The Last Chicago 2-Step

Chicago, destination for yet another work trip. So, what are we doing here? My history seems to be littered with this town in 1 form or another. Perhaps in a reality of my possible self, I moved to Chicago and regretted it. This, this lifetime has been an exercise in going here to ensure my current self that while I do like Chicago, I don’t want to live here. I do enjoy the city-proper, but it’s a very small space packed with many things to do, and lots of good eats. I’ve now had 4 different bosses in Chicago, and thus, I have come out here maybe 15-20 times in the past 10 years. Frankly I have long lost count. It’s been a bunch.

That’s what this trip has been about, another work trip to see another boss, in the same old Chicago. To be more accurate, we’ll be mostly in Naperville where my boss lives. This is a trip to come out, touch base, work on some details, and frankly to eat a bunch of food. My boss and his wife, being Taiwanese, both enjoy a good Chinese meal as much as I do. When we get together, we make sure we eat plenty of good food. That would be the case this time.

This blog post will span 2 full days, which started on Tuesday morning just after 5:00 am, when I dialed up an Uber and found that, after an inordinately long search, the wait was going to be 25 minutes. In that time, I could almost drive to Newark myself, so that’s what I did. In reality, this option would be cheaper than taking Uber so it saves the company money. I just like to zone out when going to/from the airport.

The excitement of airports and travel has long worn off, so there’s nothing of note to be said here. The first thing I do after the TSA is to check the board to ensure the flight is on time and the gate hasn’t changed. Nothing of note, so I get myself to the gate, grab a coffee, and sit down to read while I wait to board the plane.

First stop of any airport after the TSA is to check the gate.

The plane takes off, I watch 2+ episodes of The Wire, and the plane lands. Again, nothing to see here, other than the latest addition to my travel repertoire. This is an iPad holder which I was using for my indoor biking setup. Since I refactored that to use a bigger monitor and Chromecast, this is no longer needed in the basement any longer. You can latch this to the seat in front of you and drop your phone so you don’t need to hold it the whole time.

Handy addition to my travel arsenal.

Uber to Tommy’s house is expensive but quick. This company is going to price themselves out of the market soon. At $60 for a 30 minute ride, things are getting a little out of hand. Other than the price, the trip is easy, and before long, I’m at Tommy’s house and he’s sharing his bounty of Taiwanese snacks that he got from his dad 2 weeks ago. The key is the pineapple cake, which is such a rare treat to have in the US. We would bring back tons of these when we used to go to Taiwan. I found them online here, which is expensive but damn, these things are awesome.

I have not had these in maybe 8 years. As good as I remember.

We decide to get out of the house and go work, and Tommy breaks out his toy to drive us there, which is a Porsche of some sort. I don’t know enough about cars to say what kind it was. We take it to the Sparrow Coffee location in Naperville. I’ve always been a fan of Intelligentsia in the city but this place is probably better. I get a double espresso, which is amazing, and a pour-over which is also quite fantastic. Normally I would have bought a pound of coffee to bring home, but I traded in my right to do this last week, so the family could watch Into the Spider-Verse. I keep my promise and pass on buying more coffee.

Tommy’s car, or rather, his toy.
Sparrow Coffee in Naperville nails it. Probably as good or better than Inteligencia.

We get some work done, then head back to the house before the afternoon triage call starts. Tommy says that if I cover he’ll make us lunch, which isn’t a tough sell. I take the call, and lunch appears on the table.

Homemade ramen for lunch on Tuesday.

Dinner will be a gathering of the Chicago crew while I’m out here, less Chris who is in Milwaukee and wasn’t able to make it tonight. Our 1-year retention is coming up, and after that, I really don’t know how many of the original crew will stick around. We were bought out a year ago, with 12 of us in the org, and now only 9 remain. After the retention, I don’t know how many people will stick around. This could be a last hurrah of sorts for some of these guys.

We head into the city, and anyone who knows Chicago knows this word: Traffic. The drive takes over double what it should, but we talk and the drive goes by fast enough.

We head into the city, with the iconic Sears Tower (never Willis) looming high above.

