Twelve years of building schools. Fifty lessons about learning, leadership, and the people who make it all worthwhile.
Today, I turn 50.
And as I’ve been reflecting on the lessons learned over five decades of living, I’ve found myself thinking about another journey that’s shaped so much of who I am: twelve years of building learner-led schools.
I’ve shared 50 Things I Know (and a Few Things I’m Still Figuring Out) over on my personal blog. But I couldn’t help thinking about all the lessons that have come from the work I’ve spent more than a decade doing.
Some of those lessons overlap. Life and work have a funny way of doing that. Others are so intertwined that I’m not sure which taught me what. And some I might never have learned had I not taken this particular road.
My journey began in 2014, when I opened my first school—a film school.
I believed people learned best by doing. By creating something real, solving problems, collaborating, making mistakes, and taking ownership of their work. I didn’t have a name for the philosophy at the time, but the principles were already there.
When I later discovered Acton Academy, I found language, frameworks, and a community of people who shared many of those same beliefs.
And over the years, those beliefs have been tested. Repeatedly.
Because believing in learner-led education and actually building a community around it are two very different things.
I’ve learned from learners who challenged my assumptions, Guides who helped me see things differently, parents who asked difficult questions, and communities that have had to figure out what it really means to practice the promises we make.
I’ve also learned that the hardest lessons aren’t always about education. They’re about people. About leadership. About knowing when to step in, when to step back, and when to recognize that perhaps you’re the one who needs to change.
So, in celebration of my 50th birthday, here are fifty lessons from twelve years of building learner-led schools.
Some have reinforced what I believed from the beginning. Others have challenged me to rethink what I thought I knew.
And quite a few I’m still learning.
Children Are More Capable Than We Give Them Credit For
1. Children are capable of far more than we give them credit for. But capability doesn’t develop because we tell them they’re capable. It develops when they get to prove it to themselves.
2. Struggle isn’t automatically evidence that something is wrong. Sometimes it’s evidence that learning is actually happening. Our job is to recognize the difference.
3. Independence isn’t something children suddenly acquire at eighteen. It’s built through years of choices, responsibilities, mistakes, reflection, and trying again.
4. Learners don’t need to make the choices we would make. They need opportunities to develop the judgment to make thoughtful choices of their own.
5. Curiosity changes the game. One thoughtful question can open a conversation that ten minutes of adult explanation would have shut down.
6. Children don’t need us to manufacture every learning opportunity. Sometimes the most meaningful learning happens when we stop interrupting what they’re already figuring out.
7. Boredom isn’t always a problem to solve. Sometimes it’s the space where initiative begins. Assuming someone doesn’t rush in with an activity and a laminated instruction sheet.
8. Learners will surprise you. With their insight, their creativity, their compassion, and occasionally their remarkable ability to negotiate their way out of doing something difficult.
9. Being able to ask for help is a skill. So is knowing when you actually need it. The goal isn’t a child who never needs support. It’s a young person who learns how to move forward without someone constantly directing them.
10. If we want capable adults, we have to give children real opportunities to practice being capable. Not someday. Now.
Sometimes the Adults Are the Hardest Part
11. Most adults say they want independent children. What we sometimes mean is independent children who make decisions we approve of.
12. Helping and rescuing are not the same thing. One equips someone to move forward. The other can quietly teach them that they need you to do it.
13. Watching a child struggle can be harder for the adult than the child. Our discomfort, however, isn’t automatically a reason to intervene.
14. Parents don’t stop being parents when they choose learner-led education. But they may have to rethink what supporting their child actually looks like.
15. Ask better questions. “What happened?” “What have you tried?” “What do you think you should do next?” Then do the really difficult part. Listen without immediately offering your solution.
16. Curiosity and assumption cannot occupy the same space for very long. The moment we become convinced we know why someone did something, we usually stop asking the questions that might help us understand.
17. A learner’s conflict isn’t automatically a parent’s emergency or a Guide’s problem to solve. Sometimes the greatest support we can offer is helping them prepare for a conversation we’d rather have for them.
18. We cannot promise learners ownership and then quietly take it back whenever we dislike their decisions. That’s not ownership. That’s permission disguised as choice.
19. Trust is easy when everything is going well. It’s considerably harder when a learner makes a decision you disagree with and you have to let the agreed-upon process do its work.
20. The adults have to be willing to grow, too. We cannot build a culture of reflection, accountability, and continuous improvement while treating our own assumptions as untouchable.
Freedom Isn’t a Free-for-All
21. Learner-led doesn’t mean adult-absent. It means the adult’s role changes. And sometimes that requires considerably more thought, preparation, and discipline than simply telling everyone what to do.
22. Freedom and agency aren’t the same thing. Agency requires meaningful choice, ownership, and accountability. And a little chaos along the way doesn’t necessarily mean something is broken or that more rules are needed.
23. Structure isn’t the enemy of independence. Thoughtful structure creates the conditions where independence can develop.
