There are people who walk into your life like sunlight streaming through a window. They don’t arrive with fanfare. I don’t even remember the moment I met Jeff Greenfield. He simply showed up in my life during Kay Merseth’s class at HGSE —Harvard Graduate School of Education – radiating this inexplicable warmth that makes everything feel lighter, brighter, more possible.

This is my very last walk of this series. Jeff is perfect for this moment. Some people are meant to bookend your story— Barb was there at the beginning to nudge me on and Jeff is there at the end to send me off to my next adventure. Together they remind me of all I have learned and all I have to give.
Jeff and I are teachers, school leaders, and occasional goofballs. We both started our educational career in middle school. Do you know middle schoolers? As Wendy Mogel said, “They are the best people on the planet. It is the period of their greatest anguish and ecstasy of life.” And they are good at it. They’re old enough to understand complexity but young enough to believe in magic. That’s this friend. When I’m with Jeff, it’s magic.
Jeff: I mean, you can play any role you want with this on. It’s great. Like secret service. Liberty moving, liberty moving. Do you follow?
Liz: Except their mics are on their wrist. Don’t you always see them?
Jeff: Yeah, they talk into their hand.
Liz: We could do that. You could be the first person who puts his mic on his wrist and has to-
Jeff: ..walk around like this for that for a while? Na
Liz: So this is it.
Jeff: Oh, are you getting sentimental?
Liz: I am a little sentimental. And I’ve been thinking about the fact that if I make a big deal that I chose you to be the last walk, does that offend 49 other people?
Jeff: I’ll keep it a secret.
Liz: Yeah, except I just said it on the mic.
Jeff: Well, only Luke will know.
Liz: I wanted to walk with you because every time I see you, you make my heart sing. I feel like a kid all over again when I see you. And I wouldn’t do all those silly things with just everybody.
Jeff: Is that because I just pull you down to my level of emotional maturity?
That of a middle schooler, no doubt.
Jeff: I didn’t have the right certification and no teaching experience, it was a bit of a risk for the school to hire me on as a middle school teacher. And they were worried about my expertise in subject area, which, frankly, so was I. I was like, now, what is that slide rule thing again?
Liz: You were hired as a math teacher?
Jeff: I was, which is a little frightening. But the thing that I always just love so much about that age is that they really become what you expect of them. So if you talk to them like the young adults they want to be, then you really get the best out of them. And if you don’t think they’re capable of much beyond what they are in that moment, then that’s what you’re going to get.
There is so much wisdom there. Every parent and teacher of a middle schooler should have to repeat those words as a mantra…daily. They really become what you expect of them.

Jeff: What I didn’t anticipate was how much education parents needed, which I should have. I mean, I knew I’d be working a lot with adults in my role as a middle school director, which I wanted to do. I love the idea of working with both kids and people who love kids. I didn’t want to teach the same thing all day, just to kids, but got really fired up about the idea of a teaming model and everybody pulling in the same direction, even if they have different ideas about what’s best for a child. But it’s parents … It’s not so much that they’re hard. I mean, everything is hard from time to time. The best stuff is always the hard stuff at some level. But it was more a matter of them just… It’s just funny, even the smartest, most common sense people, when it’s their kid involved, they just can’t… I mean, I’m sure the same is true for me. You just can’t see it the way sometimes your kid really needs you to. So setting up education for families and trying to stay ahead of the thing that they were going to fear next.
You see… I’m tempted to just let this entire walk be nothing but the raw audio from our walk. It is a natural conversation between two people who fit that category of “people who love kids.” But I have to highlight some of the good stuff. Reiterate it for emphasis. In school leadership, parents can be hard. This is true because they love their children so fiercely …and because they are afraid. Love and fear are not opposites—they’re partners. Jeff says it was his job to “stay ahead of the thing that they were going to fear next.” What brilliance in that simple statement. Instead of waiting for parents to bring their fears to him wrapped in anger or accusation, he anticipated their worries and addressed them proactively. He understood that fear from a parent’s perspective. As parents, we send our most precious cargo into these buildings every day and trust strangers to care for them, teach them, challenge them. We drop them off at car line with backpacks that are too heavy and hearts that are too tender, and we drive away hoping—no praying—that today will be a good day. That someone will notice if they’re sad. That someone will celebrate when they finally understand fractions. Just love them.
When love meets love, fear has nowhere to weaponize. Rose Helm shared the same idea.
Rose Helm: …when we see parents who are manifesting crazy…I like to say it’s actually rooted in fear…which is actually rooted in love. And if we can meet them in the love place… We can bring the crazy level down.
It is as if they were all talking to one another. Jeff agrees, “Everything about good education is personal. You just can’t have a great school without meaningful and strong relationships all around, starting with the adults in the building.”
