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Tim Lear: The Flex Interview

When it comes to peering over the horizon, Head of School Tim Lear is all about embracing What’s Next. Mr. Lear can often be found walking with a bounce in his step through the halls, or running the same Pingry cross country trails he did when he was a student here—often interrupting himself by dashing into his house to jot down new ideas that strike him. Wherever you find him, his perpetual friendly smile and contagious enthusiasm are sure to be present, and, as of recently, a copy of The Pingry Plan rolled up in his pocket, ready to be unveiled, discussed, and shared.

 

What will the future look like at Pingry and the wider world? The Flex sits down with Pingry’s Head of School to find out he is not afraid of a little ambivalence.

 

You have this warm and tremendous ability to remain present and in the here and now; yet a Strategic Plan is all about a thoughtful and calculated vision for the future. Tell us about the importance of considering “What’s next?”

The Pingry Plan anticipates a conversation. Faculty, staff, students, alums, Board members, and parents have said, ‘Here’s what we think is on the horizon. Here’s what we want you to anticipate. Here’s what we’re thinking about as the next project or the next big thing or the next challenge and opportunity.’ I really love the fact that it serves both purposes; that it asks an anticipatory question and it starts to provide an answer that we can start working on in the here and now.

While creating the plan, we began with getting back to what Pingry is at its core. How do we operate? What is in our DNA? We ask questions. We proactively anticipate needs. We act quickly. And I really like that about Pingry.

The downside to that speed to get things done is forgetting how to slow down. As Miller says, ‘to think you have all the answers before you even ask the question.’ And so What’s Next is both an anticipation and a promise that we will consider what’s next. We will be thinking about it before it's a concern. So there’s a kind of proactive promise to that phrase.

 

Are you someone who is easily present in the here and now?

(laughs) I’m glad Ellie and the kids are not here. Yesterday, we were having dinner and I got up in the middle to write the last sentence in the Board Report that I’m putting together because something my son James said spurred an idea I wanted to add. So that is something that I’m trying to get better at.

But to the point about being present, I’ve been the beneficiary of people who were anticipating what would be best for me, or what I would be good at, before I even realized it. And the three people who had the biggest impact on me becoming a teacher and going into education are Miller Bugliari, Tom Keating, and Lydia Geacintov. Lydia was a French teacher, Chair of the Language Department and then Director of Studies. All of them are members of the Magistri.

Two of those three people never taught me. They never coached me. Never served as my advisor. Tom was my ninth-grade English teacher, my assistant coach on the track team, and then my senior-year teacher as well—he bookended my high school career and was one of my college recommenders. But Lydia and Miller and Tom reached out to me when I was in college and I would have dinner with them about twice a year. And they were, as a group, saying, ‘Have you thought about teaching?’

It was because they saw something in me that I would make a good teacher. Had they not pointed me in that direction repeatedly, my whole life would be different. And not a little bit different. Dramatically different—and not as enriching and purposeful.

I’m in the right place. I went into the right field.

So the plan is about community and role modeling and supporting students and really looking out for them long term. It’s not just words on a page, or idealistic. I know that it happens here. I’ve seen it dozens of times with current students and young alums and older alums who come back and they still want guidance from a coach or a teacher or they just want that connection. They want to remember what it felt like to be a student where people believed in them and supported them. This is that secure base.

 

When you’re struck by an idea, do you need to write it down right away?

I do.

Sometimes it’s just a phrase. [Author and commentator] David Brooks had a really cool piece in The New York Times [the other day]. His thesis was that the formula that works best is daring explorations from a secure base. The idea that you will be comfortable aspiring to go to the moon if you know that the landing base—the home base—is secure, is stable, and is there when you get back. That you have something to come back to. I read that and thought of Pingry.

We send people out into the world at graduation, which isn’t a finish line as much as a beginning. Pingry has such a strong and connected community because people know they can come back at any point.
 

We Graduate Good People. The Strategic Plans seems to be infused with this simple yet enduring belief. One line really stands out: “At Pingry, excellence is only possible through honor.” Talk about bold. Tell us what this means.

Excellence isn’t just academic. To have a mindset that you are going to fully commit to something and be fully present and show up—that is a form of excellence. And that for me bleeds into this idea that you are not the center of the universe. You have a responsibility when you’re here to show up for other people, to put as much energy out as you absorb. If you are the captain of a team or you’re the Valedictorian or you’re on the Honor Board, you have a responsibility not just to preserve your spot and build your résumé, but to turn around and make other people excellent and better.

 

It’s funny because you’re saying it in such a friendly way, but you’re saying something that is really a challenge to people, and a demand.

