Episode 325: The Secret to Courage? Brave Habits (with Todd Henry)
26 Sept 2024 · 28 min
In this Skucast episode, host Bobby Lehew interviews creativity and leadership expert Todd Henry about his newest book, The Brave Habit. The conversation begins with a brief introduction to Henry’s background—author of seven books, creator of the Daily Creative podcast, and keynote speaker for the upcoming SKUCon conference. Henry reframes bravery not as an innate trait but as a deliberate choice: the act of applying courage in moments of uncertainty. He distinguishes small, everyday brave actions from heroic, “heroic” moments, arguing that consistent micro‑bravery builds a reservoir for larger challenges. A central theme is the concept of dissonance—the gap between the “why” and the “what” of work—and how simplicity (aligning purpose with method) restores agency. Henry explains his leadership principle of “bounded autonomy,” where leaders set clear goals but give creators freedom to choose how to achieve them, a practice he calls herding tigers. He walks through the BRAVE acrostic (Block time, Review, Agency, Visualize, Express) as a weekly habit system to prepare for brave decisions. The dialogue also touches on the distinction between finite and infinite games, positioning the infinite game of lasting impact as the more courageous path. Henry warns that cowardice often masquerades as wisdom, urging listeners to recognize safe‑mode advice. Throughout, he emphasizes preparation—reviewing upcoming commitments, visualizing outcomes, and pre‑deciding intents—to shift from reactive to responsive behavior. The episode closes with teasers for SKUCon, a nod to Henry’s other works, and a brief mention of recent influences such as The Righteous Mind.
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Welcome to Skucast, the podcast for entrepreneurs in the promotional products industry. Skucast shines a light on our industry's best work, features maverick personalities, and discusses what's really involved in running a modern promotional products business. Skucast is the official special podcast of Common Skew.
Todd Henry is one of the most sought-after creativity coaches in the world. He teaches leaders and organizations how to establish practices that lead to everyday brilliance. He's the author of 7 books, including The Accidental Creative, Herding Tigers, The Motivation Code, Daily Creative, and more, which have been translated into more than a dozen languages. And he speaks and consults across many industries on creativity, leadership, and passion for work. With more than 18 million downloads, his podcast Daily Creative offers weekly tips for how to stay brave, focused, and brilliant. His latest book, The Brave Habit, offers strategies for rising to important moments in life and work. And Todd is our opening keynote speaker at SKUCon in Las Vegas on January 12th, where he will be speaking on the topic, How to Be Brilliant on a moment's notice. Todd's topic is perfect for our industry because we live in such a deadline-driven, fast ideation environment. And we just opened registration for SKUCon this week, so you're one of the first to hear about it. And as you know, SKUCon always sells out. So if you're curious, you want to learn more about the event and our lineup of amazing speakers, go to skucon.com and reserve your spot today.
Today.
But in this episode of the SkewCast, we're talking with Todd about his latest book, The Brave Habit. To hear his advice on how to be brilliant at a moment's notice, you'll have to join us at SkewCon. But for today, we dig into this topic of bravery, courage, and why simplicity is your greatest tool to fight dissonance. But first, quick question for you. Do you know our friend Anthony McNally, the brand experience manager at Vanguard Promotions? You should know Tony. He's one of the coolest guys I know who has really made an impact in New York City and on this industry. Well, Tony's joining me for a live interview on Thursday, October 3rd, 2:00 PM ET. And the interview is for the CommsCue curious. If you're not on CommsCue and you want to know what it's like to create an efficient team geared for growth through the simplicity of the CommsCue platform, a unified single source of truth to make your team's life easier., then show up to hear how Tony and his team make it happen. You can find the link in the webinar in our show notes for this episode, or hop on over to commonscue.com/events and scroll to the webinars. We'd love to see you there. Today's episode is brought to you courtesy of us at CommonsCue. We are the work-from-anywhere platform that powers your connected workflow, enabling you to process more orders and dramatically grow your sales. If you want to learn how over 800 100 distributors fuel their phenomenal growth, visit commonsku.com. And now here's our chat with our SKUCon keynote, Todd Henry.
Todd, thanks for joining us on the Skucast, my friend.
Oh Bobby, it's so good to be here.
