Education as the Great Equalizer, featuring Annie Weinberg ’10

[00:00:00] UNICEF calls middle school the second window of opportunity. There’s a lot of chaos going on and peak brain development, but it’s also this moment of peak neuroplasticity and this ability to build self-efficacy. And if you can help harness a child’s motivation and belief in themselves at that moment, there is a really high likelihood that they will begin to believe in themselves. And that course will longitudinally follow them for the rest of their lives.

[00:00:18] Laurie: You’re listening to Midd Moment, the podcast of ideas from Middlebury’s leaders and independent thinkers who create community. I’m Laurie Patton, president of Middlebury and professor of religion.

Today, we’re talking with Annie Weinberg, the founder and executive director of Alexander Twilight Academy. Located in Boston, Massachusetts, the Twilight Academy is a catalyst program designed to support students from under-resourced backgrounds. Beginning in the middle school year, ATA provides rigorous year-round academic programming, advocacy, and mentorship for a population of students who otherwise may have never gotten an opportunity to access such support.

Annie Weinberg is a 2010 graduate of Middlebury and she holds master’s degrees from Columbia University’s Teachers College and Harvard’s Graduate School of Education. As a public school teacher in New York and Boston, Annie discovered both the inspiring possibilities and frustrating limitations inherent in resource-starved classrooms and wondered if the idea of a model classroom could be expanded into an organization, one structured to meet the needs of a cohort, not just for a year but for a critical period in young lives of a generation of students.

Annie, welcome to the podcast.

So, you know, as I think about your story and read more about Alexander Twilight Academy, maybe if you could start with talking to me a little bit about how you got to Middlebury, what it was about Middlebury that gave you this idea, how did the idea come to you, and did it come at Middlebury, or were there seeds at Middlebury? And just tell us a little more about your journey and relationship to you as a Midd alum.

[00:02:03] Annie: It’s so interesting because, you know, when I began to explore colleges, I knew that I wanted a school with a lot of spirit, a school that fostered this sense of intellectual curiosity, that was a place for nerdy community builders, and people who really wanted to be immersed in an environment that really relishes the building and nurturing of relationships.

I remember arriving on campus with my dad. We’d gotten a flat tire on the way up to Middlebury. And I watched him change it on the side of the road in awe because I didn’t think he was that handy, but it was pretty incredible to see that flat tire changed in 20 minutes. So, it was off to a little rough start. I don’t think I was positioned to love Middlebury from that experience. But there was something about stepping out of fire and ice and watching the sunset over the mountains that just spoke to my heart and soul.

I think when I got to campus, what was so striking to me and almost took me off guard was the sense of community and collaboration that was immediately so welcoming to me. I remember being in this astrophysics class my freshman year because President Liebowitz told us that we should be brave and courageous in our class choices and make sure that we’re putting ourselves out there to all new opportunities.

So, you know, the person who loved humanities ended up with a freshman course load of Chinese, economics, astrophysics, and a freshman seminar on American presence biographies. And my parents were, kind of, like, “What are you doing? Because this is, kind of, this is very different than the path we thought you’d take.” But I remember being in that astrophysics class and being so refreshed and honestly taken aback by the fact that my classmates were so collaborative and kind and that—versus my uber competitive high school where there was almost a sense of competition over grades—that there was a group of people who wanted to work with me and work as a group to collaboratively solve problems. And I was just so refreshed in that sense of place.

[00:07:27] Laurie: You talk about Middlebury giving you a space to explore, to be creative, to be courageous. And then, you graduate, and there’s… studies show that the hardest years for a young adult are the first year in college and the first year outside of college. And so, what was that like when you graduated and you’d been inspired by all these people from different backgrounds and, suddenly, you’re there and you’re thinking about your own life? And how did you move to think about graduate school and education and then to create this amazing thing that we’re going to talk about in a second?

[00:08:05] Annie: I left Middlebury right from graduation because it was too emotional for me. I remember, when I was packing up my stuff, I walked into the kitchen in LaForce, which has that extraordinary view out into the fields where you can see cows and you can see Bi Hall. And I just sat there, like, tears streaming down my face, because I had built such an amazingly strong community where I felt so welcomed, valued, loved, and seen, and had such amazing friends from so many different backgrounds. And I just thought, “Gosh, when in my life am I ever going to be in such a powerful, magical community where all of my friends are within a quarter of a mile of each other?”

