Student Leadership

About Jason Kupery

Jason Kupery (@jkupery) is a Director of Learning for the Palliser School Division which serves students and families in both Southern Alberta and the city of Calgary. Jason is in his 23rd year in education and has worked as a teacher, vice principal, principal and director in his years in education. Beyond his teaching role, Jason has been heavily involved in coaching, both in the school and community, as developing and encouraging young athletes is one of his passions.

Jason believes strongly that a strengths based approach is the key to developing young people into their future potential. Students need positive influences in their lives that will not only teach them, but shape them into who they have the potential to be. Jason is dedicated to helping students find where their “deep joy and the world’s deep need meet.”

Connect with Jason: Email | Instagram | Twitter

Listen Now

Listen to the episode now on Apple Podcasts, Spotify, or on your favourite podcast platform.

Resources Mentioned

Palliser School Division (PSD)

University of Victoria – Teacher Education Programs

University of Calgary

Mentorship for New Teachers – PSD

The Transcript

**Please note that all of our transcriptions come from rev.com and are 80% accurate. We’re grateful for the robots that make this possible and realize that it’s not a perfect process.

Sam Demma (00:03):

Welcome back to another episode of the High Performing Educator podcast. This is your host and youth speaker, Sam Demma. Today’s special guest is Jason Kupery. Jason is the Director of learning for the Palliser School Division, which serves students and families in both southern Alberta and the city of Calgary. Jason is in his 23rd year in education and has worked as a teacher, Vice Principal, Principal and Director in his years in education. Beyond his teaching role, Jason has been heavily involved in coaching; both in the school and community, as developing and encouraging young athletes is one of his passions. Jason believes strongly that a strength based approach is the key to developing young people into their future potential. Students need positive influences in their lives that will not only teach them, but shape them into who they have the potential to be. Jason is dedicated to helping students find where their deep joy and the world’s deep need meet and intersect. I hope you enjoy this insightful conversation with Jason and I will see you on the other side. Today we are joined by a very special guest virtually, who was recommended by another past guest; Joyce Sonata. Today’s special guest is Jason Kupery. Jason, thank you so much for coming on the show. Please start by introducing yourself and telling everyone a little bit about who you are.

Jason Kupery (01:22):

Hey Sam. Thanks for having me. Appreciate it. Happy to be here. Yeah, so as Sam said, my name is Jason Kupery and I’m a director of learning with the Palliser school division in southern Alberta. We have some schools in Calgary, and we have lots of schools in southern Alberta as well. And yeah, I just, I’ve been an educator for 23 years now. All of my time has been spent in high school. In high schools I was a teacher. I’ve been a Vice Principal, Principal, and now a director. And a large part of my responsibility is looking after high school programming, and another big rock in my portfolio would be health and wellness as well. I shared that responsibility with another colleague in my school division. And so it’s inspiring young people and seeing them grow and seeing them do that in a healthy way is definitely a passion of mine.

Sam Demma (02:20):

What got you interested in education? Did you know when you were a student, when your teachers would ask you, what do you wanna be when you grew up that you wanted to work in education?

Jason Kupery (02:32):

Yeah, that’s a good question. I always knew that I wanted to be I’m one of those weird people that is <laugh>, identifies as introverted. Okay. do like the, do like the idea of being around people and being of influence. And so when I went to school I was big into sports like yourself. and I went to, I, I grew up in Ontario and so I went to university to play football. Nice. and essentially that’s the only reason I went to university. other than, you know, there wasn’t a real academic pursuit at that time in my life. and I heard somebody else the other day say you know, I wasn’t always the greatest student and I did get myself into a bit of trouble. and, you know, those, those skills I honed around that sort of shenanigans in my life certainly made me a better educator cuz, you know, down the line you’d have kids trying to use things on you. I’m like,

Sam Demma (03:23):

I know this <laugh>,

Jason Kupery (03:24):

I don’t think, I’m not sure that’s original. I know you’re, and here’s how I know. Cause I used that once. Yeah. and so, yeah, I think it did prepare me to be a better educator. So I went, played football didn’t get a whole didn’t get a far away with that. cuz I wasn’t going for the right reasons. and so I sort of hunkered down and went to transferred schools. I stopped playing football and I got a little more serious about my my studies. I actually became a financial advisor for a while given an opportunity I had at the time of my life. But again, still knowing that I wanted to do something different. And I eventually moved to Victoria and the University of Victoria had an awesome teaching program, and I knew at that point that I needed to apply, and I was lucky enough to get into the program and had a wonderful experience there. And the rest, as I say, is history the last 23 years, I guess, have been going, going well ups and downs. And but I do love the idea, or sorry. I love being an educator and the idea of speaking to kids lives.

