The Brave Art of Teaching

Hi Todd, thank you so much for joining me today.

Susan, it’s so good to be here. Thanks for the kind invitation.

Of course, of course. So for those who may be unfamiliar with you and your work, can you just start us off by telling us who you are, what you do, and how you came to this particular intersection of creativity, bravery, and leadership all in one?

Yeah, if I’m being cheeky, say that I like to describe myself as the arms dealer for the creative revolution. But a more expanded version of that is I’m an author. I’ve written seven books, mostly in the space of creativity and creative leadership and what it means to have to confront uncertainty every day as a professional. My background is as a creative director. I started a podcast in 2005, which was a very long time ago. This is the 20 year anniversary.

Uh, back when we had to explain to people what a podcast was, still, still did until like 2015 had to explain to people what a podcast was. Um, and that sort of became an opportunity for me to share some insights, things I was learning and meet some great people. And then that led to the first book, the accidental creative in 2011. And since then I’ve written six more books and, uh, travel all over the world and speak and teach and get to meet a lot of amazing people like yourself, get to meet a lot of amazing people and share insights with them and their audiences.

Well, congrats on such a long-term, you know, focus on such an important topic. And it’s something that we’re really passionate about here as well. How did creativity become the crooks of what you really want the world to know and become, you know, better around?

It’s so funny because if you look at my history, I studied marketing in college. like any good marketing major, I did my tour of duty in the music business as a performer. So I was a singer songwriter. had a, you know, I always liked to joke with my friends in the business that I was as successful as you can be without being successful, meaning, um, had the chance to play on a lot of great stages and open for a lot of people and made absolutely no money at all. Um, but so as a way to sort of fill in, in the midst of that, um, I started taking piano bar gigs where I would like play on a Monday, Tuesday, and then I would go out with the band like Wednesday through the weekend and play events wherever. But then like Monday, Tuesday or Monday, Tuesday, Wednesday, I would play these little piano bars. He’s like improv piano bars were like sing along where you sort of had to read the room and you had to sort of like come up with ideas on the spot and be funny and all that. And it was really interesting because I realized like there’s so much.

About what I do now that is very similar to what I was doing in that room of, you know, 200 people, 200 drunk people, honestly, uh, who were like, try, you know, you were leading the sing along, she had to read the room and do all these things. Um, and then, uh, I, ended up, I met my wife. was settled in Cincinnati, Ohio. Um, we sort of decided, you know, music business, gainful employment, marrying an amazing woman. You can have two of the three. can’t have all three.

So I decided to find a job. ended up as a creative director, which was phenomenal, leading a small team and that team grew over time. And as that team grew, I realized, my goodness, there are so many things I need to know about creativity and especially creating on demand. Cause we’re under a lot of pressure to create great ideas by 2 PM on Tuesday.

And so I started the podcast really as a way to sort of share some things I was learning, but also to invite other people to come and teach me some things that they were learning about how to do this. And it just kind of exploded from there. So my interest in this topic was really from a demand on my part to understand some of the underlying mechanics of creativity, especially creativity under pressure, creativity in the marketplace. And what I discovered was that

So many of the brilliant creators and leaders that I was encountering in the marketplace seemed to have, even if they weren’t formal, they had some practices. They had some things that they settled into over time that they did over and over and over again that kept them in the game. I always like to say that talent will get you a seat at the table, but your practices are what keep you in the game over the longterm and so that was what I was exploring and that led to the research that became the accidental creative. then, you from there, obviously it just kind of sort of things kind of took off from there. But that was kind of my entry point into this space. I am an accidental author. I had no intent of writing a book. It just sort of happened, but I’m very grateful that I’ve had the opportunity to do what I’ve done.

Yeah, absolutely. So when you were diving into these creative practices and this idea of creating on demand, it’s something that I think a lot of us actually struggle with. I have a music teaching background, so as teachers in general, or as educators, people are constantly asking, what’s your new lesson plan? How are you keeping it interesting for students? So this idea of creativity on demand is something that many of us have to work through.

