A Week in Chicago That Changed the Course of Our Lives
Earlier this year, Aaron and I stayed in Chicago for almost a week. The last time we were in the city was when we took a visit to see our long-time friend, Jimmy, who showed us both that awesome Italian grocery store, Eataly and the amazing Thorne Miniatures installation at the Art Institute of Chicago. (We had hoped to see him during this trip but, sadly, we didn’t give him enough notice as we couldn’t nail down the dates until the last minute. That meant while we were in his backyard, he was on the other side of the globe, having flown off to Madrid, Spain, I believe it was, on a spur-of-the-moment vacation to relax, tour glorious old cathedrals, and experience the local culture.)
It seems safe to say that it was probably one of the most important trips we’ve ever taken, the ramifications of which will be felt in ways that are difficult to calculate but that will no doubt reverberate for the remainder of our lives. While nearly all of our time was spent in meetings, working from the hotel, or touring real estate to give us a better idea of how we might make the city home if we end up living here for an 18-to-24-month stop-over in Illinois en route to relocating to the West Coast – something I briefly mentioned in the post on looking at office space in Southern California and that has to do, specifically, with the process of us having kids – two other things occurred.
- We came up with a plan to divest all of our operating assets, and intellectual property, related to the letterman jacket and letterman jacket award industries as part of our decision to reorder our entire careers around the asset management firm.
- We attended an incredibly helpful gestational surrogacy conference that provided us with the opportunity to sit in on panels with physicians, attorneys, and other specialists. These experts walked us through the process of having children by laying out a comprehensive roadmap of the surrogacy journey, and allowed us to hear from other couples who have built their families through surrogacy, speak with children (now adults) who had been born through surrogacy, and have question-and-answer sessions with women who had given the gift of surrogacy to others in the past. It was eye-opening in ways we didn’t anticipate but that deserves its own post in the future as we share that part of our lives with you.
During our time in the city, we called the Langham Hotel on the Chicago River home. We decided to give it a try because the location was convenient for our business needs, we had heard incredible things about it after it was named the best hotel in the United States last year, and we were thrilled with our experience when staying in the Langham Hotel in Pasadena several years ago. It turned out to be a great decision. The hotel itself is amazing but the staff really make it shine. It’s hard to describe but it was a deep competency in even the small things. They made everything easy, letting us focus on our work. From allowing us to use the boardroom on short notice and for as long as we needed (in fact, there was only a single day during the trip where they couldn’t accommodate us due to what I believe was a corporate pre-booking, in which case we were able to use the Club Lounge) to helping us gift wrap presents for our nieces and nephews, they made it possible for us stay productive. Whenever we needed to go somewhere, the car was waiting for us at the front of the building. If I needed a stack of stationary to take notes during long phone calls, problem solved. Those things add up and came together to to make it something special.
The first night, nearly everything was closed – turns out to be the story of this trip as by the time we were finished with work, few things were open – but we decided to walk around the city. It was great to see it like this. I understand why people take such pride in it.
My favorite part of the hotel was definitely the Club Lounge. The views were fantastic, the staff was always available to help, and you could be left alone to work in peace for hours at a time. There were days when I’d grab a stack of annual reports from the room, get a cup of coffee, and sit at one of the tables with my pen and highlighter, reading. They also had these ridiculously large, great-tasting glazed donuts for breakfast but the downside of that was they felt so indulgent you couldn’t help but skip lunch to make up for the nutritional sacrifice. Still, they were worth it. I get the feeling the food in this city is probably really good.
Speaking of which, we made a point to stop by Giordano’s because my brother kept urging us to indulge in one of their deep dish pizzas, which he loves.
The only bad part of the trip is that we couldn’t really enjoy much of the city because time didn’t permit us to do anything other than stick to our agenda. There were a few brief windows of time when we were able to take breaks and visit the Magnificent Mile. On one of these outings, we picked up a few things at Brooks Brothers because they were having a huge sale. We also managed to get a few small gifts elsewhere. 
Aaron and I have a lot to decide, and many of the decisions we’re facing will make sense when we start explaining the surrogacy process. For example, do we keep the house in Missouri? What does a person even do with multiple houses? We know lots of people who have them, and who seem to enjoy the convenience, but he and I prefer simplicity. Maybe that will change as we get older and have kids; pick up and go spend the summers near both grandmas and grandpas as we can work from nearly anywhere thanks to the nature of capital allocation. Still, it’s not something towards which we are drawn.
Regardless of whether a combination of favorable political laws and fate end up combining to result in us becoming residents for a couple of years, we end up having a layover somewhere else, or we go directly to California, we understand the reasons so many people love Chicago.
