COLUMN: Don’t Mind the Mess – Confessions of a tax-time lunatic

Every year around this time, I make a solemn vow: Next year, I will be organized. I will keep meticulous records. I will have neat, labeled folders. I will NOT toss receipts into random drawers, purses, or the glove compartment of my car like some kind of financial raccoon.

And yet, here we are. Again.

Tax season. That magical time of year when the Canada Revenue Agency begins to send letters that start with “We require…” and end with a mild threat and a due date. There’s nothing quite like the thrill of opening a government envelope and feeling your stomach do an interpretive dance of anxiety and dread.

This year’s tax adventure began with a letter containing words like: “legal action” and “garnish your income” which is never a good thing. Why didn’t I open this earlier? I found it in a box which contained a gas receipt from 2019, a pen that doesn’t work, and an unopened Christmas card from a local political candidate.

What followed was a full-scale scavenger hunt through every drawer, tote, and coat pocket in my house. I found receipts crumpled inside a jacket I don’t remember buying, and in a Tupperware container labeled “Cookies?” I can’t remember why I thought that was a good hiding spot, but desperate times, right?

Meanwhile, my accountant, who has the patience of Job, waits for my documents, while I wonder if I can write off dark chocolate as a therapy expense.

I’m a creative person. My filing system is less “alphabetical” and more “emotional.” I keep receipts based on how they make me feel. That lunch with a friend where we brainstormed our new book ideas? That goes in the “Hope” file. The hardware store receipt for the wrong sized furnace filters goes in the “Regret” file. The receipt for the scented candle I lit to make my workspace more “inspirational”? The “Spiritual Expenses” category.

My Internet can be a write off, so maybe I should talk to it a bit more gently. “Thanks for the support, but can you please work just a little bit faster?”

I wonder if I can claim a portion of my Netflix subscription as “research material.” Maybe not.

But among the chaos, something surprising happened. As I sifted through piles of receipts, invoices, and oddball expenses, I began to see the shape of my year—where I went, what I did, who I helped, who helped me. The business lunches where ideas were born. The printer ink for the courses that have helped me grow as a writer. The mileage to interview amazing people with incredible stories. It was all there, hidden under the dust bunnies and chocolate wrappers.

Taxes may be a nightmare, but they also tell a story—my story. It’s not just about owing money (although, yes, let’s not talk about that number). It’s a record of the hustle, the growth, the little moments of courage when I tried something new. When I said yes to an experience even though I was terrified. When I invested in myself, even if the CRA doesn’t consider flavoured coffee, gel nails or comfy sweaters as legitimate business assets.

So yes, the letters from the CRA are ominous. The deadline is looming. My desk and my kitchen table look like a stationery store exploded. And no, I still haven’t found that one invoice from March (Where are you?), but I’m slowly digging my way out of the rubble.

Hope, it turns out, is tax-deductible after all. At least in spirit.

And next year? I will be organized. I will use folders. I will track everything in real-time. I will not hide receipts in old purses and shopping bags. Probably.

Maybe the best place to put them is in a box labelled “Chocolate” where I can count on finding them.