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Episode 19 · Stang Stories

Cameron Skinner

16 Sep 2026 · 41 min

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On this episode of Stang Stories, Eileen '29 interviews Cameron Skinner '05, founder and CEO of Penhammer, based in Portugal. Cameron shares how his Milton experience, influential teachers, and international teaching — including time in the Peace Corps — shaped his career in tutoring, test prep, and school leadership.

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Welcome to another episode of the Staying Stories podcast, where we interview alumni about real experiences at Millen Academy and beyond. My name is Eileen Chi, and I'm pleased to introduce our guest today, Cameron Skinner, a graduate of Millen's class of 2005 and now works in the education sector, specifically with private tutoring. Cameron is the founder and CEO of Penhammer, a service that coaches educators as well as prepares students for standardized testing. Specializing in reading and writing, Cameron has traveled the world tutoring kids and is now based in Portugal.

Cam, thank you for taking the time to talk with me today all the way from Portugal. And let's begin with looking back at your time at Milton. So what was your experience at Milton and what were your favorite classes that you took? Great to be here and thank you for the invitation, Eileen. My time at Milton, how would I describe it? I would describe it as a time when I forged many deep friendships and was also very academically challenged. And I feel like it's a rare environment in the sense that, you know, everyone's excited to be there and excited to learn about the world and new stuff and each other. And that's a unique aspect of community as I've.

Lived and worked and traveled the world and seen all kinds of schools all over the place. I really come to understand how special Milton is in that sense. And favorite classes? I mean, I was definitely a humanities guy. Through and through, adored my English class with Mr. Chung. He really stretched me in lots of ways with my writing craft, which I continue to appreciate to this day. I had great experiences with Mr. Hilgendorf's senior seminar. He's now left and retired, but his seminar was a thing of legends back in the day. And by the way, everything I'm mentioning is just anecdotal, right? Like I had so many amazing teachers while I was at Milton.

I really can't complain. Just don't really think I ever suffered from a bad teacher once. They were all wonderful for a variety of different reasons. But one who definitely sticks out for me is Patty Smith, who's also left and retired, but she taught biology for many years And just had, a really interesting backstory and was just such a wonderful, warm person and also stretched me in all kinds of ways. And yeah, it just forced me to look at the world from a different perspective, which I really appreciate. Yeah.

And so then looking at clubs, what clubs did you do? And then within those, were there any leadership positions that you stepped into? I think I did, I forget if it was called student council, but like your student class rep, basically someone you go to if you had issues that you didn't want to directly address with an adult, but you still needed some sort of outlet. And in other ways, I was actually just really into sports and extracurriculars. So I actually didn't have much of a life in clubs. It was more around, you know, music or acting in the latter part of my career.

Or, yeah, again, sports teams, lots of sports teams. I played Ultimate Disc. I wrestled. I was on the soccer team, too. So, yeah, between all those things, I was plenty busy. And actually, I did do an extracurricular that would have been club-like. I did Miltones as well, the acapella group. But I forgot that I also did another acapella group outside of school in Brookline. So I did both two acapella groups, I think for a span of two years, if I remember right. But yeah, I enjoyed it all.

So then what is one moment at Milton that made you realize that this is where you wanted to be? Well, great question. I think for me, it was actually just an amalgamation of things like over time, because I just felt very connected with certain, the whole community, but also specific pockets of the Milton community around dorm life. So Forbes House was a place where I hung out quite a lot and just loved the guys who were there. And I would spend lots of time with them.

And, you know, just those deep friendships over time is just like, wow, this is a pretty special time of life and a unique type of place that can actually provide that type of experience and connection. I had so many teachers who clearly went above and beyond to help me out during difficult times or, you know, made themselves available for different types of conversations. And, yeah, I just always felt very supported and supported. Welcomed and was met with nothing but like love and kindness from pretty much every member of the community.

And then in what ways has Milton given you an environment to find what you're passionate about? And then did it help you decide what your career would be like in the future? Wow, there's a lot of layers to those questions. If I look back, I would have to say that again, Milton was a place that very much academically challenged me. And before I arrived there in middle school, I had also been academically challenged, but I was also like top of my class. And then when I got to Milton.

