Are COBRA premiums deductible when self-employed?
"The basic idea is that the average person can't deduct health care costs unless they're really onerous. But a business can, and as a self-employed person, you can deduct those costs from the businesses earnings... as long as the business is really generating enough profit to cover the health insurance costs. That's why most people get their health insurance from their employer, actually. The relevant IRS rules say: ""You may be able to deduct premiums paid for medical and dental insurance and qualified long-term care insurance for you, your spouse, and your dependents if you are... A self-employed individual with a net profit reported on Schedule C (Form 1040)."" For 2010, thanks to the Small Business Jobs Act of 2010, you can even deduct the premium from your income before deducting the self-employment tax (Source). I'm sure that when you get your tax returns and instructions for 2010 this will all be spelled out." "I am very late to this forum and post - but will just respond that I am a sole proprietor, who was just audited by the IRS for 2009, and this is one of the items that they disallowed.  My husband lost his job in 2008, I was unable to get health insurance on my own due to pre-existing ( not) conditions and so we had to stay on the Cobra system.  None of the cost was funded by the employer and so I took it as a SE HI deduction on Line 29.  It was disallowed and unfortunately, due to AGI limits, I get nothing by taking it on Sch. A.  The auditor made it very clear that if the plan was not in my name, or the company's name, I could not take the deduction above the line.  In his words, ""it's not fair, but it is the law!""" http://www.ehow.com/about_4625753_cobra-as-selfemployed-health-insurance.html This link makes it clear... it has to be itemized, and is subject to the > than 7.5% AGI rule. When you take the self employed health care deduction on on Line 29 of form 1040 for 2010 it also will lower your self employment tax.  See line 3 of Schedule SE.  You report your net earnings from self employment less line 29 from 1040. COBRA premiums are not deductible on 1040 line 29; to qualify, the IRS says the insurance plan must be in your name (COBRA is in your former employer's name).  H&R Block confirms this. Here is a quote from the IRS website on this topic: You may be able to deduct premiums paid for medical and dental   insurance and qualified long-term care insurance for yourself, your   spouse, and your dependents. The insurance can also cover your child   who was under age 27 at the end of 2011, even if the child was not   your dependent. A child includes your son, daughter, stepchild,   adopted child, or foster child. A foster child is any child placed   with you by an authorized placement agency or by judgment, decree, or   other order of any court of competent jurisdiction. One of the following statements must be true. You were self-employed and had a net profit for the year reported on   Schedule C (Form 1040), Profit or Loss From Business; Schedule C-EZ   (Form 1040), Net Profit From Business; or Schedule F (Form 1040),   Profit or Loss From Farming. You were a partner with net earnings from self-employment for the year   reported on Schedule K-1 (Form 1065), Partner's Share of Income,   Deductions, Credits, etc., box 14, code A. You used one of the optional methods to figure your net earnings from   self-employment on Schedule SE. You received wages in 2011 from an S corporation in which you were a   more-than-2% shareholder. Health insurance premiums paid or reimbursed   by the S corporation are shown as wages on Form W-2, Wage and Tax   Statement. The insurance plan must be established, or considered to be   established as discussed in the following bullets, under your   business. For self-employed individuals filing a Schedule C, C-EZ, or F, a   policy can be either in the name of the business or in the name of the   individual. For partners, a policy can be either in the name of the partnership or   in the name of the partner. You can either pay the premiums yourself   or your partnership can pay them and report the premium amounts on   Schedule K-1 (Form 1065) as guaranteed payments to be included in your   gross income. However, if the policy is in your name and you pay the   premiums yourself, the partnership must reimburse you and report the   premium amounts on Schedule K-1 (Form 1065) as guaranteed payments to   be included in your gross income. Otherwise, the insurance plan will   not be considered to be established under your business. For more-than-2% shareholders, a policy can be either in the name of   the S corporation or in the name of the shareholder. You can either   pay the premiums yourself or your S corporation can pay them and   report the premium amounts on Form W-2 as wages to be included in your   gross income. However, if the policy is in your name and you pay the   premiums yourself, the S corporation must reimburse you and report the   premium amounts on Form W-2 as wages to be included in your gross   income. Otherwise, the insurance plan will not be considered to be   established under your business. Medicare premiums you voluntarily pay to obtain insurance in your name   that is similar to qualifying private health insurance can be used to   figure the deduction. If you previously filed returns without using   Medicare premiums to figure the deduction, you can file timely amended   returns to refigure the deduction. For more information, see Form   1040X, Amended U.S. Individual Income Tax Return. Amounts paid for health insurance coverage from retirement plan   distributions that were nontaxable because you are a retired public   safety officer cannot be used to figure the deduction. Take the deduction on Form 1040, line 29.
