Joel Hilchey on Why Fun Belongs in Leadership

by Chris Tompkins | March 12, 2026

Season 6 of the Shaping Our World podcast is here and for the first time, you can watch the conversation as well as listen. We’re now incorporating video, giving you a chance to see these thoughtful and engaging discussions unfold in a whole new way.

In this premiere episode, speaker, author, and culture-builder, Joel Hilchey, illuminates the intersection of leadership and something we don’t always take seriously enough: fun. Joel is the author of The 6½ Habits of Highly Defective Bosses and Brainsprouting, and the founder of Beanstalk Creative, an initiative built on the belief that leadership isn’t about status or authority, but about connection. Through his work in schools, organizations, and communities across the country, Joel challenges the idea that fun somehow gets in the way of meaningful work.

The Overlooked Power of Fun

Joel argues that we often miss the value of fun because we mistakenly think fun is the opposite of work. In school and professional life, fun is frequently dismissed as frivolous or unproductive, when in reality it can be one of the strongest drivers of motivation and learning. He suggests that the real magic happens when something is both meaningful and enjoyable. If something is only meaningful, it can feel heavy and exhausting; if it’s only fun, it can feel empty or purposeless. As he puts it, “the magic spot is where things are both fun and meaningful.” In that space, people are more likely to push through obstacles, connect with others, and absorb new ideas because when we enjoy what we’re doing, our brains feel safer and more open to learning.

Why Fun Matters in the Classroom

Joel explains that fun in the classroom isn’t just about enjoyment but it actually helps students learn. When students feel threatened or stressed, the brain shifts into a fight-or-flight response and the parts responsible for deeper thinking begin to shut down.

“You can’t learn if you’re feeling threatened,” he explains, emphasizing that psychological safety is essential for learning.

Fun helps create that sense of safety and connection. Teachers who build human relationships by learning students’ names, showing interest in their lives, and sharing moments of humour, often have the biggest impact. Joel also notes that the first few minutes of a class matter most. A positive start can set the tone for the entire lesson, helping students relax, participate, and absorb new ideas. In that way, fun isn’t the opposite of learning but rather, it’s often what makes learning possible.

Leadership Starts Earlier Than We Think

Joel says that young people are often practicing leadership long before adults recognize it.

“If you think about leadership as influence, you start to see kids practicing it all the time,” he says.

Too often, we define leadership by position, titles, or authority, when in reality it often shows up much earlier as initiative, curiosity, and the desire to improve something that matters. Kids demonstrate these early leadership instincts in small but meaningful ways: organizing their collections, caring deeply about animals, or wanting to protect the environment. Parents can nurture this by noticing those sparks of interest and giving kids opportunities to act on them. Whether it’s helping a child write a letter about protecting trees or organizing a small fundraiser for a cause they care about, these moments help kids connect the dots between caring about something and taking action. Over time, those small experiences build the confidence and agency that later become true leadership.

For more on what Joel has to say on the importance of fun, listen to the full episode at the top of this post or watch the conversation unfold on YouTube!

Visit our website to discover a variety of other guests that we’ve had on the show. Shaping Our World episodes are also available wherever you get podcasts.

Transcript

[00:00:12.520] – Speaker 1
Well, hey, everyone. I’m Chris Tompkins, and welcome to the Shaping Our World podcast. This show’s all about young people and the world that they live in. Now, if you’ve been tracking with our show for a while, you know that we’re heading into Season 6. Something that’s new for this season is that we’re moving to video. Now, not only can you listen to it across the channels that you subscribe to, but you can also watch us on YouTube. Many of you who are listening to this might be like, Oh, let me go see. Now you get to see me. I don’t know if that’s a great thing or not, but you get to see our guests and you get to watch us interact and have these great conversations about how we inspire the young people that we live with and care about. As we kick off Season 6, I’m joined by Joel Hilchey. Speaker, author, and culture builder, whose work sits at the intersection of leadership and something we don’t always take serious enough, fun. Joel is the author of The 6-and-a-half Habits of Highly Defective Bosses and Brainsprouting. He’s also the founder of Beanstalk Creative, an initiative rooted in the belief that leadership isn’t about status or authority, but about connection and helping people feel like they matter.

[00:01:27.900] – Speaker 1
His work has taken him into schools, organizations, communities across the country, challenging the idea that fun somehow gets in the way of meaningful work. In our conversation today, we’ll explore why reclaiming joy, play, and curiosity might actually be one of the most powerful leadership tools we have right now. Joel’s refreshing approach to leadership invites us to think about fun and meaningful work all at the same time. Joel, it’s great to have you. Nice to meet you and looking forward to this conversation.

[00:02:08.360] – Speaker 2
Yeah, thanks, Chris. I’m looking forward to the chat. It’ll be great.

[00:02:12.620] – Speaker 1
Part of our tradition here, it’s called the Shaping Our World podcast. We want to get into your bio a little more personally. Can you tell us what shaped your world when you were growing up? What were the big influences for you during childhood and into young adult life?

[00:02:27.540] – Speaker 2
Yeah, sure. So I grew up in a little town called St. Marys In Ontario, a little town, 5,000 people and three traffic lights. They recently got a fourth. It was very exciting for them. But I grew up… I feel like a lot of kids in semi-rural places I was playing hockey. I played all the sports in town. But the big thing for me was actually music. My mom and dad put me in the children’s choir growing up. And I guess I was about third grade when I started, and it was a huge emotional lift for me at the time. I didn’t want to go. I didn’t want to go back. My mom dragged me, kicking and screaming, crying to the audition, which was just with the music teacher at the local elementary school. But I ended up staying in that choir for that one for maybe seven years or something, and it really shaped me socially. I got to travel to different countries and meet people from all over the world, these choral festivals, and just knowing that I was doing that, that was a huge impact. But then personally as well, music became part of my life from there onwards, and I still am in a performing group.