So, you know, definitely, transitioning into life, especially into finance, which was a career that I really enjoyed but was not my calling, was a harder transition. I was lucky enough to live with four Middlebury girls in a three-bedroom apartment in New York City. And the transition into finance, I think that was more of a de facto career for me. I’d seen mentors and role models in my life say, “Oh, gosh, you’d be really good at this.” And while I loved it and I loved the intellectual rigor of being in that space, I had this calling to do something else. And I always thought that I would go make money first and then use financial means to have an impact.

But I sat there in my chair one day, and I said, “What am I doing?” I’m hearing stories about District 6 in East Harlem, it is a failing district, and in New York City. And their high school graduation rates are below 50 percent. And I was called to jump into the work. I became a global history teacher at a big public high school in East Harlem—50 kids in my classroom, kids were sitting on window sills and radiators. And that was only legal to 50 kids in the classroom because there’s a… in New York, there’s a 1 to 25 ratio. And we had a paraprofessional wandering the hallway.

And during that time in East Harlem, and I was going to school at night and coming back into the classroom to teach during the day, I was just met with the greatest dichotomy of a system that had failed a group of students. So much hope and potential in these young people who are so brilliant and big-hearted and incredibly intellectually curious. And yet, a system that, because of these low expectations, had blatantly failed them.

And I wanted to be a part of a system that was a solution, where education could actually be the great equalizer. And when I think about Middlebury, you know, it’s funny, I didn’t take many education classes. I took Jonathan Miller-Lane’s Education in America, which was certainly a transformative class. And I wrote my thesis on reimagining the American dream, which I think connects a lot to my philosophy on education, that, while education in America is actually the vehicle that halts social mobility today, it should be, and has always been promised to be, the great equalizer in America.

And I think when we… you know, when we think about the origins of my story and founding Alexander Twilight Academy, it’s in that, the innate belief in young people and their stories, and in the innate belief that education should and can be the great equalizer.

[00:11:53] Laurie: So, I want to come back to that because I think it’s incredibly powerful, and I’m thinking a lot about American education, you know, every day at Midd in different ways. But I wanted to just ask you a couple of things. The first is, you were going to school at night, so tell me more about working in East Harlem during the day, going to school at night, what all of that looked like for you.

[00:12:15] Annie: I’m sitting here in a classroom with this incredible group of young people, many of whom were far wiser and more experienced in the world than I was. Some of them had been incarcerated. Some of them had their own children. And here I am, pretty fresh out of college, not knowing a ton about education, but being incredibly passionate and committed to them.

And it was really my duty and responsibility to make sure that I was doing as good of a job as their teacher as possible. So, while going to class every night was definitely a challenge and caused me to do even more work, it was what I owed the kids to be able to be a competent educator that really put my relationships with them at the forefront of everything I did, and also to create a curriculum that was really multicultural, and was able to be rigorous to push them in ways that they deserved to be pushed.

[00:13:08] Laurie: So, can we go back for a second to, you were saying, you know, you were, sort of, sitting in your chair in your finance job wondering about this. I want to dive a little deeper into that. There must have been more than you just sitting in your chair and having a thought. Like, was there a news article you read or a friendship you had or conversation or something where you, kind of, made that flip, you know, that there’s always some kind of specific thing? Or, was it a growing sensibility and a tipping point that was a moment? If you could dive a little deeper into that moment of obligation that you described earlier.

[00:14:30] Annie: Yeah. I mean, I think it comes back to the fact that my family, you know, has always believed in the power of education. And I’ve been able to have such a privileged educational upbringing, right? I’ve been able to go to Middlebury College, one of the best colleges in the world. And here I am, sitting there with so much privilege and knowing that it was my duty and obligation to use that privilege I had to make the world a better place. And what better way to do so than to invest in being a teacher?
I love building relationships. I love stories. I love helping bring out the potential in others. And I love the hard work the educational profession demands. So, it, kind of, spoke to my soul.

[00:15:12] Laurie: Yeah. And on that day, you know, when you were thinking, when you were sitting there, was that day a particularly boring day for you in your work? Or was it… what was the tipping point for you? Because you must have been feeling this for a while, right? You knew that you have this sense of obligation. I think people identify, too, you know, as raised in a privileged background. How do you think about sharing that privilege, right?

