Before our son was born, my husband and I were confident about one thing: we did not want him to go the traditional school route.
We both had strong feelings about the structure we remembered from our own childhoods — long days sitting still, and learning that felt disconnected from real life. I wasn’t taught to be excited about learning. I was taught how to temporarily retain information just long enough to regurgitate it on a test.
We became adamant hands-on learners ourselves over the years, building out a van into a tiny home to travel, then sustaining ourselves on 40 acres of off-grid property.
We wanted to create a childhood for our kids built around curiosity, practicality, and real-world experiences. Homeschooling felt like the obvious path.
At first, it felt possible
In those early years, it felt possible. We had built a steady passive income stream, so we could stress less about our work and spend more time with our son. We basically lived at the zoo, and our son learned abstract information about animals and dinosaurs at a very young age. When he was 2 years old, he asked Santa for a Quetzalcoatlus. When we weren’t at the zoo, we spent our days exploring museums, attending library programs, and enjoying hours outside.
We loved how flexible our schedule was. Our vision felt aligned with our reality. But as he grew and our work became more demanding, balancing the demands of being full-time entrepreneurs with our child’s needs became unmanageable.
Around age 3, we started to notice how social he was. He lit up when he ran around and played tag, explored a creek with other kids, pretended to be animals in the wild, or brainstormed the best ways to solve a puzzle. Simultaneously, we started to feel the weight of prioritizing child rearing versus our work. The more time we spent with our son, the less time we spent on our business. We felt the ropes of child-rearing and entrepreneurship tied to our wrists, with horses taking off in either direction.
When structured activities ended, we often resorted to educational shows or documentaries just to buy time to work. Business calls were interrupted with meltdowns. My husband and I grew irritable over splitting our capacity between two important things: income needed to pay the bills, and our son’s holistic development.
Instead of pouring fully into our son or our work, it felt like setting a cup outside in the rain and getting frustrated when it never seemed to fill up.
We enrolled him in preschool
Our son was in dire need of a type of attention we were becoming less able to give him, so we decided to enroll him in an outdoor nature preschool for two days a week.
The change in him was significant. He came home muddy and energized. He talked about friends, shared adventures, and challenges he navigated without us. At 3, he learned how to ride a pedal bike without training wheels. Watching him grow in that environment forced us to confront that our original plan had been shaped by our values, but not fully by his needs.
We ultimately moved him to a full-time Montessori program, which felt like a bridge between our philosophy and our reality. Montessori preserved the emphasis on exploration, practical learning, and independence that we cared about, while also providing the social structure and consistency he clearly needed. We put our daughter into the same school at just over a year old, and though we feel guilt that she’s not getting the same unstructured experiences he did, we see her thriving there as well.
We learned alongside our kids
Entrepreneurship has taught us something we did not expect. Flexibility is a fundamental business skill. But it’s an equally important parenting one, too. Changing course does not mean we failed. If anything, it means we are paying attention. We learned that the most important thing is not choosing the “perfect” path. It is staying responsive to who your child is becoming. Sometimes that means revisiting decisions you once felt certain about. Sometimes it means accepting that the version of parenting you imagined is not the one that ultimately serves your family best.
We had our son’s fifth birthday party at our home, and a soothing realization rested over me. Our small house was crammed with about 80 people, many of them classmates from school, all crowded around our enthusiastic son, singing him happy birthday.
We may not get to spend all day with both of our kids like we originally had planned. But my husband and I have breathing room to complete our work. Our son holds our daughter’s hand as they excitedly run into school together. And when we come home, we’re able to be a family without dividing our attention, and our children know we’re fully there with them.
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