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When I started blogging back in 2007, I never imagined it would lead me to a career in design. Or that I’d travel to visit a friend I met through blogging, spend 3 days in Chicago, pack up and move to the Midwest, and then launch a women’s lifestyle website. But here I am. For those of you who don’t know my story, I spent my entire life in California, and after spending 3 days in Chicago in 2009, decided to return a few months later (during winter) for a 1 month sublet. A few months later, on August 1 2010, I made the move to Chicago. Six years later, my life is completely unrecognizable in a very good way. Here it is, my journey to Chicago.

Journey to Chicago

I found myself going through old posts written around the time of the move and thought I’d share them here, since this month marks six years in Chicago.

Written Feb 24, 2010

This was written a few weeks into my 1 month sublet which served as a test run to see how I liked living in Chicago (and if I could handle the cold winters). A new friend I made in Chicago was friends with Jacey of Damsel in Dior, connected us, and I rented her furnished West Loop condo for just over a month. 

It is almost 3AM but I felt like I need to sit down and write. 

Moving halfway across country by yourself to a new city where you don’t know anyone isn’t easy.

I didn’t expect easy. I knew I’d be lonely. I thought I’d have moments where I wondered how I got here and still have no idea how any of this happened. I do know that I love Chicago. The people are wonderful, the city is beautiful, and the snow is magical. But being all alone 2,000 miles away from everything and everyone I know is very, very hard. This isn’t like going away to college. There’s no dorm or meeting friends in class. Everyone has their own lives and routines. And here I am, by myself, smack in the middle of it all.

I have Thursday, Friday, and Saturday plans which is an improvement from lunch last Saturday and spending the rest of the weekend by myself. I know more of those weekends will occur and I’m ok with some alone time, but working from home can mean days without any human interaction. While I can see being good friends with some of the people I have met, for now they are great people that I am getting to know.

It will take some time to find my place and form relationships with people. 

To feel like I belong. As lonely as it can be, I am happier than I have been in a long time. I do believe that struggles and longing for something will lead to happiness. To completely disclose what was going on before I left, I feel like I should tell you that J and I were seeing each other again. It’s complicated and I just cannot go into the details of a 7.5 years of a relationship, but there is so much there. I am not 100% sure of where we are, but we were and are definitely something. I do know that he’s in LA and I’m in Chicago and that I cannot go back to LA.

As scary as this is, I am so glad that I did this and don’t want to look back with any regrets. 

If there is something you have been wanting to do but you aren’t sure if you should, please go for it. Out of everyone I know, I was least likely to pick up by myself and move to a new city, but here I am. Sometimes you may need to step outside your tiny little box. As cheesy as this may sound, figure out what it is you want, and follow your dream. It will be scary but in the end, you will find your place. It will be worth it.

Published March 18, 2010

I’ve been back in LA for one week and feel so different.

I think I’ve lost that spark that I had in Chicago. This city doesn’t have that special something that Chicago has, and I am not the same girl I was just a few weeks ago. Those 5 weeks in Chicago opened my eyes to a whole new world. They allowed me to come into my own. To explore, and to just be myself. I’ve had several moments where I’ve tried to tell myself this move is too much for me to handle.

I’ve thought about whether or not I can make it work in LA and tried to talk myself out of moving.

To be honest with you, I am not past that point yet. I stop to think of the millions of people that live here–and it isn’t all bad, but in the end it just isn’t for me. I do know that. But I have my doubts. I’ve never had my own apartment in LA and wonder what that would be like. In the end, we all know I’m supposed to leave. If I was supposed to get a place in LA, I would have done that by now. That would have made more sense than moving 2k miles away, but that is what I ended up doing. I–the girl that did not fly for 10+ year–spent 5 weeks in Chicago put a deposit down on an apartment. There is obviously a reason for that.

But even when all the green lights are on and all signs point to go, it is not easy.

When I have any doubts, I remember the happiness that I felt in Chicago. That my new friends offered to help me with my apartment, discussed house warming parties, and invited me to come out with them to dinners, events, etc.

I think about the fact that all these wonderful things happened after just 5 short weeks and I wonder how amazing things will be after 5 months or 5 years. Not having close friends in Chicago is one of the hardest parts about moving there. No family, no friends, no connections. Voluntarily putting myself in this situation is something I have struggled with.

It’s a struggle

Sorry I’m so all over the place. I am exhausted right now but need to get this out.  This is a daily struggle. For all of you who said I was so strong, I am not as strong as you think I am. This is an emotional roller coaster. Yes, I love Chicago. I was happier there than I have ever been. I had so many moments where I looked out the window or walked down the street and couldn’t help but smile and dozens of moments when I looked out the window and couldn’t believe that I was in Chicago by myself with thoughts of moving there.

I still cannot believe that this is happening.

This move is a lot more permanent and a lot more real. Last time I was in Chicago I brought a few boxes and a two large suitcases. This time, I am bringing everything. I am ordering furniture and signing a lease.

As scary as this is, it is an adventure of a lifetime and I want to take it all in. This will change my life and shape the person I become. I will meet friends I never would have met, and will do things I never would have done.

Published May 7, 2010

I found an apartment

I found an apartment right before I left Chicago on March 10th and put down a deposit. I cannot believe that I have been back in LA for such a long time and no, I have not been happy here. I planned on making the move to Chicago, and even booked a flight for the morning of April 28th. I obviously did not make the move.

It gets better. I promise.

Two weeks ago, I came across a building in an area that I really like.

I immediately contacted my realtor/friend who told me she knew I’d love the building. I filled out my application and waited to see if I would be accepted without having someone co-sign. That same day, I got a call. I got the apartment. In Chicago. And I move in just a few months with the pup as soon as the first dog friendly unit becomes available.

One thing that really made me feel like I needed to do this was the support of new friends that I hardly know.

I am still scared, but I met some really great people in a pretty short time span and am confident that I’ll meet even more. This is only the beginning. And when I miss my people back in LA, they are just a few hours away by plane.

The reason I followed through

While this is the most difficult thing that I have faced so far, I keep holding on to the fact that that I do not want my story to be “I took this trip to Chicago, loved it, went back for 5 weeks and really loved it, and almost moved there but didn’t because I was too afraid”. I’d spend the rest of my life wondering what would have been. 

I am so glad that my story will be “I took this trip to Chicago, loved it, went back for 5 weeks and really loved it, so I packed my things and moved there.” I can’t wait to find out what happens next.