[00:03:43.070] – Speaker 2
But all the way through the University, I was studying engineering, but I was playing in a brass quintet for fun on the side and singing in a barbershop quartet. I sang in choirs all the way along. So for me, music was really an enormous thing. If I can add one more thing to it, when I was 15, my dad’s job changed. He worked in the cement industry, and his job changed. We moved across the continent to California. I started in 11th grade at a brand new school where I knew nobody. And my younger brother was in sixth grade at the time. And for me, a lot of people said, Oh, was that hard? Changing schools and changing your whole social environment. Maybe I was just lucky, but I had a good foundation. But I actually felt like, Oh, this is a neat chance. I can be whoever I want right now, and I can meet new people, and they don’t know me. I have no baggage here. And I got a chance to redefine who do I want to be in the world. And then I came back after 12th grade and did an extra year of high school, OAC at the time in Ontario.

[00:05:00.000] – Speaker 2
And I actually lived with that choir conductor and her two sons who had become brothers to me. I had this transition that was like, Oh, I’m now away from my parents, but not quite at university yet. When I went to university, it was really the third time that I had moved away. Each of the times I’d had this chance to think about who do I want to be. I don’t know, maybe camp is like that, too, for some people. But it’s this chance. It’s a environment. Those are some of the things. It’s like this music, and then the combination of changing physical places, I think. I got to ask, How do I want to show up?

[00:05:40.580] – Speaker 1
Well, I know, like you, how much moving around when you’re a kid. We moved every few years from when I was five years old to when I was probably 14, across the US, Australia, different places. I know a little bit about what you’re sharing. We did that about eight times in that span of time. So I totally know what you’re sharing and how that shapes you. So you mentioned a little bit about how music has stayed with you, but what shapes your world today? Like beyond your professional work, what do you do for fun?

[00:06:13.100] – Speaker 2
Yeah, sure. So I am self-employed. That is, I started in the training and development world about 20 years ago after quickly realizing that that engineering degree was awesome, but it led to doing database work. And I wasn’t really that into databases, it turns out. So I got into the training and development world, and over the years, what we’ve developed, Beans stock Creative, we now have a team of entertainers turned educators who do career skills workshops, largely in education. And we’re all about helping people find fulfilling careers and become trusted professionals. So that’s the professional side. But the personal side, where I suppose I get to practice this just as much. My wife and I have three kids of our own, a 10-year-old and twins who are eight.

[00:07:08.040] – Speaker 1
Oh, boy.

[00:07:08.610] – Speaker 2
So we have our own little living laboratory, I suppose, as every parent knows. I don’t know what we’re doing They’re like, Let’s hope this goes okay. The kids had been at a Montessori school. It wasn’t working well for them. Now my wife is homeschooling our three kids, as well as two other kids from our community. And around home, what does it look like day to day? When I’m not on the road speaking or doing training, I’m around home and I see this little community of young students, my kids and our community. And that is a really dominant factor. It’s a lot of our conversation day to day. What’s it like? How are things going here? We’re that much closer to the school experience.

[00:07:58.340] – Speaker 1
You’re probably in line with a lot a lot of our listeners who are here because they’re like, Yeah, how are we figuring this parenting thing out and what’s going on? And we’re all doing it together. I tell people the best part about hosting this podcast, and Roz, who’s our producer, is listening, too. We take notes all the time. We’re like, Oh, that’s really good. That’s helpful. Because we’re all trying to figure this thing out together, which is, again, why we do this and why you’re here today. I am intrigued with your professional journey because it’s really nonlinear. As you mentioned, you started in engineering, into teaching, and now add in juggling, singing, and now you’ve turned it into this organization that helps leaders create magnetic culture, educates teachers, and facilitates them in fun learning experiences for students. I want to get back to the impetus of all this. Was there a moment when you realized fun was not just a hobby and actually could be something of a professional focus?

[00:08:57.700] – Speaker 2
Yeah. I got involved in high school, not high school, university. So high school, I’d always been performing. I had a little juggling act through university that I would take. Some people bring their guitar. I bring my juggling balls to coffee houses and talent shows and things. And I realized I could make people laugh. So that was the first thing. Then I also got involved with a group called Engineers Without Borders, which really was… I mean, they had a chapter at McMaster University where I went, but it was really founded on the belief that engineers could solve problems that matter in the world. I thought that was really meaningful. And one of the things they did was they went out to high schools and did these presentations on water issues and food issues. I really liked doing these things. And one of the teachers, I remember them saying, Hey, that was really good. You’re really good with students. Have you considered being a teacher? I said, Oh, thank you. That’s very kind. But no, I’m going to be an engineer. I’m studying doing engineering. And I had this idea in my mind, like those other things, they’re not professional things.

