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  • Writer's pictureBryan Jun

goodbye Chicago - part 2 of 3

As many of you know, I'm leaving Chicago "permanently" this Wednesday. As the Windy City was my first home as a true adult post-college and my first real city life experience, I thought that it deserved at least 3 blog posts the reflect my thoughts and feelings. Over the course of the next three days, I'll be discussing:


  1. Things to do and eat

  2. My thoughts on Chicago as a young professional

  3. Personal reflections

Note that while the posts are to serve as a funnel from "objective" to personal, it'll be difficult to detach my subjective opinions from all of the topics mentioned. As a means of background for those of you unaware, I've lived in Chicago full time since June of 2019 following a summer internship the year prior. As the world flipped itself upside down in March 2020, I have gone back and forth between the Second City and Irvine, CA (where my family resides), but I'd identify Chicago as my "home" for the past two years.


My thoughts on Chicago as a young professional


It's rather to keep this post as objective as possible as my introduction and life in Chicago has been under such a wide array of special circumstances that I'm not entirely sure I'm the best perspective on this topic. Regardless, after being here for two years as what most call a "young professional," here are some thoughts on what it's like to start a career here in the Windy City in both a career and social perspective.


For a little synopsis on my time here, the first time I lived in Chicago was actually following my junior year in college for my summer banking internship, which ultimately became a full time offer post graduation. The 10 week program flew by, filled with excitement of a buzzing city (I've only lived in suburban areas, the regions that people during the first two weeks of school during introductions say that they're "just outside of [insert big metropolitan area here]." In comparison to other horror stories from investment banking, my internship was actually on the "chill' side and looking back it was probably one of the best summers of my life. A foodie by trade and an extrovert by genetics, I don't think I ever felt more energized by the thousands that I walked by everyday. It also helped that Chicago summers are something out of a romance movie and I won't be the first to say it may be the best summer city experience in the United States. Note that I was still under 21 this summer and I am a law abiding citizen, which could have limited my experience of the city depending on who you are.


My full time experience in Chicago started in June of 2019 and aside from extremely late night activities on the weekends, there wasn't much time for me to fully enjoy the city. I don't even fully blame banking for this as there were plenty of bankers in my class who seemed to find pockets of time on weekends and and even sometimes during the weekdays to do this - I just think adulthood hit me like a truck and I needed time to adjust. My state of mind wasn't at a place where I could "own up" to being a young professional and it felt more like I had four places that I had restricted access to - home, work, this one nightclub and church. It's hard to say I fully embraced the city during this nine month period and some of the best times during my early career was spent outside of Chicago.


Then President Trump announced the European ban, my firm went from "stop talking about COVID it wastes time" to "go home and take your monitors," all my deals died for 2 weeks and no one had any idea what was going on. I defaulted to my defense mechanism of going home and it felt like I was in high school again. I realize I've deterred from the main topic a bit so let me fast forward to August of 2020, where I think I started to fully recognize the merit of Chicago as a city for a young professional. Some brutal truths ahead, you've been warned!


If you're in finance or any form of professional services, I don't really understand why you wouldn't live in Chicago unless you have a genuine fear of the cold or you have a medical obsession with NYC. The pay is the same across the board with a significantly reduced cost of living and marginally lower taxes. The cleanliness of this city is actually unbelievable - note that the science of urban planning was literally invented here. Never in my life have I been to more of an accessible place that is perfectly laid out in a logical grid system - and this is coming from someone who grew up in bubble city Irvine, California, a perfectly planned out suburb. Nightlife could be the one "limitation," but unless you're envisioning hosting a weekly table facing times square with your Goldman friends, Chicago will be more than satisfactory for you (I'd recommend Tao or Hubbard Street as a whole). If you have the money to do that, you can also just go to NYC once a month and spend whatever you saved by living in Chicago instead. I've talked thoroughly about the food here (which I think matters a lot as a young professional) and the activities you can partake. Perhaps I have a low bar for what's fun, but even walking down Michigan Avenue is exciting. One thing I do have to come clean about is that I am somewhat of a control freak, so I think fully understanding the layout of the city and what area has what is very important to me. I realized early on that I'm not worthy of doing so with the great NYC whereas Chicago was something I could figure out within a month or so. Maybe I'll tackle NYC when I grow up.


In terms of careers, and I won't be discussing job by job as I don't know much beyond the finance scene here, there is a matter of how obsessed you are with the "hustle." Most people that didn't grow up here would agree that Chicago isn't necessarily known for the grind mentality and especially in comparison to its counterparts, I think it's notorious for its lax. You could "blame" the midwest culture or the cold weather, but I actually think this is one of the most important aspects of Chicago that people overlook. Not everyone wants to hustle 7 days a week and pay $4,000 for a studio - many people, in fact, want to make $75,000, live in Wrigleyville and go on the riverwalk for a beer every weekend. Aside from internal motivation and the occasional freaks like me from the outside, no one is pressuring you to constantly be on your A game or looking down on you for not having a blog. To the one career I can speak on, I will guarantee you that unless your end goals are Blackrock and KKR, you'll have no problem breaking into that buy side role that you dreamed of from the womb.


One thing I'll speak to that people will start squirming about is lack of diversity. I'm not really one to criticize such things nor do I think cities have a responsibility to force diversity, but if you're someone that deeply cares about the racial makeup of a city, it's definitely something to consider before starting your lease here. Probably due to a wide array of reasons like the overall makeup of the Midwest, the various feeder schools in the area, Indiana and Michigan and the Chicago Bears, Chicago probably is one of the most white cities out there. Again, I've never personally seen this as a problem and there's definitely pockets of other races that you can actively seek out, but unless you're on Michigan Avenue or other touristy spots, you're not going to get that melting pot feeling you romanticize. This in turn leads to a restricted pool of what I'd call non-white food and an "overwhelming" amount of social spots where you clearly stand out if you're a minority. I will say, I think this all depends on what you deem to be the "true American experience" and I can see arguments for both pros and cons of this aspect of Chicago. It's just something to keep in mind as you look to venture into your first couple years.


Geographical location in relativity to the United States is also rather ideal, especially if you have a lot of friends on the east coast but you don't want to live where they live. Less than three hour flights to DC, NYC and Boston (which is 90% of my friends), all at affordable prices. There's a direct train from the city to O'Hare Airport (which the end spot is the airport itself) and if you can bare the cost, the Uber ride there isn't that bad either. Screen golf exists throughout the city and if you're really into it, there's a long list of great golf courses in the north where the old money resides. If you're considering a grad school network, there's UChicago to the south, Northwestern to the north (lol) and plenty of others that my Korean name brand schools only brain won't allow me to remember. Speaking of schools, I will say the one negative thing about Chicago if you didn't go to a school around here is how strong the alumni culture is in comparison to other cities. If you didn't attend IU, UMich or Notre Dame (who almost have stronger Chicago pride than the schools actually in Chicago...) you're going to feel like an outsider. But this is probably true at other cities too, given that I've actually never lived in another city before, although I have a strong guess that NYU grads don't only hang out with each other.


For some tangible advice - if I started my time in Chicago again, I'd probably live a bit more north. Consider neighborhoods like Wrigleyville, Lincoln Park, Logan Square and Old Town. Where I live, River North, is definitely convenient, but my roommate and I are definitely the youngest people in our building and constantly being around tourists probably diluted my resident experience a bit. I'd also take advantage of the public transit a lot more than I did during my time, the city is vast and always more to explore.


These posts are simply making me sad and I'm sure tomorrow will just top it off - please move here so I can live vicariously.

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