WW: A Shift in Perspective

Sunrise over Lake Michigan with the Chicago city skyline.

I can’t believe how fast July has snuck up on us. As this weekend nears, I can’t help but think of my moving anniversaries and I’ve found myself getting sentimental more than once over the past few days. I moved to New York over Fourth of July weekend in 2012 and this Saturday also marks my two year anniversary living in Chicago. Where the heck does the time go? On one hand, it’s absolutely mind-blowing to think of how much has changed and how much life has been lived in these past two years in Chicago. (Launching a clothing line, friendships changing, family dynamics changing, friends getting engaged, friends and family having babies, some of the most fun and insane stories that I’ll never forget, getting ghosted by guys, me doing the ghosting, too, I could go on for days.) But on the other hand, I really can’t believe two years have gone by. I keep finding myself saying I moved here “last summer,” and have to catch myself and remind myself it was actually two summers ago. Doesn’t that seem like a long freaking time?!

I mean, I still remember so many specifics about the day I moved to Chicago… Walking through Central Park *sobbing* before I had to go to the airport… It being a mere 60 degrees on July 1st when I landed in Chicago… Getting to see my apartment for the first time… Shopping at Potash for cleaning supplies and picking up a two-pack of paper towels and Ellen saying, “You have storage closets now, babe. You can get the big pack.” Lauren visiting that weekend and us trying to share an air mattress using my turkish towels as blankets. (We ended up getting a room at the Drake the next night instead, haha!) My furniture getting delivered a few weeks later… Going on my first few dates in the city… My 26th birthday… I literally remember everything like it was yesterday. What I wore, how I felt, where I went, etc. Those first few months were pretty fun! It was a whirlwind getting to experience a new city, meet new friends, make new memories, decorate my apartment, and find a new normal.

But for a lot of reasons I’ll spare you, I kind of started to hate Chicago after a few months. I missed New York, but didn’t know if I could see myself moving back. I thought about moving to Dallas for a hot second. Obviously Paris has always been in the running, too. Basically, I just longed to be anywhere but Chicago. And if you’ve been following along for a while now, you can probably see that’s when I really started to ramp up my traveling. No exaggerating necessary, I was actually gone more days than I was home in Chicago in 2016. (Maybe that’s why it doesn’t feel like two years… haha!) I didn’t like being here so I just chose not to be…. Month-long trips became the new norm. And then I got back from Asia right before Thanksgiving and everything kind of came crashing down. There was a whole lot of personal shit that I’m not ready to chat about just yet, but I was already so burnt out from traveling, was trying to gear up for the holiday season (one of the busiest in the blogging world), and on top of all of that, shit basically hit the fan in every single facet of my personal life. Oh, and I stress -fractured my ankle and was in a walking boot for ten weeks. It was a fucked up few months, to say the least.

But one day, I just kind of saw the light. In the midst of what felt like rock bottom, I realized that if I didn’t like something, I was the one that needed to change it. I realized that jetting off for a month at a time was essentially me running away from dealing with shit. (Well, it was and it wasn’t. Obviously those were once-in-a-lifetime trips that I wouldn’t change for anything. I have a flexible work situation that allows me to travel, which I do want to take advantage of while I’m able to do so so freely. But still, there was some element of escapism in there, too.)

I also realized that I had been playing the victim ever since I moved to Chicago… (If you’re new around here, I randomly got evicted from my last apartment in NYC. You can read about that here. That post still makes me cry every time I read it.) I think since I definitely left New York before I “was ready” to leave, I was constantly comparing the two cities. Anything that would piss me off about living in Chicago, I would always think “This would have never happened in New York,” “This was never the case in NYC,” etc. Like, no effing wonder I didn’t like it here. I wasn’t even giving it a chance!

After a lot of soul-searching, I realized that while there were things I didn’t love about Chicago, what I actually disliked was how I didn’t feel like “myself” here. And to be totally honest, I kind of felt like I didn’t even know who that was. I had experienced so many things (both good and bad) that I sure as heck wasn’t the exact same person who moved here “last summer.”

One day over the winter, I just kind of sat myself down and was like, “You’ve got at least six more months until your lease is up. What don’t you like? What’s bothering you deep down? And how can we fix it, at least for the time being? If you want to move when your lease is up this summer, you can, but you’ve got to get your shit together until then.”