As I mentioned in the intro, Todd's book The Accidental Creative has influenced many, many creative professionals, and we are going to hear all about that in January. But really what we're here to talk about in the Skucast is a glimpse into what Todd's going to talk about at QCon. But for today, we're going to talk about The Brave Habit, which is Todd's new book. And it's a different twist on bravery, Todd. How, for example, how do you define bravery?
So often people conflate the words bravery and courage, right? They think that they're basically— that, you know, we tell people have courage, go be courageous. But to me, that always felt like it fell a little flat when I would talk to my team members and tell them to be courageous, it felt like I was telling them to jump a little higher, be a little taller, right? It's like you're telling them to have some attribute, whereas brave action, in my perception, in my research, brave action, as I'm defining it in the book, is the employment of courage in a moment of need. So it's putting courage into action, which means it's a choice. It's something you can choose as opposed to something you have. It's not a trait. It's a decision that you make to act bravely in the face of uncertainty. And so I really wanted in this book to really sort of help people understand that bravery is something you can choose, not just something that happens to you or that some people can do and other people can't do, but it's something that we can choose in the face of uncertainty every single day.
It sounds like such a minor correction, but it's huge. It's a major correction. So take, for example, you take somebody like me who might be more wired for flight than fight. And I might say something to you like, I'm just not a very brave person. I don't think I could ever be that brave. We tend tend to use those statements a lot, but you're saying it's not about who you are and how you're wired, it's about making a choice in the moment.
It is. And, and I would also say that sometimes we tend to think that bravery is about those big moments, right? It's about running into buildings, it's about storming beaches, it's about, you know, launching a business against all odds, you're risking everything. And that's not really, I think, a great definition of bravery. I think we could probably call that heroism more so than bravery. And it certainly is brave. Yes, unquestionably brave. But I think sometimes we excuse those little moments of cowardice in our lives by thinking, well, you know, bravery is for the big moments. No, bravery is for the small moments. It's how we choose to interact with someone on our team we have a difference with. Are we going to have a difficult conversation, or are we just going to let things slide and hope that they work themselves out, right? Yeah. Are we going to introduce the idea in the meeting, or are we just going to let the moment pass and, you know, hope that we don't regret the fact that somebody else comes up with that decision or that, that idea later, right? So these small acts of bravery practiced consistently over time are what give us the deep reservoir of bravery that we need in order to act bravely in the big moments.
One of the unlocks for me as I read your book was this quote, "Life is a universe of probabilities, not certainties. This means that we cannot seek certainty before we act. Instead, we must cultivate clarity." Why is uncertainty a key requirement for bravery?
Well, if everything was certain, bravery would not be required. If I knew that my risk was going to work, if I knew that launching a business was going to work, then it's not really a brave action, right? If I knew that making a financial investment was going to pay off tenfold, it's not really a brave investment, a brave decision. If I knew the other person was going to respond favorably, it's not really a brave conversation. So uncertainty is baked into our everyday interactions. It's baked into the world, it's baked into the universe. And so some people, I think, unfortunately, in their chase for certainty in their life, forego potential. You know, they, they seek certainty to the point that they are unwilling to step into uncertainty, to the point where it causes them to forfeit their potential as a professional. And I think it's really sad. And it was really the big— that was a big impetus for me writing the book, right, was to challenge people to lean into that uncertainty a little bit more. Not to take big stupid risks, as I write about in the book. You know, bravery isn't rash action. It's not bravado. It's not bluster. It's not stupid risk. Bravery is taking progressive, consistent steps in the direction of your optimistic vision and claiming agency to do so. And the more we do that over time, the more we prepare ourselves for those moments when, when big action might be required.
What you just said really helps bring it down to us that are salespeople. We might be managers. We might be CEOs of our business. Is this idea of bravery. Because you look back at very large personalities, and I'll think of folks like from Georgia O'Keeffe to Mother Teresa, both of them had talked about they've never had clarity in their life, they've never had that kind of certainty in their life, and yet they go create this body of work or they impact the world in the case of Mother Teresa in small actions all the time. We only tend to sort of ascribe bravery and courage to them in hindsight, but in actuality, it very much mapped out the way you're talking about. It was these individual battles on an individual basis, small actions with a big vision.
