
I’m a lucky guy. Sometimes when my wife travels for work I get to tag along and while it’s a work trip for her my only jobs are to explore, find good restaurants, curate a list of interesting things to see, and bless her with my company. I’m kind of like a great male escort.
The great thing about traveling is not only do you learn things about your destination, you also learn things about yourself.
Here are things I learned about Chicago.
- The Art Institute of Chicago is amazing. Easily the best art museum I’ve ever been to.
- Chicago is really walkable. Nice wide sidewalks. Great design. I think the great fire afforded them a chance to start over and really put thought into the layout. Which begs the question, why don’t we burn down Philadelphia and start over?
- The architecture is great.
- It has the largest Starbucks in the world where you can overpay for coffee and overpay for coffee inspired cocktails.

Now, most importantly, here are the things I learned about myself in Chicago. I contain multitudes. 😄
- I enjoy a good deep dish pizza. For me it’s the burned cheese around the edge. I’m glad I don’t have this available to me at home. It would be bad for my health.
- Constant wind is really annoying to me. There were a few days while I was there that Chicago lived up to its nickname. If I was one of the founders of this town I would have called it quits early on. Three days into building my log cabin I would’ve paused and been like, “You guys think it’s always gonna be this windy? Cause if it is this is not going to work for me. I get that this is a good location for trade, and it’s right on the lake, but I’ve lost two hats already and I rarely if ever fly kites so…….”
- The most important thing I learned is really something I already knew. I don’t like heights. The last thing I did before returning to the mediocre state of Pennsylvania was go to the top of the Willis (Sears) Tower. A big part of the attraction of going to the top is that you can stand in one of four glass Skyboxes that jut out from the building and look straight down 103 stories (1,353 ft.) to the ground. When my turn came to step into the box I moved right to the edge of the glass floor. The employee who’s job it is to take a picture of each visitor and try to sell it to them said, “Stand right in the middle and I’ll get your photo.” I looked back at him and said, “Yeah, I’m not gonna do that.” This is the point in my visit where I learned I really don’t like heights. Like at all. I’ve known too many builders to trust anything man made that high above the ground. I don’t know if you guys realize this but half of the crew that built the house you live in was definitely on some sort mind-altering substance. Why would this be any different?

There you go, many things learned on my Chicago trip. The last thing I learned is that if I tell my wife that I didn’t step into the Skybox she will call me a chicken and laugh.

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