In general, you should be prepared to show the IRS documentation of any expense you deduct and be prepared to explain why the expense is both ordinary and necessary.
Examples of expenses that DON'T qualify as ordinary and necessary include:
- Expenses of commuting to and from a regular workplace
- Federal income tax payments
- Country club or other similar membership dues
- Lobbying expenses or political contributions
- Penalties and fines paid after breaking a law
- Clothing, unless it's required to be worn for your business and can't be worn for everyday wear
- Personal, living, and family expenses