Chicago: A Month In

I officially hit my month-mark at work, which means I’ve been living in Chicago for over a month now. CRAZY.

Chicago Life

And it’s everything I’ve ever dreamed of!


Of course, before I lived here I imagined myself frolicking around the city, walking to and from work to my apartment, eating all the time at these fun restaurants. Now that I’m here and my 10-12 hour days between work + commute, that dream has been a little clouded.

The positives:

  • Being with my boyfriend. Honestly, as much as I was the best single girl, my life is filled with a new kind of happiness now that I have Ben. We were ready to do long distance, but obviously I’d rather be closer to him.
  • Being near my friends (+making new ones). I was so incredibly lonely in Green Bay, away from anyone I knew and the people I did know weren’t interested in the same things as me. It’s been so refreshing to be around other bloggers, up-and-coming entrepreneurs, independent and fun people. Plus, the foodies here are the best. 😉
  • Making more money. Just being honest. I’ve worked my whole life at multiple jobs, just to pay the bills. This is the first job where I’ve made enough to live. Only took 29 years …
  • Mindset. I don’t know if it’s the city, if it’s the people, or what, but this city just ignites my fire. It’s the biggest reason I decided to move here. I’ve really been focused on what I want in life (plus, watching my business-owning boyfriend helps get me excited as well) so I feel like I’m going to change my life this year and I couldn’t be more excited. 🙂
  • City life. The buildings. The restaurants (restaurant week in Chicago has been AMAZING). The coffee shops right around the corner to do work at (where I am currently). The hustle and bustle. It’s everything that I wanted and more. I can’t wait until it warms up a bit and I can walk around to see what else is in my neighborhood.


Not-so-positives: (I refuse to say negatives …)

  • Commuting. I thought I’d be able to handle the commute from the city to the suburbs. Well, I can *handle* it … I just hate it. Not only am I in the car for 2+ hours a day, most of that time is in crazy traffic. Stressful and not something I want to do for a long time! Thankfully my job has decided I’m allowed to work downtown one day a week. Cross your fingers that soon I’ll be allowed to work-from-home one day per week, because then I’ll only be driving three days a week instead of five!
  • Work. Now, please don’t take this in the wrong way! I’ve only been here about a month, but it’s been slow moving. I lovvvvve when I get to work downtown with my “clients” and I lovvvvve working with my creative team. However, I don’t have a ton of direction outside of that and I’m still pretty slow. Plus, my company as a whole isn’t at the top of their game and there’s been whispers of lay-offs, which is obviously terrifying for someone that just moved their life to a new state! I also wish I had friends at work!

So that’s my little month-in update on my move to Chicago! Any questions for me? Let me know in the comments! Have a wonderful weekend. <3


  1. Amy says:

    I love the real-ness of your new life + situation. It’s going to calm down—-so enjoy the mayhem—kidding! You sound like you’re handling change really well:)

  2. G says:

    Any way you can live closer to work??? If it’s a budget thing, think about less money spent on car/car repairs vs rent?? I used to do the same kind of commute (for 3 years…). I finally moved closer last year and it has made SUCH a difference – I encourage it if it’s a possibility! Life is too short to spend it in a car 🙁

    • Jessie says:

      There is, but I don’t want to hah! I’m looking for ways to work downtown or from home more often. I’d rather live in the city than in the suburbs. I’m with you, though! It’s just I’m doing it the opposite way – trying to find a way to work closer to where I live. 🙂

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