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Following Through

“I wish I had stayed in touch with my friends."

I wish I had let myself be happier.

I wish I had the courage to live a life true to myself, not the life others expected of me.

From “The five regrets of the dying”

Two weekends ago, I flew from D.C. to Chicago in order to see a play: Baked! The Musical.

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It's co-produced by my good friend from high school, Jordan Liu. I'm so happy I went. It's clear he and his co-producer best friend Deepak Kumar put in a lot of effort and hard work into making the play as polished and complete as it was. The show was wonderful, hilarious and emotional and thought-provoking, assembled with many genius brushstrokes. Apparently, the play sold out of its original run of shows and tickets, and the theatre had to book more sessions because it was so popular, which is a really good problem to have (or at least a better problem than “we can't fill seats”).

Chicago was great too! It was the first time I've visited since elementary school, when I went up the Sears Tower and was too afraid to look down the glass floor. Chicago has that “big city” feel, with the supertall skyscrapers that you know are really tall, but are far away enough where you get the “it's not that tall” feeling – like the Rocky Mountains:

Oh look, the Rocky Mountains. Don't worry kids, we'll be there in no time, they look so big already!

(five hours later)

Why are they the exact same size??

I got the same feeling when I was on the Staten Island Ferry and looking towards lower Manhattan. But unlike New York City, Chicago felt far more comfortable. For one, I really like the CTA, I liked it better than MTA or BART and maybe even my own beloved WMATA (apparently this point might be contested amongst my friends). Chicago's people also seemed friendlier and chiller, while New Yorkers were constantly busy and angry and flowing in the streets like worker bees. Chicago also has wider streets, with canals intersecting the city. And it was cold, really cold, and I love the cold! I'm constantly terrified of never seeing snow ever again, and it snowed while I was there. To put that into perspective, Michigan measured 60 degrees Fahrenheit during December, the same place where it used to snow six inches every winter without fail just ten years ago. Crazily enough, Chicago felt more like home than home itself felt.

It was kind of crazy going to Chicago. I'm on sabbatical at the moment and it's not like I'm rolling in money. If United Basic Economy round-trip tickets weren't $100, I doubt I would have pulled the trigger. It's also crazy for other reasons as well, that I don't really want to elaborate on here. But the absolute craziest thing about the trip was, I almost didn't make it in the first place.


Sometimes, I over-promise and under-deliver. In the past, this used to be “all the time”. I'd always bite off more than I can chew, and end up overworking, and still falling short of my original commitments. So when Jordan said he was hosting a play, and I decided to purchase tickets online, I mentioned I might be coming. Our conversation went something like this:

Me: I purchased a ticket to your play! Hopefully I can make it to Chicago!

Jordan: I hope you can make it too!

Jordan didn't say anything untoward or hint towards anything negative, but I got a sinking feeling in my stomach that I was always the friend who never showed up, always the friend who was never there. I mean, when was the last time I traveled domestically to see a friend? Never. I've never even flown in order to see a friend, because I always valued saving money, and having that temporary feeling of comfort and safety in having just a little more financial freedom.

And what did it cost me? The risk of one of the five regrets appearing when I'm still in my 20s. Which is absolutely and completely ridiculous!! I'm not married, I don't have kids, I'm not tied down in any way, shape, or form, and yet I feel a lot more alone and trapped on a regular basis than I really should (whether I'm on sabbatical or working a job).

So I decided to do something different. I recognized that I did feel bad about not showing up, and honestly a bit pissed off at myself that I let things come to this. So I purchased the ticket and didn't hesitate (too much) on making the decision.

I mean, come on. It's $100. Other friends, friends who have started companies, friends who interview at med school or residencies, spend tens of thousands of dollars on traveling, and travel cross-country every week. If I can't make $100 in an hour after going back to work, what kind of a software engineer am I even?

Jordan was delighted that I would be flying in! I made a friend happy, and that made the two months in between really happy for me 😄