Jeff: The blessing and the curse of being a school person. That the best learning happens in relationships. The deep joy comes from… You have to be there. COVID and all this virtual learning has taught us so much because especially for younger kids, it’s so dependent on… You got to have 20 kids or 15, whatever, in a room with a caring adult. That also means that the head of school or the division head has to have their ass in building, too.
I’d like to do the math of the collective wisdom of the school leaders with whom I have walked. I know there is well over 100 years of experience of creating positive cultures with meaningful relationships… the joy of being there… being present for all of the best people on the planet.
Jeff: It’s just the fact that you accumulate so much knowledge, whether you mean to or not, when you’re at something a long time and you make a lot of mistakes and you learn from them. And I’d love to be able to put that to use in some way. While I’m thinking about ways to make best use of what I’ve learned to help others or help a school community, I also have learned how important it is to keep learning. After I retired, I started woodworking. It was just liberating to not have to be right, to not have to do things perfectly. And I mean, I realized, of course, that’s the pressure I put on myself. But it just struck me when I was really starting from scratch on something that has a steep learning curve.
Liz: You really do have to humble yourself to learn something new.
Jeff: Yeah, especially something like that. I just hadn’t… So often you have skills that transfer from something else that you’ve done. Oh, my God. Nothing. Transferred. You pick up these tools, and I don’t even know what it is. So you have to be willing to start at the beginning… the excitement of learning something that’s brand new.
And I’m realizing, too, these are not linear things. These are not either ors. You could come there to be the best school administrator you could be, but it doesn’t mean that you can’t pick up these interests and these values along the way. …Life is just so much more nuanced than we, and I especially, tend to give it credit for.
Maybe the boards of our schools should require us as school leaders to learn – not through a professional development budget that sends us to conferences – to humble ourselves to learn something brand new. Embody the child who slides into a seat in a classroom every day. Develop that empathy muscle – that authenticity of making mistakes without wearing a mask of perfection. When you have worn the armor of “getting it right” for so long, it is hard to take it off. We may need to practice more often. I have mentioned before that we spend a lot of time on the launch of emerging leaders and zero time on the landing. What if transitions during leadership succession were more about the people than the position? What if we cared about the wellbeing of the outgoing leader as much as we care about the support of the new hire?
Jeff: My first two years, after I left USN, I felt like I was… It just… I mean, I would wake up constantly in the middle of some dream that was exactly what my job used to be. And that still happens today, but not with the same frequency.
Liz: What are you doing? Crossing guard or fighting with a teacher?
Jeff: It wasn’t always bad.
Liz: Oh, some of the dreams are good.
Jeff: Yeah, but they’re still so… Just my entire being was so entrenched in that role, in that identity. I’d think in the middle of the day when I was awake, would I be in a seventh grade… It’s Thursday at a quarter of two. I’d probably in a seventh grade team meeting right now. And I know that’s pretty typical. But after 20 months, and I’m still thinking that way, I thought, oh, my gosh, is this a forever thing? But surely there’s more to me than that. How do I clear my head?
Liz: So how did you clear your head?
Jeff: I just lived a little further into it, I guess. I mean, it still happens, and it probably always will, but I don’t feel controlled by it like I did before, where I’d be. I just thought, my God, if I’m going to think about this so much, why don’t I at least go into school and make some money? It’s going to be on my mind anyway. And now that I’m getting a little more distance, I’m just thinking… the big things on my calendar in the coming weeks have nothing to do with Parents Night and Alumni events and whatever. It was about something fun for me or a trip with Carolyn or seeing the kids… So that’s refreshing.
Liz: You and Carolyn really hit a nerve when you said, ‘Why do we have to wait until we’re older to do the things we want to do?’
Jeff: I’m going to be 60 in a few months. And these are supposed to be the go-go years before you get to the slow-go years. And then eventually, the no-go years. But that shit can… I mean, you don’t know.
Liz: That shit can change on a dime.
Jeff: It can.
So many walks have included the line, “Life is fragile.” We do not know what tomorrow holds. So what are you going to do with today? With this moment?
Liz: I think we should turn around.
Jeff: Is this not…
Liz: You don’t think we can go that way? You think there’s a path over there?
Jeff: I don’t know. Does it look like there’s a sidewalk?
Liz: A sidewalk. hmph
Jeff: Does it look like there’s a path over there?
Liz: Maybe
Jeff: Because if we can stay along there, I have a feeling that’s where we want to be, right?
Liz: Yeah. Oh, wow. Look, and then you get yourself lost, and then you find this amazing vista. Your call… So that’s what scares me, is they can’t…
Jeff: All right, let’s go back.
