As a freelancer, I have to pay taxes three times a year. Every time it’s time for another paperwork, I dread the process. I’ve gotten better at knowing what to do over the years, but it still takes a lot of time and causes a lot of stress.
Ever since I looked at the roads AI assistants Could make me more productive, I decided to try them out to speed up the process. I sent the same documents and instructions through Gemini, Lumo AI, and Claude to see which tool worked best.
Why I decided to try AI assistants for my taxes
Spreadsheets are literally a headache
The longest part of my tax filing is not filling out the forms, but the process of pre-sorting all the information. This includes my income, medical expenses and home office expenses. This involves exporting a year’s worth of transactions to a spreadsheet and then creating multiple sheets focused on different categories.
I’ve never been a fan of charts, but after developing chronic migraines, spending long periods of time looking at them becomes even more difficult. Using dark mode in tools like LibreOffice Calc creates inconsistencies, sometimes rendering text unreadable. Meanwhile, Google Docs and Proton Sheets don’t play well with my dark mode flags or extensions.
I’ve enjoyed the benefits of Excel’s dark mode, but I can’t use the desktop app without a Microsoft 365 subscription — and I don’t want to subscribe to an office suite that I barely use for just one function in one app.
When my tax filings came back this year, spending hours starting with the spreadsheet led to another migraine attack that lasted for days. Copilot helped speed things up (since I was still subscribed at the time), but it still required me to copy formulas to create new sheets.
Since I dismissed Copilot as an option, I wanted to see if other chatbots could do a better job when the next request came. For my test, I started my spreadsheets from scratch – just a year’s worth of transactions from my bank and credit card. I also used the free plan of each assistant to see what the experience would be like for most users.
Lumo AI: The safest, but with one big problem
He made the most mistakes
I started with Lumo AI first because it’s a tool I’m excited about. However, Lumo is Proton’s privacy-focused AI assistant My first impression of the tool was not positive. Nevertheless, I wanted to see how well it worked with my documents.
I’m not a fan of sharing my financial transactions with companies, so the fact that Lumo AI is encrypted and doesn’t use your conversations for training made it my preferred tool. Although I used its free plan, I didn’t face any problems with restrictions.
I uploaded my bank and credit card transactions using the projects feature. I then asked the chatbot to identify trends, create checklists, and also create charts that I could copy into spreadsheets.
During the process, I realized that the chatbot was not receiving all transactions accurately. For example, when I asked him to film all the operations related to my migraine medication, he missed a month. When I asked to check November, he said there was no payment that month. But when I gave him the exact date, he was able to find the surgery he missed.
This issue came up again when I was asked to bring in all my positive transactions to create a table for my earnings, excluding transactions with certain conditions. His bottom line missed about a third of my income and would have resulted in a hefty fine if I had submitted it as a final amount.
Trying to figure out why the chatbot was missing such a significant portion of revenue resulted in a loop where it just kept calculating and recalculating the results. I finally figured out where some of the inconsistency was, but could never get it to match my spreadsheet.
Gemini: The best balance
Its free plan offers useful features
Things went more smoothly in Gemini. Unfortunately, the chatbot doesn’t have a projects feature, but I was able to upload files to the chat and continue to reference them.
It handled the tasks well, although it was very prone to file creation in Google Drive. For each table he created, he saved a copy in Google Sheets. This is convenient, but can be annoying if you don’t want to use Google’s cloud documents.
I ran into a limitation when trying to create a checklist that I could copy from the chatbot. Unlike tables, I just couldn’t hit the copy mark. Instead, he wanted me to connect to Google Workspace, possibly creating a checklist in Google Keep. Since I don’t use Google Keep anymore, I would prefer a checklist that I can copy to my note-taking app.
I couldn’t see any glaring errors from Gemini, and I found some of his observations helpful for items I’d forgotten to include or exclude from the charts. However, I still couldn’t get my return to match the one I manually sorted. But at least it got very close to $100. Sorting filtered data would also be easier than working with a completely unfiltered spreadsheet.
Claude: The ultimate assistant, but with limitations
Limitation issues affected my usage quite a bit
I’ve heard great things about it Claude featuresso I wanted to see how I could use its Projects feature to analyze my documents. However, after two requests, I was met with a message that I had reached my limit. When the limit was renewed five hours later, I used my quota again within two requests.
This meant that what would take minutes with other chatbots was spread over hours with Claude. However, when I revisited the tool over the weekend (off-peak), I was able to get through the rest of my instructions without issue.
As annoying as the initial limitations were, Claude’s results were impressive. He created an interactive checklist that I can download for my tax filings. Every spreadsheet it created was available for download and use by programs on my computer. For more complex tables, the chatbot even color-codes the different elements to make them easier to distinguish visually.
It affected me the most when it came to determining my income. He suggested excluding additional items that I had not included in my prescription and asked additional questions about whether certain items should be included. As a result, it was the only chatbot that could reconcile my gross income for the year with my hand-filtered spreadsheet.
Its responsiveness made it feel like a collaboration and really helped me filter through the data more easily than just relying on my memory.
AI can be a useful partner, but it still makes mistakes
Testing different tools revealed their strengths and weaknesses, as well as my own blind spots when sorting through data. However, the experience reminded me why these tools are imperfect and should always be checked.
I’ll still probably do most of my taxes by hand because I’m very concerned about potential errors from AI. But chatbots have been useful tools in finding transactions I’ve forgotten or filtering information that’s easy for me to confirm.