I know I'm not alone when I say this, I suddenly found myself kind of in the middle of the pack. You know, I was not like the worst or the best. And frankly, none of those labels really mattered at all in a place like Milton, which I very much appreciated. It was a place where, you know, definitely multiple intelligences could be and were celebrated and valued. And I think over time, I realized that, I mean, it's kind of started at Milton now that I look back where I started to work at summer camps and things like that, like do work with youth even when I was, you know, 18 and under.

But I really enjoyed that work. And then I also had lots of models in my family with my dad and even my mom, although in most of her career, she wasn't a teacher. She actually started out as a teacher after she left her undergrad at Harvard. And then I also had, you know, my aunt and my grandmother, like just so many people. So I kind of always had that reference point in my mind. And then obviously, like also people in my family who would attend in Milton too.

And that's all to say that just I think I was brought up with just a deep love and appreciation for the value of education. And as I started to work with kids and I started to see how teachers operate and the kinds of things that they do, I really like the idea of that. And I think for a while I pushed against it actually, like in. I would even argue in college and beyond, what else could I do? What else? And I always just kept coming back to it. So over time, I learned like, yeah, that's where my passion lies.

And a lot of people, you know, refer to their work in education as a calling. And I'm not an exception to that at all. I found I have a real gift for it. Part of that is like, in my own life, I very much appreciated when teachers have made an effort to make complex things simple and ask really powerful questions. And, yeah, as I've gone through life, I've learned that those are actually just two of many, but two major components of the art and science of what I bring to teaching.

And, you know, I actually started, as I said, in summer camps, and then I ended up in the Peace Corps. I lived and worked in Rwanda for a couple years teaching students English after the country transitioned from Francophone to Anglophone. Basically, the Rwandan government called the U.S. government and said, hey, we need personnel because we don't have enough native English speakers here to actually execute on this new educational framework around an anglophone system.

So me and a bunch of other people shipped out and I learned a lot in that experience. If I remember right, I had multiple classrooms at one of the schools where I worked where I had over 50 kids in every class. And that was kind of baptism by fire. Like classroom management with over 50 children is something. And yeah, as time went on, it evolved. And I kept looking back to folks that I really admire, but also was looking ahead to who I really wanted to be.

And yeah, I just kept coming back to working with kids. And I really love helping young people understand who they are and what they want out of life. And, you know, I've since gotten into the international school realm, and I'm actually opening my own school. Well, this coming Monday. And yeah, outside of that, what you mentioned where I've dabbled in things like, well, more than dabbled, I've, launched and managed and owned a business now for many years, but in, you know, test taking and test prep and also with coaching and consulting with education organizations and educational leadership.

So, yeah, it's just one of these things where as I go, as I acquire new skills and new certifications and credentials and I have new conversations with people in the sector and, yeah, interact with different types of leadership and institutions, it's just like it always gets more interesting. It never gets old. It never gets boring. I always love, you know, establishing and building relationships with kids and again, helping them on their path, wherever that might lead them, whether it was by like pushing against it in some ways because, you know, maybe denying my own truth.

Or just accepting it and going along with some of those opportunities that came my way, whether working with, you know, in that student leadership role or with summer camps or different programming and, Yeah, it's such a rich environment. And that's the really great thing about it is just there's there's so many interesting people who are interested in so many different things. And there's so much support and so many resources for you to explore all of that.

And what better what better thing to set up your kid for success than to just put them into a, you know, petri dish of learning. And, you know, rub shoulders with other people who are, you know, smart in their own way and can challenge everyone around them. As people should be. Yeah, for sure. And then if you could go back in time, what is something that you would do differently? Or what is something that you wish you knew going to high school? I mean, there are a lot of things that I probably would have done differently, but hindsight's always 20-20.

