Last we spoke with Jeneen DiBenedetto Graham, it was summer 2020 and as the head of the upper school at St. Margaret's Episcopal School in Southern California, she was still in the thick of the complexities of Covid-19. In the more than four years since, her ability to handle the unexpected has continued to be tested as she has faced fears, uncertainty, and a chaning future. Find out how keeping service and growth at the center can keep things on track.
Last we spoke with Jeneen DiBenedetto Graham, it was summer 2020 and as the head of the upper school at St. Margaret’s Episcopal School in Southern California, she was still in the thick of the complexities of covid and retooling just about everything in anticipation of bringing students back in the fall. In the more than four years since, her ability to handle the unexpected has continued to be tested as she has faced fears, uncertainty, and a changing future.
In this episode, find out from Jeneen how keeping service and growth at the center can keep things on track…on Roads Taken Revisited with Leslie Jennings Rowley.
About This Episode’s Guest
That was Jeneen DiBenedetto Graham who is currently head of school at St. Margaret's Episcopal School in San Juan Capistrano, California. She previously was Upper School Principal from 2018 to 2023 and Academic Dean, 2012 to 2018, in addition to teaching AP psychology and serving on the Board of Trustees as a parent of two graduates of the school.
For Jeneen’s first appearance on Roads Taken, listen to Independent Education and her special bonus episode about closing her school for covid lockdown and moving to online learning.
Jeneen Graham: You know, St. Margaret's is a whole child school. That's what drew me to it. The mission is about hearts and minds, and that's really what I wanted. I wanted well educated children for my own children, but I also wanted them to be good people. And so, as I think about the human traits, character skills that we're very actively building, that's really important for the future.
Leslie Jennings Rowley: Last we spoke with Jeneen DiBenedetto Graham, it was summer 2020, and as the head of the upper school at St. Margaret's Episcopal School in Southern California, she was still in the thick of the complexities of COVID and retooling just about everything in anticipation of bringing students back in the fall. In the more than four years since, her ability to handle the unexpected has continued to be tested as she's faced fears, uncertainty, and a changing future. Find out how keeping service and growth at the center can keep things on track. On today's Roads Taken Revisited with me, Leslie Jennings Rowley.
Today I'm here on a very special Roads Taken Revisited with my friend Jeneen DiBenedetto Graham. And we are going to talk about taking the helm in all sorts of ways and what the future holds when you don't know what it holds. So Jeneen, thanks so much for being here.
JG: Of course. I'm so happy to see you again. So much has happened since we were last doing this.
LJR: So much. Because you were one of my first guests.
JG: I know.
LJR: Really one of the early ones. And it was right smack in when we were stuck in our houses and everything. And you even walked us through what it felt like to be an educator at that time, which was not any position that any of us wanted to be in, probably yourself included. But since then so much has happened. So I won't leave you to it to give us all of it, but let's do a first little bit of, if you can even think back that far on, if you want to…You had a position that made you deal with all of protocol development and then rolling it right out after we spoke with you in summer of 2020. You had a 19-year-old.
JG: Yes, I did. Yep. I had a 19-year-old who had come back from Colby College when they closed middle of March and was taking classes online in our house. And then I had, when I spoke to you, Reid had just finished his sophomore year.
LJR: So not only were you dealing with a school population, you were a mom of that school population. So talk us through, where were you and what was happening?
JG: Gosh, it's amazing what has occurred in that span of time when I think about it truly. I spoke to you in July 2020, and we were in the process of really reconfiguring our entire school. To bring back all 1,234 students with the recognition that they needed six feet of separation between them. And that’s a really significant feat for a school. But it was remarkable in Southern California because we could use outdoor space. So we were in the process of getting tents and also heaters, because we knew that it wasn't going to be long before we were going to need heat. And everybody in California was, you know, going to do education outside. So we knew that there was going to be a run on heaters. So we were, I mean, the things that we had to consider in that space, right down to how we’re going to use the microwave and the coffee maker in the faculty lounge, right? Because we, at the time, were terrified about any sort of disease transmission by touch, because we didn't really understand what was happening. We didn't know what was happening with the disease. We were lucky in Orange County, California, because we actually did have a window where we were able to open school. Many schools and metro areas in California stayed closed pretty much until the spring, but we brought students back. Initially, it was pre K through six. We brought them back. And I think it was either late August or early September. And then the other grades, we brought them back in October and we were ready and we, we were able to keep them six feet apart, but there was so much that was so challenging if we had anybody who had COVID we had to track them. So as an upper school principal, think back to your high school years..you know that you would sit in class, however many classes you had in a day, five or six in a day and every class was a different assortment of kids. So we had to contact trace everybody basically. And so we were constantly sending out emails. You've been exposed. You need to stay out of school. I mean, it was, it was true for all of us. It was triage. I mean, you know, obviously the medical system had the worst crisis and they were really having to deal with very sick people. So I can't compare what they were dealing with to what schools were dealing with. But schools were, we were really struggling. It was incredibly hard.
