The idea for the journey was born on Thursday, October 10th, 2024.

 

 

​We were driving from Chicago to Pokagon State Park in Indiana for Halle’s annual family camping trip—a four-hour stretch of open road and quiet Midwest scenery. Somewhere along the way, Jake asked, “If you could live in a different city every month, where would you go?”

​

 

​That kicked off a long, winding conversation. For the next hour or so, we talked through our dream cities, ideal seasons, what places felt exciting, romantic, or a little out of our comfort zones. It was just for fun. A travel game to pass the time. Neither of us thought it was serious.

​

​

But eventually, Jake asked, “Would you actually do something like that?” And Halle answered without hesitation: “Yeah. Absolutely.”

​

​

That changed the tone. Suddenly, it didn’t feel like a game anymore—it felt like something we might actually try. The conversation shifted. We started talking about logistics, remote work, budgets, timing. And by the time we pulled into the campground, we’d decided: we were going to do it.

​

​

We told a few family members that weekend, casually. Most of them probably didn’t believe it would happen. Honestly, we weren’t totally sure either. But the idea stuck. And it kept growing.

Now it’s real. One year. Twelve cities. And the best decision we’ve ever made on a road trip.