31 Comments

  1. KristinaMarie1
    KristinaMarie1 at

    Chicago is my twice-adopted home – I moved here with my then-husband in 2004 to start grad school. I wanted to be here, grew up in Michigan and loved urban visits, and studied here for a semester in college (during another rough winter!). We were starting our life together and planting roots. I had friends and was ready to make more and really build a life and a community. 

    In 2010, when my marriage fell apart and I was all graduated, trained and licensed, it was time for some real change – time to jolt me out of my comfort zone and do something bigger than myself. I moved to South Korea to work as a civilian counselor to our soldiers stationed there. It was the biggest adventure of my life (so far) and I embraced it. I spent a large part of my salary on travel, saw 7 countries in 8 months, and toured around Korea the rest of the time on day trips and weekend adventures. I made friends who were Korean and American, transient and stationary, and said “yes” to almost every invitation to something – an art show, a train ride, a dinner, a walk up a mountain (there are plenty of them there), a yoga class, a coffee and cupcake (awesomely and frequently paired there). I learned how to take photographs, how to be truly independent (but when not to be), that a career path can have diversions and bi-ways and backtracks, that being alone has its positives and negatives. And I learned where home was for me. 

    When it was time, I came back, re-adopting my true home and embracing another opportunity – this one a bit more traditional – knowing that I had nurtured this particular sense of adventuresomeness and I would have to work to cultivate it while living a more “normal” life. Sometimes that’s a real challenge. But it gets easier to look for all the little ways to say yes, and to find the daring and the exciting in the everyday. 

    Saya, it sounds like you need to nurture something within yourself. Its stirred, awoken, and you won’t be able to let it rest until its ventured out, fed, seen something! I can’t tell you whether you should dip your toe or jump in with both feet, but I can encourage you to stop hesitating and try whatever fancies you next. It doesn’t have to be THE adventure or the RIGHT move, it just has to be something that lets you test the waters, no matter how big of a splash you make;) 

    Its Nike time, my friend:) Keep us posted!

  2. katieaune
    katieaune at

    Fascinating. I have seen some of the exodus too. Speaking for myself, when I left to travel in 2011, a large part of it was that I was just tired of Chicago. I felt stagnant here and was bored and felt like I just didn’t have much in common with people as I had before. When I looked for places to live when I returned, Chicago ended up feeling natural to come back to, but I think more and more about leaving as well. It’s been harder than I imagined to get back into a social life and I found most of my friends moved on while I was away and I haven’t had much luck finding new people here that I really connect with. I feel more and more like Washington DC is calling my name, but it would take the right opportunity for me to actually make the leap and move.

  3. JillyMacDowell
    JillyMacDowell at

    This (substitute Pittsburgh): “I found that I didn’t love Chicago anymore and couldn’t get excited about it again. It started to feel too big, too crowded, my commute was too much, I wasn’t seeing the friends I did have as much. In my effort to try to rekindle my love for Chicago, I did some fun stuff and I was making lots of girlfriends but having a difficult time dating. I wanted to live in a smaller city where living/getting around was just a little bit easier. I needed more breathing room.”
    Yes to everything about this, Saya! Impressive data-gathering. The California exodus! All but two of my closest friends have left Pittsburgh in the 15 years I’ve been here. I came thinking it’d be three years. Instead of moving, though, I’m going to buy a second home. Pittsburgh’s blowing up!

  4. MeganReilly
    MeganReilly at

    I loved reading this Saya! Coming up on 10 years in NYC
    (with an original 2 year plan) and for some
    reason still not ready to give it up 100%, I have to say… If you can
    try another city short-term (which we both are lucky enough to do as
    entrepreneurs), it’s a great way to test the waters and get a fresh
    perspective (and YES grow your business). As someone now doing the bi-coastal thing, I’ve loved the
    change of scenery in California (awesome weather, tons of “creatives” and
    nontraditional workers, Ocean-side hiking and biking, cool people,
    healthy living, and a flourishing art and tech scene, to name just a few
    things). 
    I would tell you:
    Think about a short-term stint

    Definitely, do NOT give up your awesome Chicago apartment!

