If you’ve been in independent school leadership for any length of time, you already know that character work is happening in your school. It’s embedded in your honor code, your advisory program, your service requirements, and the way your faculty show up for students at 10 p.m. on a Tuesday. The question isn’t whether we’re forming character. It’s whether we’re doing it on purpose, and whether the pieces we’ve built actually hold together.
In a recent episode of The Table, I had the opportunity to sit down with Ryan Olson, senior fellow at the Institute for Advanced Studies in Culture and research associate professor at the University of Virginia. Ryan has spent the last three years working directly with independent school heads to explore how character is formed in schools and, just as importantly, what gets in the way. As a co-editor of The Content of Their Character and the parent of three boarding school students, Ryan brings both the researcher’s rigor and the parent’s lived experience to this conversation. What emerged was a framework that I think every student life professional and school leader should be sitting with right now.
The Real Question Isn’t What We Teach. It’s Who Students Become.
Ryan opened our conversation by reframing what schools are actually doing. The dominant conversation about education, he noted, has tilted heavily toward cognition, achievement, and measurable outcomes. Those things matter. But they don’t come close to capturing the full scope of what schools are shaping. Schools form honesty, courage, judgment, self-command, and public responsibility whether we design for it or not.
The central question, as Ryan put it, is this: what kind of human does this school make it easier to become?
That’s a question I’d encourage every leadership team to bring to their next strategic planning session. It cuts through the noise.
The Data We Can’t Ignore
Before we get to frameworks, the context matters. Ryan walked through the well-being landscape our students are navigating, and the numbers are sobering. Roughly four in ten high school students report persistent sadness or hopelessness. Three in ten report poor mental health. Two in ten have seriously considered suicide. Only about three in five say they consistently get the social and emotional support they need.
Layer on the digital dimension. Forty-five percent of teens say they spend too much time on social media. Forty percent say it hurts their productivity or overwhelms them with drama. Nearly a third say they feel pressured to post for approval. And about a third of Gen Z students feel pressure to be perfect, rising to 40 percent among girls.
But Ryan was careful to note the other side of that data. When students feel engaged at school, when they have a sense of belonging, and when they believe what they’re doing matters, they are more than twice as likely to report thriving and to feel a sense of agency about their future. That’s the opening. That’s where our work lives.
Character in Five Words: No, Yes, Here I Am
One of the most useful frameworks Ryan shared comes from the sociologist Emile Durkheim, who defined character as having three properties: moral discipline, moral attachment, and moral autonomy.
- Moral discipline is the capacity to say no. No to impulses, no to shortcuts, no to cruelty, no to making comfort or status the highest good.
- Moral attachment is the capacity to say yes to something good beyond yourself. A community, a cause, the dignity of other people.
- Moral autonomy is the here I am of ownership. The movement from compliance to judgment, from following the rules because adults are watching to acting from an internalized standard.
Ryan calls this “character in five words”: no, yes, here I am.
For a dean of students, this trio is remarkably practical. Discipline asks whether a student can regulate themselves. Attachment asks whether they belong to something worth serving. Autonomy asks whether they’ve become capable of owning their own choices. It gives us a shared language that isn’t tied to any one tradition or discipline, which is a real asset in the pluralistic communities most of us are working within.
The Four Virtues: Why “Character” Needs More Vocabulary
Ryan also introduced a four-part model of virtue that I found genuinely clarifying:
- Moral character (honesty, integrity)
- Performance character (persistence, determination)
- Civic character (citizenship, loyalty, public responsibility)
- Intellectual character (curiosity, creativity, not just achievement)
Independent schools tend to excel at performance character. We’re very good at teaching students to grind. We’re often less intentional about civic and intellectual character, the latter of which is really about the love of learning rather than the pursuit of the grade.
And then there’s a fifth layer that Ryan called practical wisdom. This is what students need when virtues conflict. If a student sees a friend cheating and is asked about it, loyalty to the friend and commitment to honesty point in opposite directions. Practical wisdom is the capacity to navigate that tension. We often don’t give students the vocabulary or the mental models to do this well, and then we’re surprised when they freeze up.
The Honor vs. Excellence Tension Is Real, and Students Feel It
One of Ryan’s most candid observations came when we talked about the tension between character formation and the machinery of selective college admissions. In his research, he found that independent schools explicitly teach honor and integrity, yet many students still conclude that the school really cares about performance and college placement.
The issue isn’t a lack of good intentions. It’s fragmentation. Schools say one thing, and students walk away with something different.
Student life professionals often feel this first. It shows up in the anxiety culture, the over-programming, the strategic extracurriculars, and the subtle message that a student’s worth is proven through accumulation. Ryan’s point wasn’t that achievement and selective college placement don’t matter. They do. But when character becomes instrumental, when service becomes box-checking, and resilience becomes the ability to perform under pressure, we’ve lost the plot.
