How I Used Gen AI to Make Doing My Taxes Less Miserable

Filing taxes in two states? Confused by vague language in tax software? Here’s how GenAI saved my sanity this season.

1. Filing Taxes Shouldn’t Require a Law Degree (But It Feels Like It)

This year, I found myself stuck in the same tax-time loop as millions of Americans—trying to decipher vague questions from my tax software while bouncing between federal forms and not one, but two state returns. I wasn’t even dealing with complicated business income or rental properties. Just your everyday W-2s, some investment info, and a partial-year move. Still, it felt like I needed a CPA, a decoder ring, and a therapist.

That’s when I realized: I have a GenAI assistant right here. Why not let it sit beside me while I file?

2. What Matters Most When Filing Taxes (and Getting Them Right)

My goals were simple:

• Accuracy – I didn’t want to get audited because I misunderstood a form.
  
• Clarity – I needed to understand why something applied or didn’t.
  
• Time Savings – I didn’t want to spend hours Googling each line item.
  

3. Using GenAI to Navigate My Tax Software Confusion

Here’s how I made GenAI part of my tax-filing toolkit:

• Screenshot Support – I took screenshots of the exact tax form sections or confusing prompts from my tax software (I used ChatGPT’s screenshot analysis feature).
  
• Conversational Clarity – I asked things like:
  “Do I have to claim income I worked in one state with the other?”
  “Can I claim mileage for a temporary job I had mid-year?”
  GenAI gave me thoughtful, conversational answers—explaining the difference between commuting and business-related mileage, helping me figure out whether my situation qualified, and even pointing me to relevant IRS documentation.
  
• Cross-Checking Logic – Sometimes the tax software would suggest something I wasn’t sure about. GenAI helped me sanity-check that logic.
  

4. AI Wasn’t Filling Out My Taxes—It Was Helping Me Understand Them

A key point: I didn’t let GenAI do my taxes. I let it help me understand what I was doing. It was like having a tax-smart friend who never gets tired of my questions.

5. Final Outcome: Confidence, Not Just Completion

Here’s what happened by the end:

• I filed in two states plus federal, confident that I understood what I was submitting.
  
• I caught two mistakes my software didn’t alert me to.
  
• I learned more this year than I ever have about how my taxes actually work—without hours of searching forums or IRS PDFs.
  

6. Takeaways & Tips for Using GenAI During Tax Season

If you want to try this for yourself next year:

• Use GenAI with screenshot capabilities so it can “see” the form you’re asking about.
  
• Be specific in your questions (e.g. “Is this unemployment income taxable in [State]?”).
  

Always double-check against your software’s guidance or IRS/state rules—but use GenAI to understand them.