Strategy to minimize taxes due to unpaid wages?
"Can I write off the $56,000 based on demand letters? Or do I need to   finish suing him to write-off the loss? No and no. You didn't pay taxes on the money (since you didn't file tax returns...), so what are you writing off? If you didn't get the income - you didn't get the income. Nothing to write off. Individuals in the US are usually cash-based, so you don't write off income ""accrued but never received"" since you don't pay taxes on accrued income, only income you've actually received. Should I file the 2012 taxes now? Or wait until the lawsuit finishes? You should have filed by April 2013, more than a year ago. You might have asked for an extension till October 2013, more than half a year ago. Now - you're very very late, and should file your tax return ASAP. If you have some tax due - you're going to get hit with high penalties for underpaying and late filing. If the lawsuit finishes in 2014, does it apply to the 2012 taxes? Probably not, but talk to your lawyer. In any case - it is irrelevant to the question whether to file the tax return or not. If because of the lawsuit results something changes - you file an amended return."
There is a shortcut you can use when calculating federal estimated taxes.  Some states may allow the same type of estimation, but I know at least one (my own--Illinois) that does not. The shortcut: you can completely base your estimated taxes for this year on last year's tax return and avoid any underpayment penalty.  A quick summary can be found here (emphasis mine): If your prior year Adjusted Gross Income was $150,000 or less, then   you can avoid a penalty if you pay either 90 percent of this year's   income tax liability or 100 percent of your income tax liability from   last year (dividing what you paid last year into four quarterly   payments). This rule helps if you have a big spike in income one year,   say, because you sell an investment for a huge gain or win the   lottery. If wage withholding for the year equals the amount of tax you   owed in the previous year, then you wouldn't need to pay estimated   taxes, no matter how much extra tax you owe on your windfall. Note that this does not mean you will not owe money when you file your return next April; this shortcut ensures that you pay at least the minimum allowed to avoid penalty. You can see this for yourself by filling out the worksheet on form 1040ES.  Line 14a is what your expected tax this year will be, based on your estimated income.  Line 14b is your total tax from last year, possibly with some other modifications.  Line 14c then asks you to take the lesser of the two numbers.  So even if your expected tax this year is one million dollars, you can still base your estimated payments on last year's tax. I guess it depends on what you mean by dodging taxes. Some could argue that legally taking advantage of tax loopholes is dodging taxes, while still perfectly legal. I think we are just talking semantics at this point. The main message is that there is nothing wrong with trying to cut your taxes. What you need to do is to reduce the withholding from your wages, or pay a smaller amount in your quarterly payments of estimated tax (if you are self-employed). To reduce withholding from wages, fill out a new W4 form  (available from your employer's HR department). There is a worksheet in the form that will help you figure out what to write on the various lines.  As a single person, you are entitled to claim an exemption for yourself, and if you have not been claiming that exemption, doing so will reduce your withholding, and presumably your tax refund. The best thing you can do here is work with the IRS to the best of your ability.  You can attempt to call them, attempt to go to one of their local branches in your area, or just hire an accountant to solve the problem.  Just be mentally prepared to write a check.   You could attempt to figure this all our yourself, but then a lot of tax law is open to interpretation.  This is why I would recommend seeking the IRS's help if you DIY.  Once you have addressed the issue to the satisfaction of the IRS agent, this will no longer be a problem.  Provided you have a good attitude (which you express in your question) and are honest, I have found them very easy to work with.  You will be a refreshing change of pace to the actual tax cheats. While I understand that you are not seeking advice on what got you your situation, I would like to offer some encouragement.  Good for you for learning from, and addressing your mistakes.  Doing this will serve you well in the future. Keep in mind that chasing after tax savings tends to not be a good way of saving money.  What is a good strategy? Making sure that you take all the deductions you are entitled to. What is a bad strategy: You asked for a book recommendation. The problem is that I don't know of any books that cover all these topics. Also keep in mind that all books, blogs, articles, and yes answers to questions have a bias. Sometimes the bias can be ignored, other times it can't. Just keep looking for information on this site, and ask good specific questions about these topics. "(Disclaimer: I am not an accountant nor a tax pro, etc., etc.) Yes, a Canadian corporation can function as a partial income tax shelter.  This is possible since a corporation can retain earnings (profits) indefinitely, and corporate income tax rates are generally less than personal income tax rates.  Details: If you own and run your business through a corporation, you can choose to take income from your corporation in one of two ways:  as salary, or as dividends. Salary constitutes an expense of the corporation, i.e. it gets deducted from revenue in calculating corporate taxable income.  No corporate income tax is due on money paid out as salary.  However, personal income taxes and other deductions (e.g. CPP) would apply to salary at regular rates, the same as for a regular employee. Dividends are paid by the corporation to shareholders out of after-tax profits.  i.e. the corporation first pays income tax on taxable income for the fiscal year, and resulting net income could be used to pay dividends (or not). At the personal level, dividends are taxed less than salary to account for tax the corporation paid.  