Transcript: Mr. O’Brien on Mindfulness, Literature, and Guidance

Good morning and welcome back to the Late Star Show. We're here today with Mr. Kevin O'Brien, an English teacher, coach, and mindfulness advocate at University School. How are you doing today, Mr.

O'Brien? I'm good. It's an honor and pleasure to be here with you guys. That's great to have you on the show.

Well, with all of our guests, we'd like to start at the beginning. So can you tell us a little bit about where you grew up and what your childhood was like? Yes, I feel like David Copperfield. I'll spare you the long version, but I'm a Cleveland native, born and raised in Cleveland.

I lived in Russell, and then we moved to Gates Mills for first grade through sixth grade. I had great teachers there that still inspire me to this day, and then I went to Mayfield Middle School, and then I was fortunate enough to have an opportunity to go to Phillips Academy and over on a full scholarship. So I had great teachers and coaches there that really inspired me, inspired me to become a teacher. You know, especially when you were younger, was there kind of subjects in school or certain topics that really just kind of were interesting to you?

I always loved to read. We didn't have cable television or all the entertainment that most families even at that time had. So my dad was a big reader. My mom's a reader.

My grandmother, my mom's mom, always gave us books for for holidays. So I love to read. I still remember the March of Dimes reading competitions in elementary school. And, and my uncle would give me a quarter for every book I read.

So I read a lot of books. And, you know, in elementary school, I loved everything. But I will note, um i think my strong suit at that time was was math and and i was very competitive with a good friend of mine uh zubin kombata and we worked our way through the eighth grade math book when we were in sixth grade it wasn't bc calculus or anything like that but i think that friendly uh uh rivalry um to have someone to work through uh math problems with was was one of the the keys to success there and and also i loved uh the performing arts in elementary school and and sadly when i got to middle school uh that uh the ability to to do uh shows and singing and choir and we did a lot of talent shows at at kate smills uh elementary and my mom coordinated a lot of those as a uh former dance teacher uh at lake erie college and and that was that was something that was a part of the community culture that they fostered, performing arts. And I think one of the great things at U.S. is that kids can be in performing arts, visual arts, and be an athlete and not be just one thing, but live their passions out in all arenas.

You know, Mr. Bryan, you kind of touched on it a little bit earlier, but you had that opportunity to attend Phillips Academy Andover for high school. What was kind of your path to that? And do you remember some of your early moments at high school?

Yes. And there are countless moments, just sort of the origins to where I'll never forget. In fact, in eighth grade, competing against university school in soccer. And I competed in soccer, basketball and track against U.S.

And I still remember some of those matches and races, games. And U.S. boys always seem to be a little taller, a little stronger. And I was a public school kid. And I remember, I think we lost and a lot of my eighth grade buddies had gone off to play football because that was the cool thing to do at that time.

So I was out there just scrapping. And then I remember the U.S. coach at the end of the handshake line kind of spun around and said, hey, where are you going to school next year? And you ever think about university school? And I looked up in my little arrogant 14-year-old self and said, I'm going to Andover.

And he's like, oh, did you apply? I just said, I'm going to Andover. And I kind of kept, you know, like I'm not going to US. But I had two uncles who were fortunate.

My mom came from a large family of seven kids and I had two uncles who had gone there in full financial aid. So when my dad had some financial difficulties, the silver lining, my uncle said is, look, you can get a full ride there. And I did. So when I showed up at Andover, I was still this kid from Ohio with a little bit of a chip on his shoulder perhaps and and like I said I was very competitive academically and then I got there and I said well and I think a lot of students at university school who might have breezed through middle school arrive at U.S. and and they realize that they're surrounded at a table with with brilliant competitive, talented young boys or young men or boys becoming young men.

And that can be intimidating. And that I certainly was at Andover at that point. There was no no singing for me. There were too many talented actors and singers.

And so I tended to be quiet at Andover and and did my best to to just keep up with the competition there. And when you're at a school with 1,200 students from all over the world, it was a real honor and a real gift to have that world-class education. So I'm grateful. And a common theme for people who go into education is that they had some mentors or people who guide them along that way kind of towards that path.