    Do give up your gym membership

    You can sustain (and grow!!) your business elsewhere

    Chicago will miss you OF COURSE! But it’s home for you so you can always return at any time.

    Good luck and keep me posted!

  5. billstreeter
    billstreeter at

    OK I read the post and I have to say the story sounds very familiar. About 90% of the people I knew when I lived there also don’t live there any more. Some of them were already leaving before I did. Most left after. I think it has more to do with why you live there than anything. I moved there to go to school and hung around for a few years after that. But Chicago is a pretty unfriendly city on a lot of levels and it just wears you down after a while. If it isn’t high rent, or crime or shitty jobs, it’s the weather or parking or getting around. And if you moved there for the creative opportunities then you soon realize that there are better opportunities elsewhere. If you live there to make money you soon realize there is better money to be made somewhere else. If you want to start a family … well it’s not really the best place to do that. So at some point, if you’re not from there, if your family isn’t there, you move on. Which is not to say that it’s not a great town. I value the time I lived there. It taught me a lot. I thought I would miss living there but strangely, after I left I never really missed it at all.

  6. stacyarmisted
    stacyarmisted at

    Love this compilation so much. Update: before I left for my travels, I was thinking of moving to Austin or Boulder when the trip was over, but I’ve completely fallen in love with Melbourne and if I miss it like I feel I will as I travel other countries I will come back and seek work here. It’s funny because the idea of living in another country wasn’t even on my radar when I left. And the only reason I came to Melbourne is because I was offered free accommodate through a Facebook group I’m part of. The best you can do is give yourself time and permission to explore and find what feels right for you.

  7. milanogirl
    milanogirl at

    I made the move from Chicago in February 2011.  I fulfilled a dream to teach English abroad in a country where my ancestors were from (Italy), and I actually had never been there before either.  I miss Chicago and my good friends dearly.  It’s almost been four years now.  I always consider the idea of moving back.  It has been a phenomenal journey rich with learning experiences.  I think in life we continue to get to know ourselves better and we are gradually revealed to ourselves.  I am trying to figure my next move, do I stay here, go back to Chicago, go fulfill another dream.  I am not sure myself.  I’m 36, too, and have always wanted to have kids.  Unfortunately there is no company to apply to for that, lol.  

    I wish I had come sooner.  I wish I  had saved more money, too.  What are your dreams?  What are your priorities?

    1. Caz
      Caz at

      Hi MilanoGirl,

      Another chicago based gal here, your age, about to leave to go teach English in Italy. Would love to chat more-if you do too, please don’t hesitate to email me!: carrie89thstreet@yahoo.com
      Fab blog Saya and the very best of luck to you!

  8. sayahillman
    sayahillman at

    KristinaMarie1 Thanks for sharing your experience! I had no idea about S. Korea, sounds like it was exactly what you needed. As was coming home.

    We shall see! I feel no pressure or stress, just excitement about the possibilities. And appreciation for Best Friend and for my job-situation.

    PS – way to step it out the other night! #FearExperiment

  9. sayahillman
    sayahillman at

    katieaune I’ve loved everything you’ve posted since before you left. Very much appreciate your detail, transparency, and including the ups AND downs. Have also enjoyed how you’ve recognized changes, both in yourself and in others/what you want in life.

    RE DC and the ‘right’ opportunity — that waiting for the perfect time always gets me, in my own life and when I see others doing it. It seems that it usually rarely comes and personally, I’d so much just do it, whatever it is, and see what happens. Before 5, 10, my whole life passes and I wonder what if and wish I had. Easier said than done x1000000 and I don’t mean to make it sound like a small decision. It’d be HUGE. I think that’s what’s driving me now… I keep waiting for a sign as to when and where and how. I’m ready to stop waiting and just leap.

  10. sayahillman
    sayahillman at

    JillyMacDowell so nice to hear from you!!!! 