[00:10:07.700] – Speaker 2
They’re just for fun. I’m an engineer. And then I got a job doing engineering stuff, this database thing. And I guess what happened was I looked around really early in this job and realized I was surrounded by people living for the evenings and weekends. Maybe that’s not fair. I was probably projecting. It was a great job, but it just wasn’t a great job for me. I was living for the evenings and weekends. It didn’t take long, but I said, I don’t know if this is the right place. Is this what I was working towards through school? And I think you can’t blame people. One of the things we try to share now is, I think people don’t know what they like until they try it. People ask me, Well, what do you care about? What do you like to do? I remember being in a job interview once, and they said, So what do you like? And it’s like, Well, I’m an engineer. I like the detail work of things. Well, it doesn’t take long with a database to figure… I don’t like the detail work of things. No, I like the idea of a database that does a lot of awesome stuff.

[00:11:15.660] – Speaker 2
But that’s not me.

[00:11:16.900] – Speaker 1
I’m not the one who’s making it.

[00:11:19.800] – Speaker 2
Oh, gosh. So that was a moment for me in retrospect. But what actually happened was I was living at a friend’s house, and I got I was borrowing her car in the first few weeks of this job that I had out of university. I got asked to do a presentation at a student leadership conference on behalf of Engineers Without Borders, actually. We talked about these extracurricular things we do that have so much impact on us. For me, this is one of them. Another speaker, another trainer guy at that conference came and said, That was really good. Have you considered speaking professionally? I said, You can speak professionally? That’s It’s a thing? It turns out there’s this whole world of training and development. People who are basically teachers, but who work in the corporate world, not in the classroom, so to speak. He said, I think you could do it. You’re really engaging with this. And we talked about it. And this sounds awesome. I remember asking a friend and myself one day in university, he was like, you know how everybody gets stressed around presentations? I wish there were a job I could do where I just got paid to do presentations.

[00:12:30.800] – Speaker 2
I don’t get stressed at all. I love being on stage. I think I’m good at it. And I didn’t realize that that’s a thing. So basically, a week after that presentation, I went back and looked around the office. It was a really bad day for commuting. It was like a two-hour commute on three busses in the rain. And I looked around and thought, I don’t want to be here. And in a very poorly thought-out decision, I typed up my resignation letter. So It made a total of four weeks that I had been on the job in the corporate world, which isn’t even really true. I was on vacation for one of the weeks, Chris. It was just really obvious to me, I don’t want to… This is not my skillset. And already I had been thinking, maybe I should go back to grad school. I like learning. I just want to learn about these specific things. This isn’t really the answer of how did I integrate fun in what I do. But this is the short professional story of I made it into the training world because Because I made a poorly thought out choice.

[00:13:33.740] – Speaker 2
My parents, as you can imagine, were thrilled.

[00:13:36.420] – Speaker 1
You quit your engineering job? Yeah. Right.

[00:13:38.940] – Speaker 2
You quit your job? I said, No, it’s okay. I’m living like a student. I’m fine in my apartment here. I can always take a serving job. If this doesn’t work out, my mom said, A serving job? Joel, you have an engineering degree. I said, No, but it’s fine if it enables me to get to what I want to do. I want to make sure I don’t disparage anyone with serving jobs because that’s an awesome career for a lot of people. So this really started me thinking, what are we pushing people towards in terms of careers? And it’s not that I didn’t value my engineering degree. In fact, I loved it. I still think like an engineer. But a thing that nobody really asked me, Chris, was like, What problem do you want to solve in the world? They always ask, what do you What do you want to be? But they never asked, What do you want to do? How do you want to contribute? What would be meaningful for you to contribute to? And I think I started asking those questions, and that was what led in the direction of, Maybe there’s something with careers that we can offer and people need this.

[00:14:46.980] – Speaker 2
And as I talked about it more, it turned out to be popular. And then in the professional world, it turns out people are asking the same thing. Other people are saying, Well, do I like the people I’m working with? Do I I feel like I’ve got purpose in my work? Is the culture good? Are the professionals, the bosses, does it feel like they care about my development or my progression in some way? This is really where it all emerged from is my little weird struggle is like, What do I want to do and how do I want to contribute? And it turns out when you ask other people that, they have good insights. But I think you’re probably already thinking like that. That’s what you do, right? You’re asking, How do we want to shape our Well, and again, before we get into the whole fun component, which I’m so interested to talk to you about, I want to pause just there for a second because you’re speaking our language here at Miskoka Woods.

[00:15:41.240] – Speaker 1
Our whole definition of leadership in our organization, Leaders are people who look at their world and say it doesn’t have to be this way, and they do something about it. Beautiful. That’s what our CEO leadership program, which is 14 to 15 year olds, they do a month with us. They know that, they memorize that ad nauseam. That’s one of the things we try to instill with them is, how are they looking at the world? What problems are they seeing or challenges or opportunities that tweak something in them? I just wonder, maybe speak to parents who are wrestling with their teenagers who feel like they’re struggling to find career, what they’re interested in, they’re thinking about, are they going to be a doctor, a lawyer, and can maybe speak in just a little bit of an encouragement for them in that journey from your own story?

[00:16:33.000] – Speaker 2
Sure. Two big ideas. The first one is you don’t have to have your life figured out by the time you graduate high school. It’s very rare for people to walk a very straight path. We ask a lot of people, how many people knew exactly what you wanted to do in high school, and you went and you did that thing, and now you still do that thing? Ask a lot of adults. You can ask yourself right now if you’re listening this. In my experience, it’s less than a third of people who they knew it, they wanted it, they got it, and they stayed it. A lot of people probably had some idea of what they liked, but then they started doing one thing, and then that opened a door to something new, and then they met a different person, and it turned out that their skill set applied in this other context that they had no idea it even existed, and then they went and did that thing for a while. That’s how life usually unfolds. It’s much more organic than, I had a plan and I followed the plan. For parents who are so stressed about, What is my kid going to do?

