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Taking a Chance: NYC Do or Die Moves to Chicago



A few years ago, I was faced with a tough decision. Stay in New York City, the center of the universe, a city I knew well and had grown up in, or take a chance and move to Chicago to work at a stellar, growing Private Equity fund. While I weighed my offers, I was ultimately left with the choice of taking a chance or playing it safe and staying in the city I knew so well. I’m not sure what got a hold of me that day, but I called my friends and family and told them that I loved them and would visit them constantly. I was going to move to Chicago in a few short months, but I would be back with them in New York in 2-3 years.

Then began the process of figuring out how to move seemingly halfway across the country. While this was daunting to start, I quickly realized that the fund I had signed with was paying for my relocation, and all I had to do was play coordinator, a task not dissimilar from IB/PE diligence processes. The next task on my list was where to live in Chicago. I talked to a few associates at my fund and was easily able to set up tours at a few buildings close enough to the office that my commute would be a measly 6-minute walk. This was a massive win in my eyes because I could live in a desirable neighborhood with ample nearby bars and restaurants while having just a short commute to work.

At this point, I was pumped for this new change and experience, and I had not even seen the apartment buildings yet. I had been paying more than I care to admit in NYC to live in a decently livable, tiny one-bedroom apartment. Upon touring the apartments my soon-to-be colleagues told me to look at, my mind was blown. This apartment was massive – 900 square feet in a new build – and had every possible amenity that I could imagine. This apartment was something that 1) does not exist in NYC outside of the Financial District (where I would never even consider living) and 2) even if it did exist in a semi-desirable Manhattan neighborhood, it would be $7,000 a month and I would never be able to afford it on my own. At this point, Chicago was starting to sound pretty nice, and I had not even moved yet.

I will choose to spare you all of the boring details here, but my move went incredibly smoothly despite some last-minute anxiety about uprooting my life. After the move was complete, in a few short weeks, it was time to start my private equity associate role. While excited, I was nervous as this was the next big step in my career. The first day came along,  and I was pleasantly surprised at how welcoming the team was.

At this point in your careers, you all know that finance is an apprenticeship model, and who you work with is incredibly important, as the only way to learn how to do your job is from your peers and superiors. I loved my time in my Investment Banking group because I was close with my team, and they all worked hard to make sure the analysts they liked were learning and improving. When interviewing for private equity roles, I paid very careful attention to how people talked about their colleagues and how they interacted with me. Based on my interviews with what would ultimately become the fund I chose to join, I felt like they were the team that I trusted the most to care about and push my development. I was so happy when, even on my first day, I already found them to be an incredibly supportive group.

While this was a great aspect of my fund, I have also found this to be true of many private equity funds in Chicago. It took me a few months to realize that being in a different city really inspired a different culture. The “Midwest nice” that I was experiencing from random neighbors and even just people on the street translated to an office setting as well. Seniors were more open and willing to talk to juniors, and everyone was and still is willing to make time for me. The events we had outside of the office (offsites, work travel, happy hours, etc.) have also had a great effect on all of our in-office relationships.

Another great aspect of the Chicago Private Equity scene is that, because it is a somewhat smaller universe of funds than exists in New York, the funds hold frequent events where you can meet juniors from other funds and understand more about other firms, investment strategies, and cultures. While this is great networking, it is an even better way to make friends with people with similar jobs/demands. Overall, the tight-knit aspect of the Chicago Private Equity scene makes it a very powerful network.

All this together has led me to have an amazing few years in Chicago, but does that mean my time is up? Am I moving back to NYC like I promised all those friends and family years ago? Perhaps not.

Chicago has proven to be an incredibly livable city. Between the ability to walk the pristine lakefront on early mornings and weekend days and the affordability aspect that has me living in my 20s, I thought I would have to wait until my late 30s (even working in Private Equity) to afford in NYC. Maybe you’ll find me in a Lincoln Park brownstone/townhome (for a fraction of a fraction of what it would cost to own in NYC). Overall, I now view Chicago as a more sustainable city and can see myself building a life here. Even if I did decide to return to NYC eventually, I would still be grateful for everything Chicago has given me in terms of both personal and professional development.



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