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37 Comments on "Words I never thought I’d say: is it time for me to leave Chicago?"

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KristinaMarie1
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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… Read more »
katieaune
Guest
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… Read more »
JillyMacDowell
Guest
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.… Read more »
MeganReilly
Guest
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,… Read more »
billstreeter
Guest
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,… Read more »
stacyarmisted
Guest
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… Read more »
milanogirl
Guest
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… Read more »
Caz
Guest

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!

sayahillman
Guest

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

sayahillman
Guest
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… Read more »
sayahillman
Guest

JillyMacDowell so nice to hear from you!!!! 

I know, Cali-Crazy over here!

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

sayahillman
Guest

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!

sayahillman
Guest

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…

sayahillman
Guest

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.

sayahillman
Guest

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.

kevinpnye
Guest
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… Read more »
sayahillman
Guest

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

HKNardini
Guest
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… Read more »
sayahillman
Guest

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.

milanogirl
Guest

@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!

cynthiarturner
Guest
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… Read more »
sayahillman
Guest

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 —

ErikaWicks
Guest
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… Read more »
OzData
Guest

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.

ErikaWicks
Guest
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… Read more »
DebbieH
Guest
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… Read more »
3SliceToaster
Guest
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… Read more »
Annetteboo19
Guest
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… Read more »
EbonyKleinman
Guest
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… Read more »
J M
Guest
I moved away a BUNCH of times, even overseas, and then kept coming back. I have deep roots here- friends I’ve known for more than 25+ yrs, some family, a ton of memories, etc. I’m also 36, and can definitely relate to the odd feeling of watching your social circles shift apart so drastically. It seems to be a hugely transitional time in life, and everyone’s sort of scrambling around to find themselves or make life changes they wish they’d done sooner, etc. I am happy to say as of right now, I have zero doubts that I want to… Read more »
Jason Silver
Guest

Writing like this is one of the many reasons why so many people love you. Thanks for sharing your reality with all of us.

Lauren
Guest

Just realized you re-posted this, when I saw it just now on twitter I thought it was a new post. After 16 years there, I left Chicago in October. Can’t name much I miss. Landed in a fantastic neighborhood in Phoenix and even though it’s hot right now, I would not change a thing.

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