The Midwesterner Takes on the Northeast: A Tale of Moving in Your 30s


A family packing for a move.Moving at any age can be challenging. Whether it is as a child or as an adult, it always comes with lots of anxiety and the fear of the unknown. All of these feelings became a reality in my 30s.

I was born and raised in a large suburb outside of Chicago called Naperville. Nicknamed “the best place to raise a family,” I am unsure if I ever thought I would move from it. I loved it. It was all that I knew. My town (I still like to call it that) had a large downtown area that, when I was a teenager and had my license, my friends and I used to cruise through the area, and that was what we would do for fun.

I liked knowing my town inside and out, the shortcuts to get places, and everything in between. Even when I moved to the city of Chicago in 2007 from the suburbs, I still felt an extreme amount of comfort. I knew my family was just a short car ride away, and the city opened up many new opportunities for me both in my career and socially. Again, in my mind, I was a true “midwesterner” and never thought I would leave my bubble of Illinois.

In mid-2017, my oldest daughter was still an infant, and we lived in a small two-bedroom apartment in Chicago. Both my husband and I worked demanding jobs in the hospitality industry, and at that time, we referred to each other as “strangers in the night,” as we had opposite schedules and saw each other so infrequently. It became apparent that a change needed to be made. We had plans to grow our family and knew that for that dream to become a reality, many things would need to change.

That first change was a rather large one. At least, it was in my eyes.

My husband had obtained his license to practice law in Illinois; however, that perfect job never came his way. Since he was originally from Connecticut, he started poking around and found an opportunity to begin his law career at a White Plains, New York firm. I was overjoyed that he had found something in the career field he had always wanted, but it meant we had to move.

A move back to Fairfield came easy for my husband. His family still resided there, and he still had many friends who lived there. I was terrified. I was terrified of where my career would go, what friends I would have, the lack of seeing my family as much as I did then, and just the location change.

I knew Illinois. I did not know Connecticut.

2017 ended, and our big move was scheduled to happen in March 2018. Looking back, I wasn’t honest with myself that we were moving. We had made the decision, but it did not become real to me until I had to give my notice at my current job – a job I loved and was so sad to be leaving.

I remember packing up my car after cleaning my office on my last day of work and driving away. I looked back, and tears began falling down my face. This was all a reality now, and I was too proud to admit that I was terrified.

The day finally came. My daughter and I boarded a plane to Connecticut (my husband was waiting on the moving truck and driving a few days later) and said goodbye to our friends and family in Chicago. It was a tough day, especially when I had to say goodbye to my parents, who I was very close with, knowing they wouldn’t be a car ride away anymore. Even at 35 years old, leaving my parents felt so terrifying. I knew things would never be the same.

When we first moved, there were so many things, mostly small things, that I couldn’t get used to; the traffic (why are there only two main highways?!?), no street lights to see where you were going at night, car tax bills, and why bars and restaurants closed so early (I was used to Chicago).

At my first restaurant job, most of my clients said, “You aren’t from the East coast, are you? You are far too friendly to be from around here.” I laugh at this now, but back then, it only intensified my dislike for where I was living.

I certainly did not come to Connecticut with the right attitude to Connecticut. So when we first moved, I didn’t make friends. I didn’t learn about the restaurants and things I could do in Fairfield County. Deep down, I think this is because I somehow thought the move wasn’t permanent. I regret many of these early decisions as they made my life and my family’s life very difficult during those first few years.

Once we bought our own home at the beginning of 2020, I knew I had to change my perception of Connecticut, as this was now my home. My goal was to build new friendships, learn about the many attractions CT had to offer, and change my attitude.

I wish I had done it sooner.

I will always identify as a “Midwesterner,” and part of me hopes I never lose those qualities that a midwestern girl has. I always have a smile on my face! It’s hard to say that it has taken me nearly five years to adapt to a new home, but I finally feel settled.

But I still put on Google maps for every location I go to in CT, even if it’s in my town!

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Lindsay lives in Trumbull with her husband, Ryan, three crazy kids (girl - 2016, and boy-girl twins - 2020), and Harley, their Shih Tzu in her twilight years. Originally from the windy city of Chicago, Lindsay met her husband when he moved from Fairfield, CT, and they decided to move back to Fairfield County as they grew their family. With a strong background in the hospitality industry, Lindsay decided to make a career change post-pandemic and is now in sales for assisted living communities. Outside of spending time with her young children and family, Lindsay enjoys volunteering for her children's schools, meeting new friends, and trying out new restaurants.


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