The Hardest Lesson I’ve Had to Learn as a Microschool Owner

By: Jennifer Kempin | March 27, 2025

Over the past year and more of building my microschool, I’ve had the privilege of connecting with other education entrepreneurs—visionaries who are creating learning environments that reflect their deepest values and beliefs about what education can and should be. But through all these conversations, one lesson has stood out as both the hardest to learn and the most empowering once embraced.

You can’t be everything to everybody.

At first, this truth feels impossible to accept. We start our schools because we want to help. We want to provide a safe, nurturing, and enriching space for children who need something different. And when families come to us with hope in their eyes, telling us they’ve finally found what they’ve been searching for, it’s tempting—so tempting—to try to mold our school to fit their needs.

But the reality is:

• Not every family will be the right fit for your school.
• Not every student will thrive in your environment.
• Not every request or expectation can—or should—be accommodated.

This has been a hard lesson for me to learn, and I will be honest that I have struggled every time these types of decisions have come up for me.

Early on, I had a family that disagreed with the way I handle behavior at my school. I don’t use punitive consequences or arbitrary rewards. Instead, I focus on supporting children in building strong emotional regulation skills, fostering a relationship of trust, and developing the ability to work through challenges with their peers.

This approach takes time and patience—there are no shortcuts. This family didn’t agree with it. While they loved many aspects of what we were building, they felt children needed harsher consequences for disruptions or not sharing. The parent was vocal about their disagreement, believing my approach was detrimental to both their children and others in the school.

I was a brand-new school. I knew my philosophy worked—I had seen it succeed in my decade of teaching and in parenting my own son. But what if I was wrong? What if the parent was right? The fear of standing firm was real.

In the end, I had to trust what I knew in my core. I wasn’t going to implement timeouts or take away free time. I wasn’t going to start handing out stickers for good behavior and removing them for bad behavior. That wasn’t the kind of school I was creating.

Once I fully committed to my philosophy, a weight was lifted off my shoulders. I knew that this family might leave, and my approach might not work for everyone, but I had to stay true to what I believed was best for kids.

That family did end up leaving—not solely because of this, but for several reasons. And when they left, I could stand confidently, knowing I hadn’t compromised my values. More importantly, I saw that when I was clear and unwavering in my mission, my school ran more smoothly, and the children thrived.

Oh, and by the way—my model does work. It works amazingly.

Building a Thriving Microschool: Standing Firm in Your Vision

To build a sustainable, thriving microschool, you must be crystal clear on who you are, what you stand for, and what makes your school unique. And then, you must have the courage to uphold those boundaries—even when it’s uncomfortable, even when you risk disappointing people, even when you feel the pull to bend.

This doesn’t mean being rigid. There’s a time and place for flexibility. But discernment is key: knowing when to adapt and when to stand firm. When to welcome a new perspective and when to recognize that a particular family or student simply isn’t the right fit for your school community.

The moment I truly stepped into this lesson, I felt stronger, more confident, and more aligned with the purpose of my school. I stopped fearing the “no” and started embracing it as an act of integrity—one that ultimately serves both my students and myself. Now, when I listen to fellow microschool founders who are still wrestling with this, I can hear their struggle. I can feel their conflict. Because I’ve been there. And I know that crossing this threshold is what will allow them to build something that lasts.

So to those just starting or still figuring it out: trust yourself. Know your mission. And don’t be afraid to stand by it. You can’t be everything to everybody—but by staying true to your vision, you will be exactly what the right families need.

How to Navigate Tough Decisions

When you find yourself being pulled in multiple directions—whether it’s a parent disagreeing with your approach, pressure from other educators to move at a different pace, or a prospective student who doesn’t seem like the right fit—take these steps:

1. Pause and reflect. Write out or talk through what doesn’t feel right about the situation.
2. Identify the root issue. Ask yourself: Does this conflict with my core beliefs about what is best for my students?
3. Gather more information. Do you need to do more research? Would insight from other microschool leaders help? Reach out to your network if needed.
4. Clarify your priorities. Determine what truly matters for your school and what aligns with your mission.
5. Make a decision—and commit to it. Once you’ve decided, stand firm. Avoid second-guessing or wavering. See it through and observe the results.

By staying true to your vision, you create a school where the right families and students will not just fit, but thrive.