Yeah. So I just finished writing something. Actually, it's going to be on next week's podcast. In 1965, I saw an interview with Mick Jagger. I didn't see it in 1965. The interview took place in 1965. There's an interview with Mick Jagger in which he was asked, and the Stones, by the way, had just had I Can't Get No Satisfaction. I can't, I can't get no satisfaction. They had had like a couple number one hits. They were sweeping the world, part of the British Invasion. And then a reporter asked, so how long do you think you could keep this going? And Mick Jagger's response was, well, I think we're pretty well set up for another year, right? In 1965. And I just saw a video the other day of like the Rolling Stones playing a stadium somewhere, you know, in like 2024. It's crazy. But in the moment, everything feels uncertain. In the moment of creating, most people have no clue whether something's truly going to be successful, truly going to be sustainable. They're just in the moment doing the thing, making the thing, pursuing a vision. And so your examples of, you know, Georgia O'Keeffe, Mother Teresa, or these people who we sort of hold up as these icons, these brave icons, or the Rolling Stones, right? Wow. Well, surely they knew it was inevitable that they were going to be these like legendary icons. No, in the moment they're just doing their thing. They're just bravely taking the next step, right? Writing the next song, releasing the next song, putting it out there, going on a tour, hoping it holds together. I think we're okay for another year, right? I mean, it wouldn't surprise me if they've been saying that for the last 60 years. Well, I think we're pretty well set up for another year, you know, right? That's what it feels like on the inside where all the risk is being taken. And yeah, I think a myth that we tell ourselves as creative professionals is that everybody else has some secret playbook that we don't have, right? We look at successful people and we think, well, they surely, they have something figured out that I don't know. And the reality is everyone is just making it up as they go. And I don't mean to be reductive, because I mean, certainly as you get experience, you know, you, you have a few more strategies and you have a little bit more experience, you can see more patterns, you have a better purview, certainly. But the reality is, when you start moving bigger rocks around and you talk to people in senior leadership, they're like, I don't know, I'm just kind of, I'm just kind of making it up as I go, right? And figure it out. Yeah, we'll figure it out. We'll just, we'll act and then we'll figure it out on the other side. I mean, that is so much of life. And And it's really sad to me, Bobby, that so many people spend their life standing on the sidelines waiting to have things figured out before they act. And they're not willing to take those small brave steps into uncertainty to start figuring things out.
That's a great point. I remember reading Howard Schultz, the founder of Starbucks, saying that the apex of his success, he was the most concerned. Like, you would think all of that success would have brought him clarity and certainty and conviction and all those things. And like you said, surely, yes, it did. It built up that muscle, but he still had to exercise that muscle of courage. Speaking of folks sitting on the sideline, you said that cowardice was often disguised as wisdom. What do you mean by that?
So the voice of cowardice in our life doesn't sound like, oh, run away, this is dangerous, right? It often sounds like, well, wouldn't it be better if, or maybe you should wait until, or, you know, it probably would be wise to. So for example, you know, maybe, maybe you should preserve your political capital now so you could spend it later, right? Or maybe you should not introduce that idea because maybe you'll have a better idea later that you'll want to preserve your voice for, right? It often sounds like the voice of wisdom. It's really just fear in disguise. It's cowardice in disguise, but it comes across sometimes as wisdom. And sometimes it comes through the voices of people we trust, right? Sometimes it's well-meaning people who are telling us things that, you know, they would do in our situation but aren't necessarily helpful bits of advice. Yeah, and so we're watching out, they kind of have our back, right? Yeah, but, but most people who care about us want us to be safe. That's what they want for us. I have a bumper sticker on my bulletin board— I'm looking at it right now— that I made for my team a couple of decades ago because I felt like we were sort of playing it safe. And the bumper sticker says, "Safety is not an option," right? Meaning that when you try to be safe, when you're trying to play it safe, that's like the most— and it's cliché now because it's so often said, but it's completely— it's cliché because it's true. When you're trying to be safe, that is often the most dangerous place you can be because it means you're not going to take risks, you're not going to try things, you're not going to experiment, you're not going to listen to those voices that might tell you, hey, push this envelope a little bit, do this thing, say the thing, you know, introduce the product. You don't do that. Instead, you just try to hover close to the middle, but that's where everybody else is already playing, right? That's where everybody else already is. And so playing it safe is the most dangerous thing you can do. And so that's what, you know, the people who care about us, they want us to be safe. They want us to be comfortable, you know. And safety and comfort are fine as a byproduct of hard work and brave action, but safety and comfort cannot be the goal. Because at some point, if you want to create great work, you're going to have to do something that's going to make you uncomfortable and unsafe for a while, at least, right?
