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From Playdates to Paychecks:

Writer: Jennifer MilanoJennifer Milano

The Chaos & Comedy of Mompreneur Life


Ever tried closing a business deal while a toddler yells "I need a snack!" for the 100th time? Welcome to the world of mompreneurs—where client calls come with background noise, “quiet time” is a myth, and snack negotiations are just as intense as business ones.


In this post, I'll dive into the hilarious, messy, and inspiring reality of balancing boss life and mom life—from using quiet time as prime work hours to why baby wipes are the ultimate multitasking tool. Whether you're a fellow business-running, kid-chasing pro or just curious about how we do it, get ready for some laughs, lessons, and a whole lot of real talk!



Welcome to the World of Mompreneurship! Above are my littles ones Edward (EJ) 6 years old and Giovanna (Gia) 5 years old.

If you’ve ever sent an email while cutting up fruit snacks or taken a business call from the front seat of your SUV while your toddler sings Baby Shark at full volume, congratulations—you’re living the mompreneur life!

Balancing a business and babies is a full-blown circus act, fueled by coffee, creativity, and sheer determination. It’s messy, unpredictable, and comes with a fair share of hilarious moments—but let’s be real, we wouldn’t trade it for anything!

So grab your (probably cold) coffee, hide from the kids for a few minutes, and let’s dive into the funniest, most relatable, and realest parts of running a business while running after little humans.


The Ultimate Multitasking Masterclass: Motherhood & Entrepreneurship Motherhood already turns you into a CEO of Chaos, so adding a business to the mix? Just another level-up!

One minute, you’re negotiating with a client; the next, you’re negotiating with a little human over why they can’t wear a superhero cape to preschool. (Spoiler: The toddler usually wins.)


Multitasking looks a little different when you’re a mompreneur:✔️ Taking client calls while changing diapers✔️ Sending emails with one hand and making a PB&J with the other✔️ Filling out spreadsheets while pretending to be in a tea party with dolls because your child want you to play with them.

The key to success? Embrace the chaos. There’s no perfect balance, only managed mayhem.


Quiet Time = Power Hour

The most sacred part of the mompreneur schedule? Nap time or quiet time.

This is the golden window where all business magic happens. The second those tiny eyes close or now in my case go in front of a screen for a little, it’s go time—a frantic race to:

✅ Answer emails

✅ Schedule social media posts

✅ Handle client work

✅ Maybe (just maybe) eat something that isn’t a leftover chicken nugget


Of course, this time is never guaranteed. Sometimes, they wake up or get bored just as you sit down to work—and that’s when we consider switching careers to professional snack distributor.


The Unexpected Perks of Mom Life in Business

As much as kids make running a business harder, they also make great (unintentional) business coaches.

  • Negotiation skills? Try reasoning with a child who wants M&M or ice cream for breakfast.

  • Time management? You learn to crush a to-do list in 20-minute increments between snack breaks.

  • Creative thinking? Have you seen the elaborate excuses kids come up with? Pure innovation.


And let’s not forget those moments when they walk into your coaching workshop on Zoom because your husband fell asleep before they did, and you have to mute your screen to yell. Peak professionalism. (yes this happened more than once). Redefining Balance: Why Mompreneurship Beats the 9-5

Let’s be real—balance is a myth. Some days, you’re a powerhouse, crushing goals. Other days, you’re just trying to keep the house from looking like a crime scene and remembering if you ate lunch.

The secret? Give yourself grace. You’re raising humans AND running a business—that’s superhero-level work.


Stop watching those TikTok videos that say, “They’re only little once, enjoy it!”—because honestly? I call BS.


Before running my own business, I worked the typical 9-5 grind. Mornings were a mad dash to get the kids to daycare between 7:30-8 AM, then I’d spend the entire day at work, only to pick them up around 5:30 PM. By the time we got home, it was a blur of dinner, baths, books, and bedtime—rinse and repeat. That wasn’t balance—that was barely time together.


Now? Running my own business has given me back time with my kids that I never had before. Is it hard? Absolutely. Do I have days where I want to quit? Of course. The self-doubt creeps in more often than I’d like to admit.


But nothing—nothing—outweighs the freedom and joy that come with building a life on my own terms. And that’s a trade-off I’ll take every time. 💛

Cheers to you!
Cheers to you!

Cheers to the Hustling, Kid-Chasing, Dream-Building Moms!


At the end of the day, mompreneurs are masters of the impossible—making playdates and paychecks work side by side. It’s exhausting, hilarious, and rewarding all at once.

So here’s to the moms answering emails in the school pickup line, taking Zoom calls with a toddler on their lap, and building empires while raising tiny humans.


Stay tuned for an epic event I am planning for MOMS building businesses. This is something you won't want to miss. Cheers to all the hardworking, kid-chasing, dream-building mamas out there! 🥂✨


 
 
 

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