Why Not Take the Biggest Write-Off I Can Get Away With?
By Jeanne Fleming, Ph.D. and Leonard Schwarz

(MONEY Magazine) – Q I donate my family's used clothing to a local charity's resale store. The store gives me a tax receipt that shows the number of boxes I've dropped off, then I estimate the value of the clothes. I've always made a conservative estimate, but my brother-in-law Alex says I'm nuts. He thinks I should write off $200 to $250 a box since "no one knows what's in it" and "everyone inflates charitable contributions on their taxes." Is he right?

A Well, he's correct that no one knows what's in the boxes. And he's also right when he implies that this form of fiddling is unlikely to be detected. But he's foolish to insist it's not wrong to write off more than the value of the items you're donating. And you are fooling yourself if you believe him.

Alex may have convinced himself that since it's impossible to put an exact value on used clothes, he's only being aggressive. But knowingly overvaluing your donation isn't being aggressive. It's being dishonest—a tax strategy that amounts to nothing less than cheating on the honor system. Sure, some people do it. But most taxpayers don't: Myriad studies have shown that the majority of Americans do not cheat on their taxes.

The real question, though, is how important it is to you to do the right thing when it comes to filling out your income tax return. If it's important, you shouldn't care how many other taxpayers take the high road with you or how likely you are to get caught by the government if you don't. Ethics, as the saying goes, is what you do when no one is looking.

Questions about money and ethics? Our ethicists are consultants who advise attorneys on people's ethical beliefs. E-mail them at right_thing@moneymail.com.

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Most stock quote data provided by BATS. Market indices are shown in real time, except for the DJIA, which is delayed by two minutes. All times are ET. Disclaimer. Morningstar: © 2018 Morningstar, Inc. All Rights Reserved. Factset: FactSet Research Systems Inc. 2018. All rights reserved. Chicago Mercantile Association: Certain market data is the property of Chicago Mercantile Exchange Inc. and its licensors. All rights reserved. Dow Jones: The Dow Jones branded indices are proprietary to and are calculated, distributed and marketed by DJI Opco, a subsidiary of S&P Dow Jones Indices LLC and have been licensed for use to S&P Opco, LLC and CNN. Standard & Poor's and S&P are registered trademarks of Standard & Poor's Financial Services LLC and Dow Jones is a registered trademark of Dow Jones Trademark Holdings LLC. All content of the Dow Jones branded indices © S&P Dow Jones Indices LLC 2018 and/or its affiliates.