The AI Sunday Drive

A line in a country song reminded me of something I’d completely forgotten: the Sunday drive. No errand, no destination. The drive itself was the point.

The idea

That feels foreign in 2026. Around Chicago, getting in the car means getting somewhere fast, with Google Maps routing me down bizarre side streets to save three minutes. I’m definitely not driving just to wander.

But I realized I do something surprisingly similar about once a week. I take a Sunday drive with AI. Sometimes Claude or ChatGPT, sometimes an open-weight model. I’m not trying to get work done. I start with something I’m curious about, and 20 minutes later I’m writing code or building something I never planned to build.

Why it matters

Curiosity teaches what use cases can’t. I’ve learned an incredible amount about AI just following ideas to see where they go.
Wandering reveals capability. Sometimes the best way to understand this technology is to use it without a use case.
Productivity still matters. I talk ROI with clients every day. Exploration is what makes those conversations sharper.

The Sunday drive moved

Maybe the Sunday drive isn’t dead. Maybe it just moved somewhere else.

Do you ever explore with AI with nothing specific to accomplish? What does your AI Sunday drive look like?

Join the conversation: see the comments on LinkedIn.

Read the full transcript

Hey, I’m Matt.

I was listening to a country song the other day, and there was a line in it about going for a Sunday drive.

And it struck me. Oh my gosh, I had completely forgotten about that concept.

When I was growing up, a Sunday drive was actually a thing.

You’d get in the car, maybe head out into the country, and just drive. You weren’t running an errand, like making yet another Amazon return. You didn’t necessarily have a destination. The drive itself was kind of the point.

And that feels so foreign in 2026.

I live around Chicago, and most of the time when I get in my car, I’m trying to figure out how to get where I’m going as quickly as possible. Traffic, construction, Google Maps telling me I can save three minutes by taking some bizarre side street.

I’m definitely not getting in the car just to wander around.

And it made me realize something.

There actually is something surprisingly similar that I try to do about once a week.

I take a Sunday drive with AI.

I like to mix it up. Sometimes it’s Claude or ChatGPT, sometimes I’ll fire up an open-weight model.

And I’m not trying to get work done. I’m usually just curious about something.

I might start asking about some completely random topic, and 20 minutes later I’m writing some code or building something I had absolutely no intention of building when I started.

And that’s kind of the point. I don’t know where I’m going.

We spend so much time talking about AI in terms of productivity and use cases and ROI. And obviously all of that matters. I do that every day with clients.

But I’ve learned an incredible amount about AI just messing around with it. Following an idea because it seems interesting and seeing where it goes.

And I believe there’s real value in that.

Sometimes the best way to understand what this technology can do is to use it when you don’t have a use case.

Just wander.

Follow your curiosity and see where it takes you.

So maybe the Sunday drive isn’t completely dead.

Maybe it just moved somewhere else.

And I’d actually love to hear if you do something like this.

Do you ever explore with AI when you’re not trying to accomplish anything specific?

What does your version of an AI Sunday drive look like?

I cannot wait to hear.

Thanks for watching.