Simon Says... Tax Season Is Giving Me An Existential Crisis
If I get one more 1099 form, I think I'll die.
Welcome to Simon Says, a weekly newsletter from Rachel Simon all about freelance life—from the inside scoop on just-published stories to advice on how to pitch to what it’s *really* like to leave a cozy full-time gig for the chaotic, unpredictable world of invoicing (jk, freelancing, but IYKYK).
You know something I hadn’t given that much thought before going all in on freelancing? Tax season. I’m not talking about having to keep a close eye on my finances all year long, since so much of most freelancers’ pay is dropped into our bank accounts pre-tax, meaning we end up owing some big $$ come filing time—I was prepared for that! I’m talking about the sheer number of forms involved with filing taxes as a freelancer: 1099s, W-2s, all the other types of paperwork that I definitely should know the names of but don’t. Like right now, I have seven different tax forms on my desk, and at least five or six more virtual ones in my inbox. And I’m still waiting on a bunch of others! It’s a lot.
As a freelancer, it’s my job to make sure that each publication I write for (and each school I teach with) sends me the right forms, and while some places are super on top of their shit and sent their tax stuff out like, two months ago, a bunch of others are… not. So pretty soon, I’m going to have to figure out every place I’m missing info from, track them all down, and then organize all the documents into one not-so-neat pile for a professional to make sense of (because god knows I certainly can’t. I’m a writer for a reason! I avoid math at all costs!).
It’s overwhelming, and expensive, but it’s a very real part of freelance life. I signed up for the good and the bad, and so if I have to have a mini existential crisis around tax season because oh my god there are so many goddamn papers and what am I doing writing for all these places anyway and wait am I even good at writing oh my god what if I’m not, so be it. Onwards!
Some Stories I Wrote Last Week
I actually only had one story published this week, because I’ve been pitching way less than usual due to that big project I’ve been talking about and a few other larger work commitments. But it’s a fun one, if I do say so myself!
It’s a roundup of 18 Valentine’s Day-themed pet gifts you can buy from Amazon (organized by price point), including heart-shaped toys, pink doggy sweaters, and even a cat tunnel featuring little hearts hanging down for the kitties to bat as they explore. Read it on People now if you’re looking to spoil your pets with some goodies this holiday.
The Inside Scoop
Each week, I’ll pick one story I’ve written (new or old, if needed) and explain how it got from pitch/assignment to publication. This week, it’s the People story on the VDay pet gifts (duh).
My editor asked me to send over some pet-centric ideas because those kinds of stories had been doing well for the publications she manages, so I pitched a roundup of VDay-themed dog toys and clothes from Target (I’d taken a look at the site and seen that they had a wide array of options). She liked the concept, but asked me to make three key changes: 1) pull the items from Amazon instead (since Amazon shopping stories were doing especially well); 2) break down the items by price point (aka under $10, under $25, and under $50, and 3) include a few cat products on the list, as well. All smart ideas that made the story more inclusive and easier to navigate!
Other Work/Life Stuff Of Note
I’ve been creating some custom crosswords for people’s weddings, which has been super cool! They’re themed around the couple getting married (i.e. “name of the college where they met”) and are given to their guests as gifts during or after the party. If you’re getting married and want one yourself (or know someone who might), order one here or shoot me a message if you have questions.
Speaking of weddings, ours is coming up in a little over two months (!) and our guest room now looks like… this.
At least Mim Mim’s happy.
Coming Up…
A few stories I’ve been waiting on should be published this coming week, I believe. But who knows! There’s always some delay…
Have a great week, everyone, and thanks for reading!
-Rachel