[00:17:38.380] – Speaker 2
Just know that if they don’t know what they want to do, they’re in the majority. They’re not in the minority. You don’t have to have it figured out by the time you graduate high school. Even in engineering, let’s say you made it all the way through engineering school, so four or five years of university. Well, it turns out, at my last check, only about a third of graduated engineers actually work as engineers. If you do engineering and end up actually working as an engineer, you’re still in the minority. But it’s not like I’m saying, don’t go to university, don’t be an engineer. I’m saying, Just know that life changes and your skill sets will apply in different ways. So that’s the first big idea. The second idea is to say, we don’t actually know what we like until we try it. And so move from a pressure on figuring it out to more of a spirit of exploration. Try stuff. Rather than thinking like, you have to figure this out and you have to be successful, try to help people explore and get exposed to different things. We only know what we know. So a lot of people end up what their parents do because they’re like, well, that’s the world I grew up in, until they happen to bump into some other field.

[00:19:09.120] – Speaker 2
And what I guess I want to say is it’s okay if we focus on the exploring a part of things, then most people go, Oh, I didn’t know this. I liked this. I met this. That seemed interesting to me.

[00:19:22.900] – Speaker 1
I think that lines up with a lot of the research we’re hearing about this generation of kids, different than maybe my generation. We’re dating ourselves. I I took Oasis as well. Nice. Myself, my parents, we had less jobs in our career. Yes. This generation is trying a lot more. They’re moving around. Some people can frame it around loyalty to occupation, but I think it’s more about trying and explore. I got into that job and it wasn’t for me, so I moved somewhere else, and I tried that. So that is lining up with where kids are at today. They’re going to be much more reticent and willing to try things than probably we were. So as parents, it’s not the freak. Your parents are like, four weeks in engineering. And for us to not freak out and know that this might be part of their journey that looks a little different than us. They’re on an exploration, like you said, to find out what really taps in, where their skill sets. And I think we’re moving to a culture and generation that skills are more transferable to different things. They’re not always as lined up. We’ve got a guy working in our Schools and Retreats program that did computer science.

[00:20:39.660] – Speaker 1
Well, now he’s working with people in recreation, but now he’s bringing his skillset when AI comes in to making schedules. So these skills are transferable in different ways. I think we’re going to see a generation of kids that will, to your point, explore more. Maybe as parents, as adults who care about kids, we can encourage that and invite that in the journey. I do want to get into fun a little bit because one of the things that intrigued us about you and your journey and what you do is this focus on fun. Little known fact, one of the things we say about Mascoka Woods, it’s a place like no other, unmatched activities led by caring staff, and the last one is, and more fun than you can imagine. That’s something about summer camp. We have grabbed hold of that. Again, this little known fact that I want to share is at Mascoka Woods, we say fun is our trademark, and we actually trademark the statement. They wouldn’t let us trademark fun, Joel, funny enough, but they allowed us to trademark the statement. So fun is our trademark, is a trademark to Mascoka Woods. So we’re speaking the same language.

[00:21:48.340] – Speaker 1
We love this, and that’s really intrigued us. So can you tell us a bit about fun and maybe in school and in professional life, why we overlook that and miss the value of it? Then we can get into what it does and why it’s important at the end of the day.

[00:22:06.620] – Speaker 2
Sure. So most people think that fun is the opposite of work. They think by definition, and in one definition, I suppose it is, fun is the frivolous this unnecessary part. But fun as the adjective, like that afternoon was fun. That’s describing something. And fun for me is like, well, I I am way more productive when I’m enjoying myself. And I have seen people be incredibly motivated by like, Oh, that’s just fun to do. I want to go and do that thing. It’s purposeful, but it’s also playful. The way I think about it is this Venn diagram of fun and meaningful. And if things are only meaningful, then it’s heavy and overwhelming. If things are only fun, then it’s frivolous and empty. But if you find Find the magic area in the middle, fun and meaningful, or as I call it, feaningful.

[00:23:04.600] – Speaker 1
There you go.

[00:23:05.390] – Speaker 2
I don’t actually call it feaningful.

[00:23:07.440] – Speaker 1
That’s a word I should trademark that.

[00:23:12.200] – Speaker 2
But to me, that area in that little Venn diagram overlap, is the magic spot, because this is where we’re intrinsically motivated, we’re creative, we’re purposeful, but also playful in how we approach things. We’re more collaborative when we’re having fun. Humans, we play, we joke, we laugh, we’re social, we’re more open-minded, we’re more resilient. Part of what I try to convince people of is when people are having fun, This is like an undervalued, undertapped resource, and it’s often very low cost. So there are techniques for how to do it. But think about it like when you’re enjoying yourself, when you’re having fun, you’ll push through all kinds of obstacles to make something happen. We’ll create obstacles just to push through them in games. That’s what a game is. I’m going to make up some rules, and then I’m going to try to outsmart the rules somehow. There are so many benefits. We learn better when we’re playing. If fun still sounds too frivolous, you could say, Well, what about play? How could we bring an element of play into this stuff? There were some stat I saw. I’m going to misquote it, but it was something like it’s been shown that to learn a new skill, it takes something like, I don’t know, 400 repetitions, unless it’s learned through play, in which case it takes 12.

[00:24:37.200] – Speaker 1
Okay.