    I know, Cali-Crazy over here!

    Where are you considering your second home? I like that idea.

  11. sayahillman
    sayahillman at

    MeganReilly I can’t believe it’s been 10 years since you left! I remember thinking what a big move, literally and else wise.

    What’s your percentage breakdown of NYC/Cali time?

    Where in Cali are you?

    I love the idea of a short-term stint, that’s most attractive to me now. Not to say I’d come back to Chicago after it was over, think I’d try out another place. And then another place. With trips home mixed in.

    Thanks for your cheers and thoughts!

  12. sayahillman
    sayahillman at

    billstreeter Seems all relative Bill. I have so many friends here who love how friendly and cheap and easy to live in it is compared with where they came from. People who’ve moved here to start a family. To make money. Etc.
    That’s what’s great about life! What works for you doesn’t have to work for others, and vice versa. There’s a home for everyone.
    Now, just to find that home for me…

  13. sayahillman
    sayahillman at

    stacyarmisted Wow, big change and update! Sounds like you have a network over there already but if you need/want more at some point, let me know. Have some folks that way.

  14. sayahillman
    sayahillman at

    milanogirl All about quality of life for me. That’s priority.

    Thanks for sharing your story! 
    Been interesting to see how many of my friends are considering non-traditional parenting b/c they’re partnerless or can’t have kids the traditional way. Foster parenting, adopting, surrogacy (both in offering and in having someone do it for them), etc.

  15. kevinpnye
    kevinpnye at

    milanogirl I actually don’t know you nor Saya, but saw this post on facebook as a recent moved-out-of-chicago-er and am doubly amazed because i moved to Milan to teach english with my fiancee and am here right now. The whole article is definitely interesting and I’m happy to share my brief input: saved up enough money, but we’re ready to have a yard and a dog and see stars at night. Thought our last hurrah in a city should be doing something totally different (i was in sales at a small software company, she’s a nurse practitioner) and signed up for classes and moved here. In any case, if you, fair commenter above, need to meet a couple of people who are recently from Chicago, we’d be glad to say hello and find some familiarity as we’ll only be here until the end of this school year.

  16. sayahillman
    sayahillman at

    Thanks for chiming in kevinpnye! And yay for strangers connecting and offering kindness. Have a great holiday!

  17. HKNardini
    HKNardini at

    THANK YOU for sharing!! I’ve lived in 7 different cities before “landing” in Chicago, and can definitely identify with that restless feeling. Maybe it’s just my name (ha!), but I’m always looking ahead to the excitement of what’s next. Because I knew this move would mean I’d stay for a good while, I promised myself I’d go on two international trips each year, so that even with a full time job, it would never feel stifling. I think having itchy feet is a good sign. It means you’re ready for your next challenge…whatever and wherever that may be. Can’t wait to follow along. You have so many people cheering you on!

  18. sayahillman
    sayahillman at

    HKNardini Itchy Feet! Ha, I love that.
    I didn’t realize you had moved so much Hope, though doesn’t surprise me — you are ADVENTURE and LIVING LIFE!
    Thanks for the rah rah rah, much appreciated.

  19. milanogirl
    milanogirl at

    @kevinpnye Is your fiancee’s name Jenna? I am Beth; I work for The English Playgroup. If so, we all had plans Saturday night to meet at Carlsberg. I’m always happy to meet with people from Chicago!

  20. cynthiarturner
    cynthiarturner at

    Hi Saya, I don’t know you, but read your posting. I left Chicago at 36 yrs old as well. Born and raised in Chicago I knew that at some point I would want to leave Illinois and try something different. I lived in the City for 13 yrs and prior to that grew up in the burbs. When my friends all started getting married and having children while I was a career girl I realized that my circle of old friends was dwindling and I was also getting tired of the winters. I researched many places and ultimately ended up in California. I love the outdoors, mountains and ocean and liked the fact that you could be active outdoors all year round. 

