Raising Children, Raising Businesses
Lessons from Two Schools, 13 Years Apart
Raising children is an extreme sport—a mix of joy, exhaustion, unpredictability, and the constant realization that no two children are the same.
Same parents, same upbringing, same environment… yet completely different personalities.
Same parents, different time, different experiences… still different.
And I’ve come to believe it’s the same with businesses.
When we "gave birth" to @kidscourtschool in 2009, I was 27. Different time, different age, different expectations.
Fast-forward 13 school sessions later, we launched @thecourthillcollege in 2021. Naturally, our first instinct was to treat it as a continuation of KCS—the way a parent might think their 13-year-old should automatically "watch over" their newborn sibling.
But very quickly, reality set in.
We realized that what worked for one would not automatically work for the other. The contexts, challenges, and even our own leadership perspectives had evolved. And just like parenting, running a second school meant unlearning, adapting, and growing in new ways.
Here are some of the key lessons we’ve learned along the way:
1. Every Business Has Its Own Identity
No matter how similar the vision and values, every school (or business) has its own DNA.
Kids’ Court School was built from the ground up, with every structure and system evolving through years of experience, trial, and adaptation.
Court Hill College was born into an era where education was rapidly changing—where digital learning, shifting student expectations, and new leadership models were reshaping how schools operate.
💡 Lesson: What worked before won’t necessarily work again. Each business deserves its own customized growth strategy, not just a copy-paste version of the first.
2. Growth Requires Different Leadership at Different Stages
When we started KCS, I was hands-on with everything—curriculum, teacher recruitment, even choosing classroom furniture. It was a start-up, and I had the energy, flexibility, and risk appetite of a 27-year-old entrepreneur.
By the time we launched CHC, things had changed. I wasn’t the same person, and the school needed a different kind of leadership—one that was more strategic than operational, more about empowering others than doing everything myself.
💡 Lesson: The leader you were at the start of your business may not be the leader your business needs as it grows.
3. People Are Not Systems (And Systems Are Not People!)
In KCS, we had built strong systems over the years—admissions processes, staff development, school culture, and more. Naturally, we assumed we could transfer these seamlessly to CHC.
We were wrong.
Why? Because systems alone don’t create culture—people do. The team, students, and parents at CHC were different from those at KCS. They had different expectations, different strengths, and different challenges.
💡 Lesson: Culture isn’t something you transfer; it’s something you build—with the people who are actually there.
4. The Power of Adaptability & Listening
In education (and in business), rigidity is a recipe for frustration.
KCS started in 2009, when physical classrooms were the core of learning.
CHC started in 2021, in the middle of a world that had been reshaped by technology, hybrid learning, and new economic realities.
We quickly realized that we couldn’t impose old solutions on new challenges. Instead, we had to listen—to teachers, parents, students—and adapt with them, not just for them.
💡 Lesson: Success isn’t about sticking to the old playbook. It’s about knowing when to rewrite it.
5. You Can’t Run at Full Speed All the Time
When we started CHC, we were tempted to replicate the speed of execution that had worked for KCS. After all, we had 13 years of experience—shouldn’t things move faster?
Wrong again.
We had to respect the growth process. Just like you wouldn’t expect a newborn to run, we had to give CHC the space to grow at its own pace—with intentionality, patience, and wisdom.
💡 Lesson: Sustainable success is not a sprint; it’s a marathon. Pace yourself accordingly.
Final Thoughts: Parenting, Business, and Growth
Just like parenting, leading multiple businesses (or schools) is a journey of learning, unlearning, and re-learning. What worked for one child—or one school—may not work for another. And that’s okay.
As we step into another year, I’m holding onto these lessons:
✅ Honor each business’s identity.
✅ Lead differently at different stages.
✅ Prioritize people over systems.
✅ Stay adaptable and listen.
✅ Pace growth intentionally.
And most importantly—embrace the process, because every new challenge is an opportunity to grow.
Have you ever experienced this in your own leadership or business journey?
What lessons have you learned from managing multiple teams, businesses, or projects?
Let’s discuss! 👇🏽
Love and Light,
DAO
#Leadership #Entrepreneurship #EducationLeadership #ScalingABusiness #BusinessGrowth #LessonsFromExperience