10/20/2026
I’m a CPA, and I recently filed my own tax return using FreeTaxUSA and ChatGPT.
Both were useful. The software helped surface questions about ESPP stock basis, rental depreciation, and deductions. ChatGPT offered planning ideas worth considering.
But neither could know about expenses I forgot to record, reconstruct my S-corp shareholder basis from incomplete information, or make planning decisions before deadlines I'd already missed.
The lesson for business owners: technology is getting very good at preparing returns and answering questions. The harder part is knowing what information is missing—and what questions to ask before year-end.
That’s where a CPA who understands your business still adds value.
Have you tried AI for tax planning?