Sam Demma (04:38):

Victoria’s a beautiful place. I, I was there in August and behind one of the residents buildings at Vancouver Island University. There’s a bunch of wild black berries that grow. I don’t know if it was the same at Victoria University, like near or around campus, but I was just losing my mind. You can go to school and then fill a bucket of blackberries for free <laugh>, it’s,

Jason Kupery (05:02):

Yeah. No, they’re everywhere on the island for sure. Yeah. It’s a, it’s a beautiful place. I, I met my wife there and she grew up there her entire life, and she wanted to get off the island. So that was I’m, I’m now in southern Alberta in the beautiful rock. So no complaints.

Sam Demma (05:18):

So from your transition from Victoria to here, tell me about the different roles you’ve worked in education at different stages of your careers.

Jason Kupery (05:28):

Yeah, so I started out as a, as a junior teacher of course. And my first job in teaching, I had you know, you have eight blocks in a four by four traditional schedule. Nice. I had seven different preps, so I taught everything from English 7, 8, 9, 10, 11 to and so it was it was a good year. it was a busy year but it helped refine me because you have to you have to learn how to multitask no question when you’re in the classroom, of course. and it keeps you on your toes when you’re preparing for so many different subjects and things like that. So it was a wonderful time in terms of the education that I received and, and the lifelong learning that it instilled in me. but it was a lot. And of course, I also coached volleyball, basketball they had a, they had a, a floor hockey team I coached there you know, led some trips and, and those kinds of things.

Jason Kupery (06:23):

And it was wonderful because again, it’s one of those things you mentioned earlier about, you know, your vocation and your passion and that coming together. And I, that certainly solidified that. And I know for a lot of teachers it has a high turnover rate in the first few years because again, that’s a lot of work. And if you’re not totally committed it it may knock you right out of the, out of teaching altogether. Right. Mm. and I found, for me, that was refining that for me, that was, yes, this is where I need to be. this is a great deal of fun and it’s amazing interacting with young people who are learning and they’re awkward and they’re silly, and they do some really dumb things, to be honest. And you get to be Yeah, I, I can help you with that because I did those exact same things. So it’s kind a neat thing for sure.

Sam Demma (07:11):

What is, sorry, continue.

Jason Kupery (07:14):

Oh, I was just gonna say, and then after that, I, I, we moved here to I, I’m in Calgary. we moved here and just progressing through the you know, continuing to do that. You, you find a new space, you’ve grown more, you’ve teach different subjects. And I just always had it in my heart that I wanted to lead. Yeah. and I had I, that, those giftings were identified in me. I was very fortunate to have some wonderful mentors and people in my life who identified those gifts and said, Hey, you need to think about this. and so I went into to administration and then eventually to a principal role. I completed my masters at the University of Calgary, I think in 2012. I was finished. and then was, was administrator in high school. And then of course, now I’m director of learning for last seven years. So that is my progression.

Sam Demma (08:03):

When you think about the mentors in your life, I’m sure there’s so many, but are there any that had a really significant impact on you that you still stay in touch with and are in communication with? And if so, what did some of those mentors in your life do for you that had a big difference?

Jason Kupery (08:21):

Yeah. So for me that, that goes quite quite a ways back. And so I was raised in a single parent home with my mother and we didn’t have a whole lot and I didn’t have a lot of positive male influence my life at the time. And so somebody my mother worked with one of her friends at work was, she was just mentioning that to her at work, and she said, oh, my husband can come by and, and take him out and, you know, hang out with him for a bit. That’d be, and, and so that was arranged, and I think that was back in, I’m dating myself here, but that was probably back in 1986, 87, oh, sooner three maybe. anyways. And so he, that mentor is still in my life. He is grandpa to my kids.

Jason Kupery (09:04):

 he helped he helped me along the way. and so that was a very significant obviously mentor in my life and now like a father. so that was the real blessing. And along the way he’s helped me on a number of occasions. so that’s the major one. But in terms of my, my career there have been so many people that have just been, you know, when you, when you see people that have something you don’t whether that be wow. Wisdom when you’re young, right? yeah, yeah. Or just the way of dealing with people or like a, like a sober second thought, like, hang on a second, have you thought about this? Because my personality is one that, hey, we gotta get this done and I’m just gonna, you know, put my head down and charge through the plate glass window kind of deal.

Jason Kupery (09:50):

Right? And we’re gonna get it done. and there’s been so many wise people in my life that have said, hang on a sec, what if, what if we did this way? Or, or, why don’t you try and just slow this thing down a little bit so that you can help other people catch up? Right? Mm. or, you know, you proceeded too quickly and now look at what happened. You created a massive mess, and now we’ve gotta go clean it up. So what did you learn from that? Right. Which is the big thing. And so the most, the most positive people in my life have, have been the ones that, cuz I’ve made plenty of mistakes haven’t, you know, pointed a finger and screamed and, or shouted or abandoned me or whatever. They’ve said, Hey, look, that didn’t go well. So what did you learn from that? And if there’s anything that I can try and help other people with in that regard, it’s that same thing. It’s like let’s get out of the guilt and shame kind of cycles here and say, yeah, everybody screws up and it’s an important lesson for you to learn, whether you’re one of my students or whether you’re a colleague or whether you’re a friend yeah. That, that didn’t go well. So what can we learn from it and how can we how can we move on in a positive way? So,