Basically, I made a laundry list of what I wanted to work on… What I liked, what I didn’t, what needed to change, what could stay, etc. I had to put myself in a lot of uncomfortable situations, had to set a shit-ton of boundaries, and had to start re-writing the narrative that I was telling myself. A simple change in your mindset can change everything. Sometimes you’ve just got to flip the script, you know?

I essentially just had to cut out all the bullshit and start back at square one with creating a life that felt more like “me.” And when you start putting that new shit into the universe, it’s wild how you’ll start attracting that right back in return. It works both ways!

It’s absolutely, positively C-R-A-Z-Y how different the last four months have been. But I can honestly now say that I’ve really started to like living in Chicago, and it’s not because of anyone specifically or anything other than a simple shift in my perspective. I appreciate Chicago for what it is (livable, clean, less expensive, slower-paced), and don’t judge it for what it’s not (New York). I hope you can see the takeaway here and how it applies to much more than a city… Your happiness depends on your mindset, plain and simple. If you’re focused on the negatives, that’s all you’re going to see.

While I had intended on spending two months in Europe this summer, I decided to stay here instead and enjoy the season that Chicago does so well. I re-signed my lease and I’ve essentially cleared my schedule for the next eight weeks. Until mid-August when I go to Croatia, I’ll only be getting on a plane to go to a friend’s wedding in July. I see places on Instagram and get the worst FOMO and I’ve had to turn down a lot of work trips, which isn’t fun, but I know it’s in my best interest to stay put for a little bit and spend some time with the place I happily call home. So let’s see what happens in year three, Chitown… Shall we?

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  1. 6.28.17
    Emily said:

    I love Chicago more than anything. No I won’t call it “the greatest city in the world” but I also think I’d need to be making over $300k to live comfortably in San Fran or NYC so yes, “livable” is key.

  2. 6.28.17
    Kaitlin said:

    Jess, I SO appreciate your authenticity and sincerity today. As a reader who has followed you from Chicago to NYC and now back to the Windy City (I’m here too!), I could definitely feel a shift in your posts last year and understand that you didn’t want or need to share what was/is going on in your personal life. Life in general is so weird as you get older! I think that has been one of the most radical things I’ve learned in my late 20’s. I thank you so much for introducing the Lively Show into my life. I could also not agree with you more, it is solely up to YOURSELF to decide what you’d like to bring into your sphere of being. I have been working on learning to train my thoughts to a positive wavelength and moving through the tough stuff myself. Know that you are not alone! I’m thinking of writing a book of all of the weird tidbits I’ve learned/thought about throughout my 20’s. Although I truly know nothing in life, I’m happy to be along for the ride. Thanks again for sharing Jess!

  3. 6.28.17
    Jess Z said:

    So great that you’ve managed to turn your situation into a positive one! Everyone deserves to feel “at home” in their home, I’m happy Chicago is doing that for you now 🙂 Thanks for sharing!

  4. 6.28.17
    Briana said:

    Wow you’ve got a lot going on! Sounds fun!


  5. 6.28.17
    Taylor said:

    Thanks for being so candid about this, Jess! As someone who also lives in Chicago, it’s kind of hard to not think about the ‘what ifs’ of where else you could live – I think it’s because Chicago is so dang livable that we think everywhere else can be like this. Also because we’re young and unattached that it’s so tempting to just pick up and move somewhere else while we can.

    I’m not a blogger and really don’t make enough money to travel as much as I’d like, I love love my weekends spent in Chicago and honestly it is what makes me love this city more and more. I think the mindset of focusing yourself in the present and not judging yourself on what others are doing / going will really help this summer – that’s always been my tactic at least!

    Thanks again for sharing (and letting me have the ability to share a little bit too!) Have a great holiday weekend!


