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.


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?


24 thoughts on “Launching a New Life in Chicago”

  1. These are great goals, Katie! And Chicago is such a fun city to explore. Plus, now that you’ll be back there, I have one more great reason to come and visit! If you want a tourist to join you for some winter fun in the next month or two, let me know! 🙂

  2. Congrats, Katie! I love your story and am always inspired and excited by people who take bold actions to pick up and follow your dreams! I can relate to many parts of your story, and can’t wait to read more on your adventures.

    Seeing your points about flying solo, meeting new friends, dancing and your fondness for sport, I’d love to invite you to take a free Zumba class with me at The Indigo Studio in River West! Open invitation, I’d love to meet you and hear more about your story!

    1. Thanks Sue! I would love to take you up on that – I’ve heard about Zumba but have never tried it and don’t even know that much about it, other than it sounds like fun! 🙂 I’ll definitely be in touch!

  3. Katie, so glad I found your blog recently as we seem to have a lot in common! I left Chicago to travel as well and although I had only lived there for three years, decided post travel that I needed a change upon return and moved to NYC. Now that I’m on my second leg of travel (this time for much longer!) I’m missing Chicago and toying with the idea of returning there rather than NYC. Its such a great city and I’m sure you’ll love it even more this time around! Can’t wait to read about it.

  4. That all sounds like a great plan, Katie! I’ve been to Chicago a bunch of times and done some of the tourist things like visit Navy Pier, the Shed Aquarium, Sue at the Field Museum, and go to the top of the Sears Tower. But I’d live to explore more. Good thing I’ll be spending a week there at the end of April!

  5. I remember after spending a year and a half abroad that I would also learn to appreciate my home more. I think it is once you have these experiences of travel you see your home through different eyes. You really want to learn and explore the world around you even if it is just a few short miles rather than hundreds of miles away.

  6. You’re welcome to join me as I start leading Chicago Architecture Foundation walking tours. I’m a completely biased source, but their membership is the one I renew annually without a thought. Known for their boat tour, their walking tours include lunchtime building, neighborhood, cemetery, parks, bus & trolley, special topic (pub crawls) – going on 2-3 tours each year easily covers the membership. I’ve met some fantastic people from around the world too. Sorry, now that I’m becoming a docent, I’m a total geek for it!

    1. Oooh, that would be great! I’ve done the boat tour multiple times but I’ve never done one of their walking tours. Will definitely check those out! Is there a particular type of tour that you’ll be leading?

  7. Congrats on rediscovering home. I discovered something similar recently also. I’m always looking for the next destination, yet it dawned on me one day just how little of Florida I had actually seen in a lifetime of living here. So I resolved to find the joy here at home, instead of searching elsewhere…

  8. good for you katie! these sound like such great goals and incentives for starting another chapter in your book.

    i love chicago. i actually heavily considered moving up there before i decided to venture to norway. i mostly love the food. the city is insanely diverse and it shows in so many ways. my best friend lives out in lincoln square around a bunch of immigrants from all around the globe and i assure you…some of my best meals have come from that little area 🙂 and i swear there are festivals every single weekend in chicago. it’s great!

    look forward to following your adventures in chicago!

  9. The more I travel, the more I see when I come back to my home town. I spot more differences between the people, and I learn to appreciate how beautiful it is right on my doorstep. I found your blog a few weeks ago when I was searching for the Tran-Siberian Railway and ended up spending hours reading through your other posts, such an adventure! I hope you find the life you are looking for back in Chicago.

  10. One of the things I loved in Chicago was my visit to Frank Lloyd Wright’s house. The tour was very interesting and walking in that area was really wonderful. Also I really enjoyed the Architecture Foundation Cruise. I learned so much in an hour, it was incredible! Make sure you do these two things.
    Do you know of the Chicago Greeters. They are volunteers who show you around for a few hours, whatever your interests are. Since you speak Russian, you could be a guide with Russian tourists. That sure could be fun.