What are some practices that you found helpful in that process?

So there are five key areas from the Accidental Creative that I talk about as what I call Creative Rhythm.

So people love to talk about balance, having balance in your life, you know, and I just want to balance this and balance that. And the reality is there’s no such thing as balance. We’re constantly moving from one thing to another, and we have to be all in wherever we go. And so I like to talk about it terms of rhythm, putting a rhythm in your life of practices that keep you stable and infrastructure to support you during those, those busy times. If you want to do anything and important, you have to have infrastructure to deliver it. and where failure happens, it’s usually because the wrong infrastructure is in place.

So the five areas are focus, relationships, energy, stimuli, and hours. Focus is about how we allocate our finite attention. We don’t realize it, but often as creative professionals, we have poorly defined the problem we’re trying to solve. And therefore it’s hard for us to allocate our attention in meaningful ways to actually solving those problems. Or we’re still trying to solve a problem from.

You have three weeks ago that has now changed because we’re not constantly redefining the problem as we’re learning things. So focus is very important. Relationships. think of creativity as a solo sport, but it’s not, it’s groups of people stumbling awkwardly into the unknown together, and, walking into dark rooms and turning on the light and saying, here’s what I see. What do you see? Here’s what I see. so we need other people in our life to help us stay engaged and focused and moving forward in a meaningful way. Energy, we’re great about, time management. We’re brilliant at time management. We have more tools at our disposal than at any point in human history. And we become more more efficient at managing our time. But the problem is we only have so much energy to give and brilliant ideas, brilliant work requires what Lewis Hyde called emotional labor. That’s putting discretionary energy, emotional energy into our work. Part of what makes creative work different is that we’re putting part of our identity into what we create.

Now our work isn’t our identity, but it’s an expression of our identity, of our perception of the world, right? And that requires emotional energy to do that because it’s vulnerable. takes risk, all those things. So we have to manage our energy effectively. If we want to, you know, to do great work consistently over time, anybody can do one great thing one time, right? But if we want to continue to do it over time, we have to manage our energy effectively. Stimuli. These are the dots that we connect Steve Jobs famously quipped that creativity is just connecting things. And it is, it’s, largely just taking two things that don’t seem like they belong together, putting them together and solving a new problem. and, but, but we have to be mindful of the dots we put in our head, the kinds of stimuli that we’re absorbing, how we’re shaping our mind. And this is even more important, I think in the age of AI, as we move into these, the world of generative AI, where we have infinite ideas at our fingertips.

Right? mean, seriously, like generating ideas is not the problem anymore. The problem is going to be how do we synthesize? How do we intuit? what is the role of taste moving forward for creative people? I think it’s going to be amplified massively. and people with taste are going to succeed in those without taste. Those who just kind of got by on being able to crank out a bunch of things and, bury it in noise. I think.

Those people are going to struggle. So we have to be good at curating our stimuli, cultivating our tastes, cultivating our intuition. And then finally is hours. Hours is about where we spend our time, but many of us think about our time as something to be spent. I just said it as a matter of fact, rather than something to be invested. Um, if we want to be effective, we have to think about how we’re investing our time, how we’re putting ourselves into projects, into ideas that may not have an immediate payoff, but could pay off.

Over the longterm when we get very busy, when we’re creating under pressure, it’s all about what do I need to do today to deliver results as opposed to how do I need to invest my time so that three weeks from now I’m better positioned to have a brilliant result. So we have to think about our time differently. So focus relationships, energy, stimuli hours. Those are the five areas. my editor, for the, for the accidental creative.

