AI for managing your finances (free tools only)
Quote from Sarah Chen on January 25, 2026, 11:00 amAnother installment of "Sarah tests AI tools so you don't have to." This time: personal finance.
Disclaimer: I'm not a financial advisor. This is what works for me and my husband.
What I use ChatGPT for:
- Explaining financial concepts I don't understand (what's a Roth conversion ladder? ELI5 please)
- Comparing insurance plans during open enrollment (paste in the plan details and ask it to compare)
- Creating a debt payoff plan with our specific numbers
- Tax prep questions ("I worked from home 3 days a week, can I deduct my internet?")What I do NOT use AI for:
- Actual investment decisions (it can explain concepts but don't ask it where to put your money)
- Tax filing (use actual tax software)
- Anything involving your actual account numbers or SSN (never paste sensitive data into AI)The insurance comparison thing alone saved us $2,400/year because it identified that the "cheaper" plan would actually cost more given our family's usage patterns. I never would have caught that looking at the plans side by side.
Another installment of "Sarah tests AI tools so you don't have to." This time: personal finance.
Disclaimer: I'm not a financial advisor. This is what works for me and my husband.
What I use ChatGPT for:
- Explaining financial concepts I don't understand (what's a Roth conversion ladder? ELI5 please)
- Comparing insurance plans during open enrollment (paste in the plan details and ask it to compare)
- Creating a debt payoff plan with our specific numbers
- Tax prep questions ("I worked from home 3 days a week, can I deduct my internet?")
What I do NOT use AI for:
- Actual investment decisions (it can explain concepts but don't ask it where to put your money)
- Tax filing (use actual tax software)
- Anything involving your actual account numbers or SSN (never paste sensitive data into AI)
The insurance comparison thing alone saved us $2,400/year because it identified that the "cheaper" plan would actually cost more given our family's usage patterns. I never would have caught that looking at the plans side by side.
Quote from Tom Richardson on January 25, 2026, 6:30 pmthe insurance comparison thing is genius. open enrollment gives me a migraine every year. just stare at 4 plans that all look the same and pick the one with the lowest premium and hope for the best.
gonna try this in october. bookmarking this post.
the insurance comparison thing is genius. open enrollment gives me a migraine every year. just stare at 4 plans that all look the same and pick the one with the lowest premium and hope for the best.
gonna try this in october. bookmarking this post.
Quote from Lisa Morales on January 26, 2026, 8:20 amSarah the debt payoff plan thing — can you say more about that? I have some medical debt from my dad's care before we got the insurance sorted and I just kind of... ignore it and hope it goes away. which is not a strategy lol. Would ChatGPT actually be helpful for figuring out a plan?
Sarah the debt payoff plan thing — can you say more about that? I have some medical debt from my dad's care before we got the insurance sorted and I just kind of... ignore it and hope it goes away. which is not a strategy lol. Would ChatGPT actually be helpful for figuring out a plan?
Quote from Sarah Chen on January 26, 2026, 12:45 pmLisa — yes! Here's what I did: I listed out all our debts (amounts, interest rates, minimum payments) and our monthly income/expenses, and asked it to create both an avalanche plan (highest interest first) and a snowball plan (smallest balance first) and compare the total interest paid and timeline for each.
It laid it out month by month. Made it feel way less overwhelming because I could see the finish line instead of just staring at a scary total number.
For medical debt specifically — also ask it about negotiation strategies. Hospitals and doctors offices will often accept less than the full amount if you call and negotiate. ChatGPT can even help you script that phone call.
Lisa — yes! Here's what I did: I listed out all our debts (amounts, interest rates, minimum payments) and our monthly income/expenses, and asked it to create both an avalanche plan (highest interest first) and a snowball plan (smallest balance first) and compare the total interest paid and timeline for each.
It laid it out month by month. Made it feel way less overwhelming because I could see the finish line instead of just staring at a scary total number.
For medical debt specifically — also ask it about negotiation strategies. Hospitals and doctors offices will often accept less than the full amount if you call and negotiate. ChatGPT can even help you script that phone call.