And, you know, working with adolescents. Adolescents need to be with each other. That is their developmental stage. That's what they need the most is social contact. So watching brand new ninth graders come in in October with masks, couldn't see their faces, and they had to sit six feet apart in every context. It's just really hard to make friends that way. So it was, it was pretty painful for me. You know, it certainly brought me back to my years of being new at school and how hard it was. In that context, when you could sit down at a table and say like, you know, I'm Jeneen. They couldn't actually find their way.
It was really, really challenging. I don't know how many ways I can say that. And it didn't stop. I think many of us were like, Oh, it will get better come January. It'll get better. No, it just kept getting worse. And so that whole year was incredibly challenging. We were so exhausted by the end of the year. So exhausted.
I remember that summer just feeling like I didn't even want to go anywhere. I just wanted to just like sleep. It was so exhausting and just really sad and scary, right? All of the above. And then the next year, I think we were really excited that it was going to be so much better, but we were still contact tracing. We were still, you know, COVID was still very much a reality for us, as it was, I think for every school. And then teachers were leaving. We were really, really lucky. Our teachers did not leave. We didn't go through what a lot of schools went through, which was amazing. I think a testament to people's commitment to the school where I am. I'm so grateful for them. I, it's still, I think about what we went through together, trauma bonds for sure.
So yeah, so that was a lot. And then the head of school at the time, let us know that he was going to be leaving St. Margaret's. And so my first reaction was, I think I put my face in my hands and just cried like a child. And then when I got a hold of myself—because I, you know love this man and he's such a good…he was such a wonderful leader—he looked at me and he said and I need you to apply. And I said, I'm so exhausted. I don't know if I can consider that. And he said, okay, well, I'll let you think about it. And then the next week he said, just checking in, just want to make sure that you're applying. And I said, I love my job. And I don't know if I have I don't know if I'm ready yet to take that step. And he said, why? And I said, mainly because I'm still trying to process everything that's happened with COVID. And I don't want to leave this division and these kids and these families. And he said, I don't usually say this, but you're going to regret this decision if you don't apply for this job. This position, this position would be wonderful for you and you are more than ready.
LJR: And I think I talked to you then
JG: Yeah, perhaps.
LJR: …right after that set of conversations when you were still going, what do I do with that?
JG: Yeah.
LJR: Cause I think you really did feel I need to stay and not only process, but you know, we've come so far.
JG: Yeah.
LJR: Let me see this through.
JG: Yes. Yeah.
LJR: But I could also tell he had gotten under your skin. And he probably was saying things that you had already heard from yourself.
JG: Well, I think the, you know, for me, what I've always wanted to do is impact the children in my care, right? That's why I went into education. And so this job would potentially give me the ability to impact a larger number of students and more directly. So that really was what I was wrestling with. I really did want that. It just felt like the wrong timing, just because of what we had already done…all endured together and how I felt nervous to leave this really tight knit community who had been through a lot together. Because, of course, if I'm leaving the upper school and running the entire school, I have less direct day to day interaction with those students and those teachers and, you know, it was going to cause me to have to stop teaching. There are lots of pieces to it that I thought, am I ready for this emotionally? So I applied and ultimately got the job. So now I'm year two in as head of school and it's been really really…it's been amazing. It's actually remarkable to think that since I spoke to you all that has happened: That we made it through Covid…
LJR: That you graduated your second son.
JG: I graduated my second son. Yes. So now we have an empty nest. We have a 16 year old dog that you can probably hear rattling around the house.
LJR: Wally.
JG: Wally is a faithful friend, a very faithful friend. And now it's my second year as head of school. The house that I'm in is owned by the school. So this is the head of school's house. So we had to move which was amazing because this is a really beautiful place to be, and it has so much history and tradition. So it's really exciting to be here and I love it. And I can have direct interaction with more students, more families. It is what I thought it would be. I do miss teaching. I think I'll always miss teaching, having those really unique relationships with, you know, less than 20 students a year. It's pretty amazing. Teaching just one class is what I, what I did, but I really, I think I'm, I'm so glad I made the decision and I definitely feel like I'm in the right place.