The net effect of corporate + personal tax is about the same as for salary (leaving out deductions like CPP.) The key point: Dividends don't have to be paid out in the year the money was earned.  The corporation can carry profits forward (retained earnings) as long as it wants and choose to issue dividends (or not) in later years. Given that, here's how would the partial income tax shelter works: At some point, for you to personally realize income from the corporation, you can have the corporation declare a dividend. You'll then have to pay personal income taxes on the income, at the dividend rates.  But for as long as the money was invested inside the corporation, it was subject only to lesser corporate tax rates, not higher personal income tax rates.  Hence the ""partial"" aspect of this kind of tax shelter. Or, if you're lucky enough to find a buyer for your corporation, you could qualify for the Lifetime Capital Gains Exemption on proceeds up to $750,000 when you sell a qualified small business corporation.  This is the best exit strategy; unfortunately, not an easy one where the business has no valuable assets (e.g. a client base, or intellectual property.) * The major sticking-point:  You need to have real business revenue!  A regular employee (of another company) can't funnel his personally-earned employment income into a corporation just to take advantage of this mechanism.  Sorry. :-/" I've given up on trying to understand how the allowances correspond to my number of dependents.   What I do instead to achieve the same end goal of having the right amount of money withheld is using a paycheck calculator. If I get paid 24 times a year (twice a month) and I figure I'm going to owe about $6,000 of taxes, then every paycheck needs to have $250 of federal tax withheld from it to make sure I am covered. Go to the paycheck calculator and play with the allowance numbers until you get $250 as the federal tax withheld and then submit a new W4 to your employer. This is the only reliable way I've found to figure this out on my own.  Because my calculations are done in dollars instead of exemptions, etc. and my taxes do not wildly fluctuate year-to-year this works well for me. Honestly its their job to pay as little in taxes as possible.  Its like any normal person who writes off work clothes as a tax deductible. Might as well do everything youre legally able to do.  The government leaves tax loopholes in the tax code, they know they are there, take advantage, lord knows your competitors are. "Yep. You're single, you're possibly still a dependent on your parent's taxes (in lieu of rent), and you're finally bringing home bacon instead of bacon bits. Welcome to the working world. Let's say your gross salary is the U.S. median of $50,000. With bi-weekly checks (26 a year; common practice) you're getting $1923.08 per paycheck. In the 2013 ""Percentage Method"" tax tables, here's how your federal withholding is calculated as a single person paid biweekly: Federal taxes are computed piecewise; the amount up to A is taxed at X%, then the amount between A and B is taxed at Y%, so if you make $C, between A and B, the tax is (A*X) + (C-A)*Y. The amount A*X is included in the ""base amount"" for ease of calculation. Back to our example; let's say you're getting $1923.08 gross wages per check. That puts you in the 25% marginal bracket. You pay the sum of all lesser brackets (which is the ""base amount"" of the 25% bracket), plus the 25% marginal rate on every dollar that falls within the bracket. That's 191.95 + (1923.08 - 1479) * .25 = 191.95 + (444.08 * .25) = 191.95 + 111.02 = $302.97 per paycheck. The ""effective"" tax rate on the total amount, as if you were being charged a flat tax, is 15.75%, and this is just for the federal income tax. Add to this MA state income taxes (5.25% flat tax), FICA (aka Medicare; 1.45% flat) and SECA (aka Social Security; 6.2% up to a ""wage base"" that $50k doesn't even approach), and your effective tax rate on each dollar you earn is 15.75% + 5.25% + 1.45% + 6.2% = 28.65%. This doesn't include any state unemployment taxes that may be withheld separately, but as the rate I come up with is pretty darn close to what you've figured (meaning I slightly overestimated your gross income and thus your effective tax rate), my bet is that SUTA's either employer-paid in MA, or it's just part of MA state income tax. It gets better, at least at the federal level: The amount of your state income taxes is tax-deductible at the federal level if you itemize your deductions. That may not be a factor for you as you'd have to come up with more than $6,100 of other tax-deductible expenses to make itemizing the better option than taking the standard deduction (big-ticket items are mortgage expenses other than principal payments, hospital stays such as for childbirth or major accident, and state and local taxes such as sales, property and income). If you can claim yourself as a dependent (meaning your parents can't), then $150 of each check ($3,900 of your annual salary) is no longer taxed for federal withholding, lowering the amount of money taxed at the 25% marginal rate. You effectively save $37.50 biweekly ($975 annually) in taxes. Get married and file jointly, and your spouse, her personal exemption, and an extra standard deduction amount (if you don't itemize) go on your taxes. The tax rates for married couples filing jointly are also lower; they're currently calculated (or were in 2012) to be the same as if two equal earners were to file separately, so if your spouse doesn't work, your taxes on the single income are calculated at the rates you'd get if you earned half as much. It doesn't work out to half the taxes, but it is a significant ""marriage advantage"". Have kids, and each one is another little $3,900 tax write-off. It's nowhere near the cost of having or raising the child, but it helps, and having kids isn't about the money. Owning a home, making charitable deductions, having medical expenses, etc are a toss-up. The magic number in 2013 is $12,200 for a married couple, $6,100 for a single person. If your mortgage interest, insurance premiums, property