About Jacqueline Butler
Meet Jacqueline Butler—an educator, leader, and lifelong learner who’s passionate about redefining what school can be. As the Deputy Head of Student Life and Wellbeing at Holy Trinity School in Richmond Hill, Canada, Jacqueline has spent the past 22 years fostering a learning environment that connects students with their passions, their well-being, and the world around them.
Her journey has taken her from the science lab to the gymnasium, always with a focus on creating meaningful, human-centred learning experiences. Right now, she’s working on integrating student life with academics, helping students develop the skills and mindsets they need to be changemakers in an ever-evolving world. She believes that in a world where humans are increasingly falling out of relationship with each other and the natural world, school needs to be a place that is based in community, where students discover, connect, grow, and take risks—without fear of judgment.
When she’s not thinking about the future of education, you can find Jacqueline hiking, skiing, or taking in a peaceful waterfront view with her husband, son and daughter. A former Queen’s University basketball player, she still finds joy in coaching, with a focus on teamwork, and inspiring young athletes to commit to something bigger than themselves.
Connect with Jacqueline Butler: Email | Linkedin
Listen Now
Listen to the episode now on Apple Podcasts, Spotify, or on your favourite podcast platform.
Resources Mentioned
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
Welcome back to another episode of the High Performing Educator podcast. This is your host Sam Demma and today we are joined by Jacqueline Butler. As deputy head of student life and well being at Holy Trinity School in Richmond Hill, Jacqueline has dedicated 22 years to reimagining education through a human centered lens. Her journey from science teacher to educational leader reflects her commitment to creating learning environments where students can discover their passions, develop as change makers, and build meaningful connections with their community and the natural world.
Sam Demma
A former Queens University basketball player turned coach, and she’s still got moves y’all, Jacqueline brings her passion for teamwork and personal growth to every aspect of her work while balancing her professional dedication with family, time spent hiking, skiing, and enjoying waterfront views with her husband and children. Jacqueline, it is a privilege and pleasure to have you on the show here today. Thank you so much for being here.
Jacqueline Butler
Thank you for having me. I was listening to some past episodes and you keep very good company, so I’m very honored to have been asked and to be here, spend time with you, Sam.
Sam Demma
I can’t wait to dive in. Can you please start by introducing yourself and just sharing a little bit about why you got into education?
Jacqueline Butler
So, so yeah, so I have been, um, a for, that’s been my whole career. And I graduated from university and took an adventure overseas to London and England to do some teaching over there, and then made my way back over to HTS and I’ve been here ever since.
Jacqueline Butler
So a really, really long time, had an early adventure, but I know a lot of people, you know, move around in their career, but I have found a place that I feel like I really belong and that I love so much. And so that’s me and kind of my little story, but I got into teaching really because I wasn’t ready to grow up yet. That’s how it started actually. And that I, all the things that I loved doing, in my youth, I felt like I could continue to do those things as an educator, and a sort of positive role model for for other young people. So, you know, I come to work every day, and I still get to sing out loud in chapel. I still get to play in the gym, whether I’m teaching or coaching. I still get to go on trips. I still get to do all of the things that I used to love to do as a kid, except just in a different role as the adult in the room now. So that’s how I got started in education.
Sam Demma
Tell me more about what brought you overseas at the start of your career.
Jacqueline Butler
So I was a student obviously in Teachers College and there were schools coming over to Queens to do some interviews. They’re doing their recruiting and I knew I was going to be in the workforce coming up really soon. And so I thought I better get some practice. So I signed up for these interviews because I’d never had a professional interview yet. And I thought this would be a great idea. So I went and sat down
Jacqueline Butler
and had some really amazing conversations with some other educators from around the world. And I never once considered that, you know a job offer would be on the table, but sure enough, it was. And then all of a sudden it was just, why not? So I really never had a plan to do it, but when the opportunity was presented to me, I didn’t have a reason not to do it. So off I went.
Sam Demma
That’s awesome. Some of my favorite memories are from my own childhood experience of traveling to Italy for six months. And I think that earlier in any career, it’s such a valuable experience to gather different perspectives from different communities around the globe. It helps shift our perspectives and have more of a holistic view on things. You’ve been in education now, you know, 22 years.
Sam Demma
How has your vision of what school can be? How has that evolved? Oh, yeah, how’s that evolved over the years?
