One of my favorite things to do when I travel or find myself with a few free hours is to just get outside and wander around.

This works especially well in cities, but it’s just as possible in small towns, neighborhoods, or any walkable area, including trails in nature or particularly interesting buildings. (For instance, yesterday, I spent an hour with a friend wandering around the high-end wholesale storefronts in the Merchandise Mart in Chicago, which is one of my all-time favorite wander destinations because it has an unlimited number of nooks and crannies to explore inside.)

Usually, I’ll pick a relative destination—like a cafe across town—as an anchor point. But it's worth noting that the destination itself isn’t the goal. I see this as more of a backup plan, a loose marker in case nothing else catches my attention along the way.

While I'm wandering, I try to pay extra close attention to things that wouldn't normally catch my eye. I'll look up and notice gargoyles on tops of buildings, or plants that grow from the middle of concrete four stories into the air. I try to take in new inputs on street level, deliberately walking down streets I visit less frequently. Maybe along the way I'll discover a coffee shop, an art installation, or notice a line outside a bakery with people hyped for the latest sugar-coated delicacy. I look for other people who are wandering too, and sometimes I'll meet a new buddy to accompany me on a segment of my adventure.

I like to this because I think intentional noticing and self-discovery are both critical parts of any creative process. Wandering unlocks creativity, and that's why I think more of us need to do it.

Wandering Around the Internet

Wandering IRL reminds me of the early internet days when I used a website called StumbleUpon. That site would randomly introduce you to fun, fascinating content, which encouraged curiosity and discovery, kind of like spinning a roulette wheel for fresh ideas. (Of course, a human version of that—Chatroulette—took off around the same time, but ultimately took a darker turn when people started to abuse the wholesome intent.)

I find it really hard to replicate the feeling of wandering digitally in the same way I experience it in real life, exploring streets and unexpected corners. The more the algorithms increasingly curate our digital experiences, we prioritize predictability over serendipity. We have to look harder to break free from our own boxes, both IRL and digitally.

We all need exposure to ideas and projects beyond our usual focus, especially if we want to improve our problem-solving skills. For me, juggling multiple professional projects means constantly taking in new information, processing it quickly, and turning it into creative output. Wandering helps me gather fresh ideas and perspectives that I can use in my work.

Interestingly, I’ve noticed parallels between wandering and using AI. The more I experiment with creative, open-ended prompts, the more unexpected and personalized results I get. It’s like bringing a wandering mindset to technology—meandering through ideas to see what emerges. This approach has helped me adapt quickly to new AI tools and make them work for me.

Activating Serendipity

If you’re feeling stuck or looking to spark your imagination, I encourage you to embrace wandering—whether that means walking aimlessly or letting your mind roam in daydreams. Sometimes the best ideas come when you’re not intentionally seeking them.

Lately, I’ve been trying a new app called BeeBot, developed by Dennis Crowley, the founder of Foursquare. BeeBot celebrates the art of wandering by surfacing hidden gems around you. It works in the background as you walk, suggesting a great coffee shop nearby, a secret jazz bar, or a tucked-away art gallery, all while you wear your headphones or Airpods. (You can sign up for the waitlist here.)

I’ve tested BeeBot in two cities this past week, and it’s been so much fun. While I don’t always change course in the moment while I'm wandering, I’ve found myself noting places to revisit later or noticing things I’d previously walked past without a second thought. What I love about this overall is how it uses technology to promote intentional, IRL discovery—without a screen getting in the way..

In an era where algorithms often narrow our view, wandering (both offline and online) is more important than ever. It’s a reminder to slow down, explore, and see where the world takes you. After all, who knows what you might stumble upon?