Improving personal tax filing with Claude CLI and Obsidian

Summary

Recently, I found myself in the same part of the year when I do my wife’s and my personal taxes here in Canada. Personal income tax filing deadline for most Canadians is usually end of April each year. It turns out this was also the first year where I had amazing AI tools at my disposal to help me with personal income taxes. Apart from work, I have been using both ChatGPT and Claude for my personal life as well, which has included varied prompts and workflows such as looking up what engine oil my car takes, or using Notion MCP to create a shopping list for building a deck in my backyard. In short, most of my personal usage has been rather rudimentary compared to my extensive and detailed workflow at work. I would not call my personal tax situation a complex one, however, given that I manage it for both me and my wife, I would want to optimize it as much as possible. While collecting all our tax related documents, forms and emails, I came up with a workflow based on Claude Code CLI and Obsidian that I found very useful in trying to get a detailed picture of my tax situation — backed by strong personal context and deterministic calculations using Python. I set up a working directory for my tax related documents and opened that as a vault in Obsidian. If you are unfamiliar with Obsidian, you are missing out a lot on what markdown can do for you especially for the agentic world so I highly recommend you familiarize yourself with this amazing tool today. Obsidian also has excellent support for viewing PDFs which I found very useful for reviewing my tax forms without leaving the app. Folder structure# Here is a sample structure that I came up with: obsidian_vault ├── main.py ├── pyproject.toml ├── README.md ├── taxation │ ├── Currency Rates │ │ ├── 2024.md │ │ ├── 2025.md │ │ └── 2026.md │ ├── Pasted image 1.png │ ├── Pasted image 2.png │ ├── PersonalTax │ │ └── 2026 │ │ ├── Wife │ │ │ ├── CLAUDE.md │ │ │ ├── Etrade Misc Docs │ │ │ ├── FILED.md │ │ │ ├── Forms │ │ │ │ └──...