Launching a New Life in Chicago

Remember when I wrote back in November about feeling unsettled and longing for my old life?

Well, I realized my old life isn’t really what I want.

If you’ve been following along since I first left Chicago in August 2011 to travel for a year, you may recall I was ready to go. My life in the Windy City had evolved over the decade that I called it home and I was feeling bored and restless and just needed to leave. At that time, I really wasn’t sure if I would return.

But as they say, absence makes the heart grow fonder.  By the time I touched down in Chicago four months ago, I was thrilled to be back. And after months of networking and interviews and seriously considering job offers in both San Francisco and Boston, I am back for good. However, now that I am finally getting settled, I am realizing I want my time in Chicago this time around to be a lot different – I don’t really want my old life back after all.

I will still run along the lakefront path and join friends to watch college football. And I will likely pick up tennis lessons again or join a volleyball league. And I still can’t wait to move back into my adorable condo when my tenant’s lease is up next fall.

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However, this time around I want to do so much more.

 
Despite living here for a decade, I have realized there is so much of the city I missed in the past. I previously lived in a bit of a bubble, rarely stepping outside of my comfort zone and falling far short in terms of enjoying all the city has to offer. Sure, I once subscribed to Broadway in Chicago and I made it to Lollapalooza a few years in a row. But I never set foot in a blues or jazz club unless I was hosting visitors. I never ventured to neighborhoods like Pilsen or Chinatown aside from a couple meals as part of a dinner club I organized. And I never did anything all by myself – if I couldn’t find a friend to join me, I didn’t go.

This time, I am determined to create a different experience for myself. Here are a few examples of how I plan to do it:
 

1. I’m going to broaden my social circle.

 
When I first moved to Chicago in 2001, my circle of friends consisted of lawyers, lawyers and more lawyers – colleagues, law school friends and a plethora of their friends who all practiced law. Even now, when I meet someone who is a lawyer, I feel an immediate connection. At the same time, that is no longer who I am – I’ve changed and I find myself seeking out people who have interests that more closely match mine now. I still have several good friends from my lawyer days and I hope we will continue to be close. But I see myself now reaching out to people I have met through things like improv class and Meet, Plan, Go – people with whom I just have more in common now.
 

2. I’m going to volunteer regularly.

 
I experimented with volunteering in the past but I never found an organization that really clicked with me.  Now, I have my sights set on two organizations whose missions really resonate: World Chicago and World Sport Chicago. I volunteered with World Sport Chicago a couple years ago when the organization’s focus was on bringing the 2016 Olympics to Chicago. Now, it promotes the development of sustainable sports among under-served youth, while also supporting the city in its efforts to bring high-level international sporting events to Chicago.  This combines two of my major interests and I want to get more involved.

World Chicago is all about citizen diplomacy – they host over 1,000 international visitors a year, many of whom are emerging leaders or up and coming professionals in their fields. Volunteers can provide homestays, host visitors for dinner or provide cultural experiences around the city. As an added bonus, a significant number of their visitors are from former Soviet countries.  How perfect is that? I sat down with their outreach director back in December and I am really excited to start working with them in my free time.
 

3. I’m going to explore Chicago’s neighborhoods.

 
I have never spent much time outside of the north side and downtown Chicago. This likely had a lot to do with a fear of standing out if I dared to wander the streets of Pilsen or the restaurants and shops of Devon Avenue. But after a year of traveling on my own through countries where I almost always stood out, I think I can handle it in my own city. I want to go beyond just going out to eat somewhere new; I want to spend a whole day in new neighborhoods, wandering the streets, checking out the shops – even participating in local festivals.
 

4. I’m going to do everything on My Ultimate To-Do List for Summer in Chicago.

 
I wrote this list in the spring of 2011, anticipating that that summer may be my last in Chicago. Unfortunately, I was so busy getting ready for my trip that I didn’t come close to checking off everything on the list. This includes checking out the free music at Millennium Park, enjoying Movies in the Parks, putting on my dancin’ shoes for Chicago SummerDance and exploring the many farmers’ markets in the city.

Cloud Gate, Millennium Park, Chicago
 

5. I’m going to play tourist in my own backyard.

 
I love playing tour guide to friends who are visiting Chicago. Unfortunately, that doesn’t happen as much as I would like it to (hint, hint to all of you who should be visiting!) and I never do anything “touristy” otherwise. I haven’t been to the Field Museum in about ten years and I have only gone to the top of the Sears Tower (I mean Willis Tower) once. My only trip to the Green Mill was when my parents visited back in 2002. And I’m not sure I have ever been to the Adler Planetarium. These are all big with tourists for a reason and I want to start enjoying them more for myself.
 

6. I’m going to fly solo.

 
I hardly ever went to anything on my own in the past. If I couldn’t find a friend to join me, I just skipped the event altogether.  As a result, I likely missed out on a lot – no, I definitely misses out on a lot. Now that I have spent a year traveling on my own, the idea of going solo doesn’t faze me as much.
 

7. I’m going to write about it all.

 
Since I won’t be doing much traveling in upcoming months, I’m going to change gears a bit and write more about rediscovering Chicago. I have met so many people overseas who have been to the United States or are thinking of visiting and very few include Chicago on their itinerary. I hope to do what I can to change that by writing about all of the amazing and diverse things the Windy City has to offer.
 

What do you love most about Chicago? What should I add to my list of things to try?

 

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