What I’ve Learned from Doing My Taxes

It’s strange.  I shouldn’t dislike doing taxes so much.  They shouldn’t make me grumbly at all.  Mine are easy compared to most people.

And I love nothing more than to be incredibly organized and have a system for everything, so taxes should just be like everything else.  It should feel good to be filing away items and adding them up.

But my setup for taxes over the years has never been perfect.

I have tried different filing systems – accordion files, file folders, receipt envelopes.  Nothing has really ever kept me fully organized like other methods I’ve set up in my office.  It’s been driving me crazy because it is what kept me from wanting to do my taxes.  Those piles and piles of receipts to sort through?  Ugh.  Please.  I’d almost rather go to the dentist.


But in assessing my systems over the years, I realized that if I combined a few of them instead of trying to rely on just one, I’d have the perfect set up.

I have a metal box that I pop my daily receipts in so that I get them out of my wallet and somewhere where I can find them.  I also keep accordion file at the front of my filing cabinet, where I keep my copies of courier receipts (you should see how big these things are and how many pages they can get up to), writing income, medical receipts (this have most certainly become bigger over the years too), etc., that keeps them filed into neat categories so that at the end of the year, I simply pull out each section and add them up.

What I realize that had been clogging my system all of these years is that I used to try and categorize ALL of my receipts.  I would have a big box of them, thinking that all I had to do was eventually go through and sort them.  You know, like once a week.

I never did this – who wants to spend time sorting through receipts when you could be out for a walk or having a nice meal at a restaurant?

So the big box became this burden at the end of the year and thus, taxes become a Herculean task that I never wanted to do.

I just did my taxes for this year, after dreading it something awful.  And you know what?  It was okay.  I wouldn’t do it instead of going to a show or having friends over, but it was really fine.  Almost fun, if you can believe it.

How can this help you though?

1.  Keep changing things up until you find something that works

Your needs will change over the years, so be sure to change your systems.  One thing I realized is that I used to purchase more, so I had more receipts.  This has significantly decreased, which helps with the amount of sales slips that I have to go through and add up.

Try out different containers, move things to a different room all together or get rid of something you’ve been using for years in order to try something new.  Products change and get better over time, so maybe there’s something better out there than that plastic file folder from 1993.

2.  Be open to change

One area I have never managed well is email. As a freelance writer, I write about 10 different topics on a regular basis. This means that I am getting emails by the ton. And despite trying different systems over the years, only in the last week have I stumbled onto something that works.

It could be just timing – I had exhausted so many other possibilities that this is best only by comparison. Or perhaps my needs are different now than they were a year ago. Or maybe my expectations.  It doesn’t matter.  What does matter is that I am open to change, to new ways of doing things.  This always leads me to finding systems that do work for me.  And the more smoothly things flow, the less time they take and the more time I have to do things that I enjoy.

3. Enjoy the routine things in your life

If you hate doing the dishes, taxes, clipping your nails – anything that has to be done over and over again, you’re going to have a miserable time.

If you can find a way to embrace these things, it will change your entire outlook and being.

I certainly don’t love washing the dishes, doing the laundry or having to create invoices, but I do try and make the best of these tasks (I don’t call them chores, because that makes them sound just awful.  Sometimes just the change of language helps…).  I use the time when I’m washing the dishes to let my mind go free and unfurl from the stresses of the day.  For taxes, I got myself a really nice calculator – it’s big and pretty and fun to use, unlike my old small one that I could barely make out the numbers.

It might be a small thing, but oh what a difference it makes!

I wish you well with your taxes this year.  I hope that they stop bringing you angst and worry and instead are just a few hours out of your day that you can then reward yourself with something wonderful.

Stephanie Dickison is the author of the recent book, The 30-Second Commute: A Non-Fiction Comedy About Writing & Working From Home, which covers her career as book, music and restaurant critic.  She has been a journalist for over a decade and now spends much of her time writing about travel, food, beauty, style and celebrities for various publications and websites.

When she’s not writing, she’s eating, cooking, organizing, filing, making lists in sumptuous notebooks (you must use your beautiful journals) and colour-coding her ever evolving calendar.

She is one of the few writers still using technology AND paper.  But at least her paper is organized into pretty file folders…