act of 2011"" is H.R.25 in the US House and S.13 in the Senate. The full text of the bill is available at the links provided. There are some fairly large consequences of implementing a fair tax.   For example, 401ks and Roth IRAs serve no benefit over non-retirement investments.   Mortgages would no longer have a tax advantage.  Luxury items would get far more expensive." As others have suggested, if you're considering taking a 50% discount on a revenue stream you feel is low risk because you're having cash flow issues paying those property taxes - I'd recommend you seriously separating these two unrelated concerns and deal with each in most financially astute manner individually. You'll keep more of your hard earned cash You don't have the hassle factor and uncertainty of trying to become proficient in an esoteric field of financial knowledge by Christmas! Without knowing specifics about your personal situation, there are two items to consider:  1. Pre-pay as many items as possible this year.  (rent/lease, insurance premiums, etc.) to reduce your profit on paper in this tax year.    2. If you don't have a retirement plan for yourself, look into it as a way to put some money aside for retirement pre-tax.  If your accountant can't help with this, perhaps find a financial planner.   Congrats though, great problem to have! Be ruthlessly meticulous about the IRS regulations for deducting a home office.  If it's allowed, it's allowed. "'Note that ""to keep an investor from lowering their tax bill"" is not an explanation'. Well, yes it is. In fact  it is the only explanation. The rule plainly exists to prevent someone from realizing a loss when their economic situation remains unchanged before/after a sale. Now, you might say 'but I have suffered a loss, even if it is unrealized!' But, would you want to pay tax on unrealized gains? The tax system still caters to reducing the tax impact of investments, particularly capital investments. Part and parcel with the system of taxing gains only when realized, is that you can recognize losses only when realized. Are there other ways to 'artificially' reduce taxable income? Yes. But the goal of a good tax system should be to reduce those opportunities. Whether you agree that it is fair for the government to prevent this tax-saving opportunity, when others exist, is another question. But that is why the rule exists." "What would be the best strategy to avoid paying income taxes on the   sale after I move to another US state? Leaving the US and terminating your US residency before the sale closes. Otherwise consider checking your home country's tax treaty with the US. In any case, for proper tax planning you should employ a licensed tax adviser - an EA, CPA or an attorney licensed in your State (the one you'd be when the sale closes). No-one else is legally allowed to provide you tax advice on the matter. Because the company abroad is befriended, I have control over when   (and e.g. in how many chunks) the earnings of the sale flow into my   LLC. So I can plan where I live when that money hits my US account. I'm not familiar with the term ""befriended"" in this context, but form what I understand your description - its a shell corporation under your own control. This means that the transfer of money between the corporation and your LLC is of no consequence, you constructively received the money when the corporation got it, not the LLC. Your fundamental misunderstanding is that there's importance to when the money hits your US bank account. This is irrelevant. The US taxes your worldwide income, so it is taxed when you earn it, not when you transfer it into the country (as opposed to some other countries, for example India or the UK). As such, in your current scheme, it seems to me that you're breaking the US tax law. This is my personal impression, of course, get a professional advice from a licensed tax professional as I defined earlier." ??  Edit: that's what I thought. Unless there is some specific tax code that I don't know about, there's no way to pass through money to the next year. But if someone on Reddit is saying something and quoting a tax law, I'd at least like to see it. "There are probably many correct answers to this question, but for most people, the main reason is qualified dividends. To be a qualified dividend (and therefore eligible for lower tax rates), the dividend-paying stock or fund must be held for ""more than 60 days during the 121-day period that begins 60 days before the ex-dividend date"". Since many stocks and funds pay out dividends at the end of the year, that means it takes until mid- to late February to determine if you held them, and therefore made the dividend qualified. Brokerages don't want to send out 1099s in January and then possibly have to send out revised versions if you decide to sell something that paid a dividend in December that otherwise would have been qualified." "I am going to keep things very simple and explain the common-sense reason why the accountant is right: Also, my sister in law owns a small restaurant, where they claim their accountant informed them of the same thing, where a portion of their business purchases had to be counted as taxable personal income. In this case, they said their actual income for the year (through their paychecks) was around 40-50K, but because of this detail, their taxable income came out to be around 180K, causing them to owe a huge amount of tax (30K ish). Consider them and a similarly situated couple that didn't make these purchases. Your sister in law is better off in that she has the benefit of these purchases (increasing the value of her business and her expected future income), but she's worse off because she got less pay. Presumably, she thought this was a fair trade, otherwise she wouldn't have made those purchases. So why should she pay any less in taxes? There's no reason making fair trades should reduce anyone's tax burden. Now, as the items she purchased lose value, that will be a business loss called ""depreciation"". That will be deductible. But the purchases themselves are not, and the income that generated the money to make those purchases is taxable. Generally speaking, business gains are taxable, regardless of what you do with the money (whether you pay yourself, invest it, leave it in the business, or whatever). Generally speaking, only business losses or expenses are deductible. A purchase is an even exchange of income for valuable property -- even exchanges are not deductions because the gain of the thing purchased already fairly compensates you for the cost. You don't specify the exact tax status of the business, but there are really only two types of possibilities. It can be separately taxed as a corporation or it can be treated essentially as if it didn't exist. In the former case, corporate income tax would be due on the revenue that was used to pay for the purchases. There would be