Originally ours was time and he said right now you have fresh and fresh is not very good Let’s change time to hours and you have fresh and then you’re fresh and it’s you know, so it’s a good way to remember it

Perfect. And there are so many nuggets in what you just shared, and I can see so many of the creative process evolving in those ways. Two that I really kind of want to kind of dive into a little bit more. The idea of emotional labor and having ourselves put into the things that we’re creating. I think it’s why creative professions like teaching, but also others, when people say it’s just a job and they don’t understand, it’s not because this is a piece of ourselves that we’re giving over, which requires vulnerability and bravery. so, and you’ve often said that bravery and creative expression are two sides of the same coin. So can you expand on that a little bit?

Yeah, I think I would add one more, I would go one layer beneath what you just said, which is that, you know, so it requires incredible vulnerability to do what teachers and artists do. And I would say that that vulnerability is sourced in something, a concept, well, the word passion, which is often misunderstood because people talk about passion as something that.

Yes, I think I like it’s something I enjoy and you certainly can enjoy the things you’re passionate about. There’s no question about it, but that’s not what makes them passions. The word passion in its root form comes to the word passio, which means to suffer. So when we say we’re passionate about something, what it means is there’s an outcome that matters so much to me that I’m willing if necessary to suffer in order to see it happen. And teachers certainly, you know, very few teachers go into education thinking, Oh, I’m, you know, I can’t wait to, I’m going to.

By a Lamborghini and a mansion and in the Hollywood Hills. I’m going to, like people don’t go into teaching because of the money and because of the fame and because of the recognition and all the things they go into teaching, because it’s like, there’s something I care about. There’s an outcome I’m pursuing and it’s worth maybe even surrendering some of those other things I might get in order to pursue this outcome, right? This thing I’m passionate about that I’m willing to suffer for if necessary.

And so as a result of that, requires a kind of surrendering of yourself to the mission, to the thing that you’re doing. So when I say, you know, that creativity and bravery in many ways are two sides of the same coin. What I mean is you’re, you’re surrendering yourself to a process where there’s potential for suffering. You’re surrendering yourself to a process. You’re putting your identity into your work. And that means you’re risking rejection. That means that somebody might say,

Well, that’s stupid. Every time I write a book, I get at least one or two. And I’ve had, you know, obviously thousands and thousands of reviews on Amazon. I don’t even read. I don’t even check reviews anymore. I did it first, think partly because I was like, am I crazy or is this, is this good? I think it’s good. And now I’ve realized like, okay, I write good books. I’m not worried if somebody, some random person is going to say something really cruel, but there are people who have said like incredibly cruel things about mean about my books on Amazon, in spite of the fact that, you know, they’re generally very well received. that’s, that hurts. That feels like rejection, you know, even though it shouldn’t because it’s like, well, that’s just one person. but, but that’s, you know, it’s, there’s a kind of vulnerability that comes with doing creative work. You’re making leaps into the unknown. You’re connecting dots. You’re saying, what about this? What about this? and so we have to exercise bravery in the face of that, because anytime we’re acting bravely, bravery and boldness is not the same thing. boldness is just doing something unexpected and brash, right? and for, for your own potential gain, that’s fine. There’s nothing wrong with that. Bravery means there’s something I care about. It’s not about me. It’s about the thing I’m doing and I’m willing if necessary to suffer, to see it happen. bravery is always empathetic. It’s about the other, it’s about the cause. And when you’re creating something for others,

There’s always a potential the other is going to reject that, which is why it’s brave. Um, and it could potentially cost you something. I have a conversation often with my author friends or with my, my leader friends in organizations. And you know, they’ll say, well, people will tell them things like, Oh, well, that’s easy for you. You know, look, look who you are. Look at the platform you have, look at the influence you have, look at the whatever they’ll say that to my, to my friends.

And my friends will say, are you kidding? mean, look at, know, if I, somebody, if this doesn’t go well, look at what I’m risking, look at what I’m, you know, putting on the line for this thing that I’m doing. think that’s why bravery is so important because you have to understand the cost and you have to be willing to take the step anyway, to bring about the change that you’re trying to bring about in spite of what it cost you. So that’s, that’s what I call productive passion. When you have that kind of productive passion, it is the kind of passion that can change the world.