taxes, medical expenditures, charitable donations, any contributions from your take-home pay to a tax-deferred savings account (typically these accounts are paid into by your employer as a ""pre-tax deduction"" and never show up as taxable income, but you could just as easily move money from your take-home pay into tax-deferred savings) and any other tax-deductible payments add up to more than 12 large, then itemize. If not, take your standard deduction. As a single taxpayer just starting out in life, you probably don't have any of these types of expenditures, certainly not enough to give up the SD. I did the math on my own taxes in 2012, and was surprised at how little the government actually gets of my paycheck when all's said and done. Remember back in the summer of 2012 when everyone was mad at Romney for making millions and only paying an effective income tax rate of 14%, which was compared to the middle class's marginal rate of 25-28%? Well, my family of 3, living on a little more than the median income from one earner (me), taking the married standard deduction, three personal exemptions, and a little extra for student loan interest, paid an effective federal income tax rate of something like 3.5%. Of course, the FICA and SS taxes don't allow any deductions (not even for retirement savings), so add in the 4.2% SS (in 2012) and 1.45% FICA and the full federal gimme was more like 9-10%." 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. "I think this is possible under very special conditions.  The important part of the description here is probably retired and rich.  The answers so far apply to people with ""normal"" incomes - both in the sense of ""not rich"" and in the sense of ""earned income."" If you sit at the top tax bracket and get most of your income through things like dividends, then you might be able to win multiple ways with the strategy described.  First you get the tax deduction on the mortgage interest, which everyone has properly noted is not by itself a winning game - You spend more than you save.   BUT... There are other factors, especially for the rich and those whose income is mostly passive: I'm not motivated enough on the hypothetical situation to come up with a detailed example, but I think it's possible that this could work out.  In any case, the current answers using ""normal sized"" incomes and middle tax brackets don't necessarily give the insight that you might hope if the tax payer really is unusually wealthy and retired." Your question begins with a misunderstanding.  When you prepare your tax return (Form 1040/1040A/1040EZ) you always try to minimize your total tax bill.  When you fill out form W4 you trying to estimate how much tax will be shown on next years tax return.  The penalty for having too much tax withheld is not having the use of the money until you get a tax refund. At the moment interest rates are very low and your economic loss is the temporary loss of access to the money. One exception would be if you are carrying credit card debt. In that case you are, in effect, paying 20-30% interest to borrow money you lending to the US Treasury for 0% interest. The penalty for having too little tax withheld is having to make a large payment with your tax return. If your pre-payments aren't at least as much as your total income tax from last year there may also be modest underpayment penalty based on the difference between your pre-payments and your total income tax from last year or this year whichever is less. A large underpayment will trigger a different larger underpayemnt penalty. The W4 combined with the withholding rates tends to over-withhold income tax for most, but not all, taxpayers. Most people don't have enough savings to pay a large tax due, which leads to more penalties and an even larger bill. Over-witholding protects the overall tax system from the consequences of those events. People tend to be very unhappy, not quietly. On balance your greatest economic benefit depends on whether or not you have high interest debt. If you do, then accurate and even slightly under-withholding will probably work to your advantage as long as you can pay next 4/15. If not, avoiding the chance of having any unexpected balance due next year may be more important. "Chris, Joe's table helps.  but think this way:  there are two ways you can pay the taxes for your side-gig:  either you can send a check quarterly to the Feds, OR, you can overwithhold at your real job to cover taxes at your sidegig.  I'd do this in ""arrears"" -- after you get your first paycheck from sidegig, then adjust your real job's withholding. Except (and Joe neglected this), you're still responsible for Social Security / Medicare Tax from your sidegig.  I suspect your income at real-job is high enough that you stop paying Social Security Tax, so at least at this time of year you won't be subject to 15.4% Social Security Tax.  However, that's NOT true for the 2.9% Medicare Tax.  Remember that because you're an independent contractor being payed without withholding, YOU are responsible not only for the Medicare (and Social Security) taxes you'd be responsible for if a regular employee, but you're also responsible for what your employer's share as well." I am actually partial to the idea of negative taxation systems, here in Australia we have the 'work for the dole' program which is essentially what the author describes, but it is inefficient and demeaning. It would be far more efficient to dramatically reduce the minimum wage and introduce a negative tax rate, or rather bracket the tax rate such that it enters negative territory at some point. This way employers can afford to employ more staff and people would still be compensated through the tax system and end up reasonably well off. So long as the compensation is fair I don't see how this is not preferable to a tax-and-transfer system where the government taxes with one hand and gives with the other? So why not talk to your employer, and ask them to pay you in gold dust? Then when tax time comes, just convert some gold dust into the amount of USD in taxes you owe.   Of course, you'd have to find farmers and shoemakers and electronic stores willing to accept payment in gold dust as well...