no personal income tax due. But it's very unlikely this situation applies as it means all profits taken out of the business are taxed twice and so small businesses are rarely organized this way. In the latter case, which is almost certainly the one that applies, business income is treated as self-employment income. In this case, the income that paid for the purchases is taxable, self-employment income. Since a purchase is not a deductible expense, there is no deduction to offset this income. So, again, the key points are: How much she paid herself doesn't matter. Business income is taxable regardless of what you do with it. When a business pays an expense, it has a loss that is deductible against profits. But when a business makes a purchase, it has neither a gain nor a loss. If a restaurant buys a new stove, it trades some money for a stove, presumably a fair trade. It has had no profit and no loss, so this transaction has no immediate effect on the taxes. (There are some exceptions, but presumably the accountant determined that those don't apply.) When the property of a business loses value, that is usually a deductible loss. So over time, a newly-purchased stove will lose value. That is a loss that is deductible. The important thing to understand is that as far as the IRS is concerned, whether you pay yourself the money or not doesn't matter, business income is taxable and only business losses or expenses are deductible. Investments or purchases of capital assets are neither losses nor expenses. There are ways you can opt to have the business taxed separately so only what you pay yourself shows up on your personal taxes. But unless the business is losing money or needs to hold large profits against future expenses, this is generally a worse deal because money you take out of the business is taxed twice -- once as business income and again as personal income. Update: Does the business eventually, over the course of the depreciation schedule, end up getting all of the original $2,000 tax burden back? Possibly. Ultimately, the entire cost of the item is deductible. That won't necessarily translate into getting the taxes back. But that's really not the right way to think about it. The tax burden was on the income earned. Upon immediate replacement, hypothetically with the exact same model, same cost, same 'value', isn't it correct that the ""value"" of the business only went up by the amount the original item had depreciated? Yes. If you dispose of or sell a capital asset, you will have a gain or loss based on the difference between your remaining basis in the asset and whatever you got for the asset. Wouldn't the tax burden then only be $400? Approximately, yes. The disposal of the original asset would cause a loss of the difference between your remaining basis in the asset and what you got for it (which might be zero). The new asset would then begin depreciating. You are making things a bit more difficult to understand though by focusing on the amount of taxes due rather than the amount of taxable gain or loss you have. They don't always correlate directly (because tax rates can vary)." I suspect that the payments were originally due near the end of each quarter (March 15, June 15, September 15, and December 15) but then the December payment was extended to January 15 to allow for end-of-year totals to be calculated, and then the March payment was extended to April 15 to coincide with Income Tax Return filing. It is important to remember that the tax brackets in the U.S. are marginal.  This means that the first part of your income is taxed at 10%, the next part at 15%, next at 25%, etc.  Therefore, if you find yourself just on the edge of a tax bracket, it really does not make any difference which side of that line you end up falling on. That having been said, of course, reducing your taxable income reduces your taxes.  There are lots of deductions you can take, if you qualify.  Depending on what type of health insurance coverage you have, a Health Savings Account (HSA) is a great way to shelter some income from taxes.  Charitable contributions are also an easy way to reduce your taxes; you don't really personally benefit from them, but if you'd rather send your money to a good cause than to Uncle Sam, that's an easy way to do it. "i think separate accounts is the simplest way to go. if the tax breaks are significant, then the inconvenience should be worth it.  you could gift or loan money back and forth. done properly, it should be technically legal (or grey enough to not cause irs trouble). specifically, they could gift you 100k$ in january and then you could gift them 110k$ in december, leaving a net gift of 10k$ for the year from you to them, which is under the annual gift tax exclusion. based on market performance, you could gift back exactly enough to hit the gift tax exclusion and keep the rest in their ""account"" with you. loans would work similarly, but the irs tends to treat undocumented or interest-free loans as weird gifts. but honestly, you might just be trading day-to-day overhead for tax audit risk. lastly, no offense meant, but i suspect that your strategy is probably just some form of martingale betting system, and you might cause some serious family strife when you eventually meet your gambler's ruin. even if everything goes smoothly, it would take some serious trust for your family to assume that you only netted them 10% roi, when your spending habits make it look like you are getting 30%. even if you used a single account, documenting the trades to their satisfaction might be more hassle than maintaining a separate account. personally, i would not trade family accord for another 2% roi." Another way to delay receipt is to delay billing. To be safe you will have to wait until the new year to send the bill, because if you do it in late December they could be super efficient and send it to you with just a few days turn around. They may being trying to spend money before the end of the year. Long ago there was a year where there were tax cuts starting January 1st.  I new of companies who allowed their employees to defer receiving their December paychecks until January. For families with two income this made a difference because they moved a month worth of one of their incomes into the cheaper year. If they weren't living month to month they could easily absorb the delay. Of course if you already sent the invoice.... The only possibility that I've seen in the past is if some of the income is for deferred services which are to be delivered in the following tax year, a portion of the income can be deferred.  Also, agree that you should be an S-corp and talk to another CPA if yours hasn't told you that yet. Reducing your income by 20k is guaranteed to lower your tax bill by less than 20k (because there are no tax rates greater than 100%).  Your goal shouldn't be to minimize taxes but to maximize total net income.