[00:15:37] Annie: I think it’s less of what was going on and more of, what was I fighting against to just doing it in the first place?

[00:15:44] Laurie: Nice. Yeah, say more.

[00:15:46] Annie: And I think it was once I got that validating job in finance, which, for whatever reason, was a marker of validation for me…

[00:15:54] Laurie: Yes.

[00:15:55] Annie: But I think, once I got it…I’ve never quit anything in my life.

[00:15:58] Laurie: Yeah.

[00:16:00] Annie: And leaving that to take a new path, I, kind of, almost wanted to stick it out for longer, even though it didn’t sit right in my heart, because I’ve never quit anything. So, leaving after a year would have just felt like a failure. But I felt so called and compelled to this work that I knew very quickly, once I began to teach and to learn about the art and science of teaching, that this was my calling. Like, education was my lifelong calling.

[00:16:29] Laurie: Yeah. I love that. And I love the way you talk about that because I think there are these really interesting moments where, once you’ve achieved what you thought you wanted, you realize that it may not be what you wanted and you really have to, sort of, rethink what your heart is telling you. And it’s sometimes not when it’s bad that that moment of reflection occurs, but rather when it’s good enough, right? And then, suddenly you’re like, “Yeah, but it’s not, it’s not, kind of, where I want to land.”

So, tell me a little more about your Columbia Teachers College experience and learning, as you said, so beautifully about the art and science of teaching. What were the things that you learned there that brought you to thinking about making access affordable and the educational experience transformative, what we all want from education?

[00:17:24] Annie: I really love the practical-based education that it provided, in the sense that I was learning skills in the classroom that I was… and directly implementing every single day. So, just the art and science of, like, how do you build a unit plan that really causes students to do deeper level thinking, not just like, how do they master these facts, but how do they more deeply understand concepts that they can connect more broadly to the world?

That was the same spirit that lit my soul on fire about education that I had at Middlebury College, where there was just this passion for learning, for learning’s sake, and this hunger for knowledge in order to make connections to the bigger world.

[00:18:24] Laurie: I think, sometimes, people misunderstand the phrase that you used about learning for learning’s sake. Learning for learning’s sake is a scholarly pursuit, and it sometimes conjures images of someone just happy in the library. But no one I know who believes in learning for learning’s sake actually says that learning stops after you’ve learned, right? Learning for learning’s sake means that you are open continually to a kind of personal transformation.

And Parker Palmer, the educator, speaks constantly about if you’re not doing your own soul work as an educator, then you’re not going to be touching, you know, the souls of others. And I think that’s such a powerful idea. It sounds like, you know, you had just come out of your own transformation. And I just need to comment that something that really strikes me that I think about all the time is, we talk about Middlebury as being really made up from its beginning of teachers and preachers. And I think that’s powerful in so many different ways. But I’m struck by the fact that you also thought about founding your academy based on the person, Alexander Twilight, that I have come to call our ancestor, right? And I mentioned that because we just had the Clifford Symposium, which is, as you might remember, when everyone gathers together in the space and talks about a particular question or issue or concern. And what we did this past Clifford Symposium was discuss Alexander Twilight’s legacy.

And he’s an archetypal teacher and preacher. That’s who he was, right? Whether it was at Middlebury, whether it was in the legislature, you know, whether it was where he went after that in Brownington, you know, there’s all these really interesting ways in which he, kind of, embodied Middlebury ideals. And I want to come back to the complexity of his legacy a little bit later on. But I’m wondering if you could talk more about the seed of your idea. And did it happen when you were at Columbia Teachers College? And did it grow from there, or did it happen after you’d been out and about, you got your degree and you were teaching some more and you saw in your workplace, saw, “I could improve it?”

[00:21:28] Annie: It’s an interesting question, Laurie. I think that, when I’ve been reflecting, I think, you know, after Columbia Teachers College and after teaching at this big public high school in Harlem, agnostic to school type, I moved to Boston and I wanted to see a different part of the system.

Again, I don’t care if it’s a private school, public school, charter school, a parochial school, as long as you’re serving kids and families well and providing them with the education they deserve, I am excited about, you know, working there. And, at the time, there’s a charter school in Boston seeming to do things really differently. And I was excited to teach with them and then help found and lead their second campus as they expanded in Boston.

