There’s a city that does something to me every time I travel there.
The skyline appears through the airplane window and something in my chest loosens. My shoulders drop. I exhale. I have lived in Charlotte long enough to call it home, but Chicago is where I feel the most alive. The food is extraordinary. The people are warm in that particular Midwestern way that still surprises me. And Lake Michigan gets more magnificent every time I see it.
I just spent a week there. Family dinners, old friends, coffee with people I’ve known long enough that we can skip the small talk entirely. I stayed at a boutique hotel on the North Side – rocking chairs on the front porch, wallcoverings that made me pause and take notice, furniture shaped like the designer had a sense of humor. All just a quick walk from the lake. Nothing about it felt like every other hotel I’ve ever stayed in, and that turned out to matter more than I expected.
One morning I met a friend at a coffee shop in a neighborhood I thought I knew. The kind of place that’s already buzzing when you arrive. I ordered an old fashioned donut that lived up to every bit of its reputation and sat there visiting for a long time, without checking my phone. I had dinner with family at a Thai restaurant where we passed spicy dishes around a table and told stories we’ve probably told before and somehow still laughed at.
I also took meetings that week. I want to say that plainly – I didn’t unplug completely, and I’m not going to pretend I did. But I took those meetings from a different city, a different chair, with a different view out the window. And somewhere between the hotel porch and the lakefront and a table full of people I love, something shifted.
The business questions I had been circling for months – the ones that felt stuck every time I sat down with them in Charlotte, started to move. Not because I carved out time to solve them. Because I stopped trying to force them.
I think about this often as someone who works with developers and property operators. People who are managing assets, timelines, budgets, and teams simultaneously, often without a real break between projects. The calendar fills up fast in this industry. There is always a reason not to go – a deal in progress, a lease-up that needs attention, a decision that feels too significant to leave unattended. I’ve heard those reasons from clients. I’ve used them myself.
But here’s what I’ve come to believe: the thinking I most need to do probably isn’t going to happen at my desk.
Research from Stanford and the University of California found that people are 60% more creative after walking or taking short breaks compared to those who stay glued to their desks. And Katie Denis, lead researcher at Project: Time Off, puts it plainly: “The productivity, creativity, bringing new ideas forward isn’t the person who’s working crazy hours. It’s someone who’s getting outside of their day-to-day.”
She’s describing what happened to me in Chicago. Not in one dramatic moment, but gradually over coffee, over dinner, on a walk to the lake. The trip worked on me the way good rest works: quietly, without announcing itself, until you realize you’re thinking more clearly than you were a week ago.
I came home with something I didn’t have when I left. Not a completed decision. Not a ten-point plan. Something more useful than either of those: perspective. The kind that only shows up when I stop white-knuckling a problem and give it room to breathe somewhere new.
If you’re a developer or operator reading this in the middle of a project cycle – and I know what that looks like. I’m not telling you to disappear for a month. I’m suggesting that the strategic clarity you’ve been grinding toward might be a long weekend away from where you found it.
The work doesn’t suffer when I leave. In my experience, it suffers when I never do.
Chicago will always be there. So will the questions you’re carrying. Give them a different backdrop. You might be surprised what moves.
