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MAILING : P.O. Box 8, Los Olivos, CA 93441
Scott shares how his background and experience have shaped his approach to teaching, leadership, and community.
We are thrilled to welcome Scott Crago as Midland’s next Dean of Academics!

Scott brings a depth of experience in education that spans field research, classroom teaching, and school leadership, including work in Chile, where he earned his doctorate. He has led experiential programs, guided schools through meaningful change, and built communities where students feel seen, challenged, and supported. Throughout his career, his work has centered on helping young people find their place and their voice. We recently sat down with Scott to learn more about his path to Midland and the values that shape his work.
I’ve always been drawn to learning through experience. Early on, that showed up in field research and time spent outdoors, which taught me how to adapt, problem-solve, and stay present in what’s happening around me. When I moved into teaching, I realized those same skills apply in the classroom.
That same instinct shows up in how I follow curiosity, whether that’s through science, teaching, or even music.
Over time, I’ve come to believe that the process of learning matters more than the outcome. Students need space to try things, make mistakes, and figure things out. That’s where the real growth happens.
That really comes from my own experience as a student.
There was a moment in high school when I thought I was going to be asked to leave. Instead, I had a teacher tell me, “We need you here. You’re an important part of this community. Now go make it right.”
That moment stayed with me. It changed how I saw myself, and it’s something I carry into my work with students. I want them to know they matter and that they have something to contribute.
It starts with trust. You can’t just tell students to take risks. You have to create an environment where they feel supported enough to try something new, even if they might not get it right the first time.
Some of the most important learning happens when things don’t go as planned. When students feel a little uncertain, that’s often when they’re doing their best thinking.
I spent time teaching in Albuquerque Public Schools, at a school where many students weren’t always experiencing that sense of belonging elsewhere. I loved that work.
There’s something powerful about helping students feel seen, especially when they might not feel that way in other parts of their lives. When students feel like they belong, everything else becomes more possible.

During Covid, I started a mountain biking program at my school. It began as a small group, but it quickly became something more.
One student showed up on a Huffy bike that barely worked and mostly stayed on the edges at first. Over time, the group pulled him in. Students came in with all different levels of experience, but what formed was a group that rode together, learned from one another, and became close-knit.
They started asking where he was if he missed practice, and you could see how much that meant to him. That sense of belonging was real.
That student went on to earn a college scholarship in mountain biking.
For me, that experience captures what education can be at its best. It’s not just about building skills. It’s about creating a space where students feel like they belong, and where they can discover something in themselves they didn’t see before.
We knew we weren’t going to make a move unless the values really aligned. You have to believe in what a school is offering.
Midland stood out right away. It’s a small, outdoor, experiential school with a strong sense of community, and that’s the kind of environment I really believe in.
What stood out even more was how authentic it felt. A lot of schools say the right things, but when you visit, it feels different. At Midland, what you see is actually what it is. That was incredibly compelling for us.
I’m excited to be fully part of the community. I don’t see my role as separate from everything else happening at the school. I want to be involved in teaching, trips, and the day-to-day life of the campus.
I’m also excited to work with colleagues in a collaborative way. I don’t think leadership is about having all the answers. It’s about listening, building trust, and working together.
More than anything, I want students to leave feeling like they belong and that they have a strong sense of who they are.
Education isn’t just about what you learn. It’s about how you see yourself and how you move through the world.
We’re really looking forward to becoming part of a community that values connection, learning, and time outdoors. That’s something that matters a lot to us.
We’re also excited for a bit of a reset, to focus on the things that matter most and to be part of a place that aligns so closely with our values.
And for the record, I still consider myself a music nerd and a lifelong fan of science fiction… a passion that once led to dressing up as Data from Star Trek at age ten. I also spent some time in a house band at a couple of dive bars in my twenties, which I’m quick to admit was not a very successful venture.

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