Don't cheat the IRS

Six women eat pizza for dinner. The check comes to $16 per woman, including tip, and each pays cash. As the waitress collects the ones and fives, one woman – then another and another and another – requests a receipt for the full amount. The waitress obliges, and four self-employed women with tax deductions sweeter than chocolate and ethics lower than the subway walk out with receipts for $96. 

I’m self-employed, too, but I’m stunned. “Oh, but it’s deductible,” one warbles. I know. “Oh, but you can only deduct half,” chirps another. True, I can fleece only half of what I spent for mushroom and broccoli topping. “Just write down my name, and say you’ve taken me out to dinner.” For 96 bucks? You irresponsible, immoral cheater.

It’s tax time, and as I organize my receipts, I wonder whether cheating is a good idea. For years I’ve been candidly clean, but I’ve started to wonder: If so many people in my supper survey cheat, why shouldn’t I?

Neither rich people nor poor like to pay income taxes, but most pay anyway. We read that the excessively wealthy are wrapped in loopholes the size of their cars, and that the tax system, created by our clever elected officials, helps the haves keep what they have. We know that poor people squeak by, paying taxes, sometimes, even on Social Security and food stamps.

But what about us poor suckers in home-based business? We deduct every pencil we purchase, every Post-It, every printer cartridge. Computers are necessities, and some folks, it seems, require new tablets and smartphones as often as Best Buy runs sales. 

Many deductions are legit, but sometimes one wonders. Once I consulted for a successful family business whose founder/president ran the company from lavish quarters facing Rittenhouse Square. The centerpiece of the office was a thrilling, 4-foot-tall copper Russian samovar, outfitted to brew coffee instead of just boiling water. As I drank its coffee, I deduced that this was the biggest tax diversion I’d ever seen in an office. (But I don’t get around much.) 

The guy liked it, had the money to buy it, had it outfitted to suit his specs – and then deducted it? Loophole or swindle? I’ll never know. But if he did, who ended up paying Uncle Sam that sum? Probably the rest of us.

So what’s on my deductible list this year? Less on postage every year, even though stamps used to be cheaper. Dues, meetings and publications. My bookkeeper/lifesaver. My computer guru/lifesaver.

Tax deductions are slippery and slithery. They slide from slightly-off-the-mark to aching-not-to-be-audited. Apparently the IRS audits fewer people than before, but I’m still chicken to cheat. 

I’ll pay for my mushroom pizza; you pay for your onions, OK? That way I can send the IRS my due and still respect my dinner partners in the morning.

Published in the Philadelphia Inquirer under a previous tax law.