6 Insane Tax Deductions Clients Actually Thought Were Legit

This post originally appeared on Forbes.

Another tax season has come to a close, and my tax pro friends around the country are likely enjoying some much-needed rest and relaxation. Hopefully, despite the crazy hours they’ve been working over the past couple months, they took a little time out of their days to laugh.


Photo by Dmitry Ratushny on Unsplash


At one firm where I used to work, two of my coworkers brought comic relief to tax season with a “wall of shame.” On one wall in their office, they’d collect the craziest and most absurd emails, notes and documents from clients. Stuff like a client dropping off a note on April 14th that says, “I can’t find any of my W-2s or 1099s, but I’m pretty sure I made $150,000 last year. We can still file on time, right?” Or maybe another client who felt compelled to attach a political screed to his tax organizer, as if his CPAs were personally responsible for the Internal Revenue Code.

Because most tax professionals I know love sharing this stuff (while safeguarding confidential client information, of course!), I asked a few of them to share some of the craziest deductions they’ve seen clients try to claim on a tax return. Enjoy!

The Sharp Shooter

Enrolled Agent Steven J. Weil, Ph.D. and President and tax manager of RMS Accounting in Fort Lauderdale, FL says one of his clients tried to deduct the cost of practicing at the firing range to increase his firing accuracy. “When asked just how this was business related, he said ‘Well, when you [tick] off as many people as I do every day at work, you need to be prepared.”

No word on the profession of Dr. Weil’s client. I’m hoping he wasn’t an IRS auditor.

The Board of Directors

I’ve seen companies deduct expenses for some pretty lavish board meetings, but Tax-Free Wealth author and CPA Tom Wheelwright’s client pushed the boundaries even further.

“One of the craziest tax deductions we’ve seen is a client who thought their boat was deductible because all of their kids were on their board and the boat was always used for board meetings,” Wheelwright recalls.

Maybe I should incorporate, appoint my six-year-old as Vice President and deduct the cost of his Legos as an honorarium?

The Philanthropist

Dr. Weil shares another story of a client who reported very little income on her tax return, despite showing up to her appointment in a very expensive car.

“I had to ask some questions to make sure that all income was being reported,” Weil recalls. “After asking about any other income and getting a negative response, I said, ‘I see you are driving a new Maserati. How can one afford that on such low income?’ To which she replied, ‘It’s a charitable contribution. You see, my boyfriend is a much older man with a wife and family, so he gave me the car as a charitable gift, to make sure I remain charitable.’”

The Match Maker

I was delighted to learn crazy tax deductions aren’t limited to the U.S. Hannah Xu, a tax accountant and founder of Xceptional Consultancy in London, says one of her clients is a relationship expert. “One of his clients successfully found a partner and got married. My client was invited to attend the wedding, which required him to fly from London to India. He claimed his flight and accommodation and argued that the purpose of the trip to India was not for leisure, but to feature a solid case study for his business to attract more clients.”

The Road Warrior

Xu shares the story of another client who took his travel expenses too far. “In the UK, if you or your employees have to travel more than five miles to work on a client’s premises and you stay there for more than five hours, you are able to claim your travel and food expenses,” Xu says. “One employee drove around the same roundabout several times until he recorded enough mileage so that he could claim his travel and food expenses tax-free.”

The Uninformed Advisor

Unfortunately, sometimes the worst advice comes from the people you are paid to give it. Wheelwright worked with a client who got terrible advice from their former tax preparer. “They actually told the client that as long as he used money from his corporation to pay expenses, pretty much everything was deductible, whether or not it had anything to do with their business.”

Spoiler alert: That’s terrible advice.

Do you have any great stories to add to this list! I’d love to hear them!


Buying a Beach House

I don’t miss much about living in Phoenix – 117 degree summers just aren’t for me – but I do miss being a quick car trip away from San Diego. We rented the same cottage in Ocean Beach every time we went. As we strolled a couple blocks to the beach or ate the best burgers and onion rings at Hodad’s, I would fantasize about buying a tiny little house in Ocean Beach and writing with the sight, smells and sounds of the ocean just outside my window.

Photo by danny howe on Unsplash

Somehow I wound up moving to the only triple landlocked state in the U.S. instead. Funny how life works.

Writing Buying a Beach House: Things to Consider for Lending Tree got me fantasizing once again about Ocean Beach. But I also realized I’m probably better off sticking to a rental.

Give it a read and tell me: Is buying a beach house on your bucket list?

Collaboration and Leadership

I had the chance to write a few articles for Parker + Lynch, the executive recruiting and consulting firm, this month. I’ve enjoyed the assignments. They give me a chance to research and write on interesting subjects.


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This assignment was no exception. I was asked to write on why collaboration is the key to great leadership.

Have you worked at an organization that suffered from a “silo mentality”?