It looks like fair-market value when you receive your virtual currency is counted as income. And you're also subject to self-employment tax on that income. Here's an FAQ from the IRS: Q-8: Does a taxpayer who “mines” virtual currency (for example, uses   computer resources to validate Bitcoin transactions and maintain the   public Bitcoin transaction ledger) realize gross income upon receipt   of the virtual currency resulting from those activities? A-8: Yes,   when a taxpayer successfully “mines” virtual currency, the fair market   value of the virtual currency as of the date of receipt is includible   in gross income. See Publication 525, Taxable and Nontaxable Income,   for more information on taxable income.Q-9: Is an individual who   “mines” virtual currency as a trade or business subject to   self-employment tax on the income derived from those activities? A-9:   If a taxpayer’s “mining” of virtual currency constitutes a trade or   business, and the “mining” activity is not undertaken by the taxpayer   as an employee, the net earnings from self-employment (generally,   gross income derived from carrying on a trade or business less   allowable deductions) resulting from those activities constitute   selfemployment income and are subject to the self-employment tax. See   Chapter 10 of Publication 334, Tax Guide for Small Business, for more   information on selfemployment tax and Publication 535, Business   Expenses, for more information on determining whether expenses are   from a business activity carried on to make a profit. You'd of course be able to offset that income with the expense of mining the virtual currency, depreciation of dedicated mining equipment, electricity, not sure what else. Edit: Here's a good resource on filing taxes with Bitcoin: Filling in the 1040 Income from Bitcoins and all crypto-currencies is   declared as either capital gains income or ordinary income, for   example from mining. Income Ordinary income will be declared on either   your 1040 (line 21 - Other Income) for an individual, or within your   Schedule C, if you are self-employed or have sole-proprietor business.   Capital Gains Capital gains income, or losses, are declared on   Schedule D. Since there are no reported 1099 forms from Bitcoin   exchanges, you will need to include your totals with Box C checked for   short-term gains, and with Box F checked for long-term gains. Interesting notes from that article, your first example could actually be trickier than expected if you started mining before there was a Monero to USD exchange. Also, there can also be capital gains implications from using your virtual currency to buy goods, which sounds like a pain to keep track of. "I don't know what the OP means when he says I want to invest in health insurance from now on so that I can use the policy after I retire. Generally, a health insurance policy covers costs incurred during the current calendar year (or specific period such as July 1 of one year through June 30 of the next year) and does not cover future periods. Indeed, many policies do not guarantee renewal when the current period ends (with exceptions for employer-provided coverage through COBRA in case employment ends). So investing in a health insurance policy meaning that you pay the premiums now, and the insurance company provides the policy in the distant future is  something that is new to me. Besides, what will the policy include? If someone had bought such a policy many years ago, say, before CAT scans and MRI were developed, would the policy cover such new developments? Or the policy would cover only those procedures, tests, and medications that are available when the policy is written and the insurance premiums start to be paid? The long-term health of the insurance company is also of some concern.  When something is offered to me with a lifetime guarantee, I skeptically ask, ""My lifetime or the device's life time or the company's lifetime?""" Your current insurance, but at full price, is available to you via COBRA.  You can also look on your states exchange or the federal exchange for insurance.  