Absolutely. And I think your distinguishing between boldness and bravery is brilliant because oftentimes when we’re in class, we’ll see students who act out in very much a bold way. You know, that they will push the boundaries of boldness, thinking that they’re being brave, but knowing the underlying motivation for what they’re doing is a key, I think, to understanding the difference between them, somebody a student being bold and pushing the boundary and a student being brave, truly brave and sharing what it is that is, you know, maybe scary for them. Now, I do know that some educators are nervous because they want to cultivate bravery, but students don’t know how or they don’t know how to cultivate that in their students. So, can you give us some ways that maybe we can cultivate that bravery?

Yeah. So there are two in my book, the brave habit. There were two things I found two common factors that tend to lead to brave decisions. and so I’ll share those and I’ll come back and offer some practical things that we can do. the, the first thing that tends to be present is an optimistic vision. meaning that we have a general sense of the, in our head, an image in our head of the thing that we want to make or the way that the things that things could be better, right? That’s what an optimistic vision is.

The second thing versus versus a sense of pessimism, right? Well, I could try, but it doesn’t matter because you know, why would I try to do this to make this thing? Why would I try to create something? It’s just, it’s not going to work out. Well, I’m not good. I’m not going to be able to do it. the second thing is present is a sense of agency to bring it about, right? versus a sense of powerlessness. So when we have a sense of agency, Hey, I may not be able to do everything, but I can do something to bring about this vision. I can get.

You know, I have the ability to at least bring part of this into being. And we all know that when you’re making art, when you’re writing books, you’re writing a song, you’re producing an album, you’re writing poetry, whatever you’re doing, it’s never in the end exactly what you intended to do. That’s just kind of a North star you’re navigating toward, but you never know exactly how it’s going to end up. You’re just pursuing this vision, right? This optimistic vision. And there’s always a gap between where you are and what you think it’s going to take to get where you want to be. You’re always having to cross that chasm. So that’s where bravery comes in. And that’s where teachers can speak into students. Hey, tell me about your vision. Tell me about what you’re pursuing. Tell me about, you know, what, because it’s easy for students to think, well, if I can’t make the best thing that’s ever been made, then why would I even try? Well, no, that’s not the point. The point is to make something that’s you. The point is to put yourself into something. So tell me about your vision. Tell me about the thing you want to make. Tell me about, you know, the the work of art that you sort of see in your head or something you saw that inspired you that you want to sort of emulate in some way. Tell me about that. Give me a sense of that vision. And, hey, maybe, you know, maybe somebody says, I want to write a symphony, right? You’re like, well, do you play an instrument? Have you ever written music before? Have you, you know, whatever.

Well, okay, maybe that’s not your thing, but how would we translate the idea of writing a symphony to a medium that you actually have some agency and that you’re actually good at? Okay, now let’s talk about that. Or maybe you could partner with someone who is musically gifted and you’re visually gifted. So what if you created something where it’s like a visual that accompanies a piece of music and it makes you feel a certain way or whatever, but speaking agency into them and saying, just because you can’t get all the way there doesn’t mean you shouldn’t take the next step in the next step, in the next step. And you can figure it out as you go. But if we want students to be brave, we have to paint a vision for them and we have to speak agency into them. And we have to nudge them and push them to take little risks along the way. Bravery always understands the cost, but it acts anyway. If you don’t understand that there’s cost involved, it’s probably not brave, right? If it doesn’t cost you anything to act or potentially cost you anything to act, then it’s probably not brave.

And if it’s easy, everybody would already be doing it. And that’s the other thing I think students need to understand is like, listen, the easy stuff’s been done. And so what hard thing are you doing every day to push yourself to take chances, to try new things? And you’re going to discover along the way, a unique voice. You’re going to discover yourself along the way. It’s not going to happen all at once. People want to come out of the gate with a unique voice. I’m a brand new thing. It’s never been seen. doesn’t, nobody, no artist in history has ever just emerged on the scene is this brilliant new voice. Everybody came up through, know, like some of the greatest impressionist painters started off as realism landscape painters, right? Like, and then they sort of discovered impressionism over time or Steve, Stephen King. I wrote about this in my book, Louder Than Words. He said, basically I copied combat Casey comic books into these little blue books he had. He would just copy them word for word because he wanted to get a sense of the feel and the style and all that.