Yeah, let's talk about the agency. Agency, the fact that gets us from, from this point of safety to making a brave decision. You, you said, quote, the greatest tool you have in your battle against dissonance is simplicity. And you mentioned that dissonance was the mortal enemy of agency. So I'm trying to figure out, well, like, what is that mechanism? So can you unpack that more? Like, what is— what does simplicity have to do with accelerating the agency of acting on something courageously?
So dissonance, as I define it, is a gap between the why and the what of our work, right? So we might very well be doing something and have absolutely no clue why we're doing it. This is very common in creative work. You know, you have these really talented people who have been told to do a project, and they're doing the project because that's their job, but they don't understand why they're being asked to do it. And so in some sense, they're being robbed of their agency because they're basically executing something somebody told them to do, and they'll do it very well because they're very talented. Yeah. But if instead you gave them a problem and said, here's why we have you doing this work, here's the problem we're trying to solve, now how would you go about solving this problem? And you let them claim agency over not just the, the project, but the mechanism by which the project is accomplished, or the method, then it completely changes and simplifies their engagement, right? So many people spend a lot of time trying to bridge that gap between the why and the what of their work. Like, I'm doing this thing, but I don't feel like it's the right way to do it, but that's what they told me to do, and I'm not sure why I'm doing it. So, so it, it robs us of agency. So when I say simplicity is the key, what what I mean is aligning the why and the what of your work, yeah, allows you to claim a sense of agency in your life. When you understand the vision that you're pursuing and why you're pursuing it, and you're allowed to choose the mechanism by which you pursue it, and you're allowed to bring something that you're really good at to the table to help you accomplish it, it really simplifies what brave action might look like for you. Sometimes we don't act because we don't feel equipped or we don't act because we think, well, this is what it's going to take in order to act. Well, not if you— not if somebody says to you, hey, I just want you to get this done, whatever it takes for you to get it done, get it done. Use whatever sense of agency you have, whatever skills you have, whatever aptitudes, platform, whatever you have, use whatever you've got to get it done. I'll let you choose the method, but I just need to get— need you to get this done. It completely changes the calculus for people. And so that's what I'm talking about. I talk about simplicity is just let people bring the essence of who they are. Don't give them something really complex to do and then say, good luck, right? Instead, say, hey, here's the problem we're solving, here's the vision we're pursuing. Now use your agency, your platform, your skills, your experience, your relationships, whatever it takes. You do whatever it takes to get it done, and I'm going to let you do that. I'm going to let you choose the mechanism.
And that releases creative people rather than constricts them. And in the sense of whoever's offering that, offering that encouragement, to do that project, then it also requires a courageous act on their part to let go and let those creators do that.
Yes. Your job as a leader is not to get work done. Your job is to lead the work. Yeah. And this is a real problem in the creative marketplace. It's why I wrote my book, Herding Tigers, right? Our job as creative leaders is to create bounded autonomy, freedom within limits. There have to be limits. We have to set boundaries because we have to preserve resources. We have to direct the flow of the work. We have to be targeting something, right? But we have to create freedom within that, which means we have to release our temptation to control. We have to release the urge that we have to like get in and make decisions with people and, you know, and instead let them direct the flow of their own work with frequent check-ins, of course, right? But that's a really, really difficult, extremely difficult thing to do. And that requires— that's why a lot of leaders fail, frankly, is because they don't exhibit brave action in their leadership, which often means releasing control in the face of uncertainty. Instead, they feel like they need to be the one making the decisions. They want to be the ones recognized for the successes. That's not our job as leaders.
Well, for those listening now, you have your third Todd Henry book to get, Hurting Tiger.
But we're going to dip in and out of these topics quite real fast.
