It took about 30 minutes of my time, and the one page that did the work is already in your policy paperwork.
Your Daily Dad Joke
Why is 6 afraid of 7?
Because 7 8 9.
Six emails and one page
The renewal notice shows up, in the mail or in your inbox. The price is a little higher than last year, same as the year before. You think about calling around. Then you picture the afternoon it would take, on hold, spelling your name for one stranger after another. So you pay it and get on with your day.
That’s why I wanted to pass this along.
You may have seen a headline this week from MoneyTalksNews saying car insurance switching hit a record this year, and yet nearly 87% of drivers didn’t shop around at all. The article says the numbers come from a J.D. Power report done with TransUnion. In the third quarter, it says, 13.2% of drivers shopped and 5.1% switched.
I don’t think most people skip it because they don’t care what they pay. My guess is it’s the afternoon.
This fall I tried it a different way. I let AI do the asking.
I pulled out the declarations pages for my homeowners policy and my car policy. That’s the page or two at the front of a policy that lists what you’re covered for, how much, and your deductibles. I marked out the policy numbers and anything else sensitive that an insurance agent didn’t need.
Then I asked AI to find local insurance agents, from different companies, that offered both home and car insurance. In my case it was ChatGPT, on a paid plan, connected to my Gmail. I asked it to write a letter saying I was looking for quotes, this was my current coverage, and I’d like a like-for-like price. I also asked each agent to tell me, from their experience, whether I had the right coverage.
It wrote a personal email to each of six agencies, attached the marked-up pages, and sent them. I read the first one, then let it send the rest. It was a very polite and nice email. That was about 30 minutes of my time. The answers came back over the next few days.
Five of the six came back and the price wasn’t a whole lot different. One, a national company, came back about $2,000 a year lower for my home and car insurance together, for the same coverage. I switched.
Here’s the part I’d want you to hear. Five out of six answers told me I was already paying about what everybody else would charge. That’s worth knowing, too. So I can’t tell you there’s $2,000 waiting for you. What I can tell you is that the asking turned out to be a small job.
And it doesn’t take AI. The page does the work. It tells an agent exactly what coverage to price, and the same short letter works if you type it and send it yourself. If letting a computer send email for you isn’t your thing, skip that part.
Like-for-like is the whole point, though. A lower price for less coverage isn’t a saving. It’s a different policy. The MoneyTalksNews piece adds one caution worth repeating: line up the new policy’s start date before you cancel the old one, so there’s never a day without coverage.
The one thing I’d do. I’d find that declarations page this week. That’s all. It usually comes in the packet the insurance company sends at renewal, and it’s often in your online account with the policy documents. I’d put it where I could find it again and look at the renewal date on it. Once the page is in your hand, the hard part is done, and the asking can wait for a quiet half hour.
Anyway, I wanted you to hear how small the job turned out to be before your next renewal shows up.
When did you last get a second price on your home or car insurance? Share it in the comments so we can all learn from it. I read every comment.
If this was important to you, share it with someone you care about.
A second price is worth having either way. It comes back lower, or it tells you the one you’ve been paying is fair, and that’s one less thing to wonder about the next time the envelope comes.
— Steve
Also on the site since yesterday: what to do when you’re in a debt settlement program and collectors are still calling, what a Boeing layoff means for a 401(k) loan, severance and unemployment, what to do with a Children’s Place gift card or return now that the company filed for bankruptcy, the real math on chasing a $200 Walmart Spark driver bonus, and what loanDepot’s new SEC filing says about two more class action lawsuits.
A longer video from me: What to Say When a Debt Collector Calls (Don’t Mess This Up!). It’s lesson one of my free class, and the heart of it is one calm sentence: “Can you please send me the validation notice in writing?”
SEE A SCAM? SAY SOMETHING. If one has landed on you or someone you love, tell me at tips@getoutofdebt.org. The ones that can warn other people may show up here. Leave out account numbers and passwords.
If this was important to you, share it with someone you care about. It’s free at yourmoneyactually.com, and I don’t sell the list. The places I actually use for my own money, and what I get out of telling you, are on one page where they’ll always be.
This is what I’m telling friends like you over coffee. But remember, you do you.