And during my time in the classroom before I transitioned into the leadership, we were the highest poverty district in the state of Massachusetts. And every single year, my class finished as the highest performing district in the state of Massachusetts, beating the affluent districts of Wellesley and Newton in terms of raw achievement. We were number one. And we were number one in the state in terms of growth.

I like to say that education isn’t rocket science. There are a lot of little things that you can do correctly to really move the needle academically. And yet, the tough thing for me, Laurie, was, despite having these brilliant years with kids who began to see themselves as students and began to see this potential in themselves, what I saw after they left my classroom is a story that, oftentimes, was exacerbated by the impacts of poverty and a story that students were not able to live out their potential. Only 20 percent graduated from high school. And the 20 percent that did, I think only 5 percent graduated from four-year colleges, in six years.

So, I was really struck by the fact that here are these big-hearted, brilliant-minded kids who deserve to be the leaders of our world and deserve to be the leaders of their communities and our communities, and yet, there was something that was happening in terms of the holistic education that they’re receiving or not receiving that we needed to change.

[00:23:34] Laurie: I don’t know if you know Shirley Collado’s College Track, but it’s a very similar idea, right? Which is, and it’s specifically focused on college, but it’s the same kind of, first of all, that quadrangle, right? High challenge, high support is the place that’s magic. All the other quadrangles don’t work, right? Low challenge, low support, high challenge, low support, high support, low challenge, right? And that looks different for, I think, every school district, you know, what that actually translates into being, but what really strikes me is that, I think, some people are, sort of, intuitively asset-based thinkers.

Before anyone comes to see me in office hours, I have them read Krista Tippett’s interview with Trabian Shorters, who is Mr. Asset-Based Thinking. And he says, you know, just exactly what you say, which is all of this talent, we’re not looking at, “Ooh, you know, he grew up in Minnesota and he thinks a lot about the experience of Black man in America. And instead of saying school-to-prison pipeline, we have to eradicate it. It’s perfectly good moral way to think about it.” He said, “No, let’s think about, where is this genius that we see in certain kinds of individuals who have had the circumstances and the love and the challenge, as you say, come out?” Why don’t we unlock that for everyone, you know?

And I think that that’s a… it sounds easy when you say it, but actually doing it and moving away from deficit-based thinking without whitewashing the challenge is, really, I think, where the best educators need to go. And, I love that you, sort of, intuitively understood this.

So, you go to Harvard Ed School and you create Alexander Twilight Academy. I wanted to have you for our listening Midd alumni audience and those beyond describe a little bit about, you know, you’re in the elevator and someone says, “What do you do?” You could just say you’re an educator, yay. You can say you create a parallel program that helps kids really unlock their potential and everyone will say yay. I know you don’t only describe it that way, though. So, how do you describe exactly what you created? And is what you just say now to someone in the elevator the same as what you said when you started at Harvard School of Ed?

[00:25:57] Annie: No, it’s very different than what I would say is, because I think when you’re in the, in the middle of deep thoughts about every aspect and every system and structure of an organization, you often get into the granular details of something that are really important to you and that light you up inside but are less important to your audience. And they can get lost in the jargon of what it is, but yet it’s so important to the concept as a whole.

But to boil it back as to what is Alexander Twilight Academy, Alexander Twilight Academy is a tuition-free longitudinal high school and college access organization. And we admit students in fifth grade and serve them really intensively through our middle school academy year-round. We have year-round coursework in math, English, seminar, writing, coding, lab-based sciences, and then a plethora of electives from art and portraiture, to game design, investing, debate, art, basketball. You name it, we have it.

In addition to these really rigorous high-acting academics, we have a component of our program that is mentorship. So, every student is paired with a one-on-one mentor. We have an aspect of the program that is explicitly focused on passion exploration, where students are being exposed to passions they might not even know exist yet. Going to the MIT robotics competition and being in a hackathon or going to the Institute of Contemporary Art or going to a Celtics game, these are all things that, as we’re nurturing the next generation of leaders, gosh, how cool is it that they are going to be exposed to these passions that are going to light them up inside and create pathways for the future?