LJR: Yeah. And I mean, it is early in this tenure of this role, but I can see a couple years down the line, one little class?
JG: Yeah. It's funny actually. So, and this was, you know, I think, how we reconnected even—me telling you that we, I had just brought on two Dartmouth 96s into my professional community. So one of them is leading our experiential ed program. And that's where I might be able to lean in because that program will not be..It's not like it meets every G block. It will have, you know, maybe eight sessions during the year. And then there'll be like a week-long end of year program where, you know, you go somewhere or do something that's more intensive and immersive, if you will.
LJR: So tell our audience who that person is.
JG: It's Dr. Ryan Carey.
LJR: Shouting out to Dr. Ryan Carey. You are coming on Roads Taken.
JG: Yes. Yes, he has to come because it's so fun and it's been so fun. So we didn't know each other at Dartmouth, but we knew so many people in common. So that's been really fun. And then we, I also hired Dr. Maryam Kia Keating and she's our director of counseling and she's also super awesome. So the three of us, when we get together, it's totally dangerous because we have so much in common just having that Dartmouth experience together together. We were there all four years together, right? Yeah, it's amazing It's really fun.
LJR: Okay, so there are things you've talked about missing and there are things that you talked about loving on a bigger scale. What are the things that you were surprised about?
JG: I think the thing that, where the surprise...There are a few surprises. I was so close to the previous head of school and I was so connected to his work. And also in that last year when he was in his last year and I was moving into the role. He gave me so much ownership. So I had like a, I had a year where we were together and he was basically handing me the role. So there weren’t a ton of big surprises. I think the thing that was making me the most nervous about the job coming in was that we were in the midst of a really sizable capital campaign. We had started in 2019 and then, you know, basically, yeah, put it on ice for a little while. But it was going to be my job to warm it back up and not just warm it up, but, you know…
LJR: Take it to the finish line.
JG: …make it come to life really. Exactly. And also just, you know, there was a whole group of parents that hadn't even heard about this project, right? So I really had to bring it to life. And that was exciting. I was, I'm really excited about the building we're about to break ground on. So all of that was exciting to me, but I had not been directly involved in leading advancement work. That was a new, that was new territory for me. And so I guess what's surprising to me is that I actually really enjoy the work because it's really, you know, at its core, it's about relationship building. It's about, you know, talking to families who love the school and want to help the school get to, you know, that next step in its future and they can be really helpful. So in many ways, they're as excited and jazzed as I am when there's, you know, a significant contribution that's going towards the work that we're doing. So it's really positive. I guess that's the word: that it's really positive work and it's not how I had imagined it. Yeah. So that is a surprise.
LJR: Yeah. And are there things that you see in this seat that you are excited to kind of push on an educational philosophy level?
JG: Yeah, so much. I mean, that's really the, that's the exciting part of a job like this one. And you know, I am, I love educational theory. I love, I mean, you know, the books that are on my nightstand are, they're all,
LJR: Page turners.
JG: They're not. I mean, you know, truth be told, I'm reading this book right now called 10 to 25, the science of motivating,
LR: Ah, that’s on my bedside. The science of motivating young people. David Yeager was just here the other day.
JG: Okay. I love this book. I love it.
LJR: Yeah.
JG: And to me, it's a total page turner. And I have been talking about how great it is. And I can see, like, people come back to me and be like, I started that book. And I don't feel like maybe they're in the same page that I am or something. I recognize that research is my jam, right? I just love it. It's so exciting to me. And I think about how to implement it. I mean, that's really impactful to think about how we best motivate that, you know, high expectations, high support. I talk about that all the time, but to have the research to support it, that's been such a gift. Oh my gosh. And it's actually, it's beyond 25. I mean...
LJR: That's right.
JG: It's like, that's how we motivate everybody. They want to have that high support, that high expectation. So anyway, I love, I love the ability to think about what's happening now, what research is available and how can I move the school forward?
Another area of great interest for me is what AI is doing to education or what it'll do to society. People who are able to do incredible work in the world moving forward are those people who can connect the dots, right? It's not enough to know a subject really well. It's one's ability to connect all of those dots. And so I think about that, whether those dots are interpersonal dots, whether they're, you know, content dots, we as humans, that is our sort of superpower to bring all this together. And if we can help kids understand what that looks like, that's why experiential education, at least in the way Dr. Ryan Carey is going to be implementing it at St. Margaret's is so exciting to me because it's really multidisciplinary. And so I It's thinking about areas of interest that kids might not have even thought go together, right? Like he and the upper school principal did a class called Coastal Connections where they're looking at the history of surfing in Orange County. They're looking at the science of surfing.
