Leaving Chicago for a New Job

Chicago has been a great city to live in the past 7 months. Though I’ve always considered myself more of a small town person, it has been really fun living the urban lifestyle. (I grew up in a city of around 6000 with the closest largest “big” city having around 65,000 people. So Chicago is huge!)

While living in Chicago, I gave up my car (for convenience and cost) and have been doing a lot more walking than I usually do. There’s some of the best restaurants in the world just a few minute walk from my apartment. When I can’t walk I take the train or bus and occasionally use Uber/Lyft or a taxi.

And, you can’t beat the view from my 8th floor outdoor pool/hot tub. (Oh yeah, there’s also an indoor cardio and weight lifting area as well as a gym where we play volleyball twice a week!)

Apartment view

Panoramic view from apartment at night

Panoramic view from apartment at night

Part of the perks of living in such a big city is that there’s always something to do. Summers here are the best. The city is active. Everyone is running around, biking, playing volleyball on the beach, listening to free concerts in the parks, and spending as much time outdoors as possible.

Since summer is so short, there are block parties and ethnic festivals it seems like nearly every day of the week. It is definitely different than a city where it is warm year round. You really need to compress everything into a short couple of months.

Source: http://frugalfrolicker.com/chicago-waterfront/

Source: http://frugalfrolicker.com/chicago-waterfront/

Source: http://frugalfrolicker.com/chicago-waterfront/

Source: http://frugalfrolicker.com/chicago-waterfront/

It has also been really fun living near the shores of Lake Michigan. Although this past summer I didn’t do as much big boat sailing as I did in the past due to work being busy, I was asked to be the bowman for a J-109 during the Verve Cup Offshore Regatta. Here’s a picture of the city skyline from that race. Chicago has an amazing skyline!

Chicago Skyline from sailboat during Verve Cup Offshore Regatta

Chicago Skyline from sailboat during Verve Cup Offshore Regatta

For those of you unfamiliar with the midwest, winters here can be bitterly cold. This winter, other than a week or so of subzero temperatures, has actually been very mild compared to the frozen tundra of Wisconsin.

I could definitely see myself living here for a couple years, but in the longterm it doesn’t really fit my personality. When I lived in Wisconsin I usually tried to get out skate skiing (type of cross country skiing) a few times a week. I lived a short 30 minute drive from some of the best cross country skiing in the country! I also enjoyed snowshoeing through the kettles (hilly area in southeastern Wisconsin created from the glaciers). Other than having access to outdoor ice skating at Millennium Park, there’s no really easy way to cross country ski or snowshoe without a long drive.

Likewise, in the summer, I really like going road biking. I brought my bike down with me and managed to make it out exactly one time. I road the entire time on the lakefront trail pictured above. While it was fun, it was always quite crowded. I really missed the wide open windy roads that I enjoyed in Wisconsin.

Holy Hilly Irish Ride in Wisconsin

Holy Hilly Irish Ride in Wisconsin

At the end of January I accepted a job near the Minneapolis area. I’ll start there soon after my contract in Chicago ends at the end of June. I’m very excited for this next stage in my professional life. Minneapolis also constantly ranks near the top of the fittest cities in America.

I’m excited to be able to do more of the outdoor activities that I enjoy. Though it is early to buy a boat or lake cabin (land of 10,000 lakes, remember?) I might splurge to buy a windsurfer. My true love for sailing is on small boats like Lasers and 420s though I’ve been doing more big boat sailing recently. There’s just something fun about being close to the water. The smaller boats are also much easier to set up. I’d be able to fit a windsurfer on or in my hatchback Subaru as well.

From an investing standpoint, I’m almost more excited. I’m going to be making more income and living in an area where the cost-of-living is much cheaper compared to Chicago.

As a quick example, I found an excellent apartment close to where I’ll be working. It is a 2 bedroom, 2 bath, end unit apartment with just under 1400 square feet for $1295/month with parking. I’m paying $1905/month without parking (which was $235/month extra) for my 720 square foot place in the West Loop of Chicago right now. No wonder I have so little money to invest this past year!