[00:24:37.920] – Speaker 2
It would sound like massive difference. I’m sure the stat is wrong.

[00:24:41.760] – Speaker 1
The point’s there.

[00:24:42.750] – Speaker 2
On that order of magnitude. It’s like 40 times faster to learn things through play. This is what kids do. This is how we all learn as kids. And then at some point we think, No, the way to learn is to sit down and study a thing. Well, most people learn experientially. So it is true that as we get older, we have the capacity to focus for longer. And sometimes that means sitting down and thinking deeper about a thing. But also, if I’m laughing and enjoying myself, whatever that is, my brain is going to feel safer, and I’m going to absorb more and make more connections. And so I learn better.

[00:25:21.380] – Speaker 1
It’s interesting because as you’re saying that, I’m thinking about there is this subtlety even inside of me that the things that are really meaningful and make a difference. They’ve got to be serious. Don’t distract me with that. Now I’m doing the real serious stuff. Where does that even come from? Because it’s your point, if it’s enjoyable, if there is some lightness and fun to it, even if it’s really, quote, unquote, serious or meaningful, I can put more into it. I can get more out of it, I’m I’m lighter. I’m not as serious in my own demeanor. Yes. As you’re saying, I was like, Oh, yeah, where does that even come from? Why do I think that? Again, we don’t have time to go through the Anthepology or sociology of all that, but I think that’s just a really interesting thing that we see. You talked about them as Venn diagram. We often see them separate. They’re two separate circles. We have fun after work, and then we work.

[00:26:25.420] – Speaker 2
Right. Here’s a neat little thing to notice, though, that everyone can maybe… Maybe you are this person in your team. Have you ever been part of a team, Chris, where in the discussion, there’s often a clown, somebody who will make a comment at just the right moment, and it brings this little light-hearted moment, bit of levity to the situation. I’m convinced now that this is like lubrication for the problem solving process. And even in conflict, if you can bring levity to how we disagree, and often an ill time joke in a serious conflict is maybe not going to go well. But gosh, wouldn’t it be great if it did movies bring this up? It’s like, oh, somebody slides in a line at just the right time. There was somebody on our team who was really good at this. He would often make the meeting just more fun. I noticed it. I think after this person left, I noticed me trying to fill that role sometimes. I actually think there’s a role. Have Have you noticed this before on your teams where often there’s a person? Oh, yeah.

[00:27:33.720] – Speaker 1
I actually, Joel, every once in a while can be that person myself.

[00:27:38.100] – Speaker 2
You get to be the person. I think we all can be because we all recognize that sometimes That’s really valuable for the group. It’s a pleasant diversion from the serious task at hand, and that little mental lift helps us come back and dive in with a little more vigor, maybe. I don’t know.

[00:27:55.870] – Speaker 1
Yeah. Well, you speak to a lot of teachers, too, and education is a from your background. I know as parents, we think about our kids spend most of their hours in school as well. But we also have teachers that might listen to this and others. Let’s talk a little bit about education and fun. Again, they’re seemingly like, Now we got to get serious, move fun to the side. From your perspective, before you get into practical, how does fun transform the learning experience? I guess it’s similar to what you’re talking about with work or tasks, but can you dive us into the classroom a little bit?

[00:28:31.280] – Speaker 2
Sure. So you can’t learn if you’re feeling threatened. If you feel threatened, your brain physiologically shuts down and the emotional reactivity, the amygdala takes over, and you And the frontal cortex, that executive function part of the brain shuts down. If we’re feeling threatened, it’s basically the fight, flight, freeze, or fawn response. And it says, get out of here and prepare to do all your future analysis from a place of safety in the sycamore tree or whatever. And that’s evolutionarily what’s happening. So we need to create a space that’s like, okay, I can be present. I feel safe. People talk about it as psychological safety. That’s what it is. When people have that psychological safety, they engage better and they think better. They actually use their brain better, the cognitive capacities. So that’s what we need to create in the classroom. Unfortunately, a lot of people, including our own, have some trauma around school or school environment or even learning. My daughter said last night, Dad, stop trying to teach me something. I said, No, I’m not trying to teach you something. I’m trying to explain that that’s what it is. You’re trying to make me think about it, and that’s what learning is, and you’re trying to teach me.

[00:29:49.680] – Speaker 2
She was pushing back. I was like, Oh, my gosh. And she physiologically, at that point, she moved away from me. We’re playing a game, right? And she laid down on the couch, and she physiologically shut down. And if we’re not having fun, that’s what happens. But some people, it just looks like silence. So a lot of people in classrooms are sitting there. They’re not engaging, but shutting down is just silent and complying.

[00:30:17.700] – Speaker 1
So how do we bring fun into the education space? I could see teachers going like, I don’t have time. We got learning to do. How do we do that in a way that helps us keep moving forward with the objectives that we have, but yet still bring some of that lightness and doesn’t feel threat? How do we do that appropriately?

[00:30:41.920] – Speaker 2
Gosh, it’s a balance for sure. Because we do have things to do. Maybe my big line is, take your work seriously, but don’t take yourself so seriously. How do you show up? How do you connect with people? Think about the teachers that had the biggest impact on you. Probably wasn’t because they were an amazing history teacher. They probably learned your name and said, Chris, how was the basketball game last night? They probably took a minute interest in your life, and maybe they joked with you for a moment, and they made a human connection first. I think our best teachers are the ones with whom we find a personal connection. Those are the ones who make the biggest impact on us. We can learn from just about anybody. We We learn information, but the most impactful teachers start with that human connection. So that’s what I would say. Start with that. We can be light as we’re doing a serious thing. The next thing I would say is that the start matters a lot more. We have a disproportionate impact on how we start things. The primacy effect is a psychological effect here. So think about the first five minutes of a class of something.