Sam Demma (10:49):

Hmm. That’s such a good reminder. I feel like sometimes when we make a mistake, we beat ourselves up for it for way too long. I, as you were explaining, that situation reflected back on one of the biggest mistakes I made in my career, speaking <laugh>. And it was when I was just starting, I was 17, and at the time, I wasn’t using a calendar to keep track of what I had committed to. And you might be able to guess her, this is going, but I basically booked a presentation with about 300 people. Some of them were in the school board that I grew up in, and it, it was at a local, a local arena. And they called me the day of the event, Sam, we’re so excited. We know that you’re starting in about 10 minutes. we just wanted to make sure that you’re nearby.

Sam Demma (11:39):

And I had totally forgot six months ago that I had booked this engagement. I didn’t put it on my calendar. And I was like, an hour and a half drive away. I instantly started bawling my eyes out, and for about two months I would walk down from my bedroom in the morning and look at my parents and go, I can’t believe I did that. And it got to the point where my parents were like, Sam, shut up. Like, you know, we’ve heard about this 60 times now, you’re not gonna make the mistake again. And it took me so long to get out of the guilt and shame period, and into the, let me learn from this, reflect on it, and build new systems so it doesn’t happen again. And I don’t think, there was like a defining moment for me where I was like, I’m gonna stop thinking about this. And I’m curious to know, like when you’ve made a mistake or when someone that you know, in the education world’s made a mistake, how do you quickly, or maybe not quickly, but how do you transition from the beating myself up to the, let’s now learn from this and move on?

Jason Kupery (12:39):

Yeah, that’s a good question. And I’ll tell you, I wish I could tell you no, none of the, I, you know, when I make a mistake, I just let it go and I, it’s gone.

Sam Demma (12:46):

Yeah. <laugh>,

Jason Kupery (12:47):

I dwell, I’m a dweller for sure. And and everybody close to me knows that you don’t have to worry about beating up on me because I’m gonna do a better job than anybody else can, right? Yeah. and so what I do, my strategy for it is to talk to people that I trust and love, right? So that’s, that’s the biggest thing. I I, yeah, it, it’s, it’s important to have people in your life that you can, that you can chat with that you can speak openly to and transparently with. and you know, it’s super important because they understand you. And, and, and none of those people say, well, here’s what you need to do, right? Mm. that’s the biggest thing. it’s not about advice. It just, it, it’s that they understand me, they know who I am.

Jason Kupery (13:28):

So, yeah. Oh, yeah, Cooper’s gonna beat himself to death on this one, so we’re just gonna stand, we’re gonna walk beside him, we’re gonna chat with ’em, we’re gonna let ’em talk. Right? And a lot of times that’s cathartic enough to be able to just to talk to somebody, talk it through, and then real, eventually when you talk it through either with the same person or with enough people, you eventually draw your own conclusions, right? Yeah. You know what, I am being kind of silly. This is, this is not as big a deal as I think it’s right. and, you know, even when it’s a big deal, you have people that you know you can love and trust that will stand beside you and, and help you through it and just, and just be there. I mean, you can use the example, your parents. I have an incredibly supportive spouse. I have some awesome kids. I have some really, really, really close friends. and I’m, so, I’m very blessed that I have that network of people in my life that I can you know, talk to when I screw up. So

Sam Demma (14:18):

I love that. And in the school building, I’m assuming that would be other people in the office as well. If you’re a teacher in, in a school, it’d be other teachers kinda leaning on your supports.

Jason Kupery (14:32):

Yeah, a hundred percent. a lot of times that’s what really makes a really tight knit school community. Like I’ve had the privilege of working on some wonderful steps where it’s just people get along they can trust each other, they can, they got each other’s backs. you know, principals got teachers backs, and we’ll help you even when you make mistakes. I’m not gonna totally, you know, I can’t defend some of those things, but I can certainly walk beside you and help you out with those kinds of things, right? you know, and, and for people who, who go into administration, those gaps tend to widen a little bit and it becomes a little bit lonelier. So finding those external sources that you can talk to and you can trust, right, is very important. And yes, of course, in the role I’m in now, you know, you have to have the right colleagues and, and they’re not all in the same school division, right? You have some great colleagues in other school divisions that can relate and empathize with some of the things that happen and, and just great people to be able to share with, and chat with and, and may have advice because they’ve been through it themselves, right? So those are important things

Sam Demma (15:28):

You, you can tell, just listening to you speak and share your ideas that you really care about this and you care about education. what about education makes you excited? Like, what gets you outta bed every single day to show up to work and put your best foot forward and try to do meaningful things?

