Can I deduct work equipment I am not required to purchase by my employer?
No, you cannot. You can only deduct expenses that the employer required from you, are used solely for the employer's (not your!) benefit, you were not reimbursed for them and they're above the 2% AGI threshold. And that - only if you're itemizing your deductions. "Old question, but in the comments of the accepted answer, I believe Nate Eldredge is correct and littleadv is incorrect. Nate copied the actual quote from the IRS guidelines, quoted below: An expense is ordinary if it is common and accepted in your trade, business, or profession. An expense is necessary if it is appropriate and helpful to your business. An expense doesn't have to be required to be considered necessary. Noise cancelling headphones certainly count as ""appropriate and helpful to your business"" in the software industry, especially with the trend of open office layouts. And because of the ubiquitous distractions inherent in the aforementioned office space, noise cancelling headphones are becoming quite ""common and accepted"" for use by developers.  I'd be more hesitant about the keyboard and monitor, as presumably the employer is providing those already. As using your own could be said to just be a personal preference over those provided, the argument that providing your own version is ""appropriate and helpful"" is a little more shaky.  I am not a tax lawyer, so don't come after me if you get audited, but my guess from reading the actual IRS guidelines is noise cancelling headphones: probably, keyboard and monitor: maybe."
"You can deduct what you pay for your own and your family's health insurance regardless of whether it is subsidized by your employer or not, as well  as all other medical and dental expenses for your family, as an itemized deduction on Schedule A of Form 1040, but only to the extent that the  total exceeds 7.5% of your Adjusted Gross Income (AGI) (10% on tax returns for year 2013 onwards). As pointed out in KeithB's comment, you cannot deduct any health insurance premium (or other medical expense) that was paid for out of pre-tax dollars, nor indeed can you deduct any medical expense to the extent that  it was paid for by the insurance company directly to hospital or doctor (or reimbursed to you) for a covered expense; e.g. if the insurance company reimbursed you $72 for a claim for a doctor's visit for which you paid $100 to the doctor, only $28 goes on Schedule A to be added to the amount that you will be comparing to the 7.5% of AGI threshold, and the $72 is not income to you that needs to be reported on Form 1040. Depending on other items on Schedule A, your total itemized deductions might not exceed the standard deduction, in which case you will likely choose to use the standard deduction. In this case, you ""lose"" the deduction for medical expenses as well as all other expenses deductible on Schedule A. Summary of some of the discussions in the comments   Health care insurance premiums cannot be paid for   from HSA accounts (IRS Pub 969, page 8, column 2, near   the bottom) though there are some exceptions.  Nor   can health care insurance premiums be paid from an   FSA account (IRS Pub 969, page 17, column 1, near the top). If you have a business on the side and file a Schedule C as a self-employed person, you can buy medical insurance for that business's employees (and their families too, if you like) as an employment benefit, and pay for it out of the income of the Schedule C business, (thus saving on taxes). But be aware that if you have employees other than yourself in the side business, they would need to be covered by the same policy too.  You can even decide to pay all medical expenses of your employees and their families too (no 7.5% limitation there!) as an employment benefit but again, you cannot discriminate against other employees (if any) of the Schedule C business in this matter.  Of course, all this money that reduced your Schedule C income does not go on Schedule A at all. If your employer permits your family to be covered under its health insurance plan (for a cost, of course), check whether you are allowed to pay for the insurance with pre-tax dollars.  The private (non-Schedule C) insurance would, of course, be paid for with post-tax dollars.  I would doubt that  you would be able to save enough money on taxes to make up the difference between $1330/month and $600/month, but it might also be that the private insurance policy covers a lot less than your employer's policy does.  As a rule of thumb, group insurance through an employer can be expected to offer better coverage than privately purchased insurance. Whether the added coverage is worth the additional cost is a  different matter.  But while considering this matter, keep in mind that privately purchased insurance is not  always guaranteed to be renewable, and a company might decline to renew a policy if there were a large number of claims. A replacement policy might not cover pre-existing conditions for some time (six months? a year?) or maybe even permanently.  So, do consider these aspects as well.  Of course, an employer can also change health insurance plans or drop them entirely as an employment benefit (or you might quit and go work for a different company), but as long as the employer's health plan is in existence, you (and continuing members of your family) cannot be discriminated against and denied coverage under the employer's plan." "According to this post on TurboTax forums, you could deduct it as an ""Unreimbursed Employee"" expense. This would seem consistent with the IRS Guidelines on such deductions: An expense is ordinary if it is common and accepted in your trade, business, or profession. An expense is necessary if it is appropriate and helpful to your business. An expense does not have to be required to be considered necessary. Office rent is not listed explicitly among the examples of deductible unreimbursed employee expenses, but this doesn't mean it's not allowed.  Of course you should check with a tax professional if you want to be sure." Chris, since you own your own company, nobody can stop you from charging your personal expenses to your business account. IRS is not a huge fan of mixing business and personal expenses and this practice might indicate to them that you are not treating your business seriously, and it should classify your business as a hobby. IRS defines deductible business expense as being both: ordinary AND necessary. Meditation is not an ordinary expense (other S-corps do not incur such expense.) It is not a necessary expense either. Therefore, you cannot deduct this expense. http://www.irs.gov/Businesses/Small-Businesses-&-Self-Employed/Deducting-Business-Expenses "It depends on what the ""true"" reason for the trip is.  