The dinner rundown goes like this. We’re off to Shanghai Terrace, which is a high-end Chinese place right off the Magnificent Mile. The food is good, but for the price you pay it’s not good enough. By far the best dish was the duck, which is worth every red (queue Chairman Mao) cent. Nothing short of fantastic. The soup buns are overrated. A few of the dishes are fine. At these prices, I need more than fine.

The desserts were tiny and expensive, but the flavors were really well-done and complex. They were solidly dessert, yet captured the essence of what Chinese sweets are all about. I think maybe still overpriced, but these were pretty unique and very tasty. We talked about the meal the next day, and both Tommy & Serena agreed with my dinner assessment.

XLB, aka soup buns, are supposed to be the best here, but we found them good-not-great.
An array of mixed dishes.
Pork belly pyramid, something I have never seen before.
The desserts were tasty, unique, and patently Chinese-influenced.
Tommy & I mid-meal, before the pyramid falls to hunger.

Less traffic on the way back made for a much faster ride home. While listening to the new Weezer album (Teal Album) on the way back, I made 2 realizations. First, this whole album is made up of covers. Second, in this car of 7 people I’m the only white person. It’s not every day I can say that. We get back home and we immediately all crash. It’s been a long day.

Aaron, me, Kai, Tommy waiting for the car after dinner.

Given my lack of sleep the night before, a large bed, and a full stomach, it’s no surprise I slept really well. Almost 8 hours later, I arise for the day feeling mostly rested, but also feeling like maybe I could sleep 2 more hours. I had opened the window a bit the night before, and turned on the ceiling fan, which cooled the room off. I sleep better in general in a colde room. Breakfast this morning is a banana, an apple, and half a croissant sandwich that Tommy threw together.

Plus another pineapple cake. I mean, if you put it on the table, I’m going to eat it.

We do a few calls, have some career discussions that span 5 different subjects, all of which extend past the borders of this blog and most will think are boring, and then the morning turns into the afternoon turns into it being time to go get something to eat. Due to timing, we decide that we’re going to have a very late lunch, then I’ll take off for the airport.

There’s a word for brunch but there’s no word for Linner or Dunch. Either way you name it, this is our meal. This will be my one main meal of the day, and today it’s Katy’s Dumplings. I assume you see the theme here? Today is a much less upscale place, and for this meal it’s myself plus Tommy & his family. The place is more hole-in-the-wall-ish but if you’ve eaten dumplings in Asia, this is the kind of place you look for. The food is good, the price is less than 1/4 what we paid the night before, and we’re stuffed when all is said and done. Solid final meal for the trip.

Katy’s Dumplings, a contrast to the upscale place of the night before.
The spicy dumplings were really good.

We wait in the lot for the Uber, and do our hugs as the car pulls up and then go our separate ways. I don’t know when I’ll next be out here, but Chicago is often on the radar so I imagine it won’t be too long. Having said that, the org has put the brakes on all travel for now, so who knows.

I get to the airport early in the hopes that I can get on an earlier flight, with no luck. The first option is to spend $75 to get on a waiting list that will never pan out. The next option is to pay $75 to get home after the family is asleep anyway. So I stick with the original plan, use one of my United Club passes, and settle into the lounge for 3.5 hours while I wait for my boarding time at 9:00 pm.

The flight back is a little bumpy but of no note. I watch 2.5 more episodes of The Wire, drop some music on my headphones when we get off the plane, and drive home to an empty highway.

In all, this trip was more about touching base with my boss and the crew, doing some work that’s best done face-to-face, talking about things that are sometimes better done in person, and of course eating good food. That we got a good coffee shop in there is a nice bonus, and the pineapple cake is a total surprise win. I’m now weighing how much I want to buy those pineapple cakes from Amazon.

It was a good trip, as it always is when I come out here and see these guys. I typically enjoy my time here, be it in the city or outside of it. There are always things I don’t have time to do, or people I don’t get to see, or food I’ve been meaning to eat, coffee I’ve been meaning to drink, and so on. A bunch of my friends that were here in the NYSE days are gone, having scattered to different parts of the country now. So much as everything in life, this place has evolved for me.

In the end, I left the house at about 5:15 am Tuesday morning and got home around 1:15 am Thursday morning, making for a total round trip time of just about 44 hours. With that, I pull into the driveway and wrap up another trip. Mark it Donny.

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