Jason Kupery (15:47):

Yes, Tim, I’ll tell you, there’s not many careers, and I know there’s, there’s a lot of great careers and there’s a lot of great people doing a lot of wonderful things, but there are not many careers that you can actually speak directly into the lives of a lot of young people, right? Mm-hmm. <affirmative> as, as challenging and as tiring as it can be, it can also be super inspiring and super wonderful. And it’s not that you know, the times that I’ve had in my career that I’ve found the most inspiration hasn’t been drummed up by me, by any stretch of the imagination. It’s been drummed up by amazing young people that have incredible ideas and that are thinking about the future as opposed to what was, what’s happened in the past and those types of things, right? and to see people grow and to see people learn is just an incredible gift.

Jason Kupery (16:38):

 and so what excites me now in this current role, because there are some degrees of separation for me is providing the structures for students to succeed, right? Mm-hmm. <affirmative>. So my job now is to develop programming and develop programs and systems and things like that, that will either help students find their passion and ignite that spark through different kinds of programs or leadership kinds of opportunities we offer. or it’s ways of finding that sort of self-actualization ways for them to you know find the rhythm be mentally well understand what it is to be healthy. These are difficult times, right? I mean, I know I’m getting old now, so it’s been a long time. But I have had, I do have teenage children, and I do, I can understand and empathize with, with what it means to grow up in those worlds, those, those vicious middle school years and the tough high school years, and you’re trying to figure out your life.

Jason Kupery (17:38):

You’re trying to figure out where you fit, who you fit in with what your future may hold. Those are extremely formative but stressful times for students. And to be able to do everything from helping somebody read and learn how to arithmetic and to make sense of the world at a young age, to guide them all the way up through adolescence and into their, you know, adulthood you know, that transition into post-secondary life. it’s such a massive undertaking and what a privilege to be able to be a part of that. so that’s what gets me up in the morning.

Sam Demma (18:14):

You mention, you mentioned at such a cool perspective. Thanks for sharing. You mentioned that some of the coolest experiences, things that got you the most excited were not drummed up by yourself, but by students. And I’m curious, can you give us some insight into what some of those things might be? On our last call, we talked a little bit about an event that you would host and that was created and co-created with kids, and I would love to hear about that, or any other ideas that come to mind.

Jason Kupery (18:44):

Yeah, there, there’s just so much inspiration out there, but we’ve, we’ve had, you know the one we were speaking about, Sam was we had a young a student in our school community that sadly passed away the year after she graduated this from some complications with the medication. and one of her big things when she was in high school, and one of the things she advocated for was organ donation. and she donated all our organs, which was an incredible gift to a bunch of different families. And, you know, we you know, sat as a staff and as administration afterwards, brokenhearted trying to figure out how to make sense of this. and you know, the one thing that I, I mentioned my affinity for sports, and some other people had some affinity for sports too. So we decided let’s do a, like a charity hockey game, and we’re gonna raise some money and give it away to the to the organ foundation around here.

Jason Kupery (19:39):

 and also raise awareness. I mean, I think that’s a big deal. And we mobilized the troops. We were really inspired by this young lady and by honoring her. and so, you know, we had some professional landing McDonald came out and played with us, and, and, you know, it was just great. We had the whole school come. We had, we raised all kinds of money. It was a wonderful event. and over the years and, and we raised a lot of awareness around organ donation and those kinds of things. And over the years we started getting letters from people. And one we had I think the next year we had somebody that had this young lady’s kidneys. Oh. And he was alive and he was thriving because he had her kidneys. So he played with us in the hockey game, which was

Sam Demma (20:23):

Super cool, crazy.

Jason Kupery (20:24):

And then the year after that, a young man from Newfoundland received her heart. Wow. And he, he reached out to us. He reached out through through the David Foster Foundation and he reached out to us and said, Hey, I’d like to come. I’m a golia. I’d like to come play. and in the mean, in, in the meanwhile, he also got to meet this young lady’s family. And I mean, it was a very emotional, you can imagine what a gift. And, and so what a gift both ways. Obviously this young lady’s heart is literally in somebody else. And is, is helping somebody live to a point where he can come out and play a game of hockey with us. and of course, the gift that he brought to the family by saying, I’m alive and well because of your daughter’s sacrifice.

Jason Kupery (21:10):

What, like, incredible. So that was, you know, those moments are are something that helped you as an adult. It puts you in awe of what young people are capable of. and again, as a teacher and as an administrator, and as a director, my, my modus operandi was always put kids in those positions to succeed. They’re not always gonna do it. They’re not always gonna take it up. Some are just gonna go through and that’s fine, and they’ll live their lives. But some really just need that extra little push or that extra little program or that extra little spark to ignite something in a passion in them. And when those types of things happen it’s just incredible what students are capable of.

Sam Demma (21:54):

You told me the same story last time, which is why I was teasing it out of you. It gave me goosebumps, and it’s given me goosebumps again. What a remarkable story of impact and what a great reminder to check the box on the paper we get in the mail when we pass away, if that’s a decision we wanna make, knowing that it could save so many people’s lives.

