Living With Kids: Jason Caldeira

If you’ve ever wondered how often I get an email from a home tour host who calls himself a Design Dad, I now have the answer: once. Jason is witty and stylish, and loves being a husband and parent…oh, I could go on and on about Jason, but I don’t want to keep you too long from his words and unique home!

So here he is: Jason Caldeira, Design Dad. Enjoy this one so much, everyone!

Hello, readers! The Caldeira posse here sending you warm greetings from an atypically blustery Chicago. (Well, atypical for mid-March, anyway. Climate change, amIright?) Allow me to introduce my adorable wife Erin, our oldest son Emmit, and our lil’ guy Julian. (Oh…and I’m Jason, the Design Dad.) 

Together we live snug as bugs in rugs in the North Center neighborhood on the north side of Chicago, a neighborhood that’s about as centrally located as you’d want to be.

A five to ten minute walk in any direction lands you in a completely new neighborhood with its own set of quirks and eccentricities. Or you can end up in Target or Whole Foods if that’s your bag. We’re also a short jaunt from the home of the World Champion Chicago Cubs. Can I get a woot woot?

Eight years ago when my wife and I decided it was time to buy a home, this neighborhood stood out to us. I’ve lived in the general area for the better part of 20 years, but she was relatively new to Chicago at the time. We both love food, and we both love a good cocktail, and there’s certainly no shortage of either on virtually every block.

As major cities go, Chicago is pretty darn affordable. Buying a house or condo is very much within reach, as long as you’re willing to make some sacrifices. With our budget, for example, we could either buy a fixer-upper of a house, in an area just outside where we truly wanted to be, or we could buy a move-in-ready condo in the location we loved. But we knew we’d be giving up square footage, storage, and most likely any chance of having a yard. But seeing as we didn’t yet have kids, those compromises were worth it to us.

Our search for the perfect home ended on our very first day of looking.

In a sense I’d say it was serendipitous, as this condo didn’t meet any criteria on our bucket list and we almost didn’t even look at it. But the photo showed these bizzaro stairs that we wanted to see in person, so we humored our realtor with a visit. We walked up the front stairs, and my wife walked directly into the master bath as I continued into the living area. She walked out and, without even seeing the rest of the unit, said, “We’re buying it”.

There was a vibe here that I still struggle to put my finger on. It feels like living in a tree house built by Scandinavian architects who were sipping Manhattans while listening to Miles Davis. In all seriousness, the unit was originally an architecture studio where the architect who rehabbed the building worked with his staff. When he retired, he converted it to living space.

The building itself is an 1893 farm house that was restored and converted to a three-flat. Our unit used to be the low-ceiling crawlspace, so the architect literally raised the roof and lined the walls with windows.

The amount of natural light – between the windows and the multiple skylights – is truly something special. Honestly, it’s about the only thing preventing us from going stir crazy during the infamous Chicago winters, when it’s possible to literally not leave the house for days at a time.

The only downside: it was much smaller than we were used to. We had accumulated a decent amount of stuff, for better or worse, and the thought of downsizing was a tad stressful, if not liberating. We also had no idea how a space like this would work with children on board, but we figured we had plenty of time to work that out.

Two months later we moved in.

Our grand vision is to eventually get a summer home using the money we saved by not buying a larger house, in a location where that money stretches a lot further. That’ll give us the much-needed outdoor space, a much-needed respite from the city, and a much-needed place to just get away. And seeing as I work for myself and from home, there’d be very little preventing us from spending considerable time away.

People ask me frequently how I’m able to work from home…in a space the size of ours…with no doors on anything but the bathrooms…five feet away from my sons’ bedroom.

What I’ve determined is it’s not a whole lot different than working in an office. Interruptions are the norm in both environments, whether it’s a coworker asking if I saw last night’s episode of The Bachelor or if it’s my son asking me – again – to watch him watch him watch him as he attempts to hop on one foot.

You learn to work amidst chaos, and the chaos I get to witness first-hand is pretty spectacular.

Speaking of work, as you’ve probably ascertained, I’m a designer. I work with a branding and marketing agency called Nerve Collective which I founded a few years back with a long-time friend and colleague. We all work from home in our respective cities, and even manage to change out of pajamas from time to time.

