How to overcome tax procrastination and confusion

Accordion Receipt File

How to overcome tax procrastination and confusion

EEven seeing the word taxes” at the top of this article gives me the willies. I am definitely not an accountant, but I have done a lot of research over the years about what I can “write off” as a self-employed artist. And while the practical details of this process are undoubtedly important, what I want to focus on this week—what I am going to try to help myself, and you, work through—are those emotions associated with taxes and money, so that we can approach that huge pile of receipts sitting in front of us with confidence.

Step 1: Acknowledge procrastination.

Say to yourself and to someone else, I am procrastinating on my taxes.” Instead of waiting until the urgency of the tax deadline necessitates immediate action, take notice of those emotions concerning money that are causing you to procrastinate. This can be done through journal-writing, meditating, daydreaming, talking to your best friend, talking to your mother, making some art, or even writing a blog post. [winky face]


When I reluctantly lift the rug of indifference, I find two main emotions underneath: anger and shame—anger at the government for its continued oppressive practices and its slow and ineffective policy-making. I am angry at my student loans and interest rates for existing, angry at my past self for buying things on credit, angry at the privilege and power of white men that make society and government policy sway in their favour to the detriment of basically everyone else. I’m angry at myself for even being angry, since I have so much more privilege than so many others. As for shame, I feel it about my debt and my difficulty saving money. I’m ashamed about being 30 years old and still not having my shit together, ashamed about not speaking out enough against the stuff I’m angry about, ashamed about not being a better singer—one that could easily just win a singing competition and pay off my loans in one fell swoop.


That’s a lot of intense emotion, and it felt good to get that out onto the page. Thanks for listening. Maybe some of your feelings are similar, and maybe they’re  different. Maybe you have emotions about my emotions. That’s ok. Just get them out somehow, so you can establish an arms-length perspective on what you are dealing with.


If you have a lot of emotion surrounding money (like I do), it might help to use the “tapping” technique, or EFT (Emotional Freedom Technique). I often use it when I feel stuck in a certain emotional rut and can’t shake the feeling no matter how much I externalize it.


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If you want to delve deeper into your relationship with money, I recommend Kate Northrup’s book Money: A Love Story” (Buy on IndieBound/Buy on I will be reviewing the book in detail on this site at some point, but wanted to mention it now. The tools and perspective Northrup offers are transforming the way I think about my money, and I am really grateful for that. The book does not satisfactorily acknowledge or critique the oppression inherent in the system that makes it more difficult for certain people to make money, and while the target audience is women, it is written from a heteronormative perspective. If you are able to work with these shortcomings, the book has great potential to help you navigate financial challenges within the context of capitalism.

Step 2: Make a plan.

How will you file your taxes? If you are using an accountant, do you have one in mind that you can call? Do you have a good relationship with your accountant, or do you need to find a new one? Do you use online software to file your taxes? Do you fill out the forms manually, on your own? Most importantly, evaluate what you did last year, if it worked for you, and if you need to change your approach. If you can take this step a month or two before the deadline, it will allow you to make the best choice for your situation, instead of using the quickest, less-ideal option.


When will you file your taxes? How long does your accountant need to process your file? How many hours does it usually take you to complete the process yourself? Set times, and keep your date with your taxes. I file my taxes using an online application, and I usually plan about an hour to do it. In reality, it usually takes me 3-4 hours. So, I recommend planning to spend as much time with your taxes as you would on a date with a friend that you haven’t seen in several months.


What kinds of documents do you need to gather and submit in order to file your taxes this year?  Are you a student? An artist? On some form of social assistance? Working full or part time? Self-employed? Make a list (using Google if necessary), and then gather the documents all in one place. Your list may include the following:
  • Receipts for business or art expenses
  • Public Transit receipts
  • Prescription drug receipts
  • T4, T5007, or other documents that show your income
  • Tax documents from your student loan providers, if you have them


If you’re self-employed or an artist, congratulations! You have now created your annual mountain of receipts. And if you’re Canadian, I have a little tool to share with you. I have developed a simple and elegant spreadsheet that I use to enter all of my receipts. It includes two pages—one to enter individual transactions, complete with a dropdown menu to place each transaction into its official tax-deductible category. The second page calculates the total amount you have entered for each category, complete with line numbers. It contains most categories for which an artist in Canada would deduct. You can get it here for the price of a couple of vegan tacos at your local anarchist café (shoutout to Le Cagibi in Montreal, where I wrote this article while eating tacos!).

The button above will bring you to Paypal. After payment is processed, click the link to return to Quill. You will be directed to a download page. The receipt counter-upper tool is a spreadsheet template that opens in your Google Drive – you need an account with Google in order to use it. If you have low income and want access to this tool, please send me an email.

This tool works well if you’re adding up receipts last-minute, but it’s also a great tool if you want to enter receipts on the go. My personal process looks something like this.
  1. After a gig, I empty out my suitcase/wallet/pockets to find all the receipts for expenses I incurred during the time I was working on the piece. Sometimes this involves travel, in which case I print receipts from my travel tickets, hotels, or anything that is stored in my email account. I dispose of receipts for non-eligible expenses.
  2. Processing each receipt separately, I enter it into my receipt counter-upper tool. I number each receipt and make a note if the information on the receipt is not clear enough for me to remember which purchase it represents. As a general rule, I try to imagine what it would be like if a tax auditor was looking through my receipts, asking myself what information I would wish I had recorded.
  3. I stuff all my numbered receipts into a large envelope with the current year written on it.
  4. If I can’t enter the receipts into the counter-upper tool right away, I use a small accordion receipt file, with labelled sections for my most frequently-used deduction categories. I physically file each receipt until I am able to digitally file it and stuff it, numbered, into my large envelope.
Accordion Receipt File

My physical receipt filing system

Step 3: Pat yourself on the back, and make an extra delicious sandwich.

Doing your taxes is time-consuming and hard emotional work, because it can unearth all sorts of feelings about society, your past decisions, the patriarchy, the government, personal agency or lack thereof, family, and the future. Celebrate, since it’s finally over… until next year.
All my love,

Rebecca Woodmass



P. S. I just couldn’t let you go without mentioning my friend Chris’s helpful and entertaining finance blog, ‘Rags to Reasonable‘. He’s a singer, actor, and money geek who specializes in helping artists. He has really reasonable rates for financial advising, too (full disclosure – he’s my financial advisor!). He published a series of posts on taxes (mostly for Canadians) here.


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