Taxation Procrastination

My job is handled as freelance or independent contractor, which means nobody is withholding anything toward my taxes, and this is the time of year I dread. Time to do the tax return. I’m putting it off as long as possible, but I’ll need to cave soon because we need to know how much more money we need to funnel into savings to pay what we’ll owe.


I’ve always done our taxes, which is kind of insane, given that I could most kindly be called mathematically remedial. I lost checkbook privileges in 1990, shortly after we bought our first house. We were buying a lot of stuff, and I neglected to write down about half of this and couldn’t be bothered forgot to balance the checkbook for four months. This resulted in some unfortunate consequences.

This task was a lot less difficult and unpleasant when I worked a regular, tax-withholding job. Now, I know I can deduct certain expenses related to my job, such as my Office 365 subscription, book marketing and promotion, and theoretically part of my internet charges and mortgage. I’ve never figured out how to do this because it seems very complicated and I suspect it involves numbers.

All year, I funnel as much of my income as possible into savings, so I can give it all back in April when I pay taxes. I leave enough in my checking account for my personal expenses. I also keep enough on hand to pay for a lot of dog stuff, including vet visits, grooming, their freeze-dried raw dog food, and the spendy but healthy chew treats I order from Best Bully Sticks.

At times, this all feels really stupid. I work long days simply to save enough to pay the taxes on the money I earn. I look at the savings account, and think, “Wow, that’s enough money for a really nice vacation, or a new deck, or to upgrade the kitchen, or do some landscaping.” But…no vacation, deck, kitchen, or landscaping for us. The savings account will by empty on April 15, and the only thing I’ll have to show for it is not being in federal prison.



I know I get benefits from the taxes we pay. Roads, parks, schools, a military to defend me, social security (which would be extra great if I could foresee any time we would actually be able to retire), public libraries…

But I also get arrogant, self-serving, clueless politicians with hidden agendas. And I do not get any sort of guaranteed healthcare, aside from a small subsidy to assist with my insurance premiums.

Friends in other countries are horrified when I tell them how much I pay per month for my health coverage, and how little I actually receive for this. Yes, I have insurance so if I am struck by a meteor or contract leprosy, we might not lose the house. But a minor hospital visit is still a hardship.

No wonder people go to Canada for prescription drugs and Mexico for surgical treatment.

I had a paragraph here about the current political climate and administration, but it made my guts feel like they were full of ground glass and barbed wire, and the last time I went to the doctor for that it cost me $4000, so…

Sometimes, I think about giving up the job and just taking a few private editing jobs for “pocket money.” But I’m in that gray area where that would mean paying a lot less in taxes, but I might not be able to help out as much or afford some of the dog-related luxuries–like regular grooming and vet care–that I currently finance.

I don’t know. If I were better with math, I could crunch the numbers and calculate whether working as much as I do is as beneficial as it should be. I do enjoy the job itself, and it keeps me busy and (mostly) out of trouble and allows me to feel less irresponsible when I hit the “buy now with one click” button on my Amazon cart full of a bunch of new dog toys.


Click it. Go ahead. Cliiiiiiiick it. It’s for us, right? Of course it is. Click!

Maybe I can get Mozzie and Oliver designated as editorial assistants, then all their food and toys and treats could be business expenses. Oliver is a standard poodle and Mozzie is a golden, so they collectively have enough intelligence that I should probably just hire them to do my taxes.

Worst case scenario, if the IRS comes to haul me away, they could distract them with their cuteness and give me time to escape.

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