Ask It SimplyHi friend,
By the end of this email, you'll know how to get AI to explain a confusing bill, lease, or medical letter in plain English, in about five minutes.
You know the feeling. A letter shows up full of codes, fine print, and words nobody uses in real life. You read it twice, still aren't sure what you owe or what you agreed to, and set it aside for "later." Later turns into a late fee.
This is a job AI is genuinely good at. Give it the confusing part, and it tells you what it means, what's being asked of you, and what questions to ask next. You stay in charge of the decisions. Here are three free tools to try, one for each step.
1. ChatGPT: the plain-English translation
chatgpt.com
The free plan includes unlimited everyday text chats (within fair-use rules), so you can keep asking "what does this word mean?" until it clicks. You can also upload a file or photo instead of typing, but cover your private details first (more on that below).
Best for: turning a page of jargon into a short, simple summary.
2. Claude: the careful second read
claude.ai
Claude has a Free plan you can use on the web, on your computer, or on your phone, with usage limits. Paste the same text and ask it to list every date, dollar amount, and deadline it finds. Two tools reading the same page is a good way to catch something one of them missed.
Best for: pulling out deadlines, fees, and "you must" lines in a lease.
3. Microsoft Copilot: your list of questions
copilot.microsoft.com
The basic Copilot is free to use on the web. You need to sign in with a free Microsoft account to use it. Ask it to turn what you learned into a short list of questions for your landlord, your insurance company, or the billing office.
Best for: getting ready for the phone call you've been putting off.
Try these prompts (copy and paste)
Prompt 1: explain it
Here is part of a [bill / lease / letter from my doctor or insurance]. I removed my personal details. Explain it in plain English, like I'm new to this. Tell me: what is this document, what is it asking me to do, how much money is involved, and what are the deadlines? If anything is unclear or missing, say so. Do not guess. [paste text]
Prompt 2: get ready to ask
Based on what you just explained, write 5 short, polite questions I can ask [the billing office / my landlord / my insurance company] so I understand exactly what I owe and why. Also list any words I should ask them to define.
Fill in the brackets and paste them into any of the three tools. For a medical bill, a good first question is to ask the provider for an itemized bill, which lists each charge.
Know your rights (medical bills)
- Surprise bills: The No Surprises Act protects you from unexpected out-of-network bills for emergency room visits, and for some care at in-network hospitals and surgery centers. (CMS)
- No insurance? Providers usually must give you a good faith estimate of what your care will cost. If your bill is at least $400 more than the estimate, you may be able to dispute it. (CMS)
- Help paying: Nonprofit hospitals are required by law to offer financial assistance programs. (CFPB)
- Questions or complaints: The CMS No Surprises Help Desk is 1-800-985-3059. (CMS)
Renting? Tenant rules depend on where you live, so check your state's laws or a local legal aid office. HUD explains your federal fair housing rights. (HUD)
One mistake to avoid
Never paste your private numbers into an AI tool. Before you paste or upload anything, cover or delete your Social Security number, account numbers, insurance member ID, full medical record numbers, date of birth, and home address. Replace them with something like [REDACTED]. AI only needs the confusing words, not your identity. And AI can get things wrong, so double-check every amount and date against the original letter, and confirm anything important with the company or office that sent it.
MONEY IN PLAIN ENGLISH · NOVEMBER LESSON
Why your first $50 matters more than you think
Once a month · about 5 minutes · education only
Welcome to our new monthly money section. Same idea as always: big topics, plain words.
A lot of people think investing is only for people with thousands of dollars. It's not. The most important thing about your first $50 isn't the amount. It's that you started.
Here's the big idea: compounding. It means your money earns money, and then that money earns money too. Think of a snowball rolling downhill. It picks up more snow as it rolls, and the bigger it gets, the faster it grows.
Illustrative example (made-up numbers, not a prediction): you start with $50 and add $25 a month. After 20 years, you'd have put in $6,050. If that money grew at a steady 7% a year, compounded monthly, it would be about $13,225.
Illustrative example, not a prediction. Real returns go up and down, some years are negative, and nothing is guaranteed. This example ignores taxes and fees.
The lesson isn't "you'll get 7%." The lesson is that time is the secret ingredient.
TRY THIS Ask any AI tool: "Explain compound interest like I'm 12, using a $50 example." Then try your own numbers in the SEC's Free Compound Interest Calculator on Investor.gov.
FREE DOWNLOAD: The $50 Starter Money Playbook A short guide to taking your first small, careful steps. Download the Free Playbook →
Education only. Not financial advice. Money in Plain English is general education, not personalized investment advice and not a recommendation to buy, sell or hold any security. Ask It Simply is not a registered investment adviser or broker-dealer. Investing involves risk, including loss of principal. Full disclaimer: askitsimply.com/money/disclaimer
Money sources: Investor.gov: Compound Interest · Investor.gov: Compound Interest Calculator · Chart: Ask It Simply, made from the illustrative numbers above.
That's it for this week
Pick one confusing letter sitting on your counter and try Prompt 1 this week (with your private details covered). Then hit reply and tell me: what kind of paperwork confuses you most? I might cover it in a future issue.
Talk soon, Dontè, Ask It Simply
P.S. Know someone buried in confusing paperwork? Forward this to them. They can join free at askitsimply.com.
Sources: ChatGPT plans and pricing · Claude plans and pricing · Microsoft Copilot terms of use (sign-in required) · CMS: Your rights and protections against surprise medical bills · CFPB: Know your rights and protections when it comes to medical bills and collections · HUD: Housing discrimination under the Fair Housing Act