I don't know. For me, I probably would have like pushed against different things. I probably would have explored even more. But then another part of me says like, nah, I feel like I did that part of life pretty all right because I definitely enjoyed my friendships for sure in high school. And yeah, so the answer is, yeah, I think I would have changed a lot of things, but ultimately I probably wouldn't have done anything different. It's all just a matter of retrospect. It's not real, you know?

I think I was like pushing in a lot of things and it served a purpose. I really don't know. That's such a great question. I don't know. Because I also am a strong believer, especially after having worked with so many people who are young and older in different walks of their life, folks just need to go through their own process. And so that's definitely what I did. I went through my own process for better or for worse. And yeah, I mean, I came out knowing a lot about myself, but I think for me, I probably would have taken different risks. I think that's how I would answer it most succinctly.

I would have taken different risks, not more or less risks, but just different risks. I mainly say that because, like, for example, I still wonder, like, maybe there was a sport I hadn't tried yet that I, you know, really would have loved and excelled at. I don't know. Maybe if I practiced, you know, my trumpet more, I would have actually been more successful as a musician. Mm-hmm. But but actually, you know, this is actually helping me. I think what I probably would have done is I kind of did like a scattershot approach to my time at Milton, where I just did everything as at the highest level that I possibly could.

And I think now looking back and now that I'm a dad and seeing my own kids, I don't necessarily think that like narrowing scope too much is a great idea because I think there's a lot of value in just trying stuff out, even stuff that you're not good at, especially if you love doing it. But I probably would have been more, I don't know, deliberate and selective. That probably would be the way I'd describe it about the things I decided to invest my time in.

Part of that is also just youth because when you're young, you think you have all the time in the world. And then you get older and realize, no, actually, it's a pretty finite thing, at least when it involves you or other human beings. And so, so yeah, I probably would have been more deliberate, more strategic, you know, for example, like with test taking, I know a lot of students now and I work with many students who have the aim of doing their SAT in their junior year.

I wouldn't necessarily suggest that for everybody. In fact, I really wouldn't. But I think if people have that sense of confidence about themselves, that that kind of thing would have been something I would have loved to have done earlier on in my high school career so I could just, like, come senior year, focus on applications and stuff. Rounding out my time at a place where I'd been so long, you know. And then was there a teacher or faculty member that has left a lasting impression with you? And if so, who is it and why? I mean, so many. So, so, so many.

Yeah, I think Patty Smith always comes to mind just because she was such bright light. And she also just had this ability to crack a joke where I would just be keeling over laughing and everyone in the classroom would be keeling over laughing. And she just had this brilliant way of relating to what is happening in the natural world all the way down to like the cellular level. And until I was in that class with her, I really never thought about the world in that way. And yeah, she's kind of like helped balance out like my purely humanity's brain.

And I really appreciate that to this day. In fact, this program I'm launching, a big part of it will be the natural world. We'll be, you know, doing experiential education out in the mountains and in flower fields and, you know, growing things with sustainable practices and all kinds of stuff. So, you know, that her, she's had a lasting impact. But I mean, I could talk all that, like Tareem Chung, there were a couple of papers I remember I turned in, I was very proud of, and they came back marked up a lot.

And I was like, God, and I'm a perfectionist. So when I see that, it's like a doomsday. But, you know, with enough, I don't know what you want to call it, exposure therapy, I guess, seeing where your errors lie and reckoning with that, I think is a valuable exercise. And, you know, especially in the age of AI, I think it's even more a valuable exercise. In fact, that's one thing I came into today wanting to explicitly mention is that what I really love about the environment and world that Milton has built is that it puts writing at the center of an educational experience.

Because a really wide and interesting variety of conversations. Yeah. You know, there are a lot of places where you could sit around a Harkness table and the conversation may not go anywhere. But at Milton, it was just like second nature. You know, even newly arrived students, they would sit down at the Harkness table and realize, okay, I got to bring my A game. There are other intellectuals in the room and we all have to interact in very real ways and back up what we're saying with evidence. And this is what it's all about. So, yeah, all of that is much appreciated. Yeah.

