The Most Exotic Tax Write-Offs That Actually Work

We hear some pretty wild questions about tax write-offs.

Can I write off my swimming pool? What about my dog? Can I take a trip to Florida and call it a business expense? What about that expensive suit I bought specifically for meeting clients?

Believe it or not, sometimes the answer is yes.

There are legitimate tax deductions out there that sound completely ridiculous until you understand the circumstances behind them. That’s one of the interesting things about taxes. It’s not always about what you bought. It’s about why you bought it and how it was used.

Take a swimming pool, for example. You can’t put a pool in your backyard, decide swimming is good for your health and send the bill to Uncle Sam. But there have been situations where home improvements made primarily for legitimate medical care qualified as medical expenses. There are rules involved, especially if the improvement increases the value of the home, but it’s a good example of something that sounds crazy until you know the whole story.

Animals are another interesting one.

No, your family dog isn’t a tax deduction just because he occasionally hangs out at the office. But legitimate service animals can qualify for certain medical expense treatment, including some of the costs of buying, training and maintaining them. Animals that actually serve a legitimate business purpose can present other tax considerations as well.

The important part is being able to explain why the expense exists in the first place.

Travel is probably where things get the most interesting for business owners.

There’s a strange belief that if you enjoyed a business trip, it somehow stops being deductible. That’s not how it works.

You can fly somewhere beautiful and still have a legitimate business trip. The IRS doesn’t require your conference to be held in the least enjoyable city in America.

If the primary purpose of the trip is legitimate business, qualifying expenses such as airfare and lodging may be deductible. You can even add personal days to certain business trips, although the personal expenses don’t suddenly become business expenses just because you checked your email from the beach.

That’s where people get themselves into trouble.

Spending $5,000 on a vacation and having one lunch with a potential client doesn’t make the vacation a $5,000 business deduction.

On the other hand, spending $5,000 traveling to an industry event, meeting clients and conducting legitimate business doesn’t automatically become a personal expense because you happened to have a good time while you were there.

Clothing is another one we get questions about.

You might spend thousands of dollars on suits because your business requires you to look professional. Unfortunately, that doesn’t necessarily make them deductible. If you can reasonably wear the clothing outside of work, the IRS generally isn’t impressed by the argument that you bought it for business.

Specialized clothing can be different. Uniforms, costumes and certain clothing that isn’t suitable for ordinary everyday wear can potentially qualify d