LJR: Tidal regions.
JG: Yeah, exactly. All of that. And then they're actually thinking about the physics of the board and how does it work? Like, how do you actually create a surfboard? And why are those angles really important? And why is that material really important? So material science. That's so fascinating to me to think that you could say to a kid, do you want to better understand surf culture and surfing in Southern California? And do you want to build your own board? Like, yeah, I want to do that. But I think the learning there is because learning is joyful, and it's meaningful, and it's relevant, right? So how do we get kids to understand that they can connect those dots and that, yes, that is the future.
LJR: And it's not like hiding the broccoli in the brownies.
JG: No. No.
LJR: Like you're saying you have to know physics, and you have to know geometry or whatever.
JG: Exactly. And, and in fact, you want to know physics.
LJR: Right.
JG: Because it's actually going to help you …
LJR: Do these cool things.
JG: Yes. Now you're going to understand the beauty of physics and maybe, you know, we go even farther and, you know, maybe you're going to need to know calculus as well. Like, I don't know. I don't know where, you know, so that's the thing that I love the most about this is that there are going to be questions that students have that the teachers are not going to be able to answer. And so what's going to happen is they're going to answer them together. That's powerful stuff, right? That makes a kid feel like, oh my gosh, I'm part of this.
LJR: And I think where you were starting with this is that AI gives us some semblance of tools of finding those connections and patterns. But yet all of the research right now is saying it can't do that alone.
JG: No.
LJR: It is the human factor.
JG: Yeah, and and what does it mean to be human? And what you know, so I think I think a lot about you know, St. Margaret’s is a whole child school That's what drew me to it. The mission is about hearts and minds and that's really what I wanted I wanted well educated children for my own children, but I also wanted them to be good people And so, as I think about the human traits, character skills that we're very actively building at St. Margaret's, that's really important for the future. Really important. I'm so proud of our kids when I see them engaging with adults, looking them in the eyes, asking really interesting questions, being polite and respectful. Think about all the skills, the very human skills that are going to be prized in this age of AI, and that's a big part of it too. So I, I really get excited when I think about the future. I know it can also be scary, but I don't think fear enables us to be really productive and innovative. So I try and stay in excited.
LJR: Yeah. And you're the one that can speak from experience because while you can say, Oh, I don't think I'm going to put my name in the hat because I like this community. There was probably some fear in that.
JG: Oh yeah.
LJNR: And you needed to get over it. [JG: Yep.] And say, I can't grow.
JG: Yep. I'm jumping in. Yep. Exactly. This is how I grow. Even though I felt, at the time, so depleted. But there was more. There was more in me, more in me than I even knew was there, right.
LJR: That's exciting to know.
JG: Yeah. I think so. I think so. Yeah.
LJR: Of course it is. What's the downside of knowing you have more to give? You just, maybe you need the vacation.
JG: I know. I just hope I don't call you and say, Leslie, so sad. Actually last year I got mono, which was so funny. My whole life, I'm going to be 51. I've never had mono before. But I was, you know, that was an indication of being just totally and completely depleted and not being able to kick it for several weeks.
LJR: Well, you've kicked a lot. Not only have you kicked things that were really hard for a long time, but now you're reaping the benefits of being on the other side of fear and growing and helping other people grow. This sounds like a great place for you now.
JG: Yeah, no, I'm loving it. I really am. It's been awesome. And it also has been nice that my kids are good and they're off in their lives. This job, it's days and nights, so it would be really hard if I was trying to do anything other than lead the school. So it's the timing in my life is actually perfect as it turns out.
LJR: Excellent. Well, thank you so much for catching us up and hopefully it won't be that long before we catch up again, but that's a lot to pack into that four years. So let, maybe the next four years won't be this…
JG: I know. Could we, could we just, yeah, have it be less eventful? That would be good. Exactly.
LJR: Yeah. Well, it's always a pleasure. Jeneen, thank you so much.
JG: Thank you, Leslie. Good to see you.
LJR: That was Jeneen DiBenedetto Graham, who is currently head of school at St. Margaret's Episcopal School in San Juan Capistrano, California. She previously was upper school principal from 2018 to 2023 and academic dean 2012 to 2018, in addition to teaching AP Psychology and serving on the Board of Trustees as a parent of two graduates of the school.
We're so pleased to be able to check back in on our guests when their roads have continued to take them fun places. Check out another example of that next week. And of course, don't forget, you can access our full archive of episodes, show notes, and transcripts at roadstakenshow.com. There's always something great to find or revisit there with my guests and me, Leslie Jennings Rowley, on Roads Taken.