Jacqueline Butler
Well, it’s interesting, I’ve been in the game a little bit longer than that, actually, not that I want to date myself, but it’s just I’ve been at HTS for 22 years. But I think that when I was younger, I felt very much like I needed to stick to the script, right? Like I was very much focused on the curriculum standards and ticking the boxes and getting done what I needed to get done. And as I’ve grown and matured and become more in tune with what my students need or the students need. I’ve been able to focus on them more as people and individuals and young growing minds and souls and spirits to be able to actually meet them where they are as opposed to like having a set goal in mind. So for me, that has been the major shift in terms of, yes, just maybe taking the curriculum standards a little more seriously when you were younger and growing into a more holistic educator that’s really, really concerned with the whole child, which can take you down many different paths, oftentimes a different path, many different times in the same day. And being the whole child being the center of what education is and what it can be, as opposed to a set path.
Sam Demma
How do you build a connection with a student to the point where you really truly understand their needs? Sometimes it feels like certain educators connect really well with their students and others want to, but struggle to do so. What do you think some of the principles are to build those connections?
Jacqueline Butler
I think that there’s probably many different answers to that question because there’s, you know, many different personalities, many different connection points for different students and the other adults in the room. But for myself personally, I always connect back to the why. Like, you know, why am I in this? Why am I doing this? And the answer is always the same. The answer is always I’m doing this for them. So if that’s in fact the case, then I can’t really get too far down the road unless I know them. So it’s about the relationship building. It’s about the questions that you’re asking.
Jacqueline Butler
It’s about caring enough to know what matters, what matters to each individual person, understanding their goals, understanding their challenges. And the really, really, really important piece, I think, is finding a way to get each student to know themself first. And taking that coaching stance in terms of helping each individual learn who they are,
Jacqueline Butler
what makes them tick, not what they wanna be when they grow up, but what they want to spend their life doing.
Sam Demma
It makes me think of some educators I’ve had that really got to know me on a personal level and understand what I was passionate about outside of their classrooms, to the point where they would teach a lesson and at the end of the lesson say,
Sam Demma
Sam, for you, this means X, And Jacqueline, for you and your passions, this lesson means X. And it just felt so personalized, despite the fact that there was another 30 students in the class. And I’ll never really forget those specific moments.
Sam Demma
Sometimes young people put a lot of pressure on themselves with so many different expectations and goals and dreams and things going on in the world. How do you think we balance that healthy ambition in a student with the challenge of them putting so much pressure on themselves these days?
Jacqueline Butler
There is a lot of pressure. It might be a cop-out, but my answer is a little bit the same. It’s just in the sense that until you really know and understand yourself, you could be tempted to be trying to do a whole bunch of different things for different people or different things for different outcomes that don’t necessarily connect with your own personal passions and your own personal you know desires and on top of that if you don’t really know yourself yet it’s really hard to know where you want to go. So in that in that sense I think it’s it’s just super important that
Jacqueline Butler
students are staying true to themselves, that they’re doing the hard work, the self-reflection, the self-awareness, they’re focused on what it means to be a good human, a good citizen of the world, and then you layer in, you know, your interests and your passions and maybe a way to make money somehow in there along the way. But staying true to yourself, I think is the key to that because then you can sort of cut the noise out, right?
Jacqueline Butler
And not have to feel like you have to be everything to everybody at the same time.
Sam Demma
One of the things you’re helping students be at HTS is change makers. Can you tell us a little bit more about what it means to be a change maker and how we foster those characteristics and skills in, in students?
Jacqueline Butler
Yeah, I think, um, in one context, a changemaker connects directly with the word impact. And if you’re able to make an impact, and that impact can be at the local level, you know, maybe in your own class, or your own school, or you can extend that impact out to the community, you can go further, and, you know, into a different country or whatever the case may be. But I think to be a changemaker means that you’ve identified an issue,
Jacqueline Butler
that you’ve learned and understood the issue, that you’ve created empathy for the people that are being affected by the issue. And then you have dedicated your time, effort and energy to find out what the need actually is not what you think the need is, but but what the need actually is. And then you put a plan in place to make a change or make a difference.
Jacqueline Butler
So I think finding opportunities and experiences that give students the skills to be able to take those steps is what it means to be a changemaker because it can be in any field, in any place. There’s no limit to what it means to be a changemaker.