And then looking back now, what do you think is the most important skill or lesson that Melon has taught you? The first thing that comes into my mind is dare to be true. Mine is actually more, my answer to that question is more and more retrospective. Like as we enter into the current moment, which, you know, again, back to AI and everyone's talking about AI, but, I think it's not going to be necessarily the massive mover and shaker that everyone's, you know, doomsaying about, but it'll definitely shake the nest.

But I think I come back to the importance of sanctuaries for open and true intellectual thought, regardless of background, regardless of anything. Just the value and importance of institutions and places where people gather and talk about big things and don't necessarily agree and. And that's OK. And in fact, everyone's life is enhanced and bettered through that disagreement because you become clear about where you stand and what you believe. And you also find areas of overlap that are really surprising and beautiful.

And I think in today's day and age with so much social isolation and, you know, siloing and all these things, it's really important to create those spaces, especially if they're not going to naturally come through the civic space, which I don't think they will. And very rarely do, honestly. But what happens in the civic space needs to be informed and educated in some way, right? So where that happens for most people is school or family or some other institution that you're heavily invested in.

So, yeah, in my mind, I'm just like, what a special and cool place to have on Earth. And I really hope it's here for a long, long, long time because the world needs places like that. And it's in desperate need of them. Yeah. Okay, so now let's transition to your college experience. You were a graduate at Tufts University. So what was that experience like there? You know, life doesn't stop when you leave high school and then you go to college. And so I think when I got to college, I was still wrestling with some of those same tensions I described before, but it was a much bigger institution.

And I would not say that a strong suit of Tufts is that it has. You know, robust advising practice. So, you know, you might be like partnered or assigned to a professor in your freshman year, but I was not the type of student to like, frankly, see that as, a valuable type of relationship to nurture. And in retrospect, I'm like, that is the most important relationship to nurture when you're in college. And so, you know, what I want to say is like, I did well and, you know, made a few friends along the way.

But I honestly did not find my experience at Tufts to be easy or necessarily even fun at times. In fact, I found it really challenging and disorienting and all kinds of things. But again, process, like I think it had immense value in my life and I learned a lot and definitely hit the books while I was there. I don't think that like maybe something to relay to, you know, upcoming graduates is that like when you when you leave Milton and then you go to another institution, don't necessarily expect it to, have all the same things or provide the same social network or, you know, everything shifts.

And for some folks, that's very liberating. For some folks, that's debilitating. For some folks, that's invigorating and exciting. It really just depends on the person. And in my experience, Like I had a lot of fun at times, but I also really did not have fun at times. And so it was a mixed bag and a lot of ebbs and flows and peaks and valleys. But it also, by the way, it nurtured like a genuine internationalism. And that's something I have to really like commend Tufts for is it's a very international place.

And so when it came to study abroad and that whole part of one's college career, if they choose, and if they're fortunate enough to have that opportunity, like I was out of the country a lot. And so I found that to be extremely valuable. I got my foundation in Spanish at Milton. I placed out of the language requirements. At Tufts. And then while I was at Tufts, I just decided I was in a foreign language class and at the last minute decided to drop it and said, I'm going to go just live in these countries and travel in these countries and learn the language that way.

And, you know, I put it to the test and, you know, I'm lucky and it worked. So that part was really cool. By three to four years out of college, I knew four languages fluently. So that's pretty cool. Yeah. Yeah. So you said that you went out for the study abroad program. Where did you go? And did you go to multiple places? Yes. So during my college career, I lived and did different things, usually some sort of like teaching or volunteer work or, you know, something like that or just purely study abroad.

And so, yeah, I lived in a place called Ayacucho, Peru. That was my first experience living in a post-conflict zone. Ayacucho, Peru is the home of a Maoist movement in the 80s, you know, now defunct, called Sendero Luminoso. Mm-hmm. And it's also in English, that's the shining path. And that was a really eye opening experience for me, extremely eye opening, not just like the current situation in that part of the world, but also like the natural beauty.

