Home » Resources » News » Keeping meticulous records is the key to tax deductions and painless IRS audits

Keeping meticulous records is the key to tax deductions and painless IRS audits

If you operate a business, or you’re starting a new one, you know you need to keep records of your income and expenses. Specifically, you should carefully record your expenses in order to claim all of the tax deductions to which you’re entitled. And you want to make sure you can defend the amounts reported on your tax returns in case you’re ever audited by the IRS.

Be aware that there’s no one way to keep business records. But there are strict rules when it comes to keeping records and proving expenses are legitimate for tax purposes. Certain types of expenses, such as automobile, travel, meals and home office costs, require special attention because they’re subject to special recordkeeping requirements or limitations.

Here are two recent court cases to illustrate some of the issues.

Case 1: To claim deductions, an activity must be engaged in for profit

A business expense can be deducted if a taxpayer can establish that the primary objective of the activity is making a profit. The expense must also be substantiated and be an ordinary and necessary business expense. In one case, a taxpayer claimed deductions that created a loss, which she used to shelter other income from tax.

She engaged in various activities including acting in the entertainment industry and selling jewelry. The IRS found her activities weren’t engaged in for profit and it disallowed her deductions.

The taxpayer took her case to the U.S. Tax Court, where she found some success. The court found that she was engaged in the business of acting during the years in issue. However, she didn’t prove that all claimed expenses were ordinary and necessary business expenses. The court did allow deductions for expenses including headshots, casting agency fees, lessons to enhance the taxpayer’s acting skills and part of the compensation for a personal assistant. But the court disallowed other deductions because it found insufficient evidence “to firmly establish a connection” between the expenses and the business.

In addition, the court found that the taxpayer didn’t prove that she engaged in her jewelry sales activity for profit. She didn’t operate it in a businesslike manner, spend sufficient time on it or seek out expertise in the jewelry industry. Therefore, all deductions related to that activity were disallowed. (TC Memo 2021-107)

Case 2: A business must substantiate claimed deductions with records

A taxpayer worked as a contract emergency room doctor at a medical center. He also started a business to provide emergency room physicians overseas. On Schedule C of his tax return, he deducted expenses related to his home office, travel, driving, continuing education, cost of goods sold and interest. The IRS disallowed most of the deductions.

As evidence in Tax Court, the doctor showed charts listing his expenses but didn’t provide receipts or other substantiation showing the expenses were actually paid. He also failed to account for the portion of expenses attributable to personal activity.

The court disallowed the deductions stating that his charts weren’t enough and didn’t substantiate that the expenses were ordinary and necessary in his business. It noted that “even an otherwise deductible expense may be denied without sufficient substantiation.” The doctor also didn’t qualify to take home office deductions because he didn’t prove it was his principal place of business. (TC Memo 2022-1)

Share:

Accounting That Speaks your Language

More Resources

How businesses can fund a buy-sell agreement

The next estimated tax payment deadline is coming up soon

Clients

Knowledge for Any Industry

Retail

View Client

Restaurants

View Client

Real Estate

View Client

Private Equity

View Client

Not for Profit

View Client

Manufacturing

View Client

Legal

View Client

Jewelry

View Client

Insurance

View Client

Health Care

View Client

Food Services

View Client

Fashion & Apparel

View Client

Sports & Entertainment

View Client

Distribution & Wholesale

View Client

Construction

View Client

Technology & Startups

View Client

Art Galleries

View Client

News + Resources

The Latest from DDK

Want to get insights right to your inbox? Subscribe to get timely alerts from DDK.
* indicates required

How businesses can fund a buy-sell agreement

The next estimated tax payment deadline is coming up soon

How can your business set the stage for organic sales growth?

Safe harbor 401(k)s offer businesses a simpler route to a retirement plan

Get Started

We’re Always Ready to Talk and Listen

Whether you have a quick question or need long-term financial strategy, our team is here to help.

Manhattan

1 Penn Plaza, Suite 660
New York, NY 10119

Long Island

50 Jericho Quadrangle, Suite 220
Jericho, NY 11753

Contact Us

© 2025 DDK & Company - All Rights Reserved.
Privacy Policy
Privacy Overview

This website uses cookies so that we can provide you with the best user experience possible. Cookie information is stored in your browser and performs functions such as recognising you when you return to our website and helping our team to understand which sections of the website you find most interesting and useful.