I remember distinctly thinking when I was a student how much easier life would be when I turned 18. Then it was when I turned 21, or when I get a girlfriend, or get married. All these milestones that we create that are real and imagined and then ‘things will get easier’ and we realize life gets much more complicated. You need people more and more, in different ways, as you get older. And I don’t want to be a part of a community that doesn’t acknowledge that and where people aren’t proactively looking out for me. And it goes back to Lydia and Miller and Tom. I was fine. I wasn’t aimlessly wandering or struggling. And yet they still said, ‘this is worth us investing our time in to make sure he at least considers teaching as an option. We think this would help him. We think it will help whatever school community he’s a part of because he has something that will make him a good teacher. And we have a responsibility to point that out to him.’ I didn’t realize I needed their advice. And yet, they gave it to me anyway.

So to me, that’s what that phrase captures. The importance of showing up for other people. Not just for yourself, and not just thinking about how successful you are, but how you are allowing other people to realize their potential.

 

This is definitely Go Big or Go Home energy. Talk to us about the importance of being bold in our ideas and actions.

Bold is a really interesting word, says the person who’s lived almost his whole life within 25 minutes of the hospital he was born in. Some people associate bold with a proverbial moonshot. As if to be bold you have to invent something. Leave home and go somewhere exotic and do something unheard of. I think when you’re a kid, being bold is asking a question in class when you really don’t know the answer. Being bold is hitting pause on your own work because you see that a friend is confused and you sacrifice your playing time or grade to spend two hours tutoring or spending time with them. Boldness is very different when you’re a kid. I also think, as an adult, everyone who is here took the bold step of working in education. That is not something I hear a lot of support for, generally. So to say I’m going to devote myself to helping other people realize their potential—that’s a bold statement in a society that doesn’t necessarily measure success that way.

So I think we’re surrounded by boldness. And if we acknowledge that and practice that, then we will execute it.

 

It’s that secure base.

Yeah. Sometimes I hear seniors say, ‘I don’t have an interesting story to tell. What makes me exceptional?’ The idea that I haven’t invented something or cured something or solved something, so therefore, I’m not bold, I’m not excellent. And instead, let’s put it in perspective. How many of us here know how to ask for help? How many of us know how to offer help? How many of us are truly selfless or present when we need to be? Most of us have regrets along those lines. So being bold is something that we can attempt every day, every class period. And you need to practice. You need to develop and practice that muscle memory before you can be bold.

 

The six priorities are “our shared work” in the coming years. We live in an often-fractured world, and yet Pingry ‘stands athwart to that tide’ that increasingly celebrates individual achievement while turning its back on shared community excellence. The emphasis in the Strategic Plan—our shared work—is increasingly rare. Tell us why this distinction is important..

We’re signaling that everybody has a role to play. We have a shared responsibility to be fluent in what this work means for our students.

 

Again, we live in a time when, more and more, the focus is on individual achievement. In some ways, Pingry’s commitment to the Honor Code feels like a throwback to a time when leaders implored, "ask not what your country can do for you, ask what you can do for your country." The Strategic Plan demands that one “places the highest value on honor and respect for others.” Tell us why a moral education matters. 

Why does it matter? I think it depends on what kind of a society we want to live in. Do we want neighbors who are looking out for us, who care about how we are doing? Or do we want to just live in our protective bubbles? I’d much rather live in a neighborhood or work for an organization where individuals want to work with and for others. Asking for help is important, but you also want people to care about you enough that they anticipate and step in when needed. Because everybody is going to need it at a certain point. Everybody.

I think outcomes are really important. College counseling was about outcomes. Running? You either won or you lost. You either ran faster or you didn’t. The things I have been involved in professionally and athletically have been outcome driven, and sometimes very black and white. You know, the stopwatch is as definitive as it gets. And yet, it’s the process that is most important. The outcome matters, but it’s certainly not the only measurement or thing of value. The kind of person you were during the process and what you do after the work is done is really important.

 

So that phrase, What’s Next, applies in smaller moments, too.

The projects that are on the horizon—those are going to be constant. And it’s important that we are involved. The extent of our involvement matters. I’m not going to tell you what you need to do, but I believe you have to show up. I don’t know that it matters where you show up in the community, or who you show up for, or how, but you have to show up in your own way. And if you do that, you will benefit, and the community will benefit.

That’s the Honor Code. You’re here, and your presence has to be felt to be known.

 

There is a well-known expression, “May you live in interesting times”. Under “Managing Success and Disappointment” it says: “Today, the only constant is change—the only certainty, uncertainty.” Tell us why change and uncertainty is a good thing. How can we embrace it with energy and hope?