Sam Demma
One of the things I noticed at HTS, every student says hello, waves, smile on their face, looking for opportunities to help each other, eat lunch with each other. Tell me more about how the school staff is intentional about building that culture of inclusion and belonging and kindness and respect and how another school may borrow some of those ideas to try and build
Jacqueline Butler
that culture within their community. So I feel like we have a really strong community at HTS and I at the same time, I’m comfortable saying that we’re on a journey and we have some growth to do in that area as well. I think we do place a lot of value on the concept of belonging. I think we we put the right vocabulary in place and we create opportunities to come together in community, which obviously fosters those relationships. And this may be a little off topic, but I think one of the biggest challenges
Jacqueline Butler
that everybody’s facing right now is that people are falling out of relationship with themselves, they’re falling out of relationship with other people and they’re falling out of relationship with the earth. And there’s a lot happening out there in the world that makes it easy for that to happen. And so I think our jobs in a school like HTS where we really do value that community and those connections and those relationships is that you have to be very intentional. Now, more I think than ever before in teaching those skills, like there’s skills connected to it. And I think, you know, for a long time, you kind of gloss over that these
Jacqueline Butler
things are happening and people are showing the signs and symptoms of belongingness and togetherness. But if we don’t focus on being intentional in terms of what we talk about, how we talk, bringing people such as yourself into our community to speak about what it means to show up in a relationship and be a positive member of a relationship, then I think we miss opportunities to really like instill those values and skills.
Sam Demma
Tell me more about the falling out of relationship with the world, the natural world. I would love to dive into that for a moment.
Jacqueline Butler
Oh man, I wish I had the answer, like, you know, this is an area for myself that, you know, causes me a little bit of internal discomfort or stress. So I think in my in my learnings and readings, as they call it the the meta crisis,
Jacqueline Butler
right, the breakdown of the interconnectedness of global systems, you know, with technology, science, information, the environment, economics, psychology, culture, politics, all these things. It’s very complicated, like it’s beyond my sort of scope of obviously fully understanding, but I can tell you that I can definitely feel it.
Jacqueline Butler
So I mean, some professional communities that I’m a part of, finding pockets of people who notice this falling out of relationship, who are open to talk about it, and who feel strongly about doing something about it, I think that’s kind of where I find a little bit of inner peace around it. But it is a major challenge that our young people have to confront, come face to face with, because, yeah, things are changing, things are different. And again, that’s why the role of us as educators is so critical.
Jacqueline Butler
Because what are we doing? What skills are we instilling? What things are we teaching and talking about that will prepare young people to be able to deal with, you know, these changes, the potential chaos, collapse, whatever you want to call it. So like, we have a really, really big, important role to play in all of this. And so, you know, I think specifically at HTS, we are really working hard to
Jacqueline Butler
potentially disrupt the way education looks and the way that we interact with our students, moving towards more of a mentorship model with our students so that they have that close relationship and we’re building in the skills in a set kind of plan, a set plan that meets the students where they are and gives them the skills that they need to be able to meet these challenges in the future.
Sam Demma
Like skill-based learning versus subject-based learning.
Jacqueline Butler
Yes, or learning the skills through a subject and being more interdisciplinary and having learning experiences with people that are not all the same age as you, you know, that are not all talking about the same subject at the same time, but really having opportunities
Jacqueline Butler
with internships and capstones and all of the different projects and programs that we’re exploring here at HDS, but to create a more like holistic, human-centered version of education that breaks down the silos and creates learning opportunities that are more authentic to us as a human being. Again, we
Jacqueline Butler
kind of school… It’s not natural in the sense of if you think of experiences where you’ve had your most authentic learning, you probably weren’t, everybody that you were with wasn’t the same age as you talking about the exact same topic as you in a room. It probably didn’t feel like that. So, how can we recreate learning opportunities that really feel more authentic to what it means to have positive learning out in the
Jacqueline Butler
world.
Jacqueline Butler
Yeah.
Sam Demma
What other things would you re-imagine in a school, you know, if you could disrupt education as a whole? Are there other things that you think would be places you’d start? Yeah, I’m curious what other things you think should, could be disrupted in the next couple of years and kind of need to be in some ways.
Jacqueline Butler
Yeah. Again, it’s a, it’s who can predict it, right? Like who can predict exactly what’s going to happen. But, um, you know, we know that technology is a game changer. We know that we can use it for good and we can use it for bad. But I think we have to separate ourselves from the concept of the four walls, right, of a building that if the pandemic taught us anything, it’s able to send students out into the world to do their internships to do their projects and, you know, be able to get their credits while doing other things at the same time. these constructs that we think must be true in order to, I’m using air quotes here, I know we’re an audio only, but to do school.
Jacqueline Butler
So yeah, that we need to kind of just look beyond what we’ve come to expect or accept as what school is.
