Ask Casey – My Reporting Career, Buying a Home in Chicago and More

I get lots of design questions from you guys, but I actually get questions about a lot of other things happening in my life, like marriage, blogging, motherhood, fashion…really every single category! So, I tackle your inquiries in my “Ask Casey” blog post series answering your questions every month or so.

Ask Casey

Ask Casey No. 3

If you want to check out previous “Ask Casey” posts, you’ll find them all right here.

The google form at the bottom of the post has helped me keep everything organized so I can slowly make my way through your inquiries.  So, if you have another question today, be sure to submit it down below.

Buying Homes in Chicago

Our home tour before and after

When buying a home, they say “location, location, location” is so important. Why did you choose the area of Chicago that you did for your recent home purchase? Why did you decide to purchase a condo rather than a single-family home as your first home purchase years ago? What do you think are the advantages/disadvantages of a condo and single-family home purchase in the Chicago area, especially for a first-time home buyer?

Casey and Finn on couch

We bought our condo, in the Wicker Park area of Chicago, back in 2015 and lived there for almost four years. We chose to go from renting an apartment to buying a condo because, at the time, it made sense to invest in a home, instead of spending money on rent. Because it was just us and we weren’t planning to start a family for a while, we knew we only needed a small condo. We chose one of our favorite neighborhoods, where we were within walking distance of absolutely everything we wanted – the best bars, restaurants, coffee shops, and more. Plus, we were within walking distance of the train so Finn could easily get to work. We did a lot of work to our condo (you can tour it here!) and ended up selling it for about $80,000 more than we paid for it, which was amazing! This money helped us when it came time to purchase our current home.

Casey and Finn sitting on the stairs

Knowing that we eventually wanted to start a family (even though our timeline wasn’t quite what we anticipated), we bought our current home in 2019. At the time, it felt ginormous with a yard, basement, and four bedrooms! Now, we are actually filling it up quite nicely. We chose this area because we wanted a family-friendly neighborhood, a yard, a nearby park, and a good school…all while staying in the city of Chicago. Our neighborhood is not quite as bustling as Wicker Park, but we do have some restaurants and coffee shops within walking distance.

Buying a home in Chicago

I think if you’re weighing the advantages and disadvantages, it really all comes down to lifestyle. When it was just us two, living in a popular neighborhood with access to everything was our priority. Now, space and schools are our priority. The price of single-family homes in the best neighborhoods of Chicago are often multi-millions of dollars, so we were not going to be able to find enough space in our old neighborhood with our budget.

Life as a News Reporter

Casey headshot, my reporting career in 2013
As a TV Host in 2013

Can you share about your time as an on-air reporter? A behind-the-scenes would be so interesting!

That life does feel like it was a million years ago, but I’ll do my best to remember the details of my reporting career! And I’ll also share some videos. (Eek, I may regret that part…some are a tad embarrassing!) I wish I had more photos of this time, but iPhones weren’t a thing yet!

While growing up, I always wanted to be a news reporter. I loved writing and storytelling and journalism just seemed like the best fit for my skills. I went to the University of Notre Dame to study Film, Television, and Theatre and I then spent each summer interning at local news channels here in Chicago. During my senior year of college, I sent my resume tape (basically a video with clips of myself reporting) to about 50 news stations all across the country. I was ready to pack up and go wherever I could get a job. I ended up taking a job in Wausau, Wisconsin at WSAW Newschannel 7.

I packed up all of my things the day after graduation and drove to a small town where I didn’t know a soul. Luckily, a few months into my stay, Finn decided to come to Wausau and find a job too, so we could be together. We only stayed for about a year, but during our time there, we made lifelong friends that we still see today.

I worked as a one-man-band reporter, which meant that I was the videographer/editor/reporter all in one. Every morning, I would come in and pitch story ideas and I would then get my assignment for the day. I’d make calls and try to be out the door as quickly as possible to go capture the interviews and video that I would need to bring my story to life. I’d then drive all over town, interviewing people, getting video, etc., and come back to the station in the early afternoon to write and edit my story. Then, I would present my story for the 5 pm and 6 pm newscasts and then record another segment for the 10 pm news. It’s hard for me to remember all of the exact details, but I believe my schedule was about 8 am-7 pm, working Wednesday-Saturday. I then did a stint anchoring the weekend news, toward the end of my time in Wausau. It was a super fast-paced job and I was just kinda thrown into the fire! But wow, I absolutely loved it, except for the shitty pay and weird hours. Here’s my reporting reel from back in the day.