Were there any teachers or mentors at Andover that really stood out to you and guided your path? Absolutely. I think of my freshman year, my English teacher, Seth Bardo, still remember the book, still have some of the books, same exact copies. My house counselor was an English teacher, Paul Cockstein, who was the head lacrosse coach.

He was a scholar and a gentleman. he went to Princeton for undergrad and had his masters from Yale. And this, I mean he I put him on a pedestal to this day and he could quote Shakespeare and Milton at practice seamlessly in a coaching point But you know there too many teachers to list My soccer coach was my calculus teacher my senior year, and I sat at his kitchen table, and he helped me through calculus. And so important at U.S. or any school to develop those relationships outside of the classroom, and takes a lot of courage to ask for help. And sometimes I was a stubborn wouldn't ask for help but my coach would say i'll see you at the table tonight and i would show up or i would meet my uh you know teachers uh at breakfast uh at boarding school so at us we try to pack a lot in so i encourage students uh to to find time to to meet with their teachers outside of class because that made all the difference in my experience you know throughout high school you also play lacrosse and then later you went on to play lacrosse at the university of pennsylvania right what position did you play when you started and how did you kind of end up on the team at penn and what was really that kind of transition look uh it's it's a long story like a lot of stories are um but great question and i was a baseball kid growing up in mayfield uh i i mentioned i did a lot of different sports uh in middle school and then uh soccer i got cut from the jv i was on the freshman team, basketballs on the JV2 team, and then lacrosse.

I knew I was going to play baseball with the travel and all that in the summer when I got home after freshman year, but I wanted to try lacrosse to my father's chagrin. But, you know, part of the story was baseball tryouts were rained out, so I was like, I'm going to try this. And I went out there. I had never worn a helmet before.

My dad said I was too skinny to play football in middle school, and if you want to play in high school, so be it. But then I got better at soccer. But I think a lot of those different skills, you know, the hand-eye in baseball and then the endurance of running the mile and 800 and track, those types of, you know, the basketball, it's basketball with sticks. So I always encourage athletes, particularly basketball, soccer, hockey, like just that, you know, there's lacrosse brings a lot of different skill sets.

And what I love about lacrosse is you don't need to be tall. You don't need to be the biggest. You don't even need to be the fastest, but if you have good hands and good instincts and do the work, things pay off. So in high school, I continued to be a multi-sport athlete.

I was a soccer captain my senior year. And my sophomore year, I had an injury. I lost that whole season after making varsity. Coincidentally, I'm still grateful to coach Brian Teeple at university school, who welcomed me to the spring break Florida trip with university school.

So part of my history and my gratitude is I played with, I graduated in 92. There were a number of great U.S. players that challenged me that spring break and still connected with. But then I even did pole vault my sophomore year, wrestled my junior year. But lacrosse, when I got to college, to answer your question, I was a midfielder.

And then within a few days david petromala who was an all-world defenseman sat me down and switched me from midfield to defense and i was a little heartbroken i i took it personally as i shouldn't have but i was very grateful and still grateful to coach petromala for for just the one year we had together my freshman year and penn i mean as all of our listeners know is a very academically challenging place like andover was how did you balance those demands with athletics and academics uh it was it was challenging it was really beyond challenging at times um i just was reminiscing a little bit uh today with mr garrett um i i thought um i would be pre-med uh that shortly that bubble popped um my uncle had gone to penn and and gave me some nice advice he was an orthopedic surgeon you say just just take chemistry and calculus and that wasn't for me um but i was an english major and i was one of two english majors uh in my four years at university at um upenn and um i had a lot of buddies uh who would ask me what are you gonna do with that um which is a common question for uh english teachers or english majors and in the back of my mind i had these great english teachers so That was something I thought of, but the the real demands of college. I was a work study student on a lot of financial aid. I was very grateful to be there. But I worked in the library 20 hours and, you know, just my college coach said you could be two.

You could do two things in college. You can have a social life and do the fraternity or academics or you could do lacrosse. So you have to pick two of those three things. And for me, I played all four years and I was fortunate to stick with it through a lot of injuries and ups and downs.

And I'm proud to say I'm part of that program. I was a captain my senior year and you didn't see a lot of kids from Ohio playing Division One lacrosse at that time. So a lot of a lot of grit. But I had great friends and there were friends and upperclassmen that encouraged me at my lowest point.

