How I Landed in Chicago

Posted on: August 29, 2017

Being a New Hampshire native that despised cold weather and winter, I naturally chose to go to college somewhere far away. I landed at Rollins College in Winter Park, FL in 2008 and didn’t leave for a winter up until last year, in January 2016. Everyone thought I was a moron for moving from Florida to Chicago in January and in retrospect, they were totally right. It was friggen COLD and MISERABLE the first few months. But hey, ya live and ya learn, right?

The most common question I got was “why!?” So, I’m here to tell ya! I lived in Florida for almost eight years, and halfway through my parents moved down from New Hampshire. Having my family close to me and constant sunshine was not a bad way to live at all. I have a strong feeling I will settle down someday near my family in Winter Park, FL, which is exactly why I left. I know the saying “YOLO” is a little overdone and lame at this point, but literally… YOLO.

I’ve always kind of unintentionally lived my life with a YOLO mentality and I think everyone should. At the end of the day, you literally only have one life, and you don’t want to look back with any regrets. Put yourself out there, even if it’s scary and you’re afraid of taking the leap. Just do it.

I was in Florida getting reallllly comfortable, working at my family company, having my family 1 mile away to lean on and support me and hanging out with the same people I had been for eight years. I did move to Boston for a summer during my Florida years, which was so fun and amazing being back with so many of my best friends, but I started looking back at my 18-year-old self and realized that I went away when I was 18 to college without knowing a single person. If I could do that at 18, I sure as hell could do it at 25. So, I told myself I wanted another challenge. A new city. Because why not? You can only pack up and move anywhere you want for a short period of your life. Once you’re married, with kids, or have a stable career, it’s a LOT harder to do so.

So, I told my family I wanted to move somewhere new for a few years while I was “young.” They were sad that I wouldn’t be living so close to them anymore, but totally understood why I wanted to try something new. They could tell I was getting bored in Florida because I was traveling practically every single weekend, exploring new cities. Like literally, every. Single. Weekend. Ask my roommate, who felt like she didn’t actually have a roommate.

As I mentioned, I was working for my family company, so I know it’s a lot easier for me to pack up and move than most people, but I consulted my Dad about it just like I would with any other boss. He said I could easily move somewhere in the Midwest because I was already covering the Midwest in my sales territory so we wouldn’t have to make any changes at work. I took about 3 minutes to think about it before I decided I was moving to Chicago.

I had been to Chicago a bunch for work and always loved it, so I figured why not try it out for real? My best friend from college lived there too, which was nice knowing I’d at least have her there. So, I did it. I packed up and moved in January 2016. I got an Airbnb for a month downtown, while I explored areas of the city to decide where I wanted to get a permanent apartment. To be honest, the adjustment was not easy, but now I’m SO happy I did it!

Even though I had one of my best friends in the city, she had her own life there. It wasn’t like she could hang out with me 24/7. I saw her once or twice a week, but I also lived alone and worked from home…alone. Not sure if any of you have lived like that before, but holy hellllllll it’s BORING! I literally could go several days without having human interaction. I would call my parents 100 times a day, just to talk to people. I’d go walking on Michigan Avenue multiple times a week, just to see and be around people, even if they were complete strangers (sounds pretty pathetic, eh?). I knew I had to make some sort of effort to meet people, so I joined a business club downtown, signed up for intramural sports teams, and reached out to college connections.

Joining intramural sports teams is such a hit or miss situation. Especially if you’re playing six person beach volleyball, you only have five chances to make a friend. I definitely joined my fair share of “miss” teams, but I luckily got a “hit” team when I played softball (no pun intended lolz). I met two girls who had also just moved to the city. One from Australia and one from London. And two years later, I still consider them 2 of my best friends.

I also started hanging out with a girl who went to my college that is from Chicago. We were a couple of years apart in college, so our friend groups never crossed paths much, but we met up in Chicago and really bonded! We’re both big foodies, so we originally just bonded over going out to trendy restaurants, but I soon discovered that she would be one of my favorite people of all time. Now, I can’t believe that we didn’t figure this out eight years ago in college!



This is a women’s bathroom in Chicago, but I won’t tell you where or it will ruin the surprise/shock.

Between my best friend, my two softball friends, and my newly-discovered college friend, I had a nice little girl gang that made my life in Chicago SO much more enjoyable. Looking back to just two years ago, so much has changed and I’m so happy I decided to take on the challenge of trying a new city. Since moving here, I have continued to meet more people, settled into a new apartment, grown our family company in the Midwest and have made so many lifelong friends here along the way. I absolutely love this city and truly feel that I have a real sense of HOME in the city of Chicago!


2 responses to “How I Landed in Chicago”

  1. Molly!!! Please leave your outfit details on every post if you dont mind. You are SO cute and look amazing in everything you wear I would love some tips!! <3

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