[00:31:59.100] – Speaker 2
Teachers will It’s all like a mind’s on activity. But gosh, I make this mistake so often with my own kids. A therapist has told me before, Don’t give an instruction until you get eye contact and a smile. I was like, Okay, so if… Now, I’m bad at this, right? I don’t do it all the time. But if I did, would I walk into the living room and say, Put the thing away. It’s time for dinner? No, I would say, Hey, what are you doing? Tell me this thing. Oh, who’s that character? Oh, and then they look at me and I go, Oh, that’s awesome. And it’s like, Have you done this all day? Yeah, he’s great. Awesome. Hey, can you put it away? It’s time for dinner. And the feeling is totally different. Now, like I said, I’m just telling myself to remind me, do this thing. So can you get a smile, a laugh, an eye contact? Can you make a connection before you give an instruction? Or as you give that command. So think about the first five minutes. If that’s fun and people are having a good time, in my experience, classes are pretty forgiving.

[00:33:12.920] – Speaker 2
You’ve probably seen this in presentations, too. If somebody in the first little bit is pretty good, and then later on, it’s like, Okay, that’s fine, but I like them. They’re good. But if the start sucks and you get a bad feeling right off the beginning, it’s a big mountain to climb to come back from that. This applies anywhere, at home, in the living room, in the classroom. What does that look like? In the office, at meetings? What do the first five minutes of a meeting feel like?

[00:33:43.460] – Speaker 1
No, it’s really good because I’m thinking about it. We do our all staff meetings weekly. They’re called our huddles, and we always have huddle fun in it. Beautiful. Sometimes they mix it up there in different places, but it’s like, what would it look like to start the meeting more regularly with with that fun aspect to, like you said, set the tone, get people engaged? I think that’s really helpful. I do think in the school system in education, too, we’ve learned how to gamify some of the learning, too, as well. Slidos and different things that… Participation, fun, minor competition, winners, prizes. I think that adds some lightness to the learning where You don’t even realize you’re learning better or differently because you’re engaged in the game. I think that’s probably another thing to add to the classroom space.

[00:34:41.120] – Speaker 2
Maybe two quick things to add to that. One is that Novelty is helpful. So variety is good. When things become too routine, our brain gets used to it, and it’s not as fun anymore. And so we constantly look for ways to add a little surprise. Maybe the second thing to say is, one of the best ways to make things not fun is to make it mandatory. So if you find that at some point, whether it’s in a meeting or in the classrooms, have you ever been part of this? Someone’s like, Okay, we’re going to start with a really fun activity and everybody has to do this. This is what you need to do now. It’s like, you’re telling me it’s fun, but I’m not so sold on it. It just doesn’t have the feeling of fun or in the business world, mandatory fun team building days. So I recognize we have a strong desire to want people to do these things. But ideally, we have more like pull energy rather than push energy.

[00:35:51.340] – Speaker 1
So can we transition into the home a little bit? Just for a lot of parents listening to this, they have less control over what happens in the classroom and different things. But from your experience, even around fun, we know that kids and young people have a lot of pressure on them growing up. Grade performance. We talked on our show with lots of people to talk about educational performance and social media, the state of the world today. There’s a lot of pressures of young people going on. How does fun weave itself into personal life? And how does it help them build resilience, sense of belonging? And what role do parents have in maybe seeing the lightning of things or fun in helping kids with some of the pressures that are on them today?

[00:36:41.280] – Speaker 2
Yeah. Okay. So I don’t have a perfect answer here. In that I am also worried about all those things, all the things for my own kids. So Jonathan Heights’ book, The Anxious Generation, the big idea of that is that we have generally overprotected kids in real life while underprotecting them online in the digital space.

[00:37:09.940] – Speaker 1
It’s a great summary. Yeah. Yeah.

[00:37:11.540] – Speaker 2
This has been on my mind a lot lately. Obviously, we were kids, not to wax nostalgic for too much, but you probably spend a lot of time outside, and the parents probably weren’t around for that time outside.

[00:37:26.160] – Speaker 1
No.

[00:37:26.860] – Speaker 2
And what they seem to be saying is that time spent unsupervised outside where the kids are in control is like an inoculation against the bad stuff that happens later on. It’s like we become more resilient in this in a real life situation, and then we can flex those resilience muscles when hard things happen to us later on. Play and fun in childhood is really important. Now, the weird thing here is that we’re actually saying maybe the adults shouldn’t be as involved as we are. We’re saying, Hey, let’s go play outside. Let’s go to the park. Let’s do something together. And as a parent, I’m like, Come on, let’s go have fun together. And it’s not that I don’t want to have positive connections. I do. But at some point, those kids are going to want to go and have fun without me. And the fun for them is that novelty, the challenge they’re like, Can we get through this? We hope that they’ve got the foundation to say, You can come and get us when there’s a problem. Please come and tell us when there’s something happening. That’s one thing that parents can provide opportunities for fun in real life, not just digital, and then take a little step back as the kids navigate their way through.

[00:38:45.640] – Speaker 2
In the virtual world, we probably need to do the opposite. We probably need to say, If you’re having fun, show me more. I want to be more involved because we’ve underprotected kids in that realm.