If you decide to deduct the trip as a business expense, then during an audit you will be asked why you had to go there. If there was nothing accomplished via the travel (that is, you worked from the hotel, met with no clients, visited no tradeshows, etc) then the expense is unlikely to be allowed. Yes, on a business trip you can do sightseeing if you wish (though you can't deduct any sightseeing specific expenses, like admission to a tourist attraction), but if you are just working while on vacation, then the trip itself is not deductible, since there was no business benefit to traveling in the first place." For the first four months of the year, when you were an employee, the health insurance premiums were paid for with pre-tax money.  When you receive your W-2 at the end of the year, the amount in Box 1 of the W-2 will be reduced by the amount you paid for health insurance.  You can't deduct it on your tax return because it has already been deducted for you. Now that you are a 1099 independent contractor, you are self-employed and eligible for the self-employed health insurance deduction.  However, as you noted, the COBRA premiums are likely not eligible for this deduction, because the policy is in your old employer's name.  See this question for details, but keep in mind that there are conflicting answers on that question. The short answer is yes you probably can take the deduction for a home office because the space is used exclusively and you are working there for the convenience of your employer if you don't have a desk at your employers office. The long answer is that it may not be worth it to take the home office deduction as an employee. You're deduction is subject to a 2% AGI floor. You can only deduct a percentage of your rent or the depreciation on your home. A quick and dirty example if you make $75k/year, rent a 1200 sqft 2 bedroom apartment for $1000/month and use one bedroom (120 sqft) regularly and exclusively for your employer. You can deduct 10% (120sqft/1200sqft) of the $12000 ($1000*12 months (assumes your situation didn't change)) in rent or $1200. However because you are an employee you are subject to the 2% AGI floor so you can deduct $1200-$1500 (75000*.02 (salary * 2% floor)) = -300 so in order to deduct the first dollar you need an additional $300 worth of deductible expenses.  Depending on your situation it may or may not be worth it to take the home office deduction even if you qualify for it. I'm not an expert, but here's my $0.02. Deductions for business expenses are subject to the 2% rule. In other words, you can only deduct that which exceeds 2% of your AGI (Adjusted Gross Income). For example, say you have an AGI of $50,000, and you buy a laptop that costs $800. You won't get a write-off from that, because 2% of $50,000 is $1,000, and you can only deduct business-related expenses in excess of that $1,000. If you have an AGI of $50,000 and buy a $2,000 laptop, you can deduct a maximum of $1,000 ($2,000 minus 2% of $50,000 is $2,000 - $1,000 = $1,000). Additionally, you can write off the laptop only to the extent that you use it for business. So in other words, if you have an AGI of $50,000 and buy that $2,000 laptop, but only use it 50% for business, you can only write off $500. Theoretically, they can ask for verification of the business use of your laptop. A log or a diary would be what I would provide, but I'm not an IRS agent. "While COBRA premiums are not eligible to be a ""business"" expense they can be a medical expense for personal deduction purposes.  If you're itemizing your deductions you may be able to deduct that way.  However, you will only be able to deduct the portion of the premium that exceeds 10% of your AGI. Are you a full time employee now or are you a 1099 contractor?  Do you have access to your employers health plan?" "To be deductible, a business expense must be both ordinary and necessary. An ordinary expense is one that is common and accepted in your trade or business. A necessary expense is one that is helpful and appropriate for your trade or business. An expense does not have to be indispensable to be considered necessary.  (IRS, Deducting Business Expenses) It seems to me you'd have a hard time convincing an auditor that this is the case.  Since business don't commonly own cars for the sole purpose of housing $25 computers, you'd have trouble with the ""ordinary"" test.  And since there are lots of other ways to house a computer other than a car, ""necessary"" seems problematic also." "I did a little research and found this article from 2006 by a Villanova law professor, titled ""No Thanks, Uncle Sam, You Can Keep Your Tax Break"".  The final paragraph of the article says: Under these circumstances, it is reasonable to conclude that a taxpayer is not required to claim a allowable deduction unless a statutory provision so requires, or a binding judicial precedent so specifies. It would be unwise, of course, to forego a deduction that the IRS considers mandatory such as those claimed by self-employed individuals with respect to their self-employment,    whether for purposes of the self-employment tax or the earned income tax credit. Until the statute is changed or some other binding authority is issued, there is no reason taxpayers who wish to forego deductions, such as the dependency exemption deduction, should hesitate in doing so. (The self-employment tax issues in the quote cited by CQM are explicitly discussed in the article as one of a few special kinds of deduction which are mandatory.) This is not a binding statement: it's not law or even official IRS policy.  You could never use it as a defense in the event that this professor turned out to be wrong and the IRS decided to go after you anyway.  However, it is a clear statement from a credible, qualified source." "The short answer is yes you can, but you have to make sure you do it correctly.  