Episode 16

How to embody courageous leadership with Todd Henry, author and Founder @ Daily Creative

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Author and Founder of Daily Creative Todd Henry, shares inspiration for marketing leaders and creative leadership.

You’ll get inspiration, insights, and more from our conversation with Todd Henry the “arms dealer for the creative revolution.” Arms dealer for the creative revolution is a fitting title for Todd as he spent two decades researching the best practices talented people can undergo to get the most out of themselves. Lucky for us, we got a sliver of his extensive knowledge in this episode. You can find more of what he has to say on his podcast, the Daily Creative, or in the many books he has written. 

In this episode, Todd shares his how-to’s for several topics ranging from courageous leadership to curing imposter syndrome. Our conversation gives you the tools needed to navigate different conflicts in your career. You’ll take away important lessons like why it is better to lead by influence, not control, and how morning routines disrupt the status quo. Tune in. 

What you will learn in this episode is about capturing the attention of big brands as a small agency from Mercer Island Group:

  • Why the future and the present belong to the curious 
  • The danger of wanting to always be liked vs being effective as a leader
  • Why a lack of conflict is often a sign of a tremendous lack of health in an organization  
  • Why leading by fear is not sustainable in the long term 
  • How to lead teams by influence, not control
  • The difference between self-awareness and imposter syndrome 
  • The key to overcoming imposter syndrome 
  • The two things talented people need from their leaders to avoid creative burnout 
  • Why managing teams and agencies through bounded autonomy sets you up for success
  • How morning routines disrupt the status quo and carve out space for your life
  • Todd’s journey from country singer to the creative leader he is today

Resources:

  • Find Todd’s newest book on what it takes to