My years being an English teacher and studying English is one of the reasons why I am very comfortable with ambivalence. I could teach Macbeth 20 years in a row and never get sick of it because it’s constantly reinventing itself for the changing times.

A strategic plan that is based on enduring values is a document and a direction that should help a community to navigate uncertainty, to make sense of it—and not be afraid of it.

 

And how can we be a nimble institution that stays true to our values—responding to those known and unknown challenges with curiosity and connection rather than judgement and fear?

A lot of it is storytelling. It’s reassuring people by giving them concrete examples and saying, what does disappointment look like? When an outcome doesn’t go your way, well, what happened next? You lose the state championship? What did everyone do the next day? I’m more interested in that. Let’s tell that story. You didn’t get into that college you wanted to? Then what happened? It’s telling different kinds of stories and highlighting different kinds of outcomes. And that’s how you become comfortable with ambivalence, with alternative endings and possibilities. 

 

The Strategic Plan notes that “Pingry’s faculty and staff are the beating heart of our school.” As a former teacher, and a former student, articulate for us the transformative impact a good teacher has on a kid.

The relationship you have with your school, your teachers, coaches and advisors, doesn’t have to end at graduation—it can deepen over time. Without supporters, advocates, and mentors, it almost doesn’t matter how talented you are, right? You need people to be able to light the way and encourage you when things don’t happen the way you think they're going to. Teachers are in a really good position to do that.

So I love the fact that relationships can deepen over time. They don’t have to be outcome driven. My relationship with Tom Keating didn’t end when my last paper was handed in and he gave me a grade. An “A”, if I remember.

If you’re willing, all of those adults will be there. That secure base will be there for you, should you wish to return to it.

 

I’m sure the students are quite eager to hear more about the planned schedule review, where it notes a focus on creating flexibility within the academic day so students can pursue their interests and passions. Tell us the vision for this, and why it's unlikely to look like students simply scrolling through their phone.

I think about the importance of having structured free time. Students need to be able to figure things out and ask questions and sit with ideas and conversations and feelings. We need time for that. My best thinking happens when I’m running or walking or eating dinner, and I’m kind of unplugged. And then suddenly something will strike me. When you’re constantly rushing from activity to activity, it makes sense to not know how to think independently or how to sit with an idea and wrestle with it. Without a quick solution, how do you sit with ambivalence if everything is structured constantly for you and everything is controlled and micromanaged?

So we’re going to review everything, and as we consider a new schedule, we will discuss making space for structured free time and build a schedule that balances structured time with free time, knowing that it will result in magic.

 

In the “Creating Space for Connection” priority, it notes “we will design inspired and dynamic spaces…”. I think The Flex readers want to know: will we be getting a new student center, and, most importantly, what kind of vending machines will go there? In all seriousness, tell us how new spaces can renew and reinvigorate community connections.

Our values and collaboration (both the end product of that work, and the process) should be visible. We want kids to gravitate toward a project or a club or an area of interest and think, ‘I want to do that’.

We can open up areas and have spaces where we can see innovation happening—ideas being designed, workshopped, and developed. And we would need some unstructured time to do that—it’s that structured free time. Pingry students and teachers are some of the most motivated, bright thinkers in education. With a little space to work on passion projects, magic will happen.

 

It’s snowing outside now, and that reminds me that two years ago you declared a no-snow snow day. What prompted that unexpected moment?

At some point, everyone needs a break. We had a winter with no snow. That’s not winter. People were tired and needed a mini-break and I hope they enjoyed the day. I also understand that my decision made life inconvenient for some, and I took that seriously; if I remember correctly, we gave the community a week’s notice. So yes, it was spontaneous, but it was Pingry spontaneity.

We need people to be at their best. And for the vast majority of the community, they needed a timeout. We have to be okay hitting pause. And it’s a little bit like that with the strategic plan. It goes back to being nimble, and being okay with ambivalence.

So yeah, I thought that was a ton of fun. Would I do it again? We’ll see.

 

And finally: what are you most excited about?

Part of it is watching and waiting for it to come to life, because I feel like we’ve been talking about it for a year and a half.

Part of me is impatient to hit the fast-forward button and do the opposite of what I just said—where the outcome isn’t the most important part, it’s the process—but I’m really excited for all of it. And it’s not up to me. I am really excited to see what other people get excited about, because we have 1,200 students, 700 families, 340 employees, and over 6,000 alumni. There are so many people who now hold The Pingry Plan in their hands. Who’s going to be inspired? What are they going to want to do? What are they going to want to fund and co-create? That to me is the fun part.

 

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Photos and video by Natalie Gonzalez 

To contact the author: Sara Courtney