    1. You can add the Frank Lloyd Wright House to the list of things in Chicago I have never seen! Definitely need to add that to the list. And I’ve heard of the Chicago Greeters but haven’t really looked into them before. I like the idea of guiding Russian visitors around and practicing my Russian!

  11. Good luck Katie! I would love to introduce you to some friends of mine in Chicago, but they are mostly lawyers! And, I like your idea of writing about Chicago – I found the same thing when I meet people from other countries – they all want to go to NYC, WDC, Vegas, LA, Disney, but never say Chicago – its unfortunate, because it is such a gem! Write well about the city I love!

  12. Yay!! Being back here is amazing and I love it more than ever. I ride my bike a lot more (since I never needed to get a car again) and there’s always something new to see, explore, or EAT! Don’t forget about all the great food all around. That’s why I started this–>
    You can check out different ‘hoods there and my favorite lists of some yummy eateries.
    2013 is going to be a great year. Welcome back Katie!

  13. Congrats on the new venture Katie! If you’re ever in the Toronto area, I would love to host ya! I myself feel I’ve explored much of the world but sometimes it’s those neighbourhoods in our very own backyard that we miss out on. The world is a fascinating place but home really is sweet home 🙂

  14. Hi Katie

    I grew up in Chicago. I’ve moved around a bit and now live in Northwest Indiana. Not that far from the city. I feel the same way that I’ve never really been a tourist. A couple of things I’ve never done is, I never been to the Art Institute, John Hancock observatory or the Air and Water Show. I also say I’m going to go back to Brookfield Zoo after a couple of decades.

    I’m an Accountant. All my friends are Accountants some of the are also lawyers.

    Looking forward to reading your new discovers. I am sure I’ll learn some things.

  15. a) Cute pic of the IE girls!

    b) Love the plan! You know how I feel about doing things solo. So many amazing things have happened when I’ve led the Solo Life. My blog has a lot of activity suggestions, if you click on Solo Life:

    c) Check out Jill’s year end review of how she explored Chicago this past year, maybe some ideas for you.

  16. This is great! I am so happy that you will continue writing on your life. I have never been to Chicago (or many places in the US telling you the truth) so I look forward to seeing this city through your eyes. As someone who does everything alone (I have little patience waiting for people), you will enjoy your time alone exploring. It is so much fun and you can go at your pace and leave when you want.
    You are no longer a lawyer? What??
    A friend and I are going to also play tourist in Toronto this summer. We are actually going to take a tourist bus and do the city. We were both born in different suburbs outside of Toronto but she now lives there and I aspire to move there. We think we know so much about the city but realize we dont know much of the history etc so we will play tourist. You have also inspired me. I am currently living in a new city (which is just ok to me) so I will make an effort to know more about the neighborhoods and people. I dont think I will be there after 2013 so might as well get it in now. Good luck in your new adventures. Sounds so fun.

  17. Katie, I love this! You captured much of how I felt when I lived there as an attorney, as well as how I’d change things up if I was there again. If you’ve never visited Ukrainian Village on the near West side, it’s worth a trip! Awesome Eastern European food at Kasia’s Deli (2101 W Chicago Ave), delicious Middle Eastern at ChickPea (2018 W Chicago Ave), and – my favorite – Flo for new Mexican cuisine at 1434 W Chicago, especially for weekend brunch (or anytime breakfast, lunch, dinner). Very comfortable to go solo and eat at the counter bar. If you see Anita, tell her Dawn-who-moved-to-the-Bahamas-a-couple-years-ago sent you! 🙂

    1. Thanks for the suggestions Dawn! And nice to hear that I’m not the only one who got to feeling that way as a lawyer in the city.

  18. This sounds fantastic Katie! I have just spent the past few days running around Sydney (Australia) playing tour guide to a friend from interstate. It’s amazing the things we can discover in our own backyard!
    I am planning to visit the United States and Chicago in particular sometime later this year… I would love to read about your beautiful city. Can’t wait 🙂

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