Once, Twice, Three Times Chicago

You don’t know what you don’t know until you know it.

On this date, eight years ago, I was in Chicago for the first time.

I was a sophomore in high school and already a very involved member of the school band and choir programs. One of the most appealing aspects of band and choir in Kasson-Mantorville is that every few years the entire music program goes on a trip to some major city. Years prior to mine had gone to such exotic places as Washington D.C. and New York City. I was pumped!

Being a “band geek” in the classical sense, I was obviously not one of those people who was only in the arts for this trip. Nevertheless, I looked forward to it. Think of the debauchery! The mischief! Shenanigans, perhaps!

The only chicanery that dude was up to was keeping that shirt tucked into those pants.

Actually, there weren’t really any shenanigans to be had, but I can definitely say that this experience opened my eyes and began pattern of thought that someday, I would like to live somewhere like that.

How different my life was eight years ago! I felt such a┬áburning desire to do something and the complete lack of knowledge and ability to do it. I didn’t know what the first step was to ridding myself of the trapped feeling that I felt.

A little over a year after my school trip to Chicago, I had begun looking for universities to apply to. It seemed to me that this was the perfect way to achieve everything that I wanted, and set my sights on really big universities in really big cities really far away from rural Minnesota. My parents, always supportive, decided that it would be fun to take me to Chicago during the summer to go on my first and only real college visit, to the University of Chicago.

Pay particular attention to the fledgling soul patch that roguish bombshell is sporting. Don’t worry: I did manage to grow it out.

Since I was like, three steps away Chicago citizenship at this point, I took it upon myself to shepherd my parents around the city. We spent a lot of time walking, both to new places and places I’d been on my trip. I even got to ride a public bus for the first time ever, with my dad! Now that was an experience: today trains, Greyhounds, subways, and city busses are old hat, but back then, it was so strange!

It sounds stupid to say now, but I felt so limited in my charmed 16-year-old life and any other lifestyle just felt hopelessly out of reach. At one point on this trip my mom asked me if I really wanted to live in such a place with big buildings and cramped apartments. I answered, emphatically and perhaps overly aggressively, yes I did.

Fast forward to 2015. I ended up at a moderately sized university in a moderately sized city, loved it, lived abroad in a smaller city, moved back, and now I had Miranda. My life had not turned out like I wanted it to back in 2010 or 2011, but at the same time I felt like my life was pretty much right on track. In March, given that it was her senior year, Miranda and I wanted to take a real spring break trip. Well, sort of: Florida was off the table. Too expensive, and we absolutely did not want to be around the kind of people who would go to Florida for spring break.

So, Chicago it was. Moderately priced. Easy drive. Reasonably priced hotel. Lots to do1.

If you’re reading this in an English class in the year 3000, you can say that this picture symbolizes how far I had risen from my previous angsty teenage self, and how I had pulled myself up by my bootstraps2.

How far had I come in my life that such a trip was even within my own realm of imagination! And how much farther had I come that I actually followed through on my dreams! In high school I spent many, many hours fantasizing about just what we did: getting in a car and driving somewhere cool, just because we wanted to.

It’s been eight years since that first trip, and I am older, and I live in New York City. I no longer really feel connected to “the youth” as I once did, but I do remember what it feels like to feel trapped. In hindsight I can say that back then I didn’t really know exactly what would make my life better, and things definitely didn’t turn out the way I had thought they would. The real problem is not that I didn’t get to live out my fantasies as I saw them back then; it’s that my vision of what life would be like was limited by what I knew at the time. And to any young person reading this: don’t worry! You’ll get there too3.

For what it’s worth though, I still struggle every day because sometimes real life is still super scary and sometimes dreams are scary too.


  1. What we didn’t realize until we arrived was that we were visiting over St. Patrick’s Day weekend, and Chicago takes that very seriously.
  2. Not really, I led and continue to lead a very privileged life where I have been afforded many opportunities that most people never get. Just throwing that out there.
  3. And I hope that when you do you don’t have a bitter feeling of regret that you listened to advice you read in a blog post.

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