Jason Kupery (22:14):

And I’m sure that decision she made has. and I just wanna, I, I just wanna share one more with you. yeah, please. We can talk about for sure. But we had a young man whose whose father passed away from cancer. unfortunately, and these guys for some reason were super into unicycles, right? Mm-hmm. <affirmative>, like, who, like how many people are <laugh>? There was like four of them. And they all just, they rode around, they ate their sandwiches at lunch in the parking lot, and they would try little jumps and things like that. and so this young man was, was sharing a story about his father passed away from cancer, and these guys come up with this brilliant idea, and I say brilliant sort of sarcastically, but it was brilliant to unicycle from B to Calgary, which is about 130, maybe 125 on a unicycle, <laugh> and to raise money.

Jason Kupery (23:01):

So they raised money for cancer research and those kinds of things. I think they raised something like 15 or $18,000. Like it was a lot. But these poor guy, they did it two days cuz it was way too much during a day. But these poor guys, and I, I drove the van behind them with the blinkers on <laugh> Road, and they rode their unicycles from BMP all the way to Calgary. and it was kind of cool in Calgary for anybody’s around here. Edward Worthy Park is just down the road. so they rode in Deady Park and their parents and their families that all had this huge celebration in the park, and they had a check presentation. you know, stuff like that. It just, like, that stuff happens more routinely than you think because young people have such inspiration and such drive, and they don’t understand quite yet what no means.

Jason Kupery (23:44):

You know what I mean? Because we, we, we get a little beaten down over the years about, oh, that can’t happen and that can’t happen. And young people just, they have great ideas. And so again, I’ve tried to be very cognizant of the fact that it’s not about saying, well, here’s what’s gonna go wrong, or here’s what could happen, or here’s this or that, or it’s, Hey, there might be some barriers. How can I help you remove those? and how can we help them? It might, it might happen differently because of certain things that we can’t do, but I’m sure we can, if we just think creatively and, and my job as a, as an trusted adult in their life would be, okay, let’s get rid of those things so you can succeed.

Sam Demma (24:16):

That’s awesome. I’m sure when you were in the schools, you dealt with a lot of those on a face to face basis because they would walk up to you and say, Hey, hey sir, I have an idea. Can I tell you about it? and now from a systems perspective, you probably hear about a lot of those things. One of the things that I think is really special about education, and you alluded to it earlier, you said, there are so many careers, but there aren’t many where you can speak directly into the lives of young people. I think one of the coolest things about education that lures most educators is the idea that they can make a positive difference in the life of a young person. What’s funny is that everything you’ve shared with me makes me believe that the young people have all made a massive difference in your life.

Sam Demma (25:03):

And I don’t think that aspect of it is, is talked about enough. and, and you just shared two inspiring stories and how it had a big impact on you. But I am curious to know in all your years working in a school, working in a classroom, has there been students who, when they first walked through your door or into the school, were really struggling and by the end of the couple years, or by the end of this semester had a real big breakthrough or transformation and yeah. Are there any stories like that that come to mind?

Jason Kupery (25:39):

Yeah, well, there’s, there, there’s plenty for sure. I think that helping students <affirmative> you know, I’m not a big fan of the idea of streaming, like saying, you know, you’re not, you’re not smart enough to do this, so don’t, don’t try. Yeah. and I’ve seen a, I’ve seen a lot and, and sometimes, you know, it is, some things are, are a deep enough level. You don’t wanna set kids up for failure, but you certainly don’t wanna say, well, don’t bother trying, because then, you know, you’re just gonna, you’re gonna end up failing, right? Yeah. So it’s a, it’s a distinction, if you will. and I’ve seen so many kids over the years flourish because you know, well, I can’t do that. I’m no good at math. That’s, that’s the easiest thing to say in, in education is I suck at math, right?

Jason Kupery (26:21):

Mm-hmm. <affirmative>. And then, okay, well, okay, I guess that’s it for you then, then we’ll, we’ll put you into something else. and I’ve always tried, I’ve used this match with my own kids too, but it’s just, no, you don’t suck at it. You just haven’t done it enough. You just have to, you need more practice, right? and, you know, trying to sort of present that mindset to students to say, try it. If it doesn’t work out, what’s the biggest, you know, fail forward, what’s the biggest thing that can happen? Right? and, you know, you gotta convince students of that, but you also have to convince their parents of course, too, right? Like, we’re gonna do this. It may not go super well, but that’s okay, right? We’ve got other room, we’ve got other spaces, we can, we, there’s other pathways. and so I’ve seen a lot of students succeed because they under, either they’ve, they’ve gone way beyond what they thought they could which is a wonderful thing.

