Twenty Years After High School, What Endures?

In late September 2026, I returned to Appian Way for a gathering of alumni from Harvard's Doctor of Education Leadership (Ed.L.D.) Program. At one point, we broke into small groups and were invited to share a particularly fond memory from our time at HGSE.

People remembered trips they had taken together. Sitting around tables wrestling with real problems. Supporting one another through difficult moments. Holding someone's baby so a classmate could participate. Visiting schools and communities and trying to understand how systems actually worked. They remembered being challenged, cared for, heard.

What also struck me was what nobody mentioned. Nobody said, "I remember a course reading packet that changed my life." Nobody named a particular assignment or recalled the grade they received in a course.

We talked about relationships, experiences, and the things we had the opportunity to do together. As I listened, I couldn't help thinking: I've just spent the past year hearing essentially the same thing from another group of former students, only this time, they were my students, and we were looking back across 20 years.

In 2002, almost 10 years before I came to Harvard, I became an adviser (teacher) at The Met, a Big Picture Learning public high school in Providence, Rhode Island. I worked closely with the same 15 students from ninth through 12th grade, “looping” with them for all four years of high school. 

On one of their first days of ninth grade, I asked them to imagine themselves many years after graduation. What would success look like?

Their answers weren’t particularly complicated. They wanted to be happy and healthy. They wanted to spend their time doing things they loved. They wanted meaningful work and enough money to support themselves. And they wanted to love and be loved by family, friends, and community.

Thirteen years later, while enrolled in an HGSE J-term course, I drafted an essay called “Ten Years After, Before You Begin.” I was wrestling with a question that has followed me throughout my career: How (and when?) should we measure whether an education has actually succeeded?

Schools and state accountability systems have become extraordinarily good at measuring things that happen while young people are in school or shortly thereafter: attendance, standardized test scores, graduation rates, college enrollment. Those things matter.

But they are limited in temporal scope; they aren't the same as a life. As one of my doctoral committee members, Clayton Christensen, so provocatively posed in a Harvard Business Review essay, “How Will You Measure Your Life?”

So last year, as the 20th anniversary of my students' graduation approached, I decided to go back to check on whether their own defined measures of success had come to fruition.

This time, I had help.

Samantha Broun, Ed.M.’96, an audio journalist, former Nieman fellow, and fellow HGSE alum, joined me in reconnecting with the students. Together we created The Advisory: Class of 2006, a five-part audio documentary built around a deceptively simple question: Twenty years later, what difference did your high school experiences actually make? 

We arranged two-hour individual one-on-one conversations between me and each student. We met back in the same advisory classroom where we had spent time together 20-plus years before.

And we listened.

We heard about careers and marriages and children. We heard about losses and second chances. We heard people reconsider experiences that looked one way at 16 and quite another at 38. And again and again, we heard about relationships: advisers, mentors, internships, families, peers, and adults who knew them well enough to see possibilities they sometimes couldn’t yet see themselves.

Not everything worked out as they had planned. Not every memory was positive. And 20 years of adult life certainly can’t be reduced to what happened during four years of high school, nor where they seemed headed immediately afterwards.

That's precisely the point.

Education is a long-haul endeavor, but we mostly measure it in short intervals. Sitting back at Harvard with my Ed.L.D. peers recently, I was reminded that this isn’t only true for adolescents. Asked what endured from an intensive graduate program, we too reached first for the human experiences: the people who challenged us, the experiences that stretched us, the relationships that continued long after commencement.

It makes me wonder what would happen if more schools did something deceptively simple: call their alumni back. Not primarily to raise money. Not to collect a testimonial. Not to prove that the institution “worked.” To ask them what mattered. And what didn’t. And what they still carry. And what they wish had been different.

And then listen.

More than two decades after I first met my advisory, I am less certain than ever that educators can know, at graduation, exactly what they’ve accomplished.

But I am more convinced than ever that we should keep asking questions, keep preserving relationships, and keep expecting that the good work we’ve done as educators should resonate well beyond graduation. Our aperture needs to pull back from short-term “outcomes,” and we need to more longitudinally inquire as to what alumni are in the process of “becoming.”