    The one mistake I made was moving initially to LA, because my Brother lived there. I thought having family there would make my transition easier which it did. However, LA is not a place for a Midwesterner in my opinion. The culture is vastly different, urban sprawl, not a lot of college educated professionals, all about “who you know” and “how can you help me”. I found the people overall to lack moral and values and I would not recommend it for any Midwesterner unless you are an actor. 

    I since then decided after many years to finally move to my dream city San Francisco. I would definitely recommend SF. It reminds me of a mini-chicago with great transportation, architecture, great restaurants and also has the city on the water. If you enjoy the mountains they are all around the city for great hiking. I also love that you can be in the city and 15 minutes over the bridge you are in total nature. It’s beautiful. Plus, if you like skiing you can still enjoy the winters at Lake Tahoe 3 1/2 hours away and if you enjoy wine, Napa is 1 hour away. I leave the city every weekend for nature hikes and/or Napa. It’s amazing how you can have the best of both worlds w/in a very short distance. 

    If I were you I would stay away from Southern California (it’s too different from Chicago) and consider Northern Cal. or Pacific Northwest (Oregon). I think this could be a great transition for you to offer you a city w/ nature. A great balance in my opinion. 

    Best of luck! Take the leap, it’s worth it. I’ve been gone now in California 10 years and although I still call Chicago home, I’m very happy with my move and SF will now be my new home. 

    Best…

  21. sayahillman
    sayahillman at

    cynthiarturner Thanks for sharing your experience! SF is definitely on my radar — so many of my folks have found their way out there. The housing costs and process scares me though! I do love Portland.
    We shall see! So many options.
    Very happy to hear your leap was a good one —

  22. ErikaWicks
    ErikaWicks at

    Funky internet, so apologies if this is a duplicate post. . .

    Taking a few days to read through this and gather my thoughts. Here’s what I came up with: I’ve lived in the Midwest, East Coast, South, and West Coast. This is my second stint in Chicago and is, for now, my permanent home. What I’ve found is that every place you leave, you miss certain things, and your heart skips a beat when someone mentions that cafe or neighborhood from your old city. But then you also discover new and wonderful things in your new home that you could never have in your old one.  Like you, I delight in exploration and discovering that “local’s” hidden gem. Some places may be harder to find culture in, but it does exist, and sometimes seeking out and cultivating it with friends is more rewarding than when it’s given to you so easily as it is in Chicago.
    FWIW, I did live in L.A. for a couple of years and loved it, yes, as a Midwesterner. No judgments on the post below, it’s not for everyone. Honestly I was surprised by how much it enchanted me – the intoxicating weather, the year-round flowers, the openness of most people and the embracing of any lifestyle,  the ability to be in the desert, mountains, at the ocean, or even in Mexico all within a couple of hours. I was not a part of “the industry,’ so had less interaction with some of the more shallow aspects of the city, although as a pop culture junkie, I also kind of thrilled being so close to the entertainment industry. What can I say – driving back from the grocery store and seeing Ben Affleck and Jennifer Garner at a movie premiere was pretty cool! Of course part of moving is finding out what truly matters to you and what you can live without.
    I firmly believe that wherever you live, you can find happiness if you seek it and create, while also still missing the old place. For me, one of the best things I discovered about myself moving around is that I’ll be okay, no matter where I am.

  23. OzData
    OzData at

    sayahillman billstreeter Saya, I agree. It’s all relative. There isn’t any universal truth about any city being universally “bad.” It depends on what a person wants in their own life. For 19 years I was happy in Chicago–snow and all. My decision to move to Portland wasn’t a Chicago-Bad, Portland-Good dichotomy. It really was a decision about what I wanted and where I could best find it.

