Take the Trip Alone

Josephine Black
5 min readFeb 19, 2024

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I recently went to Chicago to see my favorite podcast And That’s Why We Drink with Em Schulz and Christine Shiefer. I had asked a couple people off handedly to go with me and they all fell through. I knew that I wanted to see them no matter what, so I bought the ticket to the show. I asked off from work. I budgeted my gas money to have enough to go to Chicago. I was telling everyone that I was going by myself; they all were supportive and told me to be safe. I was journaling about it almost everyday how thankful I am for all of my opportunities that were making this possible for me to go see them. I was excited and ready to drive this 9 hours there and back within two days (I ended up doing it in twenty four but that’s for later). I had little to no anxiety about it either. I got a friend to dog-sit for me, and I had an air mattress for my car so I didn’t have to get a hotel there.

I took the fucking trip.

Did everything work out the way that I had planned? To an extent yes. There were a lot of things that I didn’t think about researching that I should’ve. You live and you learn. I started the drive and it seemed to be dragging. I was listening to music for majority of the drive. I had already listened to the newest episode of And That’s Why We Drink so I didn’t have that to pass the time. I thought about turning around twice. I thought to myself that they drive was too long and my back was going to start spasming, who am I to drive this long by myself in one day. But I had already bought the tickets. I already had money invested in this experience. It’s my first time going to Chicago, I had to keep driving.

When I got to Chicago it was all worth it. The awe that I had in downtown area just on the outskirts of it, I teared up. It was the most amazing feeling ever. I went straight to the theatre where the show was being hosted and went in. Me, being the anxious person I am, got alcohol right of the bat. I’m not proud of how much that costed but it’s the experience right? They literally have a drinking game at every live show. How could I not? Found my seat immediately after that so I knew where I had to make it back to. When I tell you how surprised I was that my seat was in the middle stage of the third row. I sat for a second soaking it in, and then went to explore. I found the merchandise stand, splurged and got myself a sweatshirt as well (it’s tradition for me at this point). I made my way back to my seat and waited for them to come on stage.

The show was amazing. They said that it was the longest show yet and I couldn’t have been happier. Sure my back was hurting because of the chairs but the experience was keeping my adrenaline up and I had been talking to some of the girls around me. Totally out of the norm for me but I loved it. When the show was over there was one more thing that I had to do before leaving. Deep dish gluten free pizza was on my radar, Lou Malnati’s was the restaurant that I chose to try. It was amazing. I dove right into the pizza and it was super hot and everything I wanted it to be. After getting the pizza, I went to one of the beaches that I had passed, I have a thing for beaches and just staring into the openness of the water. It’s different than the lakes back in Kansas. I stayed there for a little while just soaking it all in. Then I left and made my trip back to Kansas.

The trip back went so much quicker than before. I was planning on stopping to get some sleep but ended up back in St. Louis before I knew it and I didn’t want to stop until I was home.

I’m not the person that travels alone. I like planning with other people to share the experience with. Even while I was in Chicago I wanted to share the experience with a couple of people that I knew would love it. The thing that I’m trying to get across here is, take the fucking trip. You will have so much fun. There’s no one holding you back from doing the things that you want to do. I went to the beach at 10:45pm and stood there in the cold just to watch the waves roll in. No one was there telling me they were cold and wanted to leave. I got to stay there as long as I wanted and then I left. Am I going to go back with the people that I missed while I was there? Absolutely. I’m not saying that you shouldn’t do the opposite. Go there first with someone you know, and then go back by yourself, that’s acceptable. Just take the trip by yourself. You deserve it.

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