Secret Letters: Diary of Tax Day(s) 💵
I am a self-employed writer, and I am determined to not make Tax Day the worst day ever. Here is my tax day(s) diary.
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A Tax Day(s) Diary 💵
I am not one of those souls who rushes to get her taxes done as soon as her 1099’s arrive in the mail. I do not have an accountant who reminds me to send along my documents once the New Year arrives. And I refuse to buy into the narrative that freelancing is a less desirable lifestyle because one generally owes money to the IRS come springtime.
Handling slightly more labor-intensive taxes throughout the year is part of being self-employed full-time. After a few years, you get used to process of setting aside your predicted taxes. For me, doing my taxes with nary a W-2 in sight reminds me that I really am doing it. I really am living full-time as a creative.
Recently, I’ve been reading William Deresiewicz’s The Death of the Artist: How Creators are Struggling to Survive in the Age of Billionaires and Big Tech. He makes a great point early in the book about how creative professionals participate in the creative economy primarily by front-loading their investment—for example, you have to invest the time to write a novel before you can attempt to get a book deal. In order to make this investment, creative professionals have to organize their life such that they can “devote the lion’s share of their energy to producing” that art. This is 100% what freelancing looks like: I’ve organized my life so that I can focus my energy on making things.
Here is how Deresiewicz says it:
Can we live without artists, professional ones? The tech evangelists would have us think so. We’ve returned, they insist, to the golden age of the amateur. Folk production, just like in the good old days. So of all that art that you consume, how much is actually created by amateurs? Other than your roommate’s band, probably not very much. Have you seen your cousin’s improv troupe? Is that the only kind of art you want to have available, not only for the rest of your life but for the rest of foreseeable history? Yes, you’ll have access to everything, but what will you have access to? Someone else’s roommate’s band? Great art, even good art, relies on the existence of individuals who are able to devote the lion’s share of their energy to producing it—in other words, professionals. Amateur creativity is no doubt a wonderful thing for those who engage in it. It should not be confused with the genuine article.
So, here is my tax day(s) diary from April 16-17. I thought you might like to get a peek into what these last days before the tax deadline look like for one writer. ✍️
April 16th: Day One 💰
8 am - 12 pm
Get up, make myself a cup of coffee, feed the crying (desperate, starving, never emotionally satisfied) cat, and then sit down at my desk to keep working on a collaborative script called The Brechtfast Club that I’m writing with my friend Lucy. (It’s a parody of John Hughes’ The Breakfast Club, but make it *Brechtian.*) Rehearsals start on April 25th, and the script only has thirty pages so far. I write two steady pages and then get hungry.
Instead of making myself breakfast, I go ahead and make an Instacart order, which is not the greatest idea since I’m picking out groceries while hungry (cardinal mistake).
I order too many groceries and make myself a smoothie.
I think a little about what movie I’m going to put on while I do my taxes today. The entire process of firing up Turbo Tax and submitting my payment takes less than two hours. It’s the perfect amount of time to put on a relaxing movie (like Amelie or Chocolat or even Sister Act) and just get the task done.
12 pm - 2 pm
When the groceries arrive, I put them away and pat myself on the back for ordering so many fruits and vegetables. Then I get back to writing.
I’m trying to find a way to parody the famous “Detention Dance” from The Breakfast Club in a play set in East Germany right before the Wall is about to fall.
Things are rolling with this script. Because I know the concept, structure, and the ending, the hardest task is just getting words drafted. But I’m moving this morning. It feels fantastic. I remember that I’ve been working my whole writing life to get to the place where I can write with this speed and unselfconsciousness.