Like it was the first time I realized that there was like something over 200 varieties of potatoes, you know, learning Spanish, learning Quechua, the Indian language there, but also digging into the history and understanding, wow, here's a part of the world that has experienced significant trauma in its history. Definitely fed into lots of things that I was interested in thereafter. Yeah. And then I also lived and worked in Nicaragua. So Spanish is very heavy there.

And then obviously like post-graduation, like I mentioned, the Peace Corps in Rwanda and learning Kenya Rwanda there. Yeah. I wish I'd picked up a little more French, but French is tough for me. I don't know why. In what ways do you think Milton helped you prepare for college? Milton's harder than college. Maybe I'm wrong, but I thought it was. Milton is, And part of that is by virtue of the fact that it's, you know, a small classroom environment, low student to teacher ratio, all that.

But I would also argue like just the types of conversations you're having with people around you and the intimacy of knowing people as deeply as you do in an environment like Milton. So anyways, by the time I reached college, I actually, you know, I felt very, very well prepared, especially from a writing standpoint. I left Milton fully like challenged, prepared for the next step. And also like with, you know, lots of curiosity about the world, which then drove my next steps in my academic life.

But you can't replicate that environment very easily. And so, yeah, I just think it's a very special place that nurtures all kinds of really dynamic young minds that are, you know, actively shaping the world, which is like astoundingly cool. Yeah. And then so you received your bachelor's degree at Tufts. So is there any point when you were there that made you want to change your major or were you set on it from the beginning? I think I changed my major like six times or something. I changed it so much that I remember one time I held the door open for a guy I asked to be my academic advisor in the third iteration of me changing my major.

And he thought that he was still my advisor. And if I remember right, he passed, when I opened the door for him, he's like, oh, good to finally see you. I, you know, you haven't been in my office in years. It's like, well, little do you know, I'm not even your advisee anymore. So this is very interesting. So, yeah, I was all over the place, but I had interests in anthropology. I had interests in foreign languages. I had interests in art history, child development.

Yeah. So when it came to coursework, I was a real mongrel and just getting it from like doing all kinds of things, everything I could. But also like the flip side of that is, you know, total generalist when all said and done. And I stuck with the English track, you know, and so pretty much that just boiled down to I like talking about ideas and I love reading and I love books and I love big thinkers. And that's pretty much it. So for me, that's what it came down to is like, oh, I could, you know, go a slightly more professional track and do the child development thing.

But am I that interested in that specific type of idea? And the answer with each field was generally no, I really wanted to be a generalist. So even with it. The field of English, I was often bringing in all kinds of different authors with different academic backgrounds and thoughts about the world, you know, scientists and social scientists and physicists and all these different people because that's who I was reading. So for me, it didn't really matter the major or the choice of it necessarily.

It was more just, you know, how I decided to engage with it. Yeah. Yeah. And then when you were in college, did you have a dream future or dream job for yourself that you wanted to achieve? No, I knew what I was doing and I knew I had interests in different places, but I wasn't necessarily set. Like I didn't have a fixed mindset about it. I actually really admire Tufts has a huge pre-med population. And I really admired my classmates who were like arriving day one and they knew that they wanted to be a pediatrician or, you know, fill in the blank type of specialist doctor.

I just, I really admired that about them, but I'm just not, I'm not built that way. And I need to experience stuff. So I need to get out in the world. And yeah, so that's what I did for, I don't know, I want to say like 28, 30 years, like basically through graduate school. And then even then, like in this past decade, I'm 39 now, turning 40 in January. But I was really fortunate to sit in a meeting with a woman named Lisa Monaco, who was a visiting professor at the time and director of national security under Obama.

I believe that was her title. But she was a very important person in the administration. She literally had the office directly below the Oval Office so that if the president needed to talk to her about an emergency, then they would have immediate contact. And she's just a wonderful person. And, super knowledgeable about the world and thinks about things very differently, I find, than lots of other people. So anyways, I sat with her in this meeting for, I don't know, a little over an hour or something. And her resounding advice to me was just like, go do everything.