And then the final component for the middle school academy is high school placement. And it’s one where we piloted the model in 2018, 2019, launched in the pandemic, but we placed our first cohort who we’ve had, many of whom we’ve had since 2018, into high schools. They’re now freshmen in high schools, 100 percent of them—and again, these are all students who are incredibly gifted, high-potential, brilliant human beings who live at or below the poverty line—100 percent of them earned admission to the top high schools in the country, both the Boston exam schools and every private school under the sun. Sixty-four percent of them are going to those institutions for free, so they literally are not paying a single dime. And they’re getting a laptop, free study abroad, complete equity, and access packages, these high schools call it. And then an average student, so the students that are not in that 64 percent, the average student is paying $516 to go to an $80,000-a-year school such as Phillips Andover, Hotchkiss, Deerfield, Exeter, Choate, Dana Hall, Roxbury Latin, etc.

[00:28:54] Laurie: Yeah. I love the numbers that you have on your website about $254,000 is the average four-year financial aid award grant.

So, I want to come to what you were talking about in terms of the exploration of passion as part of your curriculum. I was looking at some of the poems and the features of some of your students on your website. And I was particularly struck with a couple of them. The first is the egg drop experiment. And the reason why I love the egg drop, it’s very clear the student is talking about force equals change in momentum over time, and momentum is mass and velocity and all these wonderful things that he’s trying to explain with this simple thing. And so, you love that.

And it could have ended with him just doing it, you know, in the classroom. But instead, he drops it out the window, and everyone’s waiting to see. And there’s this incredible sense of excitement when it actually works and there’s, like, this outburst of happiness with all of the students around watching the experiment.

And I think that really speaks to the passion that you were talking about, that you showed the sheer excitement about what it means to drop an egg out of the window. That’s the educational gold, no matter, whether you’re at ATA or somewhere else, you know, it’s a really lovely moment. And I think that really speaks to me about exploration of passion. And I’m wondering if you could talk a little bit about that part of the curriculum, because I think it’s relevant to college. It’s relevant to grade school. It’s relevant to job search, you know, etc.

[00:30:36] Annie: Yeah. In many ways, I think that our kids are coming to us with assets beyond belief. And we are incredibly lucky to get to work with young people who are such extraordinary leaders and who have these innate gifts of brilliance, intellectual curiosity, tenacity, resilience, and so much joy within them.

So, we’re really the lucky ones that get to work with our kids. But in many ways, when you understand the way America works as a country, oftentimes, as I said before, in terms of Jean Anyon’s research on the hidden curriculum of social class, our education system does more to perpetuate class order than to create class mobility. And when we think about our kids being the leaders they deserve to be, leaders who are going to change the world and make it a better place, and leaders we really need right now, we need to give them access to the full gamut of opportunities that exist out there.

And what does that mean? That means replicating privileged networks that already exist for affluent America. So, bringing in a mentorship network where they can build connections with people in different professions, see themselves in the faces and voices and stories of those people, build relationships and be able to intern and potentially work at those places and spaces.

It also means giving them the opportunity to be exposed to both lifelong passions that fill their soul and infuse love and harmony and magic into their just daily existence, as well as to expose them to passions that they might not even know exist yet in terms of career involvement. What strikes a lot of people is that you’ll meet some of our youngest students who just finished fifth grade, and they’ll ask what they want to be when they grow up. And they’ll tell you they want to be a biomedical engineer. It’s a pretty specific answer for a sixth grader, but it’s a specific answer because they’ve met biomedical engineers. And not only have they met biomedical engineers but they’ve met biomedical engineers who look like them and who have lived this story and lived this journey. And they see themselves in the skill sets, in the type of work, in the excitement about the work of that biomedical engineer.

When we think about helping our kids gain positions of power and privilege in America, we need to think about, what other levers of support can we provide to help them gain the gamut of experience and build off of the assets of their communities and their families and support that with these other levers that families from affluent backgrounds already know how to and have access to pull?

[00:33:12] Laurie: Yeah. I know. I think that that sounds really inspirational to, sort of, think about it in those contexts and that the students can tell themselves a story about their own future because someone else has told a story about their past, you know. And I think that’s really a wonderful way to set it up.

I wish we had more time. I want to end with two other things that I want to just think about. I was also really struck by, I think, the student’s name was Fortune’s, poem, about imagining leaving a war zone to enter a war zone. There was a really powerful meditation on your website from Fortune about the question of privilege, the question of violence, the question of how to think about a migrant life. It was a really beautiful poem.

