When I start to think about tax preparation, usually New Year’s Day, there’s a chipmunk in my stomach that wakes up to rummage around, causing mild anxiety. Then the sarcastic, critical voice in my head starts in…

“Yeah, I told you! The time to begin tax prep is in December of the previous year! But no! You had more important things to do!” Which means that even as early as January I was feeling guilty for not preparing my tax filing.  

Procrastinating the Dreaded Tax Filing

Tax experts estimate that up to 50% of us put off tax preparation and filing until the last minute, or at least 1 in 3, depending on your source. Many of us find the task incredibly brain-numbingly daunting, whether we’re filing individually or on behalf of multiple businesses. So we put it off, kick the can down the road, procrastinate.

Whether this is the your first year for tax filing or you’ve been doing it for a while, what can stop us cold is the horrifying reality that we have to do this every single year for the rest of our lives! So we better get our shit together. 

If you are a life-long, chronic procrastinator like me, not just for tax stuff, you’re probably familiar with the vicious cycle of avoiding the dreadful thing. It goes something like this: 

  1. Something causes anxiety. 
  2. Avoid it, which lowers anxiety. Avoidance works!
  3. Feel guilty about avoiding it. 
  4. The thing that causes anxiety is still out there. Anxiety builds.
  5. Repeat.

I know this cycle so well. I put it in our Explore What’s Next logo. It’s the anxiety hill. The lesson I have to learn over and over again is that by actually doing the thing I avoid I get over the top of the hill and onto the other side where the anxiety lowers and the thing that caused so much distress really isn’t as bad as I imagined and finally is behind me.

How to break the procrastination cycle and reduce anxiety? Here are some tips that work for me.

Breaking The Tax Filing Procrastination Cycle

  • Create a real deadline that you must be accountable for. Plan on having your filing in at least a week before the official federal date of April 15. If you use an accountant, for example, talk with them and make an appointment that works for both of you.. It doesn’t have to be an accountant. It could be a sympathetic relative, a reliable friend, even your therapist, anyone who has your back without judgment. Being accountable to someone else helps a lot. I may not be great at doing things for myself but I’ll be damned if I let someone else down!
  • You can also create mini-deadlines ahead of the major one that your partner, friend or sympathetic cousin can help you keep track of.
  • Don’t overwhelm yourself. Break down the daunting task into bite, sized, chewable bits. You can do this two different ways:
    1. Complete specific tasks one at a time.
    2. using segments of time. 

Sometimes I choose to complete a specific taskone at a time, one day at a time. One day it will be make a folder for 1099s. Another day it might be, review Quickbooks accounts.

To use segments of time I start with a timer. There’s one on your phone. Set it to five, ten, fifteen, whatever, minutes. I work for the designated time until the timer goes off, then I stop. I can choose to go one for another chunk of time or not.

A Designated Tax Filing Prep Area

Choose a designated place as free of distraction as possible. You might need a place where you can leave your work alone, unattended when you walk away and know it will be safe. An office at work or at home with a desk and a door that closes is nice but not everyone has that. 

Whether it’s the dining room table, a coffee table, or a couch in the family room, make it a place where your kids, dogs, food will not mess with your tools while you’re working.

  • Gather your tools, documents. the docs, folders, bank, receipts, statements, computer, pads of paper, pencils, pens, whatever! Get them all together at your designated place.

If your designated space is a common area like the kitchen table, have a portable box for your tax stuff that you can put in a safe place when you’re not actively prepping. I like laundry baskets for this purpose. They are the right size and have those nice handles.

Communicate With Those That Matter

  • Let your family, roommates, whoever is around, know your intention, ask for their support. Let them know it’s time limited, just this much time and then we can do something together.
  • Now you can go month by month, there are only twelve, and fill out the amounts that go into each category. For me, going month by month is less intimidating. Later I can do the grand annual totals. It might take a week to go through it all but everyday feels like such an accomplishment!
  • Lighten up! You get to pay taxes! Yay! Haha! Play music! Get up and dance whenever you want! Have your favorite beverage handy. And chocolate. Lots of chocolate!

When you add it all up and hand it over to Uncle Sam, reward yourself! You’ve done the hard thing so now it’s time to do whatever it is you’ve put off, a mani-pedi (my favorite), a meal with a pal at your special occasion restaurant, play video games! Then vow to never procrastinate doing tax prep ever again! This is a lie, of course, but it feels good for a moment to imagine this is a new year and we can reform!

dr aletta