And he became this like brilliantly unique writer. Steve Earl said, basically songwriters just copy the songs of their heroes until they discover their own voice. Right. So I think that what we have to help students understand is, everybody wants to be known for a thing, but you don’t, you don’t come out of the gate known for a thing. You emerge into becoming known for a thing over time, which means taking little risks, discovering yourself, figuring out the things you can do that nobody else can do. spent, sorry, I’m going on and on, but I spent, I spent last weekend with a friend of mine, Zach. Zach is, it’s great when your friend comes to town for work and you get to spend the whole day showing them your city, which was fantastic. It’s even better when your friend Zach is the DJ for LL Cool J and you get to watch him work and you actually get to go to the show and watch him do his thing. And Zach was telling me once, he said, you know, it’s kind of like all of us as DJs, right? Cause DJs are a unique thing. They’re taking elements and mixing them together into something new. said, it’s like,

It’s like a tree and you’ve got all these DJs hovered around the tree because the tree is stable. The trunk is stable. That’s where the money is. And you can make a lot of money just kind of doing the thing that’s expected. He’s like, but then every so often somebody steps out on a branch and they start going out on the branch farther and farther and farther. And they become notable because they’re willing to take those little risks that are required. It’s really easy to stay on the trunk and everybody’s like, why are you going out on the branch? It’s great here on the trunk. Stay here where everybody else is.

And he’s like, but it’s only out on the branch that you really like when you’re taking those risks, you discover who you are, but it’s risky because you’re getting farther and farther from what’s expected of you. And I thought I was being smart. said, well, Zach, what happens when the branch breaks and you fall off, right? Cause you get too far out of the branch. You said, that’s the beautiful part. The beautiful part is once the branch breaks, you become a seed and you become a new tree. And then people are emulating you. And I was like, that’s, that’s pretty good, right?

And so I think that’s the way we need to approach our work. Everybody starts out in the trunk, emulating, copying, developing their basic skills. But the great ones are the ones who begin to step out a little bit at a time onto the branch and they begin to move out into doing something unique. And then eventually the branch breaks, they fall off and they become a new tree trunk that everybody’s copying. That’s how great artists are forged over time.

Yeah, well, I mean, clearly you work with so many creative professionals and leaders and who have these experiences. And I would imagine, in fact, I know that if you’re going to put yourself out there, you’re going to be brave in the creative sphere. You’re also going to face fear and resistance. It’s just, I feel like those are two qualities that tag along for the ride no matter what and no matter who you are. How have you seen the most consistently creative people deal with those two tag alongs of fear and resistance and maybe how can we do, how can we work with our students to overcome some of that or at least dull it a little bit.

Yeah, I think for the first thing is just acknowledging that these are our constant companions. Like they’re not going away. You’re not getting rid of fear. You’re not getting rid of resistance. That’s the term Steve Pressfield, uh, came wrote about in the war of art, which is a fantastic book. One of the first people I interviewed on the podcast, as matter of fact, in 2007, um, cause it’s such a phenomenal book. Um, so that’s the first thing is just recognizing these are common forces. They’re there. Everybody experiences them when your favorite artist, your favorite musician walks on stage, they feel a little bit of fear, right? Like every single time, it doesn’t matter who it is, or they’re lying to themselves if they don’t, because it’s weighty, the work that we do is weighty. That’s the first thing, but the second thing is recognizing the difference between true consequences of failure and perceived consequences of failure. So talking through, okay, if you do this, what might happen if you fail?

