LOS OLIVOS, Calif.: Every parent eventually faces the same question: Will my child be ready to navigate the world without me? At Midland School, a nature based college-preparatory boarding school in the hills above Los Olivos, students build readiness gradually, by earning real responsibility and working through problems that do not come with immediate answers.
For seniors Amelie and Michael, newly appointed as Midland’s head prefects, that preparation is taking shape in two very different futures. Amelie plans to defer college for a year to attempt a mostly solo thru-hike of the 2,650-mile Pacific Crest Trail. Michael plans to enlist in the Army and pursue a path toward becoming a combat medic.
As head prefects, Amelie and Michael hold Midland’s highest student leadership role, a responsibility both see as the result of years spent earning trust. “You’re building up a trust and a reputation, and they’re not going to give you a role of leadership unless they trust you,” Amelie said. Michael’s path included becoming a job head in Midland’s Jobs Program, where every student contributes to the daily work of running the school, and a Steward, one of Midland’s trained student outdoor leaders.
Those experiences taught him that leadership does not depend on having every answer. “No one knows everything,” he said. “I like to be approachable.”
That comfort with uncertainty has taken on new importance for families raising teenagers in the age of artificial intelligence. Students now have tools that can generate an essay or propose a solution in seconds. Midland asks them to keep developing the human capacities that have to be practiced in real life.
“You’re not going to get an answer in life, especially outside,” Michael said. “We’ve got to critically think, we’ve got to put our heads together.” Amelie sees resilience as central to that process. “AI is a regurgitation machine. It is not a resilient machine,” she said. “Resilience is what allows for growth and allows for new things to be created, rather than old things to be resurfaced.”
At Midland, students practice that resilience through lived experience. Michael points to a 100-mile backpacking trip as one of his most formative experiences. Amelie describes years of Hardluck trips (wilderness overnights led by students on the Midland property) as teaching her how “to be in a really hard place and bounce back, and bounce back as many times as you need to.”
The same principle applies in daily life, where students see quickly when work is left unfinished or other people are depending on them. The goal is to build
the judgment, self-reliance, and sense of responsibility they will need long after graduation.
Two recent alumni offer a glimpse of what that kind of future-readiness can look like. Mark Gong ’17 went from Midland to Parsons School of Design, founded the womenswear label Markgong, and was named to Forbes 30 Under 30 Asia 2025 in The Arts. Maggie Tang ’18 carried an interest in food and hospitality from Midland’s kitchen to the Wharton School at the University of Pennsylvania, then founded Magic, an AI company building technology for hospitality, earning a place on Forbes 30 Under 30 2026 in Food & Drink. Tang’s work adds another dimension to the conversation about AI: powerful technology still depends on people with the curiosity and judgment to imagine what it should do in the world.
Amelie and Michael are just beginning to find their own paths. Amelie is applying to colleges including Brown, Dartmouth, and UC Santa Cruz, and plans to defer enrollment for her Pacific Crest Trail attempt. “Midland has kind of shown me that there’s reality in doing hard things, especially as a young person,” she said. “That will set me up for a level of challenge that leads to growth rather than failure.”
Michael hopes to become a combat medic because, he said, “I want to help people who don’t have adequate healthcare.” For families wondering how to prepare a teenager for a future none of us can fully predict, their stories offer one answer: give young people meaningful responsibility, real trust, and enough challenge to discover all that they are capable of.
Midland School is located at 5100 Figueroa Mountain Rd., Los Olivos, CA. For more information or to schedule a visit, contact admissions at admissions@midland-school.org or (805) 688-5114.
