Dictionary of Tax Deductions

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Edward A. Lyon, JD
TaxTuneup.com, Inc.
3416 Shaw Ave #5
Cincinnati OH 45208
513.321.2821

elyon@taxtuneup.com




Weight-Loss Programs

Deductible Medical Expense, subject to the 7.5% floor, if prescribed for a specific condition (not just to improve general health).

Wheelchair

Deductible Medical Expense subject to the 7.5% floor.

Wig

Deductible Medical Expense, subject to the 7.5% floor, if prescribed for mental health after losing hair to disease.

Withholding

Withholding is the secret to making today's income tax system work. If taxpayers actually had to write checks for their tax bills, the revolt would make the Boston Tea Party look like--well, a tea party. The vast majority of us pay our taxes through employer withholding. Our employer deducts taxes directly from our pay and sends them directly to the IRS, cutting out the middleman. (That would be us.) Withholding is actually an efficient way to collect taxes. It cuts down on time and paperwork, it ensures that tax deposits are filed regularly and timely, and it saves us the time and effort of filing our payments. It also gives rise to the annual refund for those of us who pay too much throughout the year.

Filing Form W-4 with your employer tells them how much you intend to report in taxable income. Start with your salary. Then add or subtract whatever number of exemption equivalents it takes to reach your taxable income. Your employer then withholds however much it takes to pay your bill. If your income is substantially higher than what your employer pays, you have two choices. You can have your employer withhold the extra tax or you can make extra quarterly payments with Form 1040-ES.

You'll need to make sure you deposit a certain amount by the end of the tax year to avoid penalties for underwithholding:

  • If your 2008 adjusted gross income is $150,000 or less, you'll need to withhold 100% of your 2008 tax or 90% of your 2007 tax.
     

  • If your 2008 adjusted gross income is more than $150,000, you'll need to withhold 110% of your 2008 tax or 90% of your 2007 tax. 

You're certainly safer paying the higher percentage of last year's tax. But you'll lose the use of that money during the year. (If you overstate deductions and credits, or understate your income, you can wind up owing a $500 civil penalty. If you supply false information, there's a $1,000 criminal penalty, plus possible jail time. Do what it takes to avoid a refund. But don't get greedy!)

You should review your withholding any time your tax picture changes:

  • If you have a baby (or adopt a child), file a new Form W-4 with an extra exemption as early as possible in the year the child will be born.
     

  • If you or your spouse take a new job, complete the worksheets to file a correct Form W-4 to reflect the extra income.
     

  • If you or your spouse receive a significant salary raise, review your situation to see if enough tax will be withheld.
     

  • If there will be a significant change in your Itemized Deductions, such as buying a new house, check to see if your withholding remains appropriate.
     

  • If you get a divorce, file a new Form W-4 as soon as possible in the year your filing status changes.
     

  • If there's a death in the family, file a new Form W-4 for the following tax year.

Your employer has to make your new Form W-4 effective by the start of the first payroll period ending on or after the 30th day after you submit your form. For more information, see IRS Publication 919, "How Do I Adjust My Tax Withholding?"

Work Clothes (See Uniforms and Work Clothes)

Workers' Compensation

Workers comp premiums you pay for your employees are a deductible Business Expense on Schedule C, Form 1065, or your corporate return.

Workers comp benefits you receive for injuries on the job are nontaxable income.

Working Condition Fringe Benefits

Working condition fringe benefits include anything your employer pays for you that you could deduct as an Employee Business Expense if you paid for it yourself. These benefits are deductible by your employer and tax-free to you. They include:

  • use of a company car or plane for business
     

  • membership in professional associations
     

  • education assistance for courses that maintain or improve your job skills but don't prepare you for a new position
     

  • outplacement assistance (see Job-Hunting Expenses)

Worthless Securities

Worthless securities are deductible as a Capital Loss on Schedule D the year that they become completely worthless. To claim the loss, you have to show that the security had some value the previous year (such as trading on an established exchange) and became completely worthless the year you claim the loss (such as going out of business or bankrupt). Securities are deemed to become worthless on the last day of the year for purposes of figuring whether losses are short-term or long-term. If a security is nearly worthless--trading for pennies a share, for example--consider selling for what you can get and taking a regular loss, rather than waiting for complete worthlessness.

You have seven years from the date of worthlessness to file an amended return to claim the loss. If you're in doubt whether a security is completely worthless, go ahead and claim the loss. You can always amend your return later.