This Genius Tax Day Trick Helped Me Finally Not Hate Filing My Taxes

For a few hours on one day every year, I enter the pit of despair à la “The Princess Bride.” Except instead of succumbing to a fictional life-sucking machine, I log onto a real IRS-approved website and file my taxes. Nobody likes doing their taxes, I know, but I fear I have an unhealthy hatred for this annual ritual. Despite having some of the least complicated forms to file, the process is capable of ruining my entire day — which is why I often put it off until the very month they’re due.

But this year, I thought, there must be a better way. And then I remembered my parents, and how they’ve always been kind of cheerful about filing their taxes. Why? They make a date out of it. 

Since I was young, they would each put on a slightly-nicer-than-everyday outfit and make a day out of driving to their tax professional’s office, dropping off their paperwork, and doing something simple together, like grabbing lunch, trying out a new coffee shop, or taking a scenic drive. Seeing as my mom is the person I call in the middle of my inevitable W-2 breakdown, I decided this time-tested approach to making tax day more palatable was worth a shot. I made a simple plan: I would sandwich this task I hate with things I love, and trick my brain into getting through it by taking myself on a date.

The result: My taxes are done, with time to spare! And, I actually had a really good day. Here’s my new three-step plan for making it through tax day without absolutely losing it. 

The day you do your taxes is not the day to experiment with going without coffee. I placed a pick-up order at the cafe down the block from my apartment and put on an outfit I felt cute in. Since public WiFi is not a good match for online forms with sensitive information, I took an extra loop in my walk before bringing the Americano back to my desk to dig in. 

If coffee isn’t part of your morning ritual, maybe this step looks like whipping up a tea latte with your matcha set, spending time doing a fun makeup look, or starting the morning with a meditation you love. Whatever it is, kicking off the day with something you’re excited to do is, in my experience, a good way to get the momentum going. And for me, putting taxes off until the end of the day slightly taints the earlier parts, so why not get it over with?

I am a proponent of the concept of romanticizing your life, but I’ve never allowed myself to view filing taxes as anything other than a cursèd obligation. And rightfully so, I would argue: It’s not just the baffling guessing game of how much money I’ll owe or not owe. It’s the confusing names for everything. It’s the filling out forms of it all.

But in an effort to make this year’s process somewhat painless, I decided to take a step back. What would I do if I were setting the scene for dinner with a friend, instead of typing numbers into a computer? I opened my blinds to let the sunshine in. I lit a new candle that smells incredible. I set my phone to the side so I could be present. And then I just… filled out the forms. This part was boring, I don’t like doing it! But the room was sunny and smelled nice and I was already dressed for the day. 

This is the most crucial step: Take yourself on a date, for real. Go to the theater and see the movie you didn’t get a chance to see before the Oscars. Make plans with a friend to take a day trip to a nearby site. Get a day pass to a museum you’ve never been to. Go for a really nice walk and call your favorite person to talk to. 

I booked a hair appointment for the early afternoon, so not only did I have a deadline for clicking submit but I also had something to look forward to. Then, I texted my sister to see if she wanted to meet up after. She did, and we ended up popping into a thrift store, trying out a new bakery, and going for a walk around a local arboretum. By the time I was polishing off my almond croissant, I’d all but forgotten about my taxes.