Are we talking about our walk or our life decisions once we step out of a school? Either situation fits the dialogue.
Liz: I always used to say the school would be okay if I get hit by a bus, but I don’t think that’s how the walk should end.
Jeff: No, really. It was going to be her last walk anyway.
Speaking of walks…
Jeff: It’s funny we’re walking because one year somebody else, I can’t even remember what it was, but I heard somebody talking about … the walk and talk. And so I had goals meetings in the fall with faculty, and they were all going to be walk and talks. And it was great because we could do this loop around Peabody, and it was a 25 minute thing.
… I’ll never know the road not taken, but it sure seemed like they were speaking a little more from the heart, a little less guarded, maybe because they didn’t have to sit in an office and look their supervisor in the eye.
Liz: That’s part of the goal right now. You and I are not looking at each other.
Jeff: I’m sure it is. And I look back and I’m like, why did it take me 20 whatever years to realize they don’t have to sit in a fucking office to have conversations that probably aren’t going to be even as good? But now there’s some meetings that need to happen there, but most of them probably don’t.
Liz: You’re not going to counsel a family out of your school on a walk and talk. Although maybe it would have been beneficial.
Jeff: These walks are different.
Liz: Yeah Oh.
Jeff: Very different.
Liz: Very different. And I didn’t give myself credit that this really was an occupation for the past year. But I never felt like I was working.
Jeff: That’s great.
I lose myself when I write these blogs. Every. Time. A man sitting next to me on the plane commented that he didn’t want to interrupt me. He had never seen anyone so invested in what they were doing. I hadn’t even said hello to him in what turned out to be a five hour flight. I wasn’t in seat 12C. I was walking through Central Park in my mind. I was immersed in getting Kermit’s story out of my head and onto the page…more gift… than work.
Jeff: Do you have another project bubbling in your mind? This has really inspired you or fueled you.
Liz: Sure. I have… That’s the one thing about doing Edge, is it unlocked the little piece of me that says, oh, you don’t just have to ask what if, you can try it. Hit that entrepreneurial go button. So I don’t know that I want to be a founder of a software company, but I certainly am not going to take the status quo. And I like the fact that I interviewed and presented authentically for this new position. So there’s no façade.
Jeff: Yeah, you’ve said that before. And that’s surprising because I think of you as one of the most authentic people I know. Have you felt pressure in the past to not do that?
Liz: Oh, I completely lost myself as a head of school.
But not this time. Not for PAIS.
Liz: …because I was with you, there was not a single moment that I worried about what somebody was going to think of the Executive Director of an Association being dragged along in a radio flyer.
Jeff: In a radio. I forgot that’s who they were called. That’s awesome.
Liz: But that’s because I was with you.
Jeff: Well, you’re sweet. Well, we go way back. That’s for sure.
Liz: Yeah.
Jeff: It just always felt like there’s just no pretense.
Liz: I’m not sad that this is The Last Walk. Luke will say of Chapter One, who knows what Chapter Two is going to look like.. Because without knowing it, and I know that you love me, but you haven’t listened to a single walk. That’s okay. You have actually brought up almost everything that all these walks have been about. Completely unintentionally, and I didn’t direct the conversation. I feel like you grabbed a sound bite from almost every single walk.
55 walks. One year of my life. Eric, Luke and I determined it takes almost ten hours for each walk. 33,000 minutes. More if you count the hours I spend thinking about each walk when I am not writing. And I would not have wanted to spend my time any other way. What do you want to do? They asked. I want to walk with people who want to help me figure that out, I said. I could not be more grateful. This amount of love is actually immeasurable.

Liz: Thanks, buddy.
Jeff: I love you.
Liz: I love you, too.
Jeff: That was good.
Liz: It was good.
Jeff: I’m honored to be
Liz: My Last
Jeff: …the temporary last one.
Liz: That’s it.
I started walking because I had left the job that had defined me for years, lost both of my parents within a crushing span of time, and woke up one morning not knowing who Liz Hofreuter was if she wasn’t a Head of School, wasn’t someone’s daughter, wasn’t moving through her days with the certainty of purpose. I found that I am still a learner, still curious, still willing to not know. I found that I am still a teacher who believes every single child… and adult… deserves to feel seen and celebrated and safe.
What I hope you learned… when you lose your way—and you will, we all do—find someone to walk with…and laugh. God, please laugh as much as you can. Let it transport you. Let it heal you. Let it remind you that joy is transformational and connection is everything.
Because here’s what I know for certain after fifty-five walks: We are not meant to do this alone. We are meant to walk together, to lean on each other, to hold space for each other’s joy and grief and questions and blunders. As Parker put it so well, we need to leave room for wonder.
We are meant to be each other’s sunshine.