Right after that line, Fortune says, “Oh, it’s okay, at least you learned about people who did that.” And that was this really powerful line. Of course, I’m going to, you know, focus on the poem. And I thought, this feels like a really authentic line, right? That there was something both, maybe it was slightly sarcastic, maybe it wasn’t. Maybe it was, no, it’s really good that you learned, you know. Even if you couldn’t imagine it, you can still learn it. And I thought that that ambiguity was actually quite lovely, that you weren’t quite sure. And that’s exactly what makes a good poem, that you begin to think about it in a number of different resonances.

And it also raised the question of authenticity for me. And I think, back to one of the hard conversations, you know, we had about Alexander Twilight is pretty clear that he passed as White for much of his life. And how do we think about that legacy in a way that the whole question of imposter syndrome, that people feel sometimes that they need to pass, sometimes that they’ve already given more credit than they deserve, all these kinds of questions that I think is part of the complexity of Twilight’s legacy for all of us.

And I’m wondering how you’ve encountered that as you begin to build this asset-based framing and unlock the kind of potential by providing such an incredible educational environment for folks. How do you come across these questions of authenticity and imposter syndrome and so on? Because I think it even occurs in middle school in different ways.

[00:35:42] Annie: Definitely, I think it’s critically important. I mean, all the literature shows that middle school is actually this time where you’re forming, especially for Black male identifying students, this real sense of identity. Who you are? And what are the most important identity markers to you? And what are the… how does the world see you?

And, you know, it’s interesting. UNICEF calls middle school the second window of opportunity. The first window of opportunity is early childhood. The second window of opportunity is middle school. And I think that people think about middle school and they just think about these hormonal, you know, this time where there’s a lot of chaos going on and, you know, peak brain development, but it’s also this moment of peak neuroplasticity and this ability to build self-efficacy.

And if you can help harness a child’s motivation and their belief in themselves at that moment, there is a really high likelihood that they will begin to believe in themselves. And that course will longitudinally follow them for the rest of their lives. It is critical, especially as we are thinking about growing the next generation of leaders and nurturing the assets they already have, that we are doing this deep, deep identity work with our kids.

So, one of the classes that they take, you know, for four years with us at Alexander Twilight Academy in middle school, and they continue to take all the way through high school and college, is this class called Lead. It’s a class that really focuses heavily on Marshall Ganz’s framework on story of self, story of us, story of now. So, who am I? Who is my community? And what are the issues of the day that call my heart and call me into action?

And we help our kids build a really strong sense of self of who they are, which their families do a beautiful job of helping them understand that, and the assets of their community, so that when they’re walking into these spaces and places, that may look different than the communities they come from, they’re not privileging one over the other. They’re thinking about both of them. Kind of similar to the Rudyard Kipling line, you know, walk with kings nor lose the common touch. We want our kids to realize assets wherever they go and bring their superpowers of originality and place with them to whatever community they enter.

And that’s critical. I think, when you think about Alexander Twilight and his legacy as a trailblazer and authentically entering spaces and the fact that did so much to be that first and only Black person that was elected to the state legislature prior to the Civil War, a lot of our students are becoming those trailblazers for their families. I think of Fortune. You, you talked about his poem. He’s actually at Phillips Andover Academy right now on a full scholarship. But his story is a really cool one because it talks about the impacts behind the data.

About two days after he got into Phillips Andover Academy, he called me, hysterically crying, at 10:30 at night. And any, any urban educator knows when you get that late night call from a student, you brace for impact and you wonder and worry about what you’re going to hear. When I picked up the phone and heard that he was crying, I really braced for impact. And he began by saying, he’s like, “Ms. Weinberg, you’re never going to believe what happened tonight.” He said, “Ever since I got admitted to Alexander Twilight Academy, my mom…” again, he’s one of six. He’s the youngest of six. “… my mom has been putting money aside for me to be able to go to the high school of my dreams. And when she saw that scholarship letter, she was inspired by me to invest in herself. And she drove down to Roxbury Community College and put money down so that she could become a nurse and that she could begin taking classes to fulfill her dreams.”

[00:39:26] Laurie: Wow.

[00:39:26] Annie: And I think when you boil down the community impact of what we do and the ripple effect of providing children with the trajectory transforming education they deserve, with relationships, the family where we all become a family and we embrace that notion of it takes a village, I think that that’s the transformative power of education. And that’s what education can and should be in America.