Like, you're now, at the time I was 28. And by the time I graduated from graduate school at New York University, I was 30, if I remember correctly. And so she was like, this next decade, just go. Now that you have an idea of where, you know, the general guidelines are for where you want to go in your career in life, which was education. I had this really eye-opening conversation with someone who was a real heavy hitter, and it shaped a lot of how I thought about the world.

So that's what I've been doing for the last 10 years. And eventually that led to me doing my own thing because I, you know, I worked at charter schools in the U.S. and Colorado, and then I, you know, worked at international schools, you know, and different just public schools in different parts of the world, whatever. So after doing a bunch of that, I was like, you know what? I still have a lot to learn, but I have enough in my background now where I really understand this practice of teaching and what it really looks like at a high level.

And I want to bring that to market on my own. So yeah. So now I've been running my company for almost six years and have really loved it because it's connected me with all kinds of interesting people and given me the opportunity to help them in their own journeys. Yeah. Yeah. And then. So, are there any lessons that you have learned from your entire school experience that you still use today? I hate to come back. I'm going to say, dare to be true. Because, like, literally, I think that's in the ethos. It's embedded within that is this searching for who you really are and what you're really about.

And so, yeah, I mean, that's what I've been pursuing my whole life. Like, who am I and what am I about? And how do I want to impact the world? How do I want to impact the people around me? And so the answer for me is want to help bring people together and help them see the world through different lenses and challenge their thinking on different things and also be a place where people feel accepted and heard. Yeah, so I think that's it for me is just this like drive to keep looking, searching, honing, crafting a very like a very deeply embedded growth mindset about what a life well lived can look like.

Yeah. So now shifting to your professional career, what made you want to go into the tutoring and educational business? Great question. Whole classroom instruction is very interesting on its own terms. But really with that, it's about, you know, tracking and being data driven, looking at the whole, but then also the individual within that whole, meaning the collective, the class. But it's a very, very, very different experience. And I first started to really tutor, like lean into that part of my work when I lived in Colorado and I was working at a charter school and I would do it in my off hours to make money, make more money.

But, but more importantly, I did it because it was one of those experiences where I could sit down with a kid for an hour. I would find that I was sitting with a kid and working through a concept and especially in math, because my specialty is actually math K through eight. Singapore math, I found that there was just this abundance of aha moments for kids. And as a, like very selfishly, truly as an educator, it just felt so good to teach something. And then in real time, see the impact that it was happening.

And then the pride that a kid would feel having mastered that skill. Yeah. Yeah. And, oh, you've taught in Africa, Europe and the U.S. So what was different in between south america and south america so. What was different between central america so like everywhere yeah pretty much every i gotta i gotta age is huge but i gotta go to asia and then maybe osinia and antarctica if that's there you go teach some penguins in the south so, i mean the answer is everything and that's what i found so fascinating everything is different but also there are things that are called like high impact teaching strategies or best practices, that kind of thing.

So what I found is that the cultural context in which you were operating was radically different wherever you were. Much of the time, the families and the students had the same baseline concerns. But at the same time, yeah, the way that that would manifest culturally was very different depending on where you were living and teaching. But also to go back to it, the most fascinating thing to me was you could be anywhere in the world and And high-impact teaching strategies have immense value.

And they're also easier said than done. It's like one of them, if I remember right, is like you should be asking a deep question every something like 10 to 15 seconds. You become more aware of what the tools are that actually work. But then your delivery of what that tool looks like looks very different depending on the cultural norms and cultural context. Mm-hmm. But yeah, it's fascinating living and working around the world. Love it. Yeah. And then so you have your own business at Penhammer. So what made you want to start this business and what were the challenges you faced along the way?

I mean, like I'm a bootstrapped entrepreneur. Like I the thing is, OK, you know, you know, Murphy's Law, anything that can go wrong will go wrong. And so it's more important that you persevere, take note, improve, stay flexible. But you name it. I mean, everything. I mean, my move to Portugal permanently, that alone, the number of like regulatory hurdles that I've had. I mean, I'm opening another business here in Portugal. So now and I'm working as the director of a center that I'm opening to.

