From Chicago City Life to Windy Wooded Roads

This is the 11th post in The Blog Backstage series about the Who, What, Where, When, Why and How behind Honestly Modern. Periodically, I share a peek behind the scenes about how and why all the magic happens to bring Honestly Modern to life.

In response to a few readers who have asked for a little behind-the-scenes peek into why we left Chicago and chose a new and different lifestyle for our family, here’s the first of a two-part post on why we left, what we miss about Chicago and what we love about our new stomping grounds outside of Philadelphia.

Just as we decided last spring to move from a very urban high rise in downtown Chicago to the almost rural suburbs of Philadelphia, I was reading Walkable City by Jeff Speck. I remember sitting in the backseat of my father-in-law’s car. Driving and driving through windy, wooded back roads to one of the neighborhoods we considered for our new home, I was royally dreading the amount of time I would be spending with my butt parked in the driver seat of a car once we moved. At the time, I felt like I was in the middle of nowhere. I couldn’t help but rattle off from the backseat all the benefits of urban living the author touted as we drove seemingly deeper and deeper into the Pennsylvania woods. In between my fact-spewing, I strongly questioned our decision to move with each passing twist and turn of the narrow road.

Despite the questioning, we made the move from Chicago to the Philadelphia area last summer for a variety of reasons.

Ironically, that “remote” neighborhood is just minutes from our sons’ current preschool, and now I drive those same roads almost everyday. With context and a Google map in my head (after many months of Waze on my dashboard), that school and that neighborhood no longer feel so remote to me. In fact, they’re closer to the city than we ultimately landed in our new home.

While we lived there, Chicago treated us well, superbly in fact. We arrived in our mid-twenties, married with no kids, and decided to “live it up for one year” in an expensive high rise in a swanky neighborhood. I remember that discussion like it was yesterday. We wouldn’t be in Chicago more than two or three years. We would scale back and move to a more reasonable place if we ended up staying longer. Who were we kidding?!

For seven years, we rented the same apartment amidst trendy restaurants and loads of nightclubs, blocks from Michigan Avenue and a mile from Millenium Park. We visited the clubs and lounges maybe a half a dozen times during our stint there, though we did frequent the local restaurants often before having kids. I learned more about the late-night life in our neighborhood waking in the middle of the night to feed two babies and watching from our 20th floor balcony windows than I ever did actually visiting the places.

We walked to work everyday, rain or shine, summer or winter (yes… even in the Chicago winter). When the boys were born, we walked them to their pricey daycare (one of few options in the area) a few blocks away and then trudged the mile and half to work. They attended preschool with children of the likes of expat executives from around the world, players on the Chicago Cubs and White Sox baseball teams, private equity fund managers, and others. Out at the bars, dropping off at daycare, and just about everywhere, we always felt a little out of our league. We didn’t always feel like “them” but we’d be lying if we said it didn’t feel a little “sexy”.

As time passed, the same sites and sounds that once felt like exciting hustle and bustle started to sound like annoying fire truck sirens and constant horns beeping, engines running, and HVAC systems humming and to feel like overcrowded sidewalks and long lines, pressure to poo-poo public schools for crazy expensive private schools, and a lot of cold wind on my face.

We had no family in Chicago and babysitters were hard to come by, if not prohibitely expensive. Sitters started at about $100 for the night by the time we paid for their time and for them to park in the garage in our building. Our boys loved the indoor gym, small outdoor track and swimming pool our building offered, but they were starting to outgrow the space. Our boys were obsessed with sports. We wanted to get them closer to family and give them more space to play.

Long last, I also got completely fed up with the winters.

As much as Chicago was the perfect place for the time in our lives when we arrived, we were in an entirely different phase in our life by the time we left and felt a new home would be more fitting.

Although we were ready to move for so many reasons, Walkable City and all it offered to explain why living in an urban area made people happier, healthier and wealthier churned in my head. We loved our walking commutes. What’s not to love when it looks like this?!

We appreciated all the amazing restaurants; even the corner burger joints were great for a quick dinner with the boys. We loved the diversity and cultural exposure for our boys to so many ethnicities, languages, skin colors and lifestyles that they encountered just in their small classes at school not to mention on every sidewalk and street. We lived above a full grocery store (literally), so we could run to the store mid-recipe if we realized we were missing something. We shopped several times a week.

There were various festivals and celebrations in neighborhoods across the city on any given weekend in the summer. We lived within walking distance of a legitimate beach. (My San Diego native brother-in-law never failed to remind me that they weren’t exactly Pacific Ocean beaches.) But they did the trick.

Of course we made some great friends in Chicago who we miss seeing. I’m sure we will get back to see them soon enough.

We haven’t had too many surprises about the things we miss from Chicago. All the things I mentioned that we loved have been hard to replicate in our new town. Walkable City still resonates with me and I think the author is right that urban living has so many great benefits.

But we’ve had no regrets about our move and haven’t looked back. In fact, we’ve been pleasantly surprised about just how great our new area is, how much we love it, and how much it’s just perfect for where we currently are in life.

Head on over to read more about our new digs (part two of this post) and why it’s been just right for right now.

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  1. I am reading Walkable City right now! It’s a great book. I’ll be interested to hear why you chose a more car-dependent life. I’ve lived in moderately urban neighborhoods of Pittsburgh for the past 26 years, and I’m still loving it! I had no car for the first 7 years, and we still have just one car for our family. We walk or use public transit for the majority of our day-to-day trips.

    The pressure to choose private school is one we’ve felt, too. Pittsburgh Public Schools are a mixed bag, though, and the K-8 half a mile from our house is one of the best! It’s academically excellent AND truly diverse in ethnicity, religion, income, and family structure. I hope more public schools will use it as a model!

    1. Thanks for the note! That sounds like you’ve found a really great balance. And isn’t it crazy how interesting a book about sidewalks, streets and urban planning can me?! Ha.

  2. We lived in a walkable area while we were in Hawaii and wanted to recreate some of that when we moved back to Florida. Our goal was to be within walking distance of a grocery store. Well life had other plans and we are more like biking distance from the store, but we love our house and the area that we are in. So fun to read about your adventures! Thanks for sharing on the #wastelesswednesday blog hop!

  3. I grew up on a farm that was very isolated from everything but I didn’t mind it because that was all I knew and I loved the country. When I grew up I moved to the city in an apartment which was quite a change but I adapted to it fairly quicker and loved being close to the stores and all. It took a while to get used to people everywhere and don’t think I ever got completely used to that. Since I got married we have lived in the country but not so isolated we are only a short drive to get store and such. Most of my shopping I do on line anyways and I love my privacy again. Its amazing how we can adapt to our surrounding. I’m glad you found a healthy place for your boys to grow up in. Congratulations on being featured on #WasteLessWednesday blog hop. Tweeted!

    1. Thanks for the note! That definitely sounds like a big change, and you’re right that it’s interesting how well we adapt. Thanks for stopping by 🙂

  4. Sad to see you leave Chicago but I totally understand the space issue. My wife and I almost left when we started having kids but ultimately ended up staying. Love this post!

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