[00:38:59.140] – Speaker 1
Well, the first part of what you said lines up to how we view camp, summer camps as a whole. Not just Muskoka Woods, any summer camps, because coming out of the pandemic and we’re seeing everything that was plaguing kids, they were inside, they weren’t doing new activities, they were not with their friends. They were sometimes in tumultuous situations, even in the home. We’re like, Hey, camp is the antidote to all that plagues kids. Get outside, meet new people, try activities. Again, like you said, in a safe, healthy way, be away from your parents to navigate all this stuff. Get invested with other adults that care about you. We know from research, we need a certain number of caring adults in our lives beyond our parents. It’s like camp was able to do that. You’re speaking our language to say, Yeah, that is one of the powers of camp is because it gives in a week setting or two or however long you go, but it gives kids that opportunity to do what you were to get a break from all the pressures, get outside, have fun, meet new people, try new things in a safe, regulated environment that I think for parents is like, but we’re always like, Don’t contact them Oh, they’re there.

[00:40:15.820] – Speaker 1
Let them have fun and be away. But yeah, so that definitely lines up. One of the things, just even segueing to a different topic, you talk about leadership. I think sometimes our definitions and understanding of leaders, we don’t even think about young people or kids because we’re like, Yeah, leaders are adults. They shape these things. But we’re big believers, and I know you are, of seeing leadership in a whole different vantage point. Can you talk about young people, how they’re practicing leadership often before adults or people like us would label it as leadership? Where do you see the raising leaders and leadership come up with kids and young people?

[00:40:57.500] – Speaker 2
Yeah. So even just questioning the definition of leadership. What does it mean? If we think of it as mostly about position, adults are leaders because adults have big fancy titles. That’s about position. But I know people have big fancy titles who I don’t think are that great at leadership. I know people who have no position of authority formally, but they’re incredibly influential to the people around them. Leadership is one of these loaded words for sure. If you’re a parent listening, you might think of it as, who is my kid influencing? That’s a form of leadership. And how are they influencing it? And then there’s the self-leadership thing, which sometimes you could call just initiative or drive. So I see it in all kinds of ways. Generally, people have the urge to do a thing that’s close to themselves before they have an urge to go out and do a thing to the world. Like, I want to get this stuffed animal. I want to buy this set of Pokémon cards. I’m talking about my kids here. And I want to organize these cards. Well, could I say, Okay, you organize these cards? That’s amazing. Is that an act of leadership?

[00:42:14.200] – Speaker 2
Well, it’s an act of organization, but organization is a good skill for leadership later on or now. And we tried to offer opportunities. So one of the things that parents can do is recognize when there’s a spark of interest in a kid and then try to give them an opportunity to exercise that interest. When the Green Belt was under attack, when it was being eroded and potentially sold off for development land, we talked about that with our kids, and one of them was like, Well, that’s not right. There should be trees. Okay, it’s a four or five-year-old’s understanding of the Green Belt. But we said, Well, what could we do? Well, we could write a letter. Okay. Do you want to write a letter to the government? Sure. Okay, so what do you want to say? And he couldn’t write yet, but we scribed for him. My wife, I should say. My wife is amazing at this. There are opportunities to create little acts of, Well, okay, I wish it were like this. Okay, as you said, the world doesn’t have to be as it is. Could I do something to make it better? And I think if you thought of leading Leadership, developing leadership in kids, really is just encouraging them to run with their interests when they want to do something, then you’ll help create the opportunities for them.

[00:43:44.460] – Speaker 2
One of our kids right now went to an SPCA camp last summer and loved it. And this year, they’re not running the camp. And so why not? Well, I guess there’s no funding for it, or maybe they’re changing venues or something. So what We should do a fundraiser for them. Okay. The classic kids bake sale, whether or not it raises money, of course, every parent knows. Do you know how much those cookies cost me to make when I sold them for 25 cents each? But the bake sale was about developing the kid’s sense of agency in the world. We wanted to do a thing, we put it together, we organized it, and here we are, and now we have something to show for it. Helping connect those dots, I think, is like the early flex of agency that ends up later on, say, Hey, the world is not as it should be, and I want to do this thing, and I need some other people to help me out. Entrepreneurs and founders, I don’t know that they particularly wanted to be leaders. They just wanted to do a thing and realize that they needed some other people to help get it done.

[00:44:52.560] – Speaker 1
That’s really good. We’re just coming to the near the end of our conversation, and there’s been so much to think through. I wonder just if two short-ending questions. In your books, you talk about culture as something leaders create, not inherit. What would you want to say to leaders about the culture we’re creating? Again, whether you’re 14 or 45 or older, around this idea of fun and meaningful? What’s your encouragement to think about some of the things that are really important to you in what culture we’re creating? Okay. Yeah.

[00:45:31.440] – Speaker 2
So my latest book is called The 6 and a Half Habits of Highly Defective Bosses: Serious Lessons for Accidental Managers.

[00:45:40.640] – Speaker 1
I’m going to have to pick that up. That’s really good, actually. Yeah.