And so like with every project, my confidence in handling what comes up grows, but also the experience. The expanse of the unknown and what can actually go wrong, according to Murphy's Law, also expands. And so back to your original question, what really drove me to, this type of life is that after working for enough places and people, I realized that I wanted to be my own boss, but I also wanted to create a really special place for learning and a really special place for teaching.

And so that's what I'm planning to build now. And what I'm finding as I work through this this project or projects that the baseline factor of success at least when it when it comes to education outside of like good teaching practices and creating in a beautiful environment and you know nurturing social connection all those things right but another part of that is that i think i think that a huge part of relationship building is really getting to know.

A student on their own terms and and giving them the space and listening actively enough that they know you deeply care, which I do. And it's through that process of establishing that type of trust that I think everything else is built on. And I say that because, you know, I've worked with kids who have had small bumps in their SAT scores, or I've had kids who have had huge bumps in their SAT scores. I've had kids who always struggled in their academic careers.

But what I've found, and actually this happened, I'll give you a really concrete example. Two or three weeks ago, was hired to go and teach this kid in person about the SAT. And kid was refusing to get out of his bedroom even and to come and meet with me. Stepped away, said, hey, I'll wait here, you know, come out when you're ready. Eventually he came out. And the shocking thing, Eileen, was that if you had to guess like how much of that two-hour session, by the way, how much of that two-hour session was actually dedicated to the SAT, what would you guess?

Like 30 minutes. Yeah, probably literally 20 to 30 minutes. The rest of the time, the other hour and a half, the kid was actually crying, deeply sobbing. And I felt very sorry for him and was just telling me everything about his life and world, about what he was not happy about and what he wanted to have different in his life and what he really appreciates and where his true interests lie. And that's what really drove me to this work is like having enough of those conversations and seeing how much of a deep impact it has on students that I just love, love, love doing it.

And, you know, case in point, I left the mom and dad were like, hey, tell us about his scores. And I very like I gave them a cursory explanation because I really wanted to lean on the point that like that's not really what's important here. And that's not what happened. And then a week later, mom followed up. Hey, just so you know, this is what happened during that session. And immediately just like a whole world opened up where she's like, wait, what? My kid is going through all of that? Oh my gosh, please, please, let's talk more.

I need you to help my kid. And I don't think that comes from nowhere. Is really what I think that comes from like a deep, sincere need on the part of parents and teachers like me and, you know, hopefully friends too, who see a person and they're like, that person could really benefit from, an outside perspective and a little guidance. Yeah. Yeah. So then what has being a CEO taught you? Keep things extremely simple, as simple as possible. Complexity is often your enemy, not always, but often. And then obviously back to what I said earlier, the irony of it is that a lot of my job I would define as making complex things simple.

Simplicity is your friend and complexity is often your enemy. Okay. And then some say that teaching goes both ways in the sense that not only the student learns from you, but you also learn from the student. So is this true? And what have you learned about yourself as an education specialist? Great question. Oh my God. I've learned that I'm trusting to a fault. And what I mean by that is that I operate from a place and I will continue to do so, by the way, I might be a little bit more like gather a few more data points or be a little bit more aware in certain ways now.

But as time has gone on and I met with as many students as I've met with, yeah, I know this about myself that if you tell me something, I believe it. And I continue to believe that that's the right approach because I really, really think that the baseline thing, the thing of most value and importance is that baseline understanding of trust. And so if a student decides to violate that trust in any way, that's their decision. And you as a practitioner and an adult is just to be like, okay, noted, Now what do we do?

I've really been bitten in the butt a few times with that approach. But it's also, I think, in turn, like reinforced that intense feeling of value that I have around that, I don't know, that principle of like, I refuse to not take kids at face value in what they tell me. You know, for better or for worse. Yeah. Yeah. What do you think is the key to success in balancing work and a social life? Key to balancing work and social life. That's such a great question, especially post-COVID.