If you are employed by a tech company that does contract work at a separate location and you don't get reimbursed by your employer for travel expenses, you can claim the mileage between your home and location B as a business expense, but there's a catch - you have to subtract the mileage between your home and location A (your employer). So if it's 20 miles from your house to your employer (location A), and 30 miles from your house to the business you're contracting at (location B), you can only claim 10 miles each way (so 20 miles total). Obviously if the distance to location B is closer than your employer (location A), you're out of luck. You will have to itemize to take this deduction, by filling out a Schedule A for itemized deductions and Form 2106 to calculate how much of a deduction for travel expenses you can take. Google ""should i itemize"", if you're unsure whether to take the Standard Deduction or Itemize. Sources:" "In the US you are not required to have a corporation to use business expenses to offset your income. The technical term you need is ""deducting business expenses"", and in matters of taxes it's usually best to go straight to the horse's mouth: the IRS's explanations Deducting Business Expenses  Business expenses are the cost of carrying   on a trade or business. These expenses are usually deductible if the   business operates to make a profit.  What Can I Deduct? Cost of Goods   Sold, Capital Expenses, Personal versus Business Expenses, Business Use   of Your Home, Business Use of Your Car, Other Types of Business Expenses None of this requires any special incorporation or tax arrangements, and are a normal part of operating a business.  However, there is a bit of a problem with your scenario. You said you ""invested"" into a business, but you mentioned buying specific things for the business which is not generally how one accounts for investment. If you are not an owner/operator of the business, then the scenario is not so straight-forward, as you can't simply claim someone else's business expenses as your own because you invested in it. Investments are taxed differently than expenses, and based upon your word choices I'm concerned that you could be getting yourself into a bit of a pickle. I would strongly advise you to speak with a professional, such as a Certified Public Accountant (CPA), to go over your current arrangement and advise you on how you should be structuring your ongoing investment into this shared business. If you are investing you should be receiving equity to reflect your ownership (or stock in the company, etc), and investments of this sort generally cannot be deducted as an expense on your taxes - it's just an investment, the same as buying stock or CDs. If you are just buying things for someone else's benefit, it's possible that this could be looked upon as a personal gift, and you may be in a precarious legal position as well (where the money is, indeed, just a gift). And gifts of this sort aren't deductible, either.  Depending on how this is all structured, it's possible that you should both consider a different form of legal organization, such as a formal corporation or at least an official business partnership. A CPA and an appropriate business attorney should be able to advise you for a nominal (few hundred dollars, at most) fee. If a new legal structure is advisable, you can potentially do the work yourself for a few hundred dollars, or pay to have it done (especially if the situation is more complex) for a few hundred to a few thousand. That's a lot less than you'd be on the hook for if this business is being accounted for improperly, or if either of your tax returns are being reported improperly!" Some of the deductions that are only available as payroll deductions are: There are other deductions you can take if you qualify such as HSA or IRA contributions without any employer help. The IRS Guidance pertaining to the subject.  In general the best I can say is your business expense may be deductible.  But it depends on the circumstances and what it is you want to deduct. Travel Taxpayers who travel away from home on business may deduct related   expenses, including the cost of reaching their destination, the cost   of lodging and meals and other ordinary and necessary expenses.   Taxpayers are considered “traveling away from home” if their duties   require them to be away from home substantially longer than an   ordinary day’s work and they need to sleep or rest to meet the demands   of their work. The actual cost of meals and incidental expenses may be   deducted or the taxpayer may use a standard meal allowance and reduced   record keeping requirements. Regardless of the method used, meal   deductions are generally limited to 50 percent as stated earlier.    Only actual costs for lodging may be claimed as an expense and   receipts must be kept for documentation. Expenses must be reasonable   and appropriate; deductions for extravagant expenses are not   allowable. More information is available in Publication 463, Travel,   Entertainment, Gift, and Car Expenses. Entertainment Expenses for entertaining clients, customers or employees may be   deducted if they are both ordinary and necessary and meet one of the   following tests: Directly-related test: The main purpose of the entertainment activity is the conduct of business, business was actually conducted   during the activity and the taxpayer had more than a general   expectation of getting income or some other specific business benefit   at some future time.   Associated test: The entertainment was associated with the active conduct of the taxpayer’s trade or business and occurred directly   before or after a substantial business discussion. Publication 463 provides more extensive explanation of these tests as   well as other limitations and requirements for deducting entertainment   expenses. Gifts Taxpayers may deduct some or all of the cost of gifts given in the   course of their trade or business. In general, the deduction is   limited to $25 for gifts given directly or indirectly to any one   person during the tax year. More discussion of the rules and   limitations can be found in Publication 463. If your LLC reimburses you for expenses outside of this guidance it should be treated as Income for tax purposes. Edit for Meal Expenses: Amount of standard meal allowance.   The standard meal allowance is   the federal M&IE rate. For travel in 2010, the rate for most small   localities in the United States is $46 a day. Source IRS P463 Alternately you could reimburse at a per diem rate Yes, you can deduct from your taxable profits (almost) any expenses incurred in the course of your business. See here for HMRC's detailed advice on the subject. The fact that you have salaried PAYE employment as well makes no difference.