Okay, yeah, there’s a very real risk that something could happen that you could fail, that it could impact you in a negative way. But the stories we tell ourselves about what we’ll have, I’ll be ruined. Everybody will make fun of me. Nobody will ever, you know, those artificially escalated narratives are, have to be called out and identified for what they are, their lies. And so the more we talk about true risk versus perceived risk, it tends to mitigate some of the negative effects of fear. Recognizing the real consequences is important because otherwise we’re deceiving ourselves, but also ensuring that artificially escalated consequences don’t creep in and paralyze us and prevent us from acting is very important.

I think that’s so helpful and it reminds me of Tim Ferriss’s fear maps, that of being able to sit down and just map the whole thing out, go as far and as deep as you can and look at the end result and acknowledge, first of all, is this true? Would this ever really happen? And secondly, if it could and if it did, would you be able to handle it? And in most cases, it’s yes, you know, to that or, you know, no, it’s not actually even true. So I love the idea of getting to the root of it and determining is it even true and could we handle that? So before we head out today, because, I can’t imagine, I can’t even believe it’s already been this long. I mean, I’ve learned so much from you already. One of the things that you talk about that I think is fascinating is the seven deadly sins that can cause creative stagnation. Which do you think that teachers are most prone to? First of all, can you tell our audience what the seven deadly sins are? And then can you highlight which one you think teachers might be most prone to and how we can avoid that?

Yeah. So, they are aimlessness, busy boredom, comfort, delusion, ego, fear and guardedness. I would say we’ve already talked about fear a little bit. I’d say that that’s, that’s certainly one, but I would say probably the one I would encourage people to think about the most is what I call aimlessness, which means, that you, know, that doesn’t mean you don’t know what you’re doing. It doesn’t mean you don’t understand your job or you’re, don’t, know, you’re not competent, what it means is that you lose sight of the deeper thing you’re trying to do. you can very easily hit all your marks. You can accomplish all your objectives. You can get great scores. Everybody can love you. It can look to the outside like you’re succeeding, but deep down, you know, that you’ve, you’re kind of settling in, you know, that you’ve kind of fallen into a routine, a pattern that is not consistent with the outcome that you want to have. You can settle into a place of, mediocrity and the word mediocrity comes from two words in the original language, medius, meaning middle and ochris, meaning rugged mountain. So it’s really easy to get halfway up the rugged mountain and say, close enough. We intended to go to the top, but I mean, it’s close enough. I’m having impact. It’s fine. And to lose sight of what you’re trying to do. And the way I describe it to people is you can succeed your way into failure. You can do everything that everybody expects of you and you’re succeeding to the world, but you’ve failed at the thing that you intended to do. And so it’s important that you have a sense of your productive passion. As we talked about, what is the outcome that matters so much to me that I’m willing to suffer on behalf of it, even if it means doing things that are a little bit left of field in my industry, it means I’m taking a left turn whenever everybody else taking the right turn. you know, whatever that looks like, you have to keep your eye on the outcome you’re aiming for, not the immediate ping of feedback that you’re getting from the work that you’re doing and people who do that over time, they tend to counter this deadly sin of aimlessness, which is when we’re checking all the boxes, but we’re slowly getting off course from the thing we intended to do.

So helpful and I think very resonant in what many educators face. You could very easily put in 25 years of success leading to failure in your words. I think that is very helpful. thank you for keeping us on track and keeping us mindful of that. Todd, where can our listeners find out more about you, your work and to connect with you?

Yeah, T O D D H E N R Y.com. you can also find my podcast there for 20 years. We’ve been serving up weekly ideas to help people be brave, focused, and brilliant. So it’s called daily creative with Todd.You could find it there or subscribe to the newsletter. once a week, we send out an email with some insights, some deeper dives into the podcast topic that help people again, be brave, focused, and brilliant.

Fantastic. We will put all of that in our show notes. Thank you so much for joining me again today, Todd. This was such a helpful episode and I really appreciate your insights.

Fantastic, thanks so much.