Speaking of Taxes

Catherine Price’s Salon article really could have come in handy last year, but at least I’ll reference it for next year:

I could never be happy in a traditional job. I hate fluorescent

lights. I detest working in groups. While I can get interested in just

about anything, nothing interests me enough for it to be a full-time

career. Also — and, to me, this is no small thing — the smell of

office carpet makes me existentially depressed.

So I became a freelancer — thus joining the growing armada of the

self-employed who sit at the same cafe table every day and thrust their

business cards in your face during casual conversation. For the most

part, it is a satisfying existence, a life of freedom and flexibility

and almost no personal connection to “The Office.” Then there are days

when the clock slips past noon, but I haven’t been outside, I haven’t

spoken to another human being, and I start to wonder if I’m going to

wake up one morning when I’m 70 and regret never having owned a


That was the sort of mood I was in on April 14 of last year, when I took out the tax forms I’d picked up at the library and started trying to wade through my finances.

I was still wearing the clothes I’d fallen asleep in the night before

and now was facing a floor covered with 1099s, a few W-2s, and those

pesky “estimated tax payment” envelopes that I never remembered to send


About eight hours later, I was still sitting in my room and the sun

was going down. I had reached my yearly tax breaking point, the moment

each April when I realize that, while they are technically written in

English, I have no idea what any of the documents I am reading actually

mean. I had, however, discovered for the umpteenth time that not

sending in quarterly tax payments meant I owed the government interest,

that I had to pay an additional 15 percent in self-employment tax (the

way the government collects Social Security and Medicare/Medicaid

payments from the self-employed), and that I hadn’t kept good enough

track of my receipts. Taxes are hard for everyone — but for the

freelancer, they’re a special kind of hell, one where the devil sips

martinis as you weep in the corner, struggling through your Schedule C.

What comes after are ten tips on how to be master of your tax domain, including one seemingly counterintuitive one:

Do not own a coffeemaker. I know this goes against the wisdom of

those budgeting articles (the money you save on lattes could pay for

your child’s college education!). But it’s critical for your mental

health to leave the house at least once a day and interact with real,

live humans — even if you are only talking about Starbucks. So here’s

a compromise: Identify the cheapest drink that you enjoy. Then

calculate how much it costs — in my case, $1.50 for iced tea —

compared to a $100 therapy session in which you talk about how lonely

and depressed you are. My guess? That iced tea is a bargain.

Or you could always walk in the park or something….