Jason Kupery (27:08):

And we’ve also seen kids succeed because they’ve made a wise choice, I need to go on a different direction. And there’s another path, right? And one of the things I’ve seen you know, that even, even the most driven of students and the straight A students don’t realize is there are so many different paths in life, and there are so many different ways you can take. but I think that young people and families and, you know, people in general just think that there’s a linear straight, like, I have to get here, I have to get that 95, or I’m not getting into this program. And so part of, part of what I’ve tried to do is in helping people through that journey is to say, look, there’s, there’s a ton of paths, and just because you can’t take this math or take this biology or take this whatever there are other ways to do it, and we can get you there.

Jason Kupery (27:51):

And, you know, in, in a, in a world of instant gratification, it’s hard to understand, Hey, maybe you should take another year of high school, or maybe you need to take another course. Well, and I need this to happen now. It, it doesn’t need to happen now. But I know that’s a hard message for some people to hear. But in order to succeed, you may need to try a little bit, you know, a different way or, or it may take a little bit longer, but that there’s nothing wrong with that. There’s no shame in that, right? to be able to take a different path in life to succeed. and the other piece is helping students identify you know, the traditional classroom or the book learning or the, those kinds of things aren’t what I love to do. That doesn’t mean you’re not smart, it means you’re brilliant in other ways.

Jason Kupery (28:30):

Mm-hmm. <affirmative>. And so trying to provide students an opportunity to, whether it’s work with their hands or build something or problem solve in a different way you know, helping students understand their own aptitudes and their own, you know, brilliance is, it’s one thing to tell them, it’s another for them to discover for themselves, right? And so, again, as educators we try to create the conditions for students to do that. You know, if you, if you allow for different modalities of teaching in your classroom, and the student says, ah, I, now I can see because I, because I made it up with my hands, now I can see why it’s important, or now I can make the connection with the learning. quite often education is learn this regurgitate it, and now you know it without that real life connection and without that, without that sort of cementing or anchoring the learning it’s very difficult.

Jason Kupery (29:21):

It’s why most times when you, I mean, you’ve done it, I’ve done it a thousand times, where you, you, you study you and then you, you drill everything into your head for eight hours before the test or whatever, and then you forget 60% of it by the time you walk out the door, right? Because it’s like, I got what I needed to do, I accomplished, I got the mark. and so I’ve accomplished that. but have I really learned, so anyways, sorry, I’m rambling. I’m just saying that allowing students different ways to learn helps ’em flourish. And I’ve seen that so many times where students have had that aha moment, like, ah, now I know this is what I’m good at. and I mentioned to you earlier as well, the idea of post-secondary is frightening to a lot of people. It was frightening for you.

Jason Kupery (29:58):

It was frightening for me. Yeah. it’s a huge transition. And so I just had this conversation earlier today with some, some educators around students feel too much pressure. We have to stop asking them what they’re going to do. And I a hundred percent agree what I, what we need to ask. And the question I’m trying to change within our school division here is what do you love to do? Yeah. Because if we, if you can tell me what you love to do or what really gets what gets you up in the morning, you asked me that question earlier, what gets you up in the morning? And then we could connect it to a different career. but if you think that you can only be a teacher, a doctor, a lawyer, an engineer, or whatever, then those opportunities don’t blossom for you because, oh, I’m not good at that, so I’m never gonna be an engineer, and I just, I can’t do this kind of math, so I won’t go on to do sciences. Well, there’s a thousand other things you could do out there that would bring you joy and would meet the world’s needs. So we just have to figure out what that is for you.

Sam Demma (30:47):

I got goosebumps like five times while you were just, just sharing those ideas because one, I was the student who took the fifth year and the gap year and thought I was falling behind. And I was, I was interviewing another educator Sarah daddario from a school in California, and I try and talk to diverse, you know, amount of educators, and she was sharing something similar that her students were going through, putting so much expectations on pressure on themselves to start the next step right when they finished high school, even though they weren’t sure what they were doing. And she shared this beautiful analogy about going to parties, and she said, this is the analogy that I give my students. She and she, she asked me a question, if you were going to one of your friend’s parties, what are all the different ways you could get there?

Sam Demma (31:36):

And I started listing off all these random ideas, ride my bike, ask my mom for a drive, hit your ride with the, with the taxi guy, called a pizza delivery person and ask him to pick me up. I could walk there, I could roller blade, I could scooter, I could get a helicopter and fly. Like I started giving some funny answers. And she’s like, well, all of those are valid options and they’ll all get you to the final destination, but every single one of them takes a different amount of time and a different set of steps. And that’s how I try and encourage, she, she was explaining that’s how she encourages their students to think about their pathways. That you will all end up at a party. It might not be the same party based on your different interests, but you’ll all end up somewhere.

Sam Demma (32:16):

Your choice of transportation is what will make your life unique and interesting. And I just keep thinking about that whenever I think about pathways and adding so much pressure on ourselves. and then the other thing you mentioned in your second point was this idea that students have five options, an engineer, doctor, lawyer, you know, what we think we, we wanna do. and what we really should try and do is figure out what they love. And I, I thought about an artist who I really look up to, his name’s Russ, and he makes music, and he grew up thinking that he lacked discipline and wasn’t a hard worker, but later in life realized that it was actually the work that made him not very disciplined and not work hard because he just didn’t enjoy it. But when he found the thing that he loved, he was in the studio every day making music, and now he’s one of the largest independent artists on, on the planet.