24. Our promises are not marketing language. They’re operating principles. And principles don’t stop being principles because practicing them becomes uncomfortable.
25. A community contract isn’t a decoration for the wall. If learners help establish the standards, they also need meaningful opportunities to uphold them, question them, and hold one another accountable.
26. Accountability isn’t punishment. It’s understanding that our choices affect ourselves and others, and taking responsibility for what happens next.
27. We don’t get to move the finish line simply because someone is struggling to reach it. We can offer support, examine the process, and ask better questions. But changing an agreed-upon standard to avoid discomfort teaches a different lesson than the one we promised.
28. Natural consequences are powerful teachers. Discomfort, frustration, and failure aren’t inherently unsafe. Unless there’s imminent danger or a genuine safety concern, we should be careful not to interrupt the learning simply because we’d rather spare someone the experience.
29. Community doesn’t happen because people share a building, a schedule, or a philosophy. It develops when people practice listening, disagreeing, repairing relationships, contributing, and honoring commitments. Especially when they don’t feel like it.
30. Not every learner or family will thrive in the same environment. That’s okay. Being committed to our philosophy doesn’t mean pretending it’s the right fit for everyone.
Building a Learner-Led School Will Change You
31. Believing education can be different is one thing. Building an organization that can sustain that difference is an entirely different education.
32. A powerful philosophy doesn’t pay the bills, hire great Guides, communicate with parents, or build effective systems. You still have to run the business. Preferably well.
33. Culture isn’t what we say we believe. It’s what we practice when those beliefs are tested.
34. A Guide isn’t simply a teacher who stopped lecturing. Great guiding requires preparation, observation, restraint, excellent questions, and the judgment to know when intervention supports agency rather than robs learners of it. And none of that is easy.
35. A curious question can change an entire conversation. A leading question disguised as curiosity doesn’t. Learners are remarkably good at knowing the difference.
36. You can believe deeply in learner-led education and still make decisions that undermine it. I’ve done it. The question is whether we’re willing to recognize those moments, own them, and adjust.
37. Not every challenge is a philosophy problem. Sometimes it’s a communication problem, a staffing problem, a systems problem, or a decision you’ve been avoiding because you already know it’s going to be unpleasant.
38. Protecting our promises doesn’t mean refusing to evolve. We should question our tools, systems, and practices constantly. But we shouldn’t abandon foundational commitments simply because someone would prefer a more convenient outcome.
39. If every important decision still runs through the founder, we haven’t built a self-sustaining organization. We’ve built a very demanding job with a compelling mission statement.
40. Perhaps the hardest part of building a learner-led school is realizing that you have to practice the same agency, ownership, accountability, and self-leadership you expect from everyone else. No founder exemption.
It Was Never Just About School
41. Agency isn’t something children need and adults have already mastered. Plenty of grown-ups are still waiting for permission, avoiding decisions, or hoping someone else will take responsibility.
42. We say we want capable, independent people. Then we create systems that reward compliance, dependence, and asking permission. And somehow, we’re surprised by the results.
43. Control can look remarkably like care. Especially when we’re convinced that our experience, intentions, or expertise give us the right to make someone else’s decisions.
44. You can love someone, support them, and want the very best for them without taking ownership of their life. That applies to learners, employees, partners, friends, and our own children.
45. Accountability without meaningful choice isn’t ownership. If someone has no real influence over a decision, we should be careful about holding them responsible for an outcome they couldn’t shape.
46. The way we respond when someone makes a mistake reveals more about our culture than any beautifully written statement about growth mindset.
47. Curious questions aren’t just educational tools. They change relationships. They challenge assumptions. They create space for understanding where judgment might otherwise take over. And frankly, more adults could benefit from practicing them.
48. The systems we build reveal what we actually believe about people. Do we trust them to think, choose, contribute, and grow? Or have we designed everything around preventing them from getting it wrong?
49. Sometimes the agency gap isn’t something we’re creating for others. It’s the agency we’ve surrendered ourselves. Through habit, fear, expectations, responsibility, or the stories we’ve decided are true about who we are.
50. Building humans who can lead themselves begins with examining how we lead ourselves. And after twelve years of asking others to do exactly that, I eventually had to turn the question on myself.
The Work Continues
Twelve years of building schools has taught me that the promises we make matter most when they’re tested. And that the work of developing capable, self-directed humans requires us to keep examining our own choices, assumptions, and leadership.
Somewhere along the way, those lessons became personal. I began asking myself whether I was practicing the same agency and self-leadership I encouraged in others.
That question inspired my TEDx talk, Live Like You Lead, and eventually my first book, THE AGENCY GAP: Why We Keep Creating Dependence—and How We Build Humans Who Can Lead Themselves.
The book explores the agency we take from others, the agency we surrender ourselves, and what it takes to build people and systems that encourage ownership rather than dependence.
Get an early look at THE AGENCY GAP.
I’m grateful to the learners, families, Guides, and fellow founders who’ve shaped these lessons along the way.
And I’m looking forward to what we learn next.