My professional career has been a tad eccentric, designing for everyone from small agencies, web shops, and b2b ingredients conglomerates to independent bands, area boutiques, and Oprah Winfrey. But I found my sweet spot just over a decade ago when I decided to go on my own.

My wife is a designer-turned-cheesemonger who decided when our first son came along that she would fulfill her childhood dream of becoming a stay-at-home mom.

I consider myself extremely lucky to be able to be at home with my wife as both my sons grow up. It is, however, not without its challenges. It can be hard to find work/life balance when my life and my work take place in the same location.

And to an extent, my work is my life. I love being a designer. It’s my hobby and my job. It’s something I carry with me at all times, and always have. Design informs almost every decision I make, especially when living in a home that many would describe as minimalist.

When we announced we were starting a family, we were constantly asked “So…are you going to stay in the city?” And we often got the good ol’ “Ya know, babies come with a lot of stuff!”

But really, they don’t. Babies come with nothing, and they’re happy with very little. We just buy them stuff to make our job as parents easier.

My wife and I found that we never needed a changing table – we used the floor. We didn’t need a diaper genie – we used cloth (for a while, anyway).

In a sense, being labeled as minimalist and living in a home with very little storage forced us to be incredibly mindful of everything we purchased. If it didn’t have a home or a purpose we couldn’t live without, we didn’t buy it. It continues to be a small sacrifice we’re willing to make in exchange for staying in the city.

Chicago is an absolutely fantastic place to raise kids. It really is. Don’t believe all the negative press.

It’s far from perfect, and there’s plenty of room for improvement on all fronts, but at the end of the day the people that live here are warm, kind, and active in their communities. It’s a city full of decent, hard-working people with Midwestern charm. I’ve lived near Chicago my whole life, and in Chicago for over 20 years, and it’s difficult to imagine being anywhere else.

When you become a parent you truly see Chicago shine. Activities for kids are everywhere, every weekend. The museums are world class, the parks are spectacular, and the walkable nature of the city makes getting from event to event relatively painless. Our sons particularly love the Peggy Noteabart Nature Museum, the Shedd Aquarium and the Art Institute…not to mention the Santa Train, which is a Christmastime must-do.

Emmit and Julian are also way into music. As a professional amateur musician I’d like to give myself credit, but I think their love of music comes naturally to them even without my genes. One of my proudest moments was when Emmit told me his favorite singer was Ella Fitzgerald. (I mean…c’mon.)

They both take music classes, dance and sing all day long, and much to our dismay consider every surface in the house their own personal drum set. Sigh. But I’m certain there’s little I’ll miss more about their childhood than watching them belt out a Justin Roberts tune or improvise a song – at the top of their lungs of course – while banging on a painfully out-of-tune ukulele.

My cheeks hurt from smiling just thinking about it.

I love watching the kids develop their own sense of style. I have a pretty defined personal aesthetic, and my wife does as well, and we both work really hard at not forcing that on our kids. They need the freedom to make mistakes, to dress like kids, to wear what they feel expresses their moods, to figure out who they are, to listen to the music that speaks to them, and to play with the toys that get their creative juices flowing.

We guide them along the way, but try to be conscious of sitting back and letting them go where the wind takes them. Sometimes that’s playing with our couch cushions for hours. Other times it’s playing with our couch cushions for hours. But sometimes, when the mood strikes, they even play with our couch cushions.

Our home doesn’t have space for a dedicated play room, so most toys are relegated to the boys’ bedroom. But we make exceptions within reason throughout the entire house – after all, this is their home, too.

So it’s not uncommon to see a tiny tractor hiding out in our plants, or a Lego space shuttle flying over our glassware. Their Lego table moves about the house, tiny cars drive over every surface, construction paper piles up in the corners, and everything seems to end up taped to the walls at some point. And that’s ok.

I want my boys to remember their first home fondly as a place where they played, laughed, explored, and learned.

I’m not going to lie, though…I’m secretly hoping they never outgrow Legos, blocks, and creative and imaginative play so our place doesn’t get overridden with Ironman, cheaply made plastic whatevers, and Minecraft everything. But I guess we’ll cross that bridge when we come to it.

