Ask Casey No. 9
The truth about summer with kids, organized chaos, and why we rarely leave the house on Friday nights
Welcome back to Ask Casey, one of my favorite series to write because I get to answer your thoughtful, funny, and very real questions.
These came straight from Instagram DMs and story replies, but if you have something you want me to answer next time, drop it in the comments. I always pull from there for the next round.
What’s your summer survival strategy with two kids?
I’m trying my best to go with the flow more.
Every week and every day looks different around here. The kids are in a million different camps and activities, so we’re constantly juggling different drop-offs, schedules, lunches, and locations.
During the school year, we’re out the door by 7:05 am and on our way to school. But in the summer, mornings are a lot looser, and many camps don’t start until 9 am. We often don’t set an alarm and the kids naturally wake us up around 6-6:30 am. Somehow, I feel like I’ve lived seven lives by the time they leave the house!
It’s funny because you’d think having more time would make things easier, but I actually find it harder to get everyone up, fed, dressed, and out the door when there isn’t a strict timeline. The kids get absorbed in playing, and before you know it, the house is wrecked, and everyone is still in their pjs.
Then I come home halfway through the morning and have to switch gears into work mode for a few hours before it’s time to do it all over again.
That said, I’m really trying to enjoy this season. I’m leaning into the chaos, eating a few more popsicles (our freezer is always stocked!), and letting the kids run through the sprinkler. I’m not naturally a laid-back person, so I’m doing my best to moonlight as one during these summer months.
What’s one thing you’ve changed your mind about since becoming a parent?
Oh man. I used to think my kids would always look put together and wear the cutest clothes. No graphic tees here! Ha. What a crock.
My kids now wear the wildest combinations imaginable and fully dress themselves. Nothing matches, oftentimes things are on backward, they only care about being comfortable, and honestly, I just want them to be somewhat clean.
If they have clean clothes on, brushed hair, and brushed teeth, I consider that a huge win. No Pinterest-worthy matching outfits over here.
How do you stay organized with so many different platforms (Instagram, Substack, blog, book, TV, and radio)?
I’m very Type-A and genuinely love systems and organization.
I live and die by my Google Calendar. That’s where I schedule all of my content for Instagram, Substack, and the blog.
For radio, I go in once a month and record several segments at a time. We put those dates on the calendar in advance, and I usually spend the day before writing all my scripts. I then go live when I’m there on a particular DIY topic during the noon business hour.
TV requires a bit more coordination because we film four segments at once, so there are projects, supplies, and wardrobe to think about as well.
And then there’s the book, which is a whole other beast that I fit in whenever and wherever I can.
It’s a lot, and honestly, I wouldn’t be able to manage it all without a system. I’ve written a lot about how I organize my time over the years, but I’ll link to my most recent post because it has lots of good tips.
What’s one family tradition your kids love that surprised you?
Our Friday movie night is definitely the most loved tradition in this house, and not just by the kids. It’s honestly become one of my favorite parts of the week, too! By Friday, we’re usually all worn down and a night in is just what we all need.
There’s something really nice about intentionally not going anywhere on a Friday evening and simply staying home with popcorn and frozen pizza.
The kids spend the entire week talking about what movie we’re going to watch, and I hope it’s a tradition that sticks around for years and years.
Finn is also in charge of birthdays, holidays, and all of the fun extras around here, and the man goes all out. I’m talking balloons, signs, decorations, and little treats for even the smallest holidays.
If it were up to me, I definitely wouldn’t do nearly as much, but he absolutely loves it, and so do the kids.
What’s bringing you joy right now?
My word for 2026 has been JOY, and I feel like I haven’t done a great job keeping you all updated on how it’s going.
If I’m being honest, I’d probably give myself a B-.
It’s not that I’m unhappy, but I wanted this word to help me become more grounded, carefree, and present. I wanted to approach everyday moments by asking myself, “How can I inject a little more joy into this?”
Whenever I actually remember to do it, I notice a difference. I’ll turn on music, make the kids have a dance party with me, light the nice candle, or sit outside in the sunshine for a few minutes just because.
The challenge isn’t doing those things. It’s remembering to prioritize them.
I will say that warm weather, longer days, and sunshine have been bringing me so much joy lately. Chicago is absolutely fantastic this time of year. There’s so much to do, the weather is incredible, and everyone is outside constantly.
People always ask if we have summer travel plans, and the answer is almost always no, because this is the season to be here and soak it all in. If you want to visit Chicago, visit June through September…Chicago really shines!
That’s it for this edition of Ask Casey!
Have a question for the next one? Drop it in the comments below.
Casey---your posts are always so genuine and authentic. Love reading them. (And your son's jersey? Well, I looked at that and thought how I'd never seen a Cubs logo on the back like that--then I read he likes to wear it like that!)