  24. ErikaWicks
    ErikaWicks at

    Funky internet, so apologies if this is a duplicate post. . .
    Taking a few days to read through this and gather my thoughts. Here’s what I came up with: I’ve lived in the Midwest, East Coast, South, and West Coast. This is my second stint in Chicago and is, for now, my permanent home. What I’ve found is that every place you leave, you miss certain things, and your heart skips a beat when someone mentions that cafe or neighborhood from your old city. But then you also discover new and wonderful things in your new home that you could never have in your old one. Like you, I delight in exploration and discovering that “local’s” hidden gem. Some places may be harder to find culture in, but it does exist, and sometimes seeking out and cultivating it with friends is more rewarding than when it’s given to you so easily as it is in Chicago.
    FWIW, I did live in L.A. for a couple of years and loved it, yes, as a Midwesterner. No judgments on the post below, it’s not for everyone. Honestly I was surprised by how much it enchanted me – the intoxicating weather, the year-round flowers, the openness of most people and the embracing of any lifestyle, the ability to be in the desert, mountains, at the ocean, or even in Mexico all within a couple of hours. I was not a part of “the industry,’ so had less interaction with some of the more shallow aspects of the city, although as a pop culture junkie, I also kind of thrilled being so close to the entertainment industry. What can I say – driving back from the grocery store and seeing Ben Affleck and Jennifer Garner at a movie premiere was pretty cool! Of course part of moving is finding out what truly matters to you and what you can live without.
    I firmly believe that wherever you live, you can find happiness if you seek it and create, while also still missing the old place. For me, one of the best things I discovered about myself moving around is that I’ll be okay, no matter where I am.

  25. DebbieH
    DebbieH at

    Does Saya’s mother get a vote in this discussion?

    I purposely didn’t say anything about where she went to college (Boston), knowing that if I kept my mouth shut, she might come back to Chicago.  Besides, by then I was ready to take a sabbatical from being a hands-on mother.  
    So, waddya know — my grand plan worked!!   For 15 years so far.
    Now, it looks like I need another grand plan.  Can you give me a couple months to figure this one out?
    If not, my first thought is, how about moving near an Amtrak line west of the Mississippi?  

    Very crafty of you to leave town right after you posted this blog.

  26. 3SliceToaster
    3SliceToaster at

    No, Saya, you’re not imagining things.  I know five people who moved from Chicago to Nevada and California in 2014.  And since being in Nevada, I’ve run into three more people who moved from Chicago in the last two years.  All of us say the weather was the primary reason.  Taxes, corruption, and affordability are secondary causes.

    The great thing is that with so many Chicagoans out here, you can get anything you want from Chicago.  There’s a grocery store down the street that has a huge Chicago section with probably 30 or 40 different Chicago items from Jay’s potato chips to Al’s Beef.  And there are Chicago-themed restaurants and bars opening every other week.

  27. Annetteboo19
    Annetteboo19 at

    Saya, I have thought about leaving Chicago for years now. After last years winter I decided this year was a last ditch effort. This winter I planned a trip to a warm place every month. Being a business owner myself I was able to do just that. You mentioned going to Secrets. Funny enough, I just got back from there about two weeks ago. In two more weeks I leave for Florida for three weeks. So far this nomadic existence is working. This winter also hasn’t been as bad as last. My biggest problem is I haven’t found a place that is warm that I’m in love with. When I first moved to Chicago it was love at first sight. There are only a couple of other cities I feel that way about and they are both not in warm climates. I can literally pick up tomorrow and move somewhere. I have a job where I can work from anywhere in the world. So why haven’t I done it yet? Friends. They are my family and it would be really hard to leave. I struggle with this question of leaving constantly and yet the years tick on, and I travel more and more. I just figure one of these days I just won’t come back. =)

  28. EbonyKleinman
    EbonyKleinman at

    You went very in depth for why your friends are moving out of Chicago! I think there are a lot of different reasons for why someone wants to move and it’s tough for the people that stay behind. A good friend of mine moved to Washington state last year and it’s been really hard to not be able to see her in person. She wants everyone to come live up in the Pacific Northwest with her, but I like living where I am right now. Sure, there are always things that will bother you about a particular place, but there are also things to love too! I would miss the place where I live if I were to ever move to another state. I’m sure I could love another state in a different way, but it won’t be the same.

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