So I still remember some of those conversations when I was at my lowest. So it was hard to balance all that. So forgive me the long-winded answer, but it's a commitment. Yeah.

And then moving on to after graduation, you became an English teacher. I know you taught at WRA, and then you also coached lacrosse there and then transitioned to US. Can you take us kind of through that journey just of after graduating up until this point? Yes, and it was certainly an odyssey.

After college, I was asking a lot of big questions as to what is next. I spent some time in New York City working both at a hedge fund and then working in film production. and then 9-11 happened and I was downtown in Manhattan on my way to work at a film house in Tribeca. And we all know what happened that day and I witnessed a lot that day So that changed the trajectory Our offices were closed for two weeks Being assistant to the president of a film company didn't seem as glamorous as it did two weeks before that. And I gave notice.

I ended up moving to Miami briefly to work with a friend of mine from from high school who was inspired by Hoop Dreams. and the book Friday Night Lights, who was an Andover grad. And I worked as his assistant. I held the boom mic on Friday night games in Miami-Dade County filming. And it was the interaction between the teachers and coach, the players and coaches.

And then I reached out to some people who I worked at camp in New Hampshire for five summers. And I had some great mentors there. and before I knew it I was the head lacrosse coach at a small school in Potomac, Maryland. I was there for four years, four seasons as head coach and then I was at Western Reserve for eight years and I loved my time at Western Reserve Academy but eight years at a boarding school it was time for a new challenge. So I moved to Episcopal Academy for a couple years.

My dad passed in my second year and and wanted to make a change and then i was at the hill school for three years until eight years ago an opening opened up at university school and i came home so uh five schools over 23 years and first time at an all-boys school but it's it's it's it's a special time and i think it's a great time to be at university school so i'm excited do you remember some of those kind of first days teaching at us obviously we've heard a lot of teachers kind of talk about some of those moments but obviously you're a pretty experienced teacher coming into us were there any surprises or just new things that you had to learn on the fly yes and and i think um still learning the the competitiveness between you know students at university school and a boys culture um having worked at a in a co-ed environment um i experienced some not to stereotype or centralized boys as you know maybe sometimes a little reticent to participate so i noticed right off the bat i'm like wow these boys are really engaged and and and then i realized like they don't stop talking uh whereas some of the boys uh in previous experiences might have been a little bit more uh preserved uh so it was um a curiosity here with boys um and and i think the values here at university school uh taking their work seriously uh for the most part and and then instilling that sense of responsibility uh i think there's a a true sense of loyalty and and brotherhood here uh that they're trying to help each other um they'll give each other a hard time at times but uh i think there is a um you know a wonderful culture and i think of culture as it's cultivating those values and practicing those values, not just preaching the shorthand RLC. But I think there are a lot of pros and cons to every school boarding versus day, but I think university school offers a boy to be his full self and to try things and take on a lot of challenges like you guys both do in all all aspects of your your careers um you know what do you find kind of most unique about teaching specifically later as you start practicing mindfulness really a lot more what is kind of mindfulness connection with english and how did you really kind of get into mindfulness uh there's a lot of ways i can answer that and that's a that's a wonderful way of asking that question. I think of mindfulness more as a practice. It's an action of stepping back without judgment, observing, taking a deep breath, pausing, and then offering some space between how we respond to something mindfully versus how we react emotionally so i think we have you know culture of hot takes and this that and the other uh so just to to look at um literature um with emotional intelligence to recognize what is this character feeling what does this character need what is in the way of what they need how are these feelings manifesting because these needs are not met i think there's a lot of great critical thinking that you can do with some ability to recognize and understand what's driving the character.

And then more importantly, how that relates to our own stories. The story I'm telling myself feels real, but is it true? I'm not going to get into college. I hear that on the weekly after a bad test or a bad quiz.

And it's not, that feels real, like honoring, you have permission to feel that, but so that discernment, you know, that feels real, but is it true? So that's a question I ask. The story I'm telling myself right now, is that helping or hurting me right now? So these are questions I try to instill with journaling as a mindfulness practice.

