My journey to Chicago is a story I’ve shared before, but any time I hit a big milestone like today, I can’t not think about how much my life has changed in the past seven years in Chicago. It was those years that brought friendship, a new career, love, and for the first time in a long time, happiness. 

Seven Years In Chicago

For those of you who don’t know my story, in November 2009, I visited Chicago for 2 nights with my friend Kelsey. We met through blogging, naturally. And I know it sounds crazy, but I got off the train in Lincoln Park and knew I was home. So I went back to Los Angeles, cried, planned, and returned to Chicago to sublet a place for one month on February 1, 2010. To a city that “seemed nice”–a city where I knew absolutely no one, to see if it was in fact, the home I thought it was. And to see if I could handle the winter because pre-Chicago, 50 degrees was freezing.

February came to an end and I wasn’t ready to leave.

I extended my sublet through March 15th. So I found a real estate agent and looked at places on Craigslist, and even put down a non refundable deposit on a studio in the West Loop. I had a plan. But back to that last day in the city, which is one I hope I never forget. I walked from the West Loop to The Bean in my leather jacket, feeling so incredibly cool and like a true Chicagoan–wearing leaving my North Face at home when it was in the 40s. To that spot in the picture above, on a slightly more grey day than the one in this photo. I stood there overlooking Michigan Avenue and didn’t want to leave, but needed to sort things out and home and get the rest of my stuff.

The thought of actually starting over shook me to the core.

I would be completely alone. No family, a few acquaintances, and a job where I worked by myself from home. But I reached out to the one blogger I knew of in the city asking for recommendations and she invited me to dinner and an event where I met a few other girls. That real estate agent invited me out for a manicure and drinks after looking at apartments, then for drinks again, and I made another friend through her. One who sent me a text a week after I left to check in and see if I needed any help.

Are these people for real? 

So I flew back to LA and quickly realized how unhappy I was being back.

My ex boyfriend was a bit of a sociopath (mean, manipulative, and generally terrible), and I just couldn’t shake him. I had a few close friends (still do) but I was in a rut and needed needed that fresh start. But I woke up in tears every morning terrified of this big change, and gave up my deposit when I backed out of that apartment.

I went back and forth but found a place in River North online.

So I flew back to see the place with my new real estate agent friend, who also invited me to stay with her a few months later. I remember hoping there would be a sign that this was my city, and this is where it gets really good. I took a cab to a bar that I can’t remember the name of, threw my stuff in the back of her car, and celebrated as the Hawks won the Stanley Cup. The city went wild. Fireworks everywhere.

I was home.

We saw my new apartment the following day, I put down a deposit, and started planning my move. But the tears didn’t stop and I was still so afraid to leave LA. And this is where it gets even better.

My now friend Anne put down a deposit for me to design her blog since that’s what I did before starting The Everygirl.

So I sent my initial follow-up email and then this.

“I don’t usually do this but need to say one more thing. I wanted to tell you that I used to read your blog and that your story has been an inspiration to me. Mine hasn’t been an easy one–an 8 year relationship with a few not so big but constant lies, lots of drama, and I am now leaving LA on Aug 1 for a move to Chicago! Hopefully after hearing that you can tell me how amazing Chicago is. I am miserable in LA and need a change. Terrified & in a constant state of worry/panic but hoping it will be great for me.”

And (some of) her reply

“Danielle! Your email made me cry! What is this–you are moving HERE to Chicago??? I’M back in CHICAGO, not in DC! I just moved back in April bc I missed it terribly! You have a friend here in me for sure! I promise you you will love it!”

I had put down another deposit and things were in motion, but it was on that day that I finally booked my one way ticket home. And Anne’s home was the first place I went after I got settled in and my mom returned home to Los Angeles. Buddy is the only thing that would be in my life right now aside from friends back home and my family. Every friendship, love, my job, and every single experience that has happened since this day seven years ago has happened because I decided to take a chance on this city for a month.

I can’t believe how unlikely I was to do this.

I didn’t fly for about 10 years after 9-11, went to college 90 minutes from home, and went right back to my hometown when I graduated. Out of everyone I’ve ever come across, I was probably least likely to pick up and move across the country by myself, so if you’re struggling right now, please give yourself some credit. You are stronger than you think and whatever it is, I promise that you are more than capable of getting through it.

Anne gave me so much hope when I was second guessing my move, so while I’m not an expert, I’m here to brainstorm a big change or listen to what you’re going through. And sometimes it helps to talk to someone you don’t really know. So if you want advice from me or anyone reading this, leave a comment, or feel free to email me or send a direct message on instagram.