Trust Along the Trail: Reimagining Middle School
Awkward middle school photo of Jennifer D. Klein, author and editor of the WSCB Chronicle
I invite you to do something uncomfortable: take a minute to remember who you were as a middle schooler.
I’ve prompted hundreds of adults with this question, and I can count on my hands the number who recall those years fondly. Most groan, laugh nervously, or shake their heads.
I myself remember the deep desire to “fit in,” to be “cool,” and the incredible pressure I felt socially. I remember not seeing much purpose in what I was learning, so my energy went into quietly rebelling against the rules—always in search of my peers’ and, if I’m being honest, girls’ attention and admiration.
My middle school experience probably looked a lot like yours: four walls, bells to tell us when to move, passes to go to the bathroom, textbooks full of facts to memorize. It was a system designed for order and efficiency, not for identity or purpose.
And yet, that’s still how we often frame middle school today. A time to endure. A time to get through. A time we have to “just survive.”
What If Middle School Wasn’t About Survival?
What if, instead of survival, middle school was about discovery? What if those years were seen not as something to “get through,” but as the most critical stretch of a young person’s journey?
This is where trust comes in. Middle schoolers don’t need more rules to manage or hoops to jump through. They need the freedom to try, to fail, to recalibrate, and to keep climbing.
For the past 15 years, my work in education has unfolded in mountainous regions—from the Rockies of Colorado to the highlands of Guatemala. Maybe that’s why I often find myself reaching for mountain metaphors to make sense of schooling. Even if you’ve never set foot on a trail, the lessons of hiking resonate with the challenges young people face.
On steep mountain paths, the shortest route to the top—straight up—is impossible. The only way forward is through switchbacks, those zigzagging trails that feel slow and frustrating but make the climb possible. And just when you think you’ve reached the top, you sometimes encounter a false summit—a ridge that looks like the peak, but isn’t.
Middle school is full of switchbacks and false summits. And the only way learners can navigate them is if we trust them. As Cruzer, a recent graduate, put it, “Once you feel like you’ve got something, you kind of stop trying… I hit that in seventh grade. I thought I was good, and then it got harder. I had to catch up again, and by the end of eighth I was back up.”
His story is a reminder that growth rarely follows a straight line. When we give young people the trust and space to stumble, recalibrate, and climb again, they don’t just reach the summit—they build the resilience to keep climbing the next one.
Keeping Trust at the Center
Embark learners collaborating with Middle State Coffee to roast professional coffee
Middle schoolers are often described in deficit terms: distracted, disrespectful, disengaged. The message we send, whether intentionally or not, is that they can’t be trusted—with their own choices, their own voices, their own time.
But in my experience, when we lead with trust, middle school learners almost always repay that trust by exceeding our expectations.
At Embark Education, where I served as Head of School, we built our model around trusting middle school learners with freedom: freedom of movement, freedom of schedules, and freedom to make mistake after mistake before putting it all together. It wasn’t always easy. But it was powerful.
Initially, Cruzer was someone who struggled mightily to stay organized. Traditional systems had labeled him “irresponsible.” He had brilliant thoughts in his mind, but was challenged to put them on paper—especially when asked to do them in a constrained period of time. But when we trusted him with more autonomy—paired with coaching and reflection—he slowly built the muscles of responsibility on his own terms. For Cruzer, he needed extended blocks of time under his control and the ability to lead others even when he was working to lead himself.
The breakthrough didn’t happen in a straight line. It came in fits and starts—zigzags on the trail. And there were plenty of false summits, moments when we thought he’d “arrived,” only to realize the climb wasn’t finished. By eighth grade, though, he was leading project teams and advocating for himself with clarity and confidence.
Trusting middle schoolers doesn’t guarantee a smooth path. It guarantees a human one.
Why Trust Matters in the Middle Years
Between ages 11 and 14, young people are commonly:
Testing boundaries and constructing identity.
Hungry for agency, yet deeply in need of guidance.
Yearning to belong while terrified of rejection.
Capable of abstract thought, creativity, and leadership—if we let them practice.
Too often, schools respond to middle school learners with control: rigid schedules, bells that fracture the day, rules designed more for efficiency than growth. We may keep order, but we lose engagement.
When educators respond with trust, we invite agency, even if not always expressed in the ways we might want. We send an important message: You are capable. We believe in you. That belief is foundational to deeper learning. Cruzer remembered, “They let me make mistakes and learn from them, but when I really needed help, they showed up. That helped me grow.”
Designing for Trust Along the Trail
We know from research on adolescent development that the middle years are a time of profound change: the brain is pruning and rewiring, novelty-seeking is high, sensitivity to peers is heightened, and identity is beginning to take shape. These traits can make middle school feel turbulent—but they are also the very levers we can design around.