I like to say sometimes you have to write to figure it out. And I think of writing as a way of downloading all these stories that we have in our head and then gives us some space and, you know just to kind of vent paper is more patient than people says Anne Frank so that's something that I like to you know instill in students is that reflective practice I like that and especially now in our current state of things with technology in the digital world and social media it seems there's less and less time to kind of think and just be present so what do you try What do you think is important, especially now, for us to just focus and be present? Are there ways that we can do that? And what is the importance of that in today's world?

I mean, it may be everything. What makes us human? And the word discernment I think is one that I really embraced Particularly let say with AI large language models generate language this this sounds real but is it true just as we spin stories in our head that feel real but are they true and I think in a need you can get a product very quickly from technology from AI but I think it's more about the process how we get there how we listen and communicate I think this conversation is a testimony to storytelling, to asking questions and listening. But with mindfulness, I think part of it is slowing down to step back and ask, what do we want?

What do we really want? Is it just to get the job done? How are we going to enjoy this practice? us, how we're going to find joy in this work. And this is a school that designed for challenges, designed, you know, kids are going to struggle here by design.

And how do we kind of embrace that process with resilience and grit? And I witness boys do it all the time, especially over four years. And I'm really proud of the graduates. And how have you seen the technology and social media impact?

Because you've been teaching for a you've seen before that world and now. How have you seen it impact your students in the classroom and is there space for technology and AI in education? What would that be? I mean, that's the ultimate question probably.

And I think we're gonna have to work collaboratively to figure that out. And I think of integrity, is this your story? How are students really honing that skill of telling their story with authenticity? And I think we have a responsibility to prepare students for their future.

So consideration, these are practicing school values and preparing students for an AI. I think mindfulness does have a place for it because we are so quickly socially media conditioned. You know, everything is coming at us. And I think we have to be mindful of the neuroscience of cognitive load.

We are inundated digital dementia. And to keep it very simple, I come back to this idea of learning equals attention plus engagement and memory. So I ask, like, what are they going to remember? okay are students engaged and do i have their attention and fighting for attention and attention economy is really hard as i'm trying to have students engage with books and reading and the hard work of writing and revision so um it's daunting um but i think we got to kind of come to the table and have that conversation you know day in and day out you know you kind of talk about this reflection piece but obviously you must have reflected on what kind of success looks like and especially succeeding over what kind of challenges and large challenges in everybody's life so looking back over your time what does success really look like to you and how do you kind of measure it uh that's there's a lot of ways to answer that question depending on how you define success and when i when i meet with uh a young alum especially when they you know they're back from fall break how are you how's it going and i i hear them there's great energy um and i like to ask are you prepared do you feel prepared oh i'm so ahead of my peers and i think even students who have struggled here and because they've struggled here they are prepared for what's next you know so you know not that college is going to be easy and some feel it's easy but i i think there's a lot of things that students have to do here and then when they get to college they have the tools so they can be successful in what they get to do what they choose to do i know there are a lot of things you rather not do um and feel you have to uh having this conversation i hope it doesn't become a chore and what you've given to this community is a real gift and having these stories as an archive. But, you know, to be successful, you know, at the end of the day, you know, it's a sense of, you know, you've done your best and that's about it.

You know, do you kind of have a favorite quote or motto or some sort of line that you really live by that really kind of guides you in everything that you do? I guess one I like to offer, and I probably say it too much, and it comes from a great book by Oliver Berkman. We have a finite amount of time, attention, and energy. So best be mindful is my addition to it.

So to make good use of that time, because just like that, the bell is here. You know, we always end with our one question. What is your why? obviously being kindest leader in reflection introspection you must have had time to thought about what was the driving force behind everything you do whether it's on the lacrosse field in the classroom or just your day-to-day what's really the motivation that pushes you to truly become someone that's been just such a mentor and role model to so many here uh there's a lot of simon and say next you know why you know start with why and I would just say um to be kind and that's um something I fall short of so I share that with humility and we get frustrated and down but like my why is like life life is hard um but students here can do hard things and I remind them that almost on the daily um so you know I I think we have all loved and lost loved ones um so my why is just honoring the teachers i've had uh the coaches um my family um and that's why i do what i do well mr brian it's been great having you on the show today thank you so much for taking the time to share your insights and experiences with us and to our listeners thank you so much for tuning in and we'll hope you'll join us next wednesday for the next episode of late start show thank you mr brown thank you both and it's a real honor thank you