I won’t be changing my lifestyle to accommodate the higher income (other than traveling more!) but will become much more active with buying stocks and options trading. I really look forward to sharing this next stage of my financial life with you all. I’ll also continue to make updates to my investing spreadsheets, as time allows.

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14 Responses

  1. amber tree says:

    Hey Scott,

    All the best with your new job and new city life.
    From a FIRE point of view, it looks like you are making a great move: earn more and spend less!

    Chicago is a city that is high on my wish list. There is the lake and the vivid city life – 2 things I like. a visit to Tastytrade and the CBOE would be the cherry on the cake.

    Happy easter
    amber tree recently posted…how to seize an investment opportunityMy Profile

    • scott says:

      Hi amber tree,

      I agree on both counts. Investing will be awesome. I just hope the markets cooperate so I can get some good values still. On the Chicago side, it is an awesome city. The lake is amazing. And the summers here are hard to beat, especially if you like running or playing beach volleyball.

      Visiting tastytrade and the CBOE are things that I still hope to do before I leave.

      Have a good Easter too!

  2. John says:

    Good Luck to you, Scott, on your new job. Sorry to see you leave Chicago but it sounds like you will be in an equally nice place. And its not that bad of a drive back here to visit friends! Keep up the good work!

    • scott says:

      Hi John,

      Thanks! In the grand scheme of things, it really isn’t that far away. Plus, my parents live about 2.5 hours north and my brother is a little over an hour north (in Milwaukee). It wouldn’t be hard at all to make the trip down when I’m home visiting my family.

      Looking forward to the new challenges! I’ve heard really good things about Minneapolis too (the nearest big city to me). It is always ranked as one of the most fit cities in the world, which is right up my kind of alley!

      Take care and thanks for commenting,


  3. FerdiS says:

    Congratulations on the new job and promotion, Scott! The change should be good for your health and wealth, so it seems like a great move… We’re living in a very expensive part of the country, so I’m quite envious of the rent you’ll be paying! Best of luck and I’m looking forward to hearing about more of your adventures.

    Take care
    FerdiS, DivGro

    • scott says:

      Hi FerdiS,

      Thanks a lot! More expensive than Chicago? You must live on one of the coasts. When I hear about rental/ housing prices in those places, I realize that in the grand scheme of things, Chicago, for a big city, isn’t really that bad. The Midwest is nice in that regard.

      I’m very excited and also a little nervous for starting a job with so much responsibility. But, that’s what the last 10 years of training have been for!

      Have a good weekend,


  4. DivHut says:

    Thanks for sharing your news with us. Good luck with your new job in MN. Seems like you really enjoyed living in Chicago by your descriptions and photos. Still have yet to visit IL and MN but probably not in the winter time as you mentioned the bitter cold.
    DivHut recently posted…Dressing Up Your Dividend PortfolioMy Profile

    • scott says:

      Thanks, DivHut. I’m going to miss the city but more so the good friends that I’ve made. I’ll definitely be visiting them in the future. And, hope to invite them up to my lake house in MN, if I ever get one of those! I’m preparing for the move now and have an apartment lined up, but won’t be actually moving until the end of June.

      Unless you like skiing or snowmobiling, then it is probably best to visit MN in the summer. Chicago doesn’t have much of that kind of outdoor stuff in the winter, but definitely has plenty to do indoors in the winter. It still gets cold though!

      Take care,


  5. Best of luck with you new job and new city. I’ve traveled to Minneapolis a few times on business. I really like it there. It’s very clean, and the people are really nice. The extra money you save by living is a less expensive are will really help you add t your retirement funds.
    Investment Hunting recently posted…Stock Buy – Royal Bank of CanadaMy Profile

    • scott says:

      Hi Investment Hunting,

      Everyone I talk to has nothing but good things to say. I’m pretty excited!

      Thanks for the comment.


  6. Scott,
    Thanks for sharing the news and photos with us! Congrats on your new job. Looking forward to more posts.
    Take care

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  8. Hello there, Scott! Thank you for sharing story, your article is a big encourage for those having afraid to deal something risky. By the way, congrats for your new job.
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