Starting. Again. On Purpose. What a Compressed Learning Community Taught Me About Launching a School Year

Those of us who have helped our schools launch new years wrestle with the question of how to design early days — faculty meetings, student orientations, welcoming activities — without defaulting to "wash/rinse/repeat" cycles we've run before. The familiar routine offers comfort but risks the chance to engage everyone's vulnerable, open learning stance — theirs and ours.

Student leaders at Putney carry primary responsibility for welcoming new students into the community. I used to coach them to be alert to a specific risk: using a new student's vulnerability to assuage their own nerves about returning to school in a new grade, with new responsibilities. No one intends to manage their own anxiety by aggravating someone else's. But like our students, we all approach a new year with some measure of excitement and trepidation, and it is entirely normal to manage that uncertainty by reaching for what is certain and familiar — including the parts of our work and our rhythms that have come to feel routine. The trouble is that the people who most need us awake and present for their needs — the new student, the new family, the new colleague — are the ones who pay the price when we unintentionally prioritize our own return instead of designing theirs.

This summer I led EXPLO's middle school summer program — a residential and day program for 530 students on the Wellesley College campus, run as two consecutive two-week sessions. Most students attend one session; some are returning alumni; and a small number stay for the full four weeks. The staff work the whole run — arriving ahead of the students and remaining through both sessions. The adults build a community from scratch, then do it again immediately, for a mostly new set of students, with no time to rest on what they'd just built and few returning students to carry the culture forward. I recognized the shape of this from CITYterm, the semester program my wife Kate directed and where I taught from 1998 to 2003 — a longer cycle, but the same underlying logic: a community that forms, does its work, and dissolves, with continuity carried almost entirely by the adults who stay across cycles.

Where does the real work of continuity live in a program like EXPLO's? A two-week session doesn't have time to tap or build institutional memory or much tradition. Students learn it from whatever the adults, returning alums, and a small handful of four-week students, choose to share. Because many of our frontline staff are college students themselves — gifted, committed, and also new to their role as educators — the work of holding and communicating the culture falls to the managers and administrators they report to. It's a parallel process: those staff need to hear it clearly from their supervisors in order to convey it effectively to their own students.

A program like EXPLO doesn't get the option of coasting. It cannot lean on the comfort of the familiar, because its structure doesn't accumulate familiarity. Renewal has to happen for every two-week session to launch. Naming the values, translating them into clear behavioral expectations — that scaffolding matters at every developmental stage, for a 25-year-old advisor as much as for a twelve-year-old student.

This summer I watched a small version of that truth play out on a residential floor. Two advisors, fatigued by a difficult few days, had stopped holding a line that seemed almost too minor to name: that students needed to be in their rooms at 10pm check-in. It wasn't defiance in any dramatic sense — a kid brushing his teeth a few minutes past the cutoff, another hoping to reach the vending machine, redirection met with a shrug. But the boundary didn't hold. Within days, the same floor that couldn't manage "be in your room by 10:00" couldn't manage much else either. The advisors, by their own account, no longer felt they could reasonably take their group off-site for an evening in town. Nobody had drawn a line connecting a missed check-in to a lost excursion, but the line was there. Once students learn an adult's boundary is negotiable in one place, they test whether it's negotiable elsewhere and the adults who let the small boundary slide don't notice they've also signaled something about the big ones.

This logic isn't confined to summer programs, and boarding school colleagues will recognize a form of this in, of all places, grade inflation. When a "B" means "solid, unremarkable work" in October and means "turned things in" by February, it isn't a grading-policy drift; it's the same unheld boundary. It’s the 10pm check-in, wearing a gradebook instead of a curfew. The people reading the signal include families and college counselors. The faculty member down the hall, deciding whether to hold their own line next semester, reads it too. I've discussed with a colleague their wrestling match about softening a rubric rather than having another hard conversation with a family.

As a Head, I sat with a teacher and parent (who was a board member) and backed the teacher's response to the child's misbehavior under real pressure and watched what that decision taught the rest of the faculty about whether standards were real. These conversations were not about grades or our affection for or bias toward a student. Both were about whether the adults meant what they'd said — the same question a floor answers, without anyone asking it out loud, once it learns that "lights out" doesn't quite mean lights out.

Which brings me back to those student leaders at Putney. The risk I used to coach them to watch for in themselves was the unconscious process by which they managed their own fear of the new year by letting incoming students hold all the anxiety instead — a natural way of convincing ourselves we're strong by reinforcing someone else's weakness. A boundary is one of the first things a new student, a new colleague, a new family learns to read, long before they've learned anything else about a place. It's a school's most honest form of self-introduction, repeated daily to people who are still deciding whether to believe what the adults here say. Which is exactly why it can't be inherited from June, or from last September, or from a decade of doing it this way.

A boundary held out of habit is already halfway to disappearing. It has to be built again, out loud, by people who see its role in the renewal — literally, the re-starting — of community. Community will always be a function of returners and new members, so "making it new again" is inevitable. The question is how we are intentional about it.

Most schools do have a choice. A school with forty years of history has earned the right to assume its culture is understood and that is precisely the risk. Culture that feels self-evident to those of us who've lived inside it for years is, to everyone arriving this September, an open question. Every fall, a meaningful fraction of any school community — new students, new families, new faculty, sometimes a new head — is encountering the place for the first time. For them, September isn't a resumption. It's a new beginning.

That's the invitation I'd offer colleagues heading into the coming weeks, and the question I'd offer trustees who want to understand their Head's job well. Don't ask only whether the opening days were warm, well-organized, or true to form. Ask whether they were built this year — deliberately, out loud, with the people who most need the welcome to be visible — or whether they were simply run again, because running them again is what steadies the adults doing the running.

The comfort we reach for in the first days of school is real, human, and not free. Someone is usually paying for it. The schools that do this well are the ones whose leaders remember, every single year, that they are not resuming something. They are founding it, again, on purpose.

John Barrengos is Senior Consultant at EXPLO Elevate and Head of the EXPLO Middle School Program. He is a former head of school.