Sam Demma (33:12):

And I think it’s really important that we don’t judge students based off of the things they don’t like doing. And I’m sure there’s a lot of things that we have to do, even if we don’t like it, and that’s a part of the journey as well. But I really like that you’re trying to help students figure out what they love and then craft the pathway from there. do you have any examples of and I’m putting it on the spot here, but of like a student who came to you and said this is what we’re, we’re, we’re passionate about and you helped kind of create a different pathway or brainstormed ideas around it?

Jason Kupery (33:49):

Yeah. well, I think that the most, when I, when I, I don’t about a specific example per se of one that’s jumping in my head and right at this moment, I’m, I’m, I’m sure I’ll think about 20 when I get, when I, that’s

Sam Demma (34:01):

OK <laugh>.

Jason Kupery (34:05):

 but I think that it’s, it’s more around helping students understand there’s a stigma that exists with certain careers, right? Mm-hmm. and, and so, you know, the trades are things that people that, that aren’t good at school do, which is ah which is seriously flawed. Obviously. I don’t want somebody who doesn’t know what they’re doing, building my house or <laugh>

Sam Demma (34:28):

Putting,

Jason Kupery (34:29):

Renovating my kitchen or whatever, right? and you know, there’s that, that sort of, these are lesser than skills, which is so not true. you know you know, the saying is, I’m educated, but I’m all that smart. And and that’s the same, goes like, I have a master’s degree, but you put a hammer in my hand, I’m gonna end up hurting somebody, right? <laugh>, most <inaudible>, I’m sure before anybody else <laugh>. and, and so I really wish, that was one thing that I developed more as a skill, right? Yeah. so just, just helping students understand that, that their gifts are extremely valuable no matter what they are, and they can be used for something. Again, it’s that the biggest thing was is that, that the world’s deep need and, and your deep joy intersecting, right? That’s where it’s at. Like Russ, you know, Hey, I found a medium that I am passionate about and that I want to pursue.

Jason Kupery (35:24):

So I’ve seen more of, of that I should say, in in, you know, where kids are so driven to, to get onto this, and they’ve fallen out of that, and really, and then they’ve come to me later and said, Hey, I’m doing this now I’m, I’m working my hands, or I’m, you know, a paramedic or I’m this or that. And, you know, it changed my life just thinking about, you know, how to you know, striving so much for something that was almost unattainable and, and, you know, at the expense of my mental health and other things in my life. and then when I realized that this was actually my gifting I was able to succeed. So

Sam Demma (36:00):

I love it.

Jason Kupery (36:01):

As we talk, I’ll think of a, of an example. I just didn’t expect to come up with that, but I should have that off the top of my head for

Sam Demma (36:08):

Sure. No, I’m putting you on the spot here. And it’s funny, it makes me think about situations where I have a conversation with someone and then five minutes after the conversation ends, I’m like, God damn, that’s, that’s what I wanted to say. You know? But you, you did a perfect job answering that, and I appreciate it. It’s really apparent that at the core of a lot of your thinking and decisions is the end user, which is the student. and I’m sure there’s ways that the the staff are a part of your, your planning as well because you’re at the, I guess, overarching level now. I’m curious, like for all the educators that are listening to this who are starting their first year of teaching, if you could bundle up your wisdom and experiences and go back in time and tap Jason on the shoulder when he was just starting and say, Jason, this is what you need to hear. What would you have told your younger self? Not because you would’ve changed your path, but because you thought it’s helpful advice to hear at the start of a career in education?

Jason Kupery (37:09):

Yeah, great question. I would say, you know, first and foremost and, and to, to, to sort of connect it to the last question you know, when it’s not so much that people have re retooled and done something and now ta-da, I’m happy. Yeah. it’s more about the kids that had a really, really, really hard time with a, because of circumstances in their life growing up unstable families drugs, alcohol, poor decisions and those are the ones that are, that are throwing things at you or telling F off or, and I just, young teachers and, and people in education, I mean, the one thing I would say is, please look past that. I mean, there is trauma in those kids’ lives, and that trauma-informed practice is really, really important because while it is that person standing in front of you, that young person standing in front of you screaming or throwing a fit or punching a snot at somebody else or whatever it’s not to see that that student or I is a terrible person or deserves some kind of punitive justice or those types of things that, that that young person needs some love in their life and needs somebody to look past that.

Jason Kupery (38:23):

And so when I’ve had people come back to me and say, Hey, thanks for, you know, because you, you because you intervened and because you had enough patience and because you didn’t kick me out and because you didn’t make my life harder, I look at I’m now a success and I wanna come back and say thank you. Those things mean a lot to me, obviously. I mean, they mean a lot to a lot of educators, right? But we tend to, and I’m no different, we tend to look at that and say, oh, that kid’s driving me crazy. I just want ’em outta here. Right? Just get out. and it takes far more patience and understanding to sort of try and look through that and try to reason and try to understand where that young person’s coming from to be able to speak into their lives.