But I encourage you to go check it out because just spending time in that idea of dissonance and simplicity is huge for us. But in your acrostic where you spell out the word brave in your book, B for block time for reflection, R for review your life and work. A for take agency, V for visualize better possible future, E for express your intent and mission for the week. What does it look like to make brave choices this week? I like how practical that is. Why for the week? And of the 10 of those, is there one that's a linchpin to the others?
Yes, because the reason I put that in the book is because most people want to do the right thing, but they're reacting in the moment, not responding. The key to all of the— really all of the work I've done so far, The Accidental Creative, which I'm going to be talking about at SKUCon, right? The key to that is if you want to be brilliant at a moment's notice, you have to begin far upstream from the moment you need a brilliant idea by building practices into your life to prepare you for the moment when you need to be brilliant, right? Same thing applies to bravery, brave action. If I look at my calendar for the week and I see these are the meetings coming up on my calendar, if I look at my calendar or my task list and I say, oh, I know I have a pit in my stomach about this conversation. I know in that moment, I know this person's going to try to power up on me. I know that I'm going to have to say some difficult things. I know that's going to be hard for me. And I know in the moment, if I haven't pre-made that decision, that I am very likely to react. And reacting means retreating and hoping things go away, hoping things get better or worse. I'm going to react and like power up on them and have some— and say something I don't mean to say. So I'm going to get ahead of that by reviewing my upcoming commitments.. I'm going to look at the agency that I can take in those relationships. How can I claim agency in that conversation? I have a pit in my stomach about to make sure that I am bringing the right perspective. I'm going to pre-decide how I'm going to conduct that conversation. What's my vision? That's the V part for an optimistic, better future with that relationship. What would be the ideal in that relationship? Right. I'm going to get ahead of it and I'm going to express my intent, which means I will in this conversation, I will be firm, direct, clear, yet compassionate, empathetic, and I will have a listening mindset with the person I'm speaking with. But I'm not going to back down because I know that my perspective is right. But I'm going to listen and be empathetic to their perspective because I know that that's what's going to create a valuable relationship moving forward. So my intent is that our relationship will be stronger. After the conversation. By getting ahead of that, you're preparing yourself for those brave actions in the moment. You're gearing yourself up for it. It's the same. I mean, I, I, it— I really don't like it when people draw parallels between things like combat and business, right? Sure. But there's a reason why the military trains so hard and why they prepare for so many different contingencies. You know, it's because in the moment when things go crazy, because nothing ever goes according to plan, right, you need to Oh, this, this feels familiar to me. Yeah, I've done this before. Okay, I know exactly what to do here. At least I've done something similar in the past, right? So in the face of uncertainty and chaos and fear, I'm not making those decisions in the moment. I'm not reacting. I'm responding based upon my training. And the same thing applies in everyday life and work on a much less dangerous scale. But the same thing applies. We need to prepare ourselves ahead of time for those moments.
Todd, I rarely take this license, but I'm going to ask the audience to forgive me. I'm usually asking questions on behalf of the audience, and I take pride in trying to make sure I ask questions on behalf of the audience. But I have a question for myself because I found out that there's a book we've both been impacted by, Finite and Infinite Games, James Kars. And you have this quote, and I want to quote it at length, that ends with this. It's your quote from your book. Brave people are driven by principles and causes. But here it is in its entirety. In his book, Finite and Infinite Games, philosopher James Kars argued that many people are often playing the wrong kind of game at the wrong time. A finite game is where one— one where there are clear rules, clear winner, loser, and a finite time frame. For example, football, baseball, and cricket. Everyone understands the rules and there's a clear scoreboard that determines the winner when time runs out. On the other hand, infinite games are for those which there is no end. Rather, the goal of an infinite game is to keep the game going. For example, while CEO may say we're going to beat the competition and be number one, there's no such thing as winning business. Instead, the goal is continual growth and the pursuit of results that matter to the organization. Why did you throw this in that particular book?