As much as I adore fatherhood, I wish someone had told me to do this parent thing sooner, because it’s exhausting being a 40-something dad with two kids six and under. (And my wife does the heavy lifting. I just work here.)

Young parents have energy that older parents just don’t have. But at the same time, I barely knew who I was in my 20s and 30s, so how could I have possibly been someone’s dad?

Besides…it took me over 30 years to meet the love of my life. And without her I can’t even imagine where I would’ve ended up. But I know it wouldn’t have been here, with two sons I love so much my heart hurts.

Sometimes life is about being patient until the stars finally align.


So much I want to discuss! But first, a big thank you to you, Jason, for putting yourself out there! I appreciate your honesty and sense of humor. It made my day.

First, this: “I have a pretty defined personal aesthetic, and my wife does as well, and we both work really hard at not forcing that on our kids. They need the freedom to make mistakes, to dress like kids, to wear what they feel expresses their moods, to figure out who they are, to listen to the music that speaks to them, and to play with the toys that get their creative juices flowing.” What a refreshing and so hard-to-do philosophy. Especially when they want to leave the house in a mix of plaids and summer satin, with a side of dinosaur tail. And shoes on the wrong feet.

And then this: “We guide them along the way, but try to be conscious of sitting back and letting them go where the wind takes them. Sometimes that’s playing with our couch cushions for hours. Other times it’s playing with our couch cushions for hours. But sometimes, when the mood strikes, they even play with our couch cushions.”

I’m reminded of Donald Robertson’s Instagram hashtag #buythemnothing. So true, right? What are your kids playing with right this minute?

P.S. – Are you living with your own kids in a unique way? Are you interested in sharing your home and experiences with us? Let me know! We love to be inspired! And it’s a lot of fun…I promise! I should also mention, I have a goal to bring more diverse points of view to Design Mom this year. So if you don’t see yourself or your community reflected here, let’s make it happen — send in your details, or recommend a friend! Take a peek at all the homes in my Living With Kids series here.

42 thoughts on “Living With Kids: Jason Caldeira”

  1. The stairs at the end of the tour, are they called “ships stairs”? And are those tree-like ladders functional? Our family is apartment-dwelling with 2 kids, (though it’s not a beautifully designed one like yours). Do you keep all of your stuff in your home, or do you have other storage areas (we pay off-site storage.)

    1. Hi, Melissa!

      I’m not sure if the stairs have a formal name, but my friends affectionately refer to them as “widow makers”. They look stranger than they feel – if you don’t look down, they feel like normal stairs. But trying telling that to my middle-of-the-night-need-to-check-on-the-kids self.

      We keep everything that we use frequently inside our home, and thankfully we have a sizable storage unit in the basement and a one-car garage that we use for seasonal items, luggage, storage, etc.


      1. Oh… and the tree-like ladder is semi-functional. Back when the unit was an architecture studio, they kept several large plants up where the big yellow C is now. They used that ladder as a way to access the plants for watering. We decorate it at Christmas, but otherwise pretty much ignore it.

        And amazingly enough the kids have never shown any interest in climbing it! (Knock on wood…)

  2. This was lovely. I always love seeing smaller spaces, as we also are a work-at-home family, living in a relatively small space. It’s so encouraging to see others doing the same! I loved the observation that babies come with nothing. We also skipped the changing table and diaper genie. :)

  3. I love this home and this family! The notes about raising kids in a city are so on point, I feel that same way about NYC. btw “It feels like living in a tree house built by Scandinavian architects who were sipping Manhattans while listening to Miles Davis.” might be the best sentence ever.
    Also, who makes the coffee table in the living room?

    1. Hi, Nora! Thank you so much for the kind words! And yes, we feel the same about NYC as well. (My wife lived in Manhattan right before moving to Chicago and meeting yours truly.)

      The coffee table was our first – and pretty much only – attempt at baby-proofing. We got rid of a chunky rectangular table and opted for this Craigslist find, which is an Eames reproduction. Search for “Eames molded plywood coffee table” and you should find a plethora of options.