You generally will not get your new company to provide money for COBRA or a policy not offered by your employer. But you can always ask. I have known of some companies that will provide money or vacation days to employees that get their insurance via TRICARE (for retired military). Also you will have to watch open seasons. When you start with the new company you have 30 days to join their program. If you don't signup in time, you have to wait for either a life event, or the next open season - which only happens once a year. If COBRA runs out before you get the new insurance in place you will have a problem. Note that open season may lead the start of the new policy by weeks or months. "You're asking explicitly about $250K+ wage earners. Well, believe it or not, but this is the most discriminated group of people in the US tax code. This is what is called ""the upper middle class"". People who still have to work for a living, but treated as if they're rich (I don't consider people who must work to keep up their life style as rich). Many of the deductions cannot be taken by them. Lets go over the list Keith made: You mentioned losses - you cannot deduct gambling losses (in excess of gambling income), and you cannot deduct passive (rental real estate, for example) losses. While for rental real estate there's a small amount of losses you could deduct, it phases out well below the $250K line (can be deducted against passive income, or when disposed of the property). 529 plans are not deductible (in fact, its a gift subject to the gift tax). Bottom line, being a high earner with wages only means you pay the most tax. You either find a way to become self employed and have a lot of business deductions on your schedule C/1120S, or switch to capital gains. You can marry an unemployed partner, it will make your life slightly easier." FSA is a convenience to allow you to pay day care expenses with pre-tax money.   It sounds like neither you nor your wife are eligible through an employer, so you can't use one. If you do not use FSA, then at tax time you can deduct the cost of day care from your gross income.  In the end the effect is the same.  Just keep track of your expenses. There is no tax code I know that would grant you such a privilege. And it just isn't practicable. In your examples, you always sold your product and were thus able, in retrospect, to give a value to your work. What if you don't sell your product? What if in one case your worked hour is reimbursed with one price, with the next product at another (i.e. difference in margin)? No, it won't work like that.  And by the way, I think you might have got some definitions upside down. What you want is a salary that your own company pays out to yourself and you can deduct from other profits. But as long as you can't afford to pay yourself a salary, and you don't have access to investors who are willing to front you the money, the time invested is your personal investment and cannot be deducted anywhere - though it might pay off nicely in the long run. That's the risk entrepreneurs take. It sounds like something is getting lost in translation here. A business owner should not have to pay personal income tax on business expenses, with the caveat that they are truly business expenses. Here's an example where what you described could happen: Suppose a business has $200K in revenue, and $150K in legitimate business expenses (wages and owner salaries, taxes, services, products/goods, etc.) The profit for this example business is $50K. Depending on how the business is structured (sole proprietor, llc, s-corp, etc), the business owner(s) may have to pay personal income tax on the $50K in profit. If the owner then decided to have the business purchase a new vehicle solely for personal use with, say, $25K of that profit, then the owner may think he could avoid paying income tax on $25K of the $50K. However, this would not be considered a legitimate business expense, and therefore would have to be reclassified as personal income and would be taxed as if the $25K was paid to the owner. If the vehicle truly was used for legitimate business purposes then the business expenses would end up being $175K, with $25K left as profit which is taxable to the owners. Note: this is an oversimplification as it's oftentimes the case that vehicles are partially used for business instead of all or nothing. In fact, large items such as vehicles are typically depreciated so the full purchase price could not be deducted in a single year. If many of the purchases are depreciated items instead of deductions, then this could explain why it appears that the business expenses are being taxed. It's not a tax on the expense, but on the income that hasn't been reduced by expenses, since only a portion of the big ticket item can be treated as an expense in a single year. Most items used in business have to be depreciated; you get to deduct a small fraction of the cost each year depending on the lifetime of the item as per IRS rules. That is, you cannot assume a one-year life for an electronic item  even if it will be obsolete in three months.  Some items can be expensed; you get to deduct the entire cost in the first year but then if you don't stay in business, e.g. you get a job paying wages and are no longer self-employed, you have to recapture this and pay taxes on the amount recaptured in the later year.  With respect to consumer-type electronics such as an iPad or laptop, it helps to have a separate  item for personal use that you can show in case of an audit.