Because I think that it takes great— it takes bravery to choose to play an infinite game as a creative professional. It's so much easier to focus on the finite games, meaning it gives us a greater sense of certainty when I know if I just make this many sales, I'm going to be the top salesperson in the organization, and then that game just resets every year, right? Now I get to do it again versus my job is to try to advance the mission of the organization and to help the organization succeed and to help us gain, you know, do whatever it is that we do through the organization to make people's lives better. And oh, as a byproduct of that, I'm going to work really hard and maybe I'll be the top salesperson. It's fine to set goals in that way, but that's not the game I'm playing. Ultimately, the game I'm playing is the infinite game of trying to create good for the people that we serve. That's the way I look at my work and my business and my writing and my speaking and everything. Like, I'm not out there trying to gain notoriety or fame or beat somebody else. I'm trying to just do as much good in the world as I can. And my hope is that as I'm playing that infinite game of getting more and more people involved with the work that I do, equipping them to be better and better at what they do, that's an infinite game. And the net result of that is hopefully my business will succeed, you know, more people in my organization will be successful, all of that. But At the end of the day, that's the game I'm playing, is the infinite game, which is a much more courageous game to play. It's much easier to say I'm going to go out and try to like hit my sales targets and, and beat everybody else in my organization, but that's a very finite game to play. Yeah. And I think a very unsatisfying game in the end as well.
Oh, I totally agree. I think Viktor Frankl talked about success being a byproduct of— not the product, but byproduct of what we do. And I think the reason why I ask it is people that get into this industry, it's a very complex creative industry. So we have creative professionals that enter a complex supply chain and industry that are manufacturing and making. And it's, it's really one challenge after another. And I have this theory that people stay in this industry, never get out, because they're— they end up involved in an infinite game. And, and that's what actually is a very compelling part of the business. So we only have a few more minutes. I want to ask you this, Todd, and obviously I could have talked to you for an hour. What, what, you know, we're heading to SKUCon. You are going to open up SKUCon for us and talk about The Accidental Creative, which has been one of the most influential books for creative professionals. It's how to be creative in a moment's notice, which this industry needs badly. What's one surprise you can spoil for us here on the SkewCast about your talk at SkewCon?
So the surprise is going to be, for, for a lot of people, that being creative is not what you think it is. Creativity is not what we often think creativity is. So my— the surprise is I hope that I can reframe for people creativity as problem solving. Creativity is everyday things we often don't think of as creative, and that hopefully I can raise the bar for people on how they think about how approach everyday actions in their life and their work through a creative lens and hopefully challenge people to, to be better at what they do and to expand their perception of what's possible for them in their everyday lives and work as they build infrastructure into their life to support that ambition.
Love it. Todd, one last question. Has there been a book, movie, or podcast interview or anything that's really impacted the way you think lately?
Yeah, it's a really, really great question. So the book that really, I think, really kind of impacted me as much as anything is I've been recently reading, rereading The Righteous Mind. Sorry, I keep going to call it The Elephant and the Rider. The Righteous Mind, which is about how we make moral decisions in our lives and our work and the nature of morality. And sort of the— you've probably heard the elephant and the rider metaphor before, right? It's really just sort of helped me rethink the way that organizations make decisions and why we make the decisions that we make inside of organizations. I work with a lot of leaders. It's really sort of helped me understand, especially in the wake— I'm just gonna get a little deep here— but in the wake of COVID how many people are experiencing reverberations organizationally on a guttural level, right? On an emotional level, they're still experiencing reverberations emotionally that maybe we don't recognize cognitively. We don't We don't recognize them on the surface, but how many people are still working out their emotional responses to something that happened a couple of years ago when we realized, oh, the entire world can stop for a year. Business can stop. Millions of people can lose their life. It was a very, it was almost like a World War II kind of moment for the world without it being obviously a World War II. It wasn't a war, but, and so it really has helped me sort of reframe and rethink how leaders are making decisions in the face of, I think, some of the reverberations of COVID Sorry, that was maybe not quite the response that— That was a great response.
Really great response. 'Cause I think most of us are nodding our heads going, "Oh, you're exactly right." Yeah. Exactly right. Todd, thanks for joining us on the Skewcast, and we will see you in Vegas in January, my friend.
All right, I'm so looking forward to it. It's gonna be a great time. All right, see you then.
Thanks so much for tuning in to this episode of SKU Cast. Be sure to keep up with our latest content by subscribing to SKU Cast on iTunes or to our blog at community.commsku.com. Until next time, friends, thanks so much for listening.
Mm-hmm.