[00:39:49] Laurie: Yeah. It’s a great, beautiful story.

My final question, I wish we didn’t have to stop, but thinking about, where does Alexander Twilight Academy grow next? You know, you’re clearly really successful, powerful in terms of the stories. You’re still in the space of, “Wow, you know, this can really work.” You’re placing your first few cohorts and so on. And I know that’s where you’re going to be focused for the next couple of years. But imagine where ATA is in 10 years. What does that look like? And how do you think about your own success? I bet there are a number of different pathways that you can imagine. Tell me a little bit about what that looks like for you as you, you know, wake up in the middle of the night and sketch stuff out or wherever you might do that work.

[00:40:59] Annie: I think the good thing about the career that I’ve chosen and, really, the life’s work that I’ve chosen is that, you know, in this time of extreme tragedy and despair, like, I’m able to wake up every single morning and feel really hopeful and optimistic about the future of our world, because I know these amazing young people who, when they’re at the helm, like, our world is going to be so much of a better place.

And I think that’s the big picture dream for Alexander Twilight Academy, that our students have built this network of people who look like them and who have grown up with them, who can be those allies and disruptive changemakers in America.

When Fortune is the governor of Massachusetts and Monty’s an activist in Roxbury and Corey has created this incredible tech startup and Jennifer is, you know, working for the Innocence Project, like, they’re going to be adults that they can call upon. And they can lead real stories of impact and change in America.

So, I think the big dream for Alexander Twilight Academy is to have them continue to build upon the experience of Alexander Twilight Academy and go out into the world and give back, you know, and really be positive community members, and also, to make the world a better place. I think that that’s one of the cool things in our admissions processes that we really gauge for. It’s who’s intellectually tenacious, who’s committed and motivated enough to do a 10-year program. And then, additionally, who really wants to make the world a better place? Who is that changemaker that really wants to lead and find ways to make the world better?

So, that’s something that I think about a lot. I mean, in the next few years, we’re going to be building out this high school model because our oldest kids are 9th graders. We will have five cohorts of students as of July, which is the official start of our school year. And then, you know, in 10 years from now, we will have our first group of kids that have graduated and will be well into their first job.

So, it’s a really exciting prospect about where this can go and how this model can possibly scale across the country, because, Laurie, you’re right. I mean, you said it before. Like, this is the type of education that every child deserves. And I was just lucky enough as a child at Middlebury and as a child that went to, you know, an extraordinary high school where I got that type of education that, like, nourishes soul and has you develop the skills of critical thinking, creativity, communication, collaboration, and problem solving that help you become an agile leader and learner for the 21st century and be prepared for the jobs we don’t even know exist yet. And I think, if we can help our students realize, both the joy of learning and also just have those practical habits of mind, they’re going to be taking over the world. And I can’t wait to see it.

[00:43:50] Laurie: Well, Annie Weinberg, it’s been so fun to talk to you. You know, I mentioned earlier about the teachers and preachers legacy of Middlebury. And even though it looked really different in 1800 than it does in 2024, you are absolutely embodying the best of what we all feel that Middlebury can give the world.

So, thanks so much for coming on and for all the vision that you bring to your project. You really are continuing the Middlebury legacy of teachers and preachers, but in a 21st-century mode. And you’re also part of the educational legacy of the Class of 2010 that has done so much in this area. So, it’s so exciting to have you, and I can’t wait to see what you do next. Thanks, again.

[00:44:38] Annie: Well, thank you, Laurie. It’s a real honor to be with you today. And, you know, the next step of excitement for me is, now that we have one group in high school, we got to start converting them early to be, to really have that Panther pride, because you know these schools are going to be fighting over them. So, that’s the next step on this journey.

[00:44:54] Laurie: Okay, right. That’s the real future. All right. Okay, duly noted. Thank you very much.
We’d like to thank Annie Weinberg for joining us in conversation today. Midd Moment is hosted by me, Laurie Patton, president of Middlebury. The podcast is executive produced by Matt Jennings, editor of Middlebury Magazine, and produced, engineered, and edited by Caitlin Whyte and the terrific folks at the podcast agency, University FM. Research on this episode was provided by Jessie Raymond.

For more conversations like this, subscribe to Midd Moment on Apple Podcasts or wherever you get your podcasts. Thank you for listening.