Character Is Sourced, Caught, Taught, and Sought
In The Content of Their Character, Ryan and his co-researchers identified five components of how character is actually formed in schools:
- Sourced in a tradition that provides moral grounding
- Caught through modeling and absorbed from what adults around students actually do
- Taught through explicit articulation, not necessarily in a lesson, but somewhere
- Sought through practice, where students try the skills and strengthen them
- Surrounded by a cultural context that either strengthens or undermines the work
That last one matters enormously. Our schools exist inside a broader culture, and that culture isn’t neutral. Part of our job is to understand what counter-moves we need to make so that what we’re building inside the school walls can survive what students encounter outside of them.
Why Student Life Is the Center of This Work
Ryan’s research has led him to a conclusion I want every head of school to hear: character is caught in the cracks and crevices of the school schedule. It’s caught in how adults correct students, whether peers include them, what happens after harm, what gets celebrated, and whether belonging is conditional on a certain kind of success.
Which means student life is central. As Ryan put it, student life leaders are the custodians of the school’s most formative spaces. Orientation. Conduct. Advising. Traditions. Residential life. Family partnerships. These aren’t the peripheral programs. They’re the places where character is actually formed.
This is the drum I’ve been beating for a long time, and it was affirming to hear a researcher of Ryan’s caliber say it plainly. If we want character formation to be real, we have to elevate the student life function and give those professionals the resources, the voice at the table, and the institutional authority to do the work.
Restorative Practices as Formation in Action
Ryan described restorative practices as one of the clearest examples of character formation at work, because restorative practice joins four things that character formation requires: truth-telling, accountability, repair, and reintegration.
Restorative work doesn’t excuse harm. It makes the moral meaning of harm clearer. It teaches students what repair requires, lets them practice it, keeps them engaged with the community throughout the process, and moves them from passive compliance to moral ownership.
Student life leaders sit precisely at the intersection of conduct and belonging, which is exactly where restorative practice lives. If your school is serious about character formation and hasn’t invested in restorative practices, I’d put that on this year’s short list.
Differentiating for Character the Way We Differentiate for Academics
One of the most forward-thinking points Ryan raised is that we’ve developed remarkably sophisticated approaches to differentiated academic instruction. We don’t expect all students to take the same courses or play the same sport. We recognize that students come in with different strengths, interests, and starting points.
But when it comes to character formation, we often run a one-size-fits-all program.
Drawing on the work of British sociologist Margaret Archer, Ryan noted that students come to us with very different internal conversations, what Archer called modes of reflexivity. Some students are critically evaluating whether what we’re teaching is worthwhile. Some are all-in and eager to be formed. Some are instrumentally focused on career outcomes. Each of those students needs to be engaged differently if character work is going to actually land. Our sophistication in thinking about human formation, Ryan argued, needs to catch up to our sophistication in thinking about academic instruction.
The Question That Predicts Thriving
Late in our conversation, Ryan shared something that has stayed with me. He recently spoke with Andreas Schleicher, who leads education work for the OECD and oversees the PISA assessment. When PISA surveys 15-year-olds, one of the questions that most strongly predicts achievement and overall thriving is this:
If you returned to your school three years after you graduated, would the teachers and staff be excited to see you?
Sit with that for a moment. That’s a question about belonging, about the quality of relationships, about whether students experienced themselves as seen and valued. And it correlates with the things we say we care most about, including academic achievement.
That’s the quiet argument for elevating student life as a strategic priority. Belonging is not soft. It’s predictive.
Where to Start: Diagnosis, Not Aspiration
For any head of school or student life leader reading this and wondering where to begin, Ryan’s advice was refreshingly practical. Start with diagnosis, not aspiration.
Ask the questions that actually surface what’s happening now:
- What do we explicitly teach about character and values?
- What are students actually doing, and what are they concluding about what we care about?
- Where does our system reward something other than what we say we value?
- Where are we misaligned?
Then pick one or two leverage points. Advisory. Honor processes. Family communication. Orientation. Discipline systems. Ryan’s cohort of independent school heads each chooses a single problem of practice to work on for a year, meets monthly to talk through what they’re seeing, and builds from there. That disciplined, integrated approach is how durable change happens.
The Hope, and the Work
Ryan closed with something worth holding onto: 95 percent of parents in his team’s survey work say they want their children to develop strong moral character, to be honest, dependable, capable of loving others, and willing to work hard. The aspiration is there. Independent schools have the assets to meet it: bought-in families, coherent adult cultures, strong traditions, close communities, and student life structures that can make formation tangible.
The work, as Ryan said, is correcting the fragmentation. It’s naming the pieces we already have, integrating rather than adding, and being honest about where our systems are rewarding something other than what we say we value.
If you’re a head of school, a division director, or a student life leader thinking about how to take this work seriously, I’d start by listening to the full conversation with Ryan. Then gather your team and ask the diagnosis questions together. The frameworks he offered, the five words, the four virtues, the five components, the nine practices, give us shared language to work with. And language is where integration starts.
To learn more about Ryan’s work, visit the Institute for Advanced Studies in Culture or explore the Character Compass assessment designed to help schools begin this diagnostic conversation.
Thanks, as always, for pulling up a chair at the table.
