Two stories, thirty years apart.

I

I was 16, freshly armed with a driver’s license, and ready to explore the world beyond my neighborhood. I’d like to say my newfound freedom led to wild, Ferris Bueller-style adventures, but the reality was far less cinematic. Instead, my first big solo mission involved a financial misadventure that would stick with me for years.

Now that I was officially allowed to drive, my mom wasted no time putting me to work. One day, she sent me off to get the oil changed on our Toyota Previa. If you’ve never seen one, it’s an odd, egg-shaped minivan. Ours was silver, and I called it the Silver Bullet—which was a stretch, but made me feel less insecure about driving a minivan.

I rolled up to Jiffy Lube, feeling responsible and grown-up, and asked for a simple oil change. But when the guy came back, it wasn’t just about oil anymore. He rattled off a laundry list of additional problems the car supposedly had—things that sounded important but went right over my head. What I did understand was that the total bill was going to be $400.

As a teenager, I had no clue that quick oil change places make their real money by upselling extra services, and no one had prepped me for this. So, when the guy said it all needed to be done, I nodded and handed him my mom’s credit card.

When I got home, my mom was livid. It was a while before she ever handed me that credit card again.

II

Fast forward thirty years to 2024. I drive my first BMW, and I had not learned that these cars are service nightmares. This one was no exception. Recently, it started acting up, so I took it to the shop. This time, instead of a guy trying to upsell me face-to-face, I got a tidy PDF estimate emailed over. But even after all these years, I was back in the same spot—dealing with asymmetric information. I didn’t know if the list of repairs was legitimate or if they were trying to sneak in unnecessary extras.

The most expensive line item was an oil pan gasket replacement. I had no clue what that was or how much it should cost. So, I uploaded the PDF to GPT and asked if the pricing seemed fair. It analyzed the document and said the pricing was generally reasonable, with a few nuances. But I know better than to take a GPT answer without some careful examination. I tweeted about it, asking if anyone knew what an oil pan gasket should really run me. Sure enough, someone who knew someone with a connection at a BMW dealership got back to me and confirmed that everything checked out.

III

This isn’t just about cars. Anytime you find yourself in an environment of asymmetric information—where you don’t have enough knowledge to make informed decisions, and the person you’re dealing with does—this is a great time to ask AI. The most accessible stuff, even the free version of ChatGPT with poorly worded questions, will return good food for thought.

I’m not saying AI will replace an expert, especially someone who’s spent years honing their craft. But getting in touch with an expert requires having one in your network, or being willing to pay for their expertise. AI, on the other hand, is free and at your fingertips. It’s something you can use in the moment, without waiting or paying a premium.

And while I still get a twitch whenever I pass a Jiffy Lube, at least now I know that the next generation of sixteen-year-olds has a better chance at navigating these waters. They’ve got an always-available advisor in their pocket, ready to help them ask the right questions before they hand over that credit card.

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Thanks to early readers: Jason Blydell