Steve Strauss: Let's hear it for taxes! Wait, what?

Q: Steve, Can I just say that the thing I really don’t like about being self-employed is that doing my taxes is so much more difficult than when I had a job. It almost makes me want to go back to the bad old days of having a boss . . . almost! – Ken

A: No, no one enjoys doing their taxes, but let me be a contrarian for a moment (or more than a moment if you ask my wife):

Taxes are actually one of the best things about being self-employed, not one of the worst.

Let me explain with a personal story. My first real job was with a big law firm in San Francisco. Although I no longer practice (having come to my senses long ago, thank you very much), back then, keeping up with expectations was pricey. I had to own several expensive suits, go out to lunch every day (and take people to lunch), grab cabs to and from the courthouse (this was long before Uber boys and girls), take continuing legal education, and so forth.

As I said, it wasn’t cheap. What made matters worse was that none of these expenses were tax deductible because I worked for someone else and didn’t own my own business.

All of that changed when I went off on my own, hung my shingle, and started my own law office. Seemingly everything became deductible and I became goodtime Charlie. “Lunch is on me!” “No worries, I’ll pick up the fare!”

My wallet became George Costanza-esque, bulging with receipts.

The IRS says that when you are self-employed or otherwise own a business, all “ordinary and necessary” business expenses are deductible from your gross income. According to IRS.gov,

“An ordinary expense is one that is common and accepted in your trade or business. A necessary expense is one that is helpful and appropriate for your trade or business. An expense does not have to be indispensable to be considered necessary.”

Do you see what a boon that is, why I say that taxes are your friend and not your enemy when you own a business? No, I am not telling you that that TV you charged is tax-deductible (unless you use it for business) but what I am telling you is that a whole host of things that you paid for when you had a boss are deductible when you are the boss. Consider:

Auto expenses: While you cannot deduct the cost of your commute (Uncle Sam says that is personal expense), other business related mileage is in fact deductible, for example, driving to meet a supplier.

Tickets to a show or the game: If you are taking a business colleague out, that is a deductible entertainment expense (50% of the cost).

Healthcare: Let’s not step into the healthcare minefield except to say that when you are self-employed and you buy your own insurance, it is tax deductible.

Home office: That extra bedroom becomes a sweet business expense if you start to use it for your business. Here’s the rule: The part of your home that you use for business can be deducted if it is 1) used exclusively for the business, and 2) is your principle place of business or where you regularly meet with customers.

Your office supplies are also a deduction.

Periodicals: Magazines, newspapers, websites, and other content you purchase for business fit the bill.

Professional licenses and association dues: While I have always had to pay bar association dues, they became a deductible expense after I started my own business.

Are you sensing a pattern here? I hope so. The point is, while nothing is certain but death and taxes, at least taxes are a little less painful when you own your own business.

Steve Strauss, @Steve Strauss on Twitter, is a lawyer specializing in small business and entrepreneurship and has been writing for USATODAY.com for 20 years. E-mail: sstrauss@mrallbiz.com. Website: TheSelfEmployed.