It’s tax season in Canada. Every year I sift through a year’s worth of receipts, grab stuff from all over the house and web, and package it all up for my accountant. I had an home-brewed Excel summary format I’ve been using for over a decade and it is meh.
Of course this called for an AI assist this year. The key data point for me, in thinking about how professions will change in the coming years, is that clients will come better prepared, presumably with both better inputs and questions. And yes of course I wonder at what point I’d be comfortable just doing it myself.
I now have:
- Much better knowledge of what the professional will be looking for and why
- A new format far better aligned to what their needs
- Better questions and a clear expectation for how I expect the returns will go
- A new filing system and workflow that I could further optimize next year. In particular, including an Inbox for dumping files which could potentially trigger automated periodic processing (because why wait until the end for this brutal process – why not have it happen automatically and even alert me to any concerns)
Receipt image processing (Feb 2026): (I know there are many SaaS solutions for this): Asking Gemini and Claude to parse photos of 20+ receipts still does not work. Gemini was strongest and would max out on photos of around 7 receipts.
Browser Automation is both wild and feels like a transitional kludge: Grinding through service provider sites to download invoices is now an Agent task, between now and whenever some protocol gets widely adopted to make that go away.
Next year’s tax season is going to be noticeably smoother.