What does it look like to design a middle school that helps learners navigate switchbacks and false summits with courage? Following are some of the strategies we used at Embark.
Embark learners including Cruzer presenting to group of visiting educators on their journeys
Freedom of Movement
At Embark, learners weren’t confined to a single classroom. They moved between learning spaces, community partners, and even local businesses. That freedom created both missteps and opportunities: forgotten materials, missed transitions, but also moments of responsibility. Adolescents crave novelty and exploration; structured freedom channels that drive into responsibility instead of rebellion.
Flexible Schedules
Instead of 45-minute blocks that reset seven times a day, we built in stretches of learner-directed time. This wasn’t just about efficiency—it was about agency. Learners had to decide when to push forward on their own work and when to support their peers. Sometimes they used the time well, sometimes not, but each choice was practice in awareness: balancing self with others. In early adolescence, when the brain is primed for social learning, these negotiations build both agency and empathy—the foundations of independence.
Mistakes as Learning
False summits teach us that “not yet” doesn’t mean “not ever.” Learners were encouraged to submit drafts, revise, and reflect openly—with adult support—about what went wrong. Risk-taking paired with reflection is essential to growth. In the middle years, when pruning and rewiringin the brain heighten sensitivity to feedback, framing mistakes as practice rather than failure is critical to confidence.
Learner-Led Conferences
When learners led conferences with families, they didn’t just report progress; they owned their story—the climbing, slipping, and recalibrating. Adolescents are in the thick of identity formation, and voicing their own journey strengthens their emerging sense of self more than any adult summary could.
Community Connections
Projects rooted in real-world issues showed learners that setbacks weren’t fatal, they were feedback. Whether designing for a local business, working with community partners, or planning our school trip to Santa Fe, learners saw that their efforts mattered. Because belonging and relevance are heightened needs in adolescence, authentic audiences turn compliance into genuine contribution.
An Example in Action: Keller’s Climb
At Embark, I watched these strategies come together in Keller’s journey. He thrived when working independently and often finished assignments quickly. In a traditional system, that might have been the summit—task completed, success achieved. But when asked to lead two project teams to roast professional coffee to be sold to the public, Keller hit a false summit. At first, he stepped back entirely, giving his teammates full freedom; the work stalled and many beans and dollars were wasted. Then he swung to the other extreme, micromanaging every move until frustration grew on all sides.
With coaching, reflection, and the structures around him—flexible project time, authentic community work, the chance to share progress publicly—Keller began to understand that leadership was less about control and more about balancing freedom with responsibility. He learned to set goals, support peers, and make space for mistakes. By the end of eighth grade, Keller wasn’t just finishing work, he was guiding others toward the next summit, equipped with skills he wouldn’t have developed without trust, support, and an authentic challenge.
Seeing the Climb Through a Parent’s Eyes
As a parent of young children, I already see the beginnings of false summits. My five-year-old daughter thinks she’s mastered something—riding her bike or number recognition—only to discover she hasn’t quite yet. The frustration is real. But so is the joy when she realizes she can try again and go further.
As she approaches the middle years, I want her schools to embrace those moments, not shield her from them. I want educators who see the switchbacks and false summits not as problems, but as essential parts of the climb. Because if she learns to see mistakes as lessons and setbacks as practice, she won’t just survive middle school—she’ll emerge with a clearer sense of who she is and the confidence to keep climbing, no matter what mountain comes next.
A Call to Reimagine Middle School
What if we stopped asking: How do we get kids ready for high school?
What if instead we asked: How do we help kids trust themselves enough to keep climbing, even when the summit isn’t in sight?
Middle school is not a waiting room. It is the most important stretch of the trail. And when we design for trust—when we allow learners to experience freedom, setbacks, and recoveries—they emerge with resilience, confidence, and purpose.
On the other hand, when adults try to carry learners up the mountain, they may move quickly in the short term, but learners miss the chance to build the strength and confidence they’ll need for the climbs ahead. And when we keep them on too tight a rope—controlled at every turn, with little room to explore—we squander the most opportune moment for discovery: the middle years, when identity and resilience are taking shape.
The real opportunity of middle school is not to get learners through, but to let them climb.
The summit will come in time. But it’s the switchbacks and false summits along the way that prepare learners to get there. Our challenge as adults is to trust middle schoolers enough to let them climb—and to walk alongside them as they do.
Brian Hyosaka is the founder of Switchback Strategies, supporting middle school families better understand adolescence and find success in these critical years, and helping schools bring learner-centered ideas to practice. He previously served as Senior Director of Programs and Head of School at Embark Education, where he helped transform a learner-centered middle school into a nationally recognized model of innovation. He has also taught in dual language schools in Denver and Guatemala, and served as a public Montessori school leader in Denver Public Schools. Brian lives in Denver with his family, is an avid biker, poor dad joker, and still believes middle school can be magical!