Sam Demma
When you think of your own educational experience, can you identify a few mentors or caring adults that had a big impact on you? And if so, what did those specific individuals do for you that made all the difference?
Jacqueline Butler
So therein lies the lesson, right? So here I am talking about how, you know, the constructs of school maybe don’t serve us as human beings, but at the end of the day, I have had amazing experiences in school, just the way that it is now. And the interesting thing is because of the relationships. So that will never change, right?
Jacqueline Butler
You mentioned it as well. The power of the relationships with you that you have with other people is like the number one indicator of happiness.
Jacqueline Butler
Right?
Jacqueline Butler
The more positive relationships you have in your life, the happier you’re going to be. Even when there’s crap. You know what I mean? Like even when things are rough, if you have positive relationships and the same is true with school,
Jacqueline Butler
like if you have those positive relationships around you, you can still accomplish all these wonderful things. So, for me personally, I had coaches in high school, I had coaches in high school, I had coaches in university. The difference for me was that it was about me. Like they wanted to know what my goals were.
Jacqueline Butler
What do you want to accomplish? What matters to you? What’s challenging you these days? How can I be helpful? So to me, again, just having that personalized connection with somebody who has your best interest at heart
Jacqueline Butler
is a difference maker in terms of how you’re gonna be successful. So if you know that somebody is caring about you, if you know if somebody knows what your goals are and where you wanna be and is there to support you and guide you, you have that person that you can go to
Jacqueline Butler
that you can ask the questions. I think that’s what makes the big difference, yeah.
Sam Demma
You mentioned coaches and I know that athletics have played a large part of your entire life. How has your background in athletics and coaching influenced your approach to educational leadership and student development?
Jacqueline Butler
Yeah, it’s really about the people working towards a common goal.
Jacqueline Butler
Yeah. It’s about the people working towards a common goal.
Jacqueline Butler
It’s about putting others ahead of self. It’s about, you know, you have to practice as hard as you want to play, right? So, you know, what do you, what do you, right? What are you doing when you’re not in the big game to enable you to deserve to win the big game is really important.
Jacqueline Butler
It’s a little off topic, but I saw something recently that I really loved and it’s so simple. The person’s name is Dr. Becky. Now, I’m sure she has a last name, but it wasn’t shared. She’s from Duke.
Jacqueline Butler
She’s from Duke. And her concept of the difference or the space between not knowing something and knowing something, right? Being pure frustration, right? The difference between when you don’t know something
Jacqueline Butler
and you do something is filled with frustration. It’s uncomfortable, it’s hard. And then you get to the point of where you know it and you have this huge sense of accomplishment. So it’s the same with sport, right? You’re not doing well and then you are doing well.
Jacqueline Butler
What happened in between? That’s the magic, right? And the skill that we need to put in place, whether it be athletics or education, is this concept that she calls frustration tolerance. And I thought, oh my goodness, like that is so simple, yet so amazing. So if we can, you know, help young people or old people, any, any to stay to the course through the frustration. The more that we can practice frustration tolerance, the more successful we will be
Jacqueline Butler
in terms of reaching our goals and getting to where we want to be when the going gets tough. So I think whether you’re talking about athletics, whether you’re talking about, you know, academics or education, how can you stay the course? How can you stick with something when you know it’s hard? Some people call it resilience, some people call it grit,
Jacqueline Butler
but the real skill of it is how do you live in that uncomfortable space between not knowing something and knowing something and have the skill to be tolerant through frustration?
Sam Demma
I think it’s such a cool way to look at growth. One of my friends always said, Sam, I hope you find something to struggle well on. It made me think of that. Life is about choosing things worth struggling for. And then it’s how much can we struggle? How frustrated can we, how much can we tolerate before we make a decision to try something else or keep moving forward? So I love that idea. And Dr. Becky from Duke, last name that we don’t know, we appreciate you.
Jacqueline Butler
We appreciate you. I loved it.
Sam Demma
This has been such a lovely conversation about what it means to build a relationship with a young person. Some of your insights that you’ve pulled from athletics and coaching and how, you know, how has you like looking through a lens in education, the importance of building community and some of the disruptions that may happen in education in the future.
Sam Demma
And that relationships are still at the center of all the work that we do in a school building and how important those are. I really appreciate your time and the work that you’re doing at HTS. I hope it continues for a very long time. Keep up the amazing work. You’re helping lots of young people and I look forward to crossing paths again soon.
Jacqueline Butler
Thank you, Sam. It’s been a pleasure.
Join the Educator Network & Connect with Jacqueline Butler
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.
