AI Found $5,000 I Had Missed

I have been using AI in my work for a while now. But some of the most practical wins have been personal.

I have a Health Savings Account that I intentionally do not spend down. Instead, I pay medical expenses out of pocket and let the HSA grow as an investment account. The idea is to withdraw it in retirement with no penalty. Triple tax advantage. It is a solid strategy; it also means I need to track every eligible expense in case the IRS ever asks.

I had started a spreadsheet and a folder structure to manage this. After a while, it became tedious enough that I kept putting it off.

So I handed it to Claude Code. I gave it a folder of receipts and documents, along with a set of instructions. It organized the files, built a ledger of eligible expenses by year, and generated documentation that future me (or future AI) can use to keep it up to date.

It also found roughly $5,000 in eligible expenses I had missed.

That is the part that stuck with me. Not just the time saved, but the fact that it caught something I would not have. That is AI as a practical tool. Not a demo. Not a gimmick. Something that quietly does useful work.

I am curious what unglamorous problems you have handed off to AI lately.