Jason Kupery (39:08):

And it’s not like you have to, okay, now I’m gonna tell you everything you need to know, and I’m the best just, Hey, I’m here to listen and I’m, I’m going to be a safe place for you to come and, and be yourself. that changes lives. There’s no question. and so my encouragement would be, a lot of these people have a lot of people that, that give you a hard time or will give you a hard time in your career, are carrying a lot of, they’re carrying a pretty heavy backpack, if I can use your

Sam Demma (39:34):

Analogy. <laugh>

Jason Kupery (39:35):

<laugh>. and, and that’s, and that’s something that’s so extremely important to understand and to try to speak to them in a way that they can hear and know that they’re safe and cared for, because they’ll still make dumb decisions, but they’ll, they’ll always thank you because you stay, you stay beside steadfast. so I guess please don’t give up too easily on, on people that give you a hard time because they got a lot going on. The other thing I would say to young educators, and I do, and I do say that now because we do have what’s called the teacher induction program here. So it’s called Tip for

Sam Demma (40:11):

Sure. Yeah.

Jason Kupery (40:12):

 is don’t let the, the jaded, angry nature of the profession seep into your brain. And I’m not suggesting that’s pervasive, but it, it can happen. All you need is one teacher that, you know, is jaded or disaffected or, you know, kids are lazy or yeah. Whatever. And that sort of can flavor the water and it can get inside your head because that was my experience, right? You know, I had some, some teacher sponsors or whatever that the people that helped evaluate me and helped me through in my early years you know, weren’t always the most possible profession, <laugh> and, you know the, the 40 kids or the 35 kids and, you know, the half of them are criminals and those kinds of things. Right? those are the kinds of things you’re here as a young teacher and you just don’t start believing that.

Sam Demma (40:57):

Yeah.

Jason Kupery (40:58):

Cause it really does impact your ability to speak into people’s lives when you start to see them differently as opposed to who they really are beneath that tough exterior.

Sam Demma (41:07):

Mm. I love it. It’s like the advice don’t judge a book by its cover. And I think it applies so deeply in education, especially with young people, and you’re speaking from experience because you started it at the beginning of this podcast saying that you did some silly stuff as a student <laugh>. So I and we all did, you know, I think back to when I was grade seven and got suspended and we don’t have to get into the details of the silly incident, but I remember coming home and uncontrolled be crying and my dad not, you know, scolding me, but saying, let’s go talk to your principal. And bringing me back to school and sitting in the office and my principal at the time instead of seriously punishing me, he asked me a lot of questions and kind of forced me to reflect on the choice I made and why maybe it wasn’t a good choice and what I learned from the experience.

Sam Demma (42:02):

And I ended up having a two day suspension but it was a it was a very kind gesture, and I learned so much from it. So I’ve had personal experiences and I think a lot of students do. So I appreciate you sharing that, and I appreciate you coming on the podcast and talking about your experiences and beliefs around education. And if there’s an educator who listens to this and wants to ask you a question or send you a message, what would be the most effective way for them to reach out and get in touch? Not that we’re gonna fill your inbox, <laugh>.

Jason Kupery (42:33):

Yeah, yeah. No, I mean, I’m, I’m always willing to, to share and collaborate with others. I think it’s awesome. Yeah, email’s the best way and I can certainly share that with you if you wanna attach it somehow or whatever.

Sam Demma (42:43):

Sure. Awesome. Sounds good. Jason, thanks again for, for coming on the podcast. Really appreciate your time and energy. Keep up the great work, and I’ll see you soon.

Jason Kupery (42:52):

Okay. Thanks, Sam. Appreciate it.

Sam Demma (42:55):

I believe that educators deserve way more recognition, which is why I’ve created the High Performing Educator Awards. In 2022, 20 educator recipients will be shortlisted, each of whom will be featured in local press. invited to record an episode on the podcast, and spotlighted on our platform. In addition, the one handpicked winner will be presented with an engraved plaque by myself. I will fly to the winner’s city to present this to them and ask that they participate in a quick photo shoot and interview on location. The coolest part, nominations are open right now, and they close October 1st, 2022. So please take a moment to apply or nominate someone you know or work with that deserves this recognition. You can do so by going to www.highperformingeducator.com/award. We can never recognize educators enough.

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The High Performing Educator Podcast was brought to life during the outbreak of COVID-19 to provide you with inspirational stories and practical advice from your colleagues in education.  By tuning in, you will hear the stories and ideas of the world’s brightest and most ambitious educators.  You can expect interviews with Principals, Teachers, Guidance Counsellors, National Student Association, Directors and anybody that works with youth. You can find and listen to all the episodes for free here.