  4. Love this home tour and love Chicago. We’ve been in the city for just under 10 years. We live not too far from this author’s neighborhood. Our two kids love it.

    1. Hi, Tamara! Thanks for the kind words. The bookshelves were leftover from when this was an architecture studio. If you look at the photos of my office, the desk and the shelves that are up high used to run the entire length of the unit on both sides in order to accommodate the studio’s staff. When they converted it to a living space they left all the shelving cubes behind. Thank goodness they didn’t throw them out!


  5. Love this tour! I see in the comment above that the bookcases were left behind by the architect. Do you happen to know what brand they are? I’m talking about the ones that look like stacked rectangular boxes–they are fantastic and exactly what I’ve been looking for.

  6. This blog post is my favorite Living with Kids, yet! Jason, you are a hysterical writer and with such a knack for design. I would read more from you in a heartbeat. Gabrielle, you kicked off this blog post perfectly in the opening line.

    Bravo, you two! More, please, thank you ;)


  7. I’m always super impressed with people’s homes filled with toys and kid’s things still manage to look so stylish! Well done. And love the fairy lights in the bedrooms. I also love that your wife’s childhood dream was to be a stay-at-home-mom. It’s a role I love, but never thought I’d choose, so it’s sometimes a struggle for me. Lastly, please tell me about the blue artwork with the sweet little tugboat. I love that so much.

    1. Hi, Julie! Thank you so much for the kind words. My wife struggles with being a stay-at-home mom pretty much daily…it’s the hardest job in the world. But for us it was important that we both had this chance to spend as much time with the kids as possible. It’s amazing how fast it flies by even when it drags!

      The art over the bar we found in Portland on our first anniversary. I wish I could remember the artist’s name, but I do remember his story. He’s a graffiti artist that draws elaborate ballpoint pen line drawings inside books and magazines in libraries, book stores, etc. He transitioned away from graffiti from what I remember and now creates artwork like what we have; felt designs glued on top of pen drawings. There’s just something so endearing about it.

      If I can track down his information I’ll come back here and post it.


      1. Hi Jason! Were u able to find out who the artist is? When I was browsing on which article I want to read, yours caught my eye bcos of that beautiful art in thumbnail. Oh and I love the article! Love your house, design and so homey too!!!!

  8. Leg lamp. Mr. T. Espresso. Killer decor. A sweet bar. And a beautiful family. You da’ man! Good to see you all on here.

    1. Thanks, Jasna! We definitely have plenty of days of full-on grouchiness – don’t let the picturesque photography fool you. But overall yes, I’d like to think we’re pretty happy. :)

  9. This is probably my favorite Living with Kids! Very witty and fun. That condo made me change my mind about condos.

  10. Thanks, Grace! It changed our mind too. Chicago condos (affectionately referred to as “Chicandos”) went up everywhere during the early-2000s real estate boom, and sadly a good majority of them had little to no character. (Think big red brick cube.) But with just a little digging, there are still plenty of gems to be found in pretty much every neighborhood.


  11. I’m completely homesick! We moved from Chicago about 2 years ago and the transition to suburbia is tricky – yes, there are yards and parking (and we moved closer to family which is hard to beat) but man, your post made me ache – like you said “decent, hard-working people with Midwestern charm” …and style – solid, bona fide style. Your condo with its architecture and your decor and the museums and the music and walking and never not hearing your kids – it was just so familiar and bittersweet.
    Go Cubs!

    1. Thanks for the comment, Annie! Yeah, it’s a hard city to leave, that’s for sure. Who knows what the future holds… but as the kids grow I’m guessing a larger space will be inevitable. Until then, we need to soak up every ounce of what the city has to offer!


  12. Love this home! Thanks so much for sharing.

    Jason, can you tell me the brand/maker of the white cubby wall setup in the 3rd to last picture? Thanks!

    1. Hi, Cambria!

      The wall cubes are Urbio, a product I Kickstarted several years ago. You can buy them online at, and I believe I’ve seen them at the Container Store in the past. I highly recommend them!


  13. No picture of the master bathroom that sold your wife on the condo?? What a tease!
    Otherwise, I really enjoyed your tour and philosophy on living with (and working around) your kids.

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