A self-employed caterer recently asked me:"I cut my hand while prepping food before a big event...

A self-employed caterer recently asked me:

"I cut my hand while prepping food before a big event, but instead of going to the hospital (which was covered in full by insurance), I paid $500 for a doctor to come to my worksite and stitch up the wound so I could stay on schedule instead of incurring a huge loss and an unhappy customer. Can I deduct that?"

Here is the breakdown:

Medical expenses are generally considered personal under IRS rules, even if they happen during work hours.

However, in this case, the medical care itself was free and the $500 was a business driven decision to avoid downtime and disruption before a critical deadline. The argument? This wasn’t about health care; it was about protecting income.

We approached this carefully, categorizing the payment as part of broader professional services, not as a medical deduction.

While aggressive positions should be avoided, reasoned and well documented ones can be defensible, especially when the goal is business continuity, not personal benefit.

Yes, there is still some risk a super strict auditor may disallow this, but the caterer had a very good argument why this was ordinary and necessary for his business.

Always think before you deduct, but don’t automatically say “no” to an expense just because it involves a doctor.