And also, by the way, as an entrepreneur, because I now lead all these different projects. I am the point person. I am the person who people go to and say, oh, what do we do here? It's so important to be deliberate and purposeful. If you're not going to be deliberate and purposeful, then you are immediately gaining yourself the opportunity to be fully present. And presence is the thing, is the most important thing. I would say in one's like general life and also in their in their work you're more efficient when you're present in your working life and you're more emotionally in tune in your own life at least i am with my kids when i say okay now is the time to be with my kids for example phone in the other room computer off in another room i'm with my kids that's what i'm doing and every time i find that like there's bleed there or like the i break that rule or stretch it it is just not it's just not how I would like to live.

So yeah, I think, again, a lot of it has to do with establishing with yourself where your personal boundaries are, and then carving out time and being purposeful with your time so that you can give everything the energy that you want to and you believe it deserves. Because otherwise, we're all just scattered. And I see this as someone who's deeply knowledgeable about this topic, because not only am I a teacher, but I suffer from ADD. So much of my life is corralling my attention.

And then once I actually sit and have attention, I have great attention. But corralling attention is a challenge for me. So it's even more important for me to be purposeful. Yeah. And then so... I know we touched on this earlier, but in the age of AI, for you as an educational specialist, do you use it at all? How do you use it? And what do you think will help us or not help us in the near future? I see it purely as an efficiency tool. That's it. I would say that I'm moderately savvy with AI.

I'm not nearly as savvy as some other people I know. But for example, with the school that I'm opening, much of that would not have been possible without AI. Because it's an efficiency tool. It helped me do things in a very, very, very efficient way. They're very true. Because you can prompt AI, but it can't read your mind. And yeah, so I think, so for me, as an educational practitioner, I have a very clear line in my mind between the age of 16 and younger, or even maybe 18 and younger, and 16 and older, or maybe 18 and older.

I'm leaving that two-year window because I don't know exactly where the literature will land ultimately. But if, you know... Technology in classrooms to date has been any like guide or indication about what AI would do in an educational landscape. It is not anything positive, truly. It's going to be a massive waste of money for all these institutions. It's going to create a generation of people who maybe can't think critically because they don't need to have an attention span, even if they want to have an attention span.

So yeah, what I really hope is with AI is that it's like the opening up of like another level of human intellect as opposed to a dumbing down and a like an intellectual crutch for people. And I think that brain development has a lot to do with that. And I'm very lucky because I was born in 1987. I still remember a time before computers, at least before they were like abundant and prevalent and everywhere, ubiquitous. And so, yeah, I think there's immense value in like a low tech or no tech, depending on one's, you know, upbringing for quite a long time.

And I think, honestly, a lot of countries are coming to that conclusion and banning things like social media because they're realizing it's addictive nature. So I don't think AI is any exception to that. Adults and practitioners, it's an immense tool for doing a lot more, much more efficiently. And for everyone who is, again, 18 or 16 and under, I would highly encourage them to know what it's about and what it can do. But I do not think that that should be at all a focus. Definitely not.

But maybe even a part or aspect of your true educational career. I think you're doing yourself a huge disservice in the long term. Yeah. So good question. Yeah. And then so finally, if you had one message you would like to share, what would it be? One message I would share. I think I just underscore the value of curiosity and exploration and like that old adage of not all those who wander are lost, you know? I think that's so true. I think we need to place more value in our lives and society on, I hate to say it, but like inefficiency, like daydreaming, imagining, being somewhere else mentally.

I really do believe that there's immense value in creativity and imagination. And I think that those things are mostly nurtured in what my dad would describe as the fertile void. So like there's maybe nothingness like, oh, I'm bored. That's the classic example of that. Right. Think something up. Imagine why not? It's within your powers. Another thing my dad used to say to me growing up, oh, I'm bored. Oh, I thought you were smarter than that. Right. Like there's so much to this world that I think that there's like a seriously understated value in doing nothing and seeing where your brain goes.

Yeah, yeah. Okay, so thank you so much for your time and have a great evening. You too, Eileen. Great to chat. Thank you.

Transcript supplied by the publisher with the episode.

Podcast

Stang Stories

Teddy Ellis · Society & Culture · English

A platform to engage Milton’s students and alumni through conversation.

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