My first paid design invoice was dated September. When I started organizing taxes, I used that date as the beginning of everything.
Then I found a July domain receipt, an August client proposal and the subscription I had bought while still deciding whether to freelance. They all said something different about what I was doing at the time.
Build a timeline, not just a pile of receipts
CRA says a business must have been carried on in the fiscal period for a business expense to be deductible. Establishing when it began can require distinguishing preliminary business operations from spending made before a business actually existed. The first sale is useful evidence, but not a universal start-date rule. CRA's start-up expense guidance.
I wrote down when I offered services, approached prospective clients, accepted commitments and acquired the things needed to deliver the work. I kept proposals, emails and receipts beside those dates. The point was to describe the activity honestly, not to choose whichever date produced the largest deduction.
Keep the purchase questions separate
Even after the business start date is established, every purchase still needs its own classification. A personal experiment, ordinary operating expense and durable asset are not interchangeable. Equipment may require capital treatment; a mixed-use subscription needs a reasonable business allocation.
I also kept records of items I already owned before using them in the business. A later change to business use needs its own valuation and tax review, rather than a recreated purchase receipt.
My folder now began before September, but it didn't claim that everything in it was deductible. It gave the person preparing my return a timeline and the evidence to make that decision. That was more useful than my original rule: start at the first invoice and hope nothing earlier matters.
Checked October 20, 2026. See equipment and supplies and record retention.
