Act Like You’ve Been There 

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A candid street-level photograph of a busy urban sidewalk with blurred motion, showing a lone traveler walking with a purposeful, steady stride past crowds of pedestrians.

What’s the best way to explore a new city?

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Wow, this is a tough question to ask a guy who doesn’t travel nearly as much as he would like to. But I do have some experience with exploring cities.

First and foremost, I will say that the internet is an absolute godsend when it comes to getting information together, planning out vacations, making itineraries, and things of that sort. And smartphones make it all the easier. Now you don’t have to carry around a clunky map or even print out a route from MapQuest for directions. It’s easier than ever to walk around a new city and not look quite so much like a tourist.

For the most part, when I go to a new city, I usually go in there for one or two particular things. With me, it usually ends up being attached to going into a major league baseball stadium. I’ll go to Milwaukee, Chicago, or Atlanta for that matter, and I will basically find out what I need to know in order to get parking, get to the stadium, and get back out. But I’m even getting to a point now where I feel like I need to do two games at that stadium just so I can actually take everything in.

And I think that’s the rub of any vacation in general. If I’m gonna travel somewhere like Italy for instance, I wanna see as much of the touristy stuff as I can. However, I don’t want it to get to a point where the vacation itself feels like a chore—where I’m so committed to a rigid itinerary that I feel like I’m not actually enjoying what I’m seeing as much as I am just checking items off a list.

Sometimes I do try to make a little bit more out of the tourist side of things. I brought up Atlanta earlier; I made a handful of trips down there back when I was living in Charleston since they were only about four or five hours apart by car. The first few times there, I wanted to check out the touristy stuff—the World of Coca-Cola, Centennial Olympic Park, the CNN building, things like that.

But probably the most extensive “prep time” I’ve had for going somewhere was my first trip to New York City about 25 years ago. X1 and I were still married at the time. And although we were in school, she was hell-bent on getting into a classroom to teach as soon as possible. She wanted to attend a meeting for Teach for America, a program that brings people into the teaching profession from other fields, usually helping them get provisional or emergency certification so they can hit the ground running.

As for me, I really didn’t have any interest in moving to New York City or doing Teach for America, so I decided to go to a Yankee game instead. I got online and started looking up maps for the subway system so I could navigate around. While we were there, we also decided to check out some of the bigger tourist stops. We were only there for the weekend so we didn’t have a ton of time, but we did hit the Statue of Liberty, the Empire State Building, and navigated through the business district, including the area known as “Ground Zero” in the aftermath of the 9/11 attacks. X1 and I must’ve been doing something right because, on more than one occasion, I had other tourists asking me for directions. So I either didn’t look like a tourist, or I looked like I knew what the hell I was doing, to my credit.

It’s hard for me to compare how that NYC trip would look today because I haven’t done a big city trip like that with a modern smartphone in hand. But I think it would feel a little different; the world just seems so much smaller because of our instant access to knowledge and information.

That said, smartphones are a double-edged sword when it comes to travel. Most people are so obsessed with filming everything or taking a billion pictures that I think they end up looking more like tourists. If you see someone standing frozen in the middle of a crowded sidewalk filming every single second, they’re a dead giveaway.

It’s funny to me how travel agencies are still open and functioning today. I know sometimes they get discounts for hotels and things like that—in fact, Guillaume has started his own travel agency as a bit of a side hustle—but for the most part, I think the internet has made traditional travel agencies obsolete.

So if I was to give someone advice on how to navigate a new city, my two pieces of advice would be: do your homework in advance, and try not to look like a tourist whatever you do. A lot of it comes down to a little bit of Midwestern stubbornness. Avoid standing there staring straight up at the skyscrapers the whole time. Just act like you’ve been there before. Even if you don’t know where you’re at, at least pretend and carry yourself like you are exactly in the place that you are supposed to be at that given moment.


Rebuilding a life takes grit, consistency, and a lot of ‘Option C’ thinking. Having crossed the 1,000-day milestone, I’m now charting the territory beyond. The mission remains the same: No glitz. Just the work. New to the blog? Start your journey here to see the blueprint and the ‘Tricorder’ perspective behind the rebuild.

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The article “act like you’ve been there “first appeared on Rebuilding Rob.

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One response to “Act Like You’ve Been There ”

  1. justrojie Avatar

    if i’m going somewhere, i’ll ask Claude to make an itinerary for my vacay by listing things i’m interested and want to eat. I can then pick and choose what I want to do from that list.

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