I left Wisconsin in 2011 and headed to St. Louis. There, I worked as an on-camera host and video producer for Anheuser-Busch. This job was a lot slower-paced than my news career had been, plus I had videographers and editors at my fingertips to do those parts of the job for me. That was great, because the quality of my work skyrocketed thanks to those pros! I traveled a lot for this job, heading around the country to interview wholesalers, cover Bud Light events, and even interview celebrities. Here’s a look at my hosting reel and my producer reel to get a sense of the kind of stories I did.

I ended up starting the blog while I was working there because, if I’m honest, I was kinda bored. I was used to the “go go go” life of a news reporter and at Anheuser-Busch things were much slower. I spent about three years in St. Louis and then moved to Chicago to work for WGN as a producer, where I won two Emmys for a Home Improvement Show I produced.

It’s interesting looking back on my decade-long career in TV and video. I feel like much of it was setting me up for where I am today! And no, I don’t have any plans to return to television, unless it is in a DIY/design capacity.

Pregnancy After Loss

2021 recap sharing our baby announcement

Trigger Warning: Discussing Loss & Miscarriage below.

I know you have written about your pregnancy with Rory after the loss of your baby boy. I am in a similar position now. I lost twins at 12 weeks this past fall, and now I’m at 12 weeks with a new baby. Have you found with more time passed that the pain and grief of that loss have become more manageable? For me, it has been helpful to read what you have put out in the world about loss, pregnancy, and motherhood. It has helped me feel less alone and I appreciate the vulnerability and courage it takes.

First, my heart goes out to you and the loss of your sweet twins. Yes, I would say that, for me, the loss has become much more manageable over time. But is it because of the amount of time that has passed or because I now have two living children in my arms? Honestly, it’s probably a bit of both. I still think about the baby we lost – not every day like I used to, but he is on my mind often. What would our life look like if things went differently? It especially hits me right around the time of year that I lost the baby and whenever it snows. (The first snowfall of the season happened the day I found out we lost him, so the snowflake has always been our symbol for him.)

And I know this next part won’t be helpful to hear, but for me, my pregnancies were both filled with lots of anxiety and fear. I was scared at every weekly ultrasound and every appointment. Heck, every time I went to the bathroom I was afraid I might find blood. It wasn’t until my babies were safely in my arms that I could breathe a sigh of relief. (But then new anxiety took over as I worried about my babies!) This was my experience and it is may be different than yours, but I think it’s helpful to know that whatever you’re feeling is normal and not wrong.

Parenting Resources

Do you mind sharing sources that have been helpful for pregnancy, feeding, sleep training, and other development-related books/articles for kids?

Before I get to my recommendations, please note that you don’t need to read or do any of these things to be a good parent. I think we put so much pressure on ourselves as parents (moms especially) to do everything “right.” We think we need to read the right things, feed our kids the right foods, and get our kids on the right schedule. Every family and child is so different, so figure out what works for you! I’m someone who likes to follow experts, read non-fiction books, and immerse myself in research, to be as well-informed as possible. Finn takes on other parenting roles, while I focus a bit more on development, schedules, etc., and pass along the most important info to him. With that being said, here are some resources I’ve used over the past two years…

  • During Pregnancy: I always say that pregnancy and birth are such a tiny blip on the radar when it comes to parenthood and everyone’s birth experience is so different. I would spend your time reading more about what happens AFTER the baby arrives, but that’s just me!
  • Moms on Call: When it comes to schedules and “sleep training” we are a Moms on Call family. I recommend getting their book for 0-6 months and having it handy. (It’s short and more of a reference guide.) This is how we got our kids on a feeding schedule and sleeping through the night by 12 weeks.
  • Baby Led Weaning: We’ve done baby-led weaning for both of our kids and it has been fantastic. I share all of my favorite resources and courses in this blog post.
  • Big City Readers: Around 9 months or so, I started doing virtual classes from Big City Readers with Rory. We’ve since purchased their Ready to Read program and Rory loves it. I’ll soon start those classes with Ellis too.
  • Lovevery Baby Toys: From the start, my generous mother-in-law gifted Rory the toy subscription to Lovevery Baby. We still get age-appropriate toys every month, along with a guidebook with ideas for play at that particular stage. We’ve saved all of those toys and now use them for Ellis.
  • Oh Crap! Potty Training: This is the book we used to potty train Rory. I love her straightforward approach. It took a few weeks, but Rory is now doing amazing without diapers!
  • Development Resources: Now that Rory is officially a two-year-old, my new homework has been learning about discipline and the development of toddlers. Here are a few of the books and resources I’ve found to be helpful…

For me, motherhood is all about learning and growing, right alongside my kids!

Submit Your Questions

Have a question you want to be answered? Use the google form below and I’ll answer it in the next Ask Casey post.


The Year of Casey

Hey there!

I’m Casey Finn, the voice behind The DIY Playbook. I’m a Chicago gal teaching you how to design, DIY, and maintain your home…by yourself! Learn more about me right here.

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