[00:45:43.520] – Speaker 2
It was a joy to write, honestly. And really, I was writing it for myself because I, like about 80 % of people, stumbled into a position of leadership. I didn’t… Okay, I guess I’m leading people now. And I I’ll end the book with this idea that I stumbled into, but it really is about knowing your values. At one point, I wrote down, How do I want my team to be? I wrote down a couple of words, I don’t know, happy, proud, and grateful, or something. And then I thought, well, who do I need to be in order for my team to feel like that? I think I wrote down like, kind, fun, generous CEO. I put those words on a little sticky note and over to the side, and And I don’t always live up to that, I think. But when I’m making tough decisions, I try to think like that. How do I want to be remembered here? How do I want to be seen? And what I maybe ask people is like, what do you want your impact to be? Could you sum it up in a few words? I think the thing I’ve realized recently that the umbrella thing that I want to do in the world is help create professionals and leaders that people love working with.

[00:47:04.040] – Speaker 2
I want to create the type of people who you go, I’m so glad they’re on my team. I’m so glad to be working for this person. I want to create these go-to trusted professionals. I think you get there by asking simple questions. Parents, how do you want to be remembered? Or in the workplace culture, how do I become a leader that people love working with? Maybe that’s not the only way to show up. Maybe that’s just my bias for like, that’s what I want to create. Maybe some people want to be leaders that got more done despite being hated. I don’t know. But that’s not my target person. So ask that question, what would it look like right now to be the professional that people love working with? Are my actions building trust or breaking trust? Am I having enough fun while still taking the work seriously? I think if you’ve got a few of those guiding questions and guiding thoughts, and if the values are clear, then through all the chaos of life, Are you going to make perfect decisions? No. But you’re going to make good decisions most of the time. That’s all anybody can ask for.

[00:48:21.360] – Speaker 1
Yeah, that’s amazing. Maybe just finally, what advice would you have for parents, teachers, mentors, adults that have kids in their lives that they really care about, about how to really steward this idea of fun in a young person’s life?

[00:48:37.780] – Speaker 2
I guess I’d try to bring attention to things, those fun and meaningful things. Help people identify what they enjoy and help people identify what seems meaningful for them. Sometimes we’re so close to our own values that it’s hard to see them. It’s hard to verbalize them. I don’t know if anybody has ever said this to you. The guy who said, Hey, you’re really good at this thing. Have you considered doing that? Sometimes we need an outside perspective to help us identify, Oh, this is a talent we have. I think similarly, sometimes we actually need an outside perspective to tell us, Hey, it seems like you really enjoy this. It seems like this is really a sweet spot for you, or it seems like you really care about this. By other people reflecting it to us, it gives us a chance to internalize that and verbalize it a little bit more or be a little more specific about who we are and what we care about. So that would be my advice for parents, I think, is use the phrase sounds like or it seems it looks like, or it looks like and reflect back what you’re seeing in that young person.

[00:49:51.360] – Speaker 2
It seems like you really care about this. It seems like you’re really lit up when you work with this thing. It seems like you’re really passionate about this idea. It seems like you really enjoyed helping that friend of yours.

[00:50:05.300] – Speaker 1
I just will add a little anecdote for all of us parents in there. In order to do that, we got to be paying attention. We got to be looking and creating space to see that, to be able to speak into it. I know myself as a parent, too, it’s easy to go frantically through our day and miss that. And so my invitation to myself hearing that is, where am I creating space to actually notice those those things about my daughter or the young people in my life? Because I can’t speak into it if I don’t see it, right? And so how do I create some space to be able to do that?

[00:50:40.110] – Speaker 2
Hits in the middle right here, Chris. Yeah, absolutely. So as we say, we’re all figuring this out together.

[00:50:47.720] – Speaker 1
A hundred %. You, me, all of our listeners trying to make sense of our kids in the world they live in. That’s why we do this. And thank you for being here today, for being in this conversation, Joel. Just maybe a quick thing. If parents or teachers are listening to this and they want to know more about you and maybe even get you to come speak and all that, where can we find you? And encourage us on that.

[00:51:09.600] – Speaker 2
Absolutely. My website, joelhilchey.com. That’s the easiest one. If you want to try the free highly defective boss assessment, you can go to joelhilchey.com/bosses. And you can, I’m sure put those links in the show notes if you want or whatever. Or you can find the book wherever you buy books. Apparently, it’s out there. So it’s all good. This has been a real privilege, Chris. Really enjoyable to chat with you.

[00:51:36.220] – Speaker 1
Joel, honestly, it’s been great. Invigorating conversation. And we probably could go for another hour. Totally. I’m sure of it, but maybe we’ll have you on later at another date. But thanks for your time today. Really appreciate the conversation.

[00:51:48.640] – Speaker 2
You bet. Take care.

[00:51:51.580] – Speaker 1
That’s it for today’s episode. If hearing from Joel Hilchey made you rethink leadership, learning, and the role of fun in the lives of young people, why don’t you head over to muskokawoods.com. There you’ll find a blog post with key takeaways from this conversation and a link to listen again. You can also follow the links to Joel’s stuff that he talked about and maybe pick up one of his books. But either way, thanks for tracking with us today, and we’ll see you next time on Shaping Our World.

About the Author

Chris Tompkins is the CEO of Muskoka Woods. He holds a degree in Kinesiology from the University of Guelph, a teacher’s college degree from the University of Toronto and a Master’s degree in Youth Development from Clemson University. His experience leading in local community, school, church and camp settings has spanned over 20 years. His current role and expertise generates a demand for him to speak with teens and consult with youth leaders. Chris hosts the Muskoka Woods podcast, Shaping Our World where he speaks with youth development experts. He is an avid sports fan who enjoys an afternoon with a big cup of coffee and a good book. Chris resides in Stouffville, Ontario with his wife and daughter.
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