OK. I know a lot of people take trips by themselves all the time. You all go galavanting around the globe without a care in the world. I’m so happy for you. And I am also a little jealous of you. But the fact is, I am not one of you.

I always tell myself I should take trips by myself. There are a million places I want to visit, and since all I need to work is my computer and my brain, it’s almost a waste for me not to be constantly on the road, because it would just be so easy!

But you know what else is easy? Sitting on the couch at my house with my fiancee and my dog, snacking and watching TV. That’s actually a lot easier, if we’re going to be honest here.

And so, there it is. I’m that person. Is it because I’m in a relationship? Because I’ve gotten lazy? Because the appeal of the comforts of home now outweighs the appeal of adventure?

Well, I’d have to think about that some more. But what I do know is that I haven’t taken a trip by myself in years….

…until this weekend! Yours truly is in Chicago, soaking up the 32 degree weather and the deep dish pizza like an injection of freedom straight to the jugular. It’s glorious. There are, however, a few tips that I’d pass on to anyone in my situation…and I know you’re out there…

  1. Ask your cab driver for advice about what to do. Especially if you only have a few days, he or she can tell you what parts  of town to focus on.
  2. Bring cash. Speaking of cabs, your debit card is not so useful when trying to pay for one.
  3. Remind yourself in advance that ghosts are not real. I forgot how scared I am of ghosts until…well, about three hours ago.
  4. Plan, but not too much. If you don’t plan at all, you (or I) could easily wind up staying in your hotel room all week, curled up in front of the TV in a robe, pretending that since you’re in a different city, you have no responsibilities at all! Wheee! But that would not be true, and it would also be kind of a waste of time. Know what you want to do on your trip, and give yourself the flexibility to do it when you feel like it.
  5. Carry a map. And read it when you need to. Will you look like a tourist? Yes. But will you also then not be lost well into the night? Also yes.

BONUS TIP: Don’t be afraid to eat in restaurants and drink in bars alone! You don’t have to get all Elizabeth Gilbert about it, but you also don’t have to feel self-conscious. A solo diner/drinker isn’t a new sight to anybody, and it’s really fun to sample local cuisine while drinking. Don’t deprive yourself of that joy because you’re worried about how you’ll look, or that you’ll have no one to talk to. All the more reason to order extra courses to keep your mouth busy.