  6. 6.28.17

    I love this post, Jess, and really appreciate your honesty. I think the tough thing about New York is that it’s NOT an easy place to live. It kicks you when you’re down, and it kicks you when you’re up. But as you obv know, there’s something really special about it. It’s easy to play the comparison game. I definitely do the same thing as you, but in the opposite way — since I’m from Chicago, whenever I go home it’s easy to think ‘Life would be so EASY here!’ Rent would be cheaper, my apartment would be bigger, my mom would be a quick drive away (I could have a car, too!) I have a lot keeping me in New York (career + alllll my friends from college) so it’s not a move I’ve thought about with much seriousness. Basically what I’m saying is I feel like it’s so normal to have this feeling like you’re being pulled in a zillion directions. When you’re young and unattached, it’s easy to feel like you can go anywhere, and this is the time to do it! I think it’s great you’re going to spend the summer in Chicago — it’s such a great place to be in the warmer months, and I think embracing life there even more so will only help improve your outlook on the city. I’m heading back to Chicago for a week on Sunday and I can’t wait! Hope you have a lovely 4th. x

  7. 6.28.17
    Ashley said:

    I can totally relate to this! Sometimes you have to change, not your situation! Loved reading this!

  8. 6.28.17
    RSD said:

    Holy shit.

    I moved to DC from the South in June 2015, and I have been sooo miserable a majority of my time here. It has gotten significantly better since I began dating my SO in the fall, but your paragraph about disliking about how you don’t feel yourself in Chicago are exactly the words I have been looking for two freaking years.

    As I said above, meeting my SO (… and making friends outside of politics… and going to therapy….) has helped significantly because I CAN be myself, but before I felt like I was constantly having to be someone I wasn’t/keeping up appearances and leaving town for the weekend and going on looooong vacations because I wanted to be as far away from DC as possible.

    I don’t really comment on blogs or anything, but I just wanted to respond because I FEEL YOU. I’m working on being more positive myself, but it can be hard. I’m glad I read this post, because it gave me a way to verbalize the weird/icky feelings I’ve had since I got here.

  9. 6.28.17
    Amanda said:

    Jess, I love your honesty and openness in this post. I lived in NYC for 9 years before moving to SF last summer. The shift has been a huge one and it’s extremely challenging to NOT compare everything to NYC. I felt very ready to leave, but at the same time, miss so much about it (glad I’m not alone in how I feel!). It’s so great that you were able to take a hard look at your life and focus on the changes you can make to improve your outlook on life. I’m definitely inspired to shift my perspective and make the changes that will allow me to live the life I want (just gotta figure out what this still…hmmm). Wishing you a great year three in chi!

  10. 6.29.17
    Katie said:

    Beautiful picture of the city in this post! Hope this year treats you well in Chicago. When the travel bug bites you again, you should look into going to New Zealand. It’s so beautiful and unlike any other place in the world. Our Winter is their Summer. So you could spend time there during the cold winter months here! 🙂 It’s a truly magical place.

  11. 6.29.17
    Katrina said:

    This was a really great, thoughtful, well-written post. Glad you’re finding your happy. Live your best life, girl.

  12. 6.29.17
    Nancy said:

    Thank you Jess for being honest and real which is a rarity on social media now a days. It is true that if there’s something you don’t like it’s up to you to change it and the fact that you had that internal struggle and felt bold enough to share with your audience speaks volumes to how much you’ve grown as a person. We all get caught up playing victim and not taking responsibility for our decisions but it’s knowing what to change and acting on it that makes the world of difference. Thank you for sharing a piece of yourself with us 🙂

  13. 6.29.17
    chicago1970 said:

    Love your blog (even though I’m in my 40’s!) I’m from Chicago but spent three years in NYC during my late 20’s. I think of living in NYC as a rite of passage — a tough yet unforgettable experience. But once you’ve “been there, done that” there are so many other big things in life to do. Much bigger things.

  14. 6.29.17
    PIC said:

    Great post bb. <3 you

  15. 7.6.17
    Ashley said:


    I liked this post; it was refreshing to see something raw and real.

    I’m a Chicagoan and have always dreamed about moving away to a different city with much warmer weather (talking about you, San Diego) but have always held back because of family and affordability.

    However, my life is falling apart right now and I’ve been seriously contemplating a move if it continues to get worse, but that would be “running away” from the issues at hand. Moments like these really make you search inside yourself to figure yourself out – so I totally relate to you and this post!

    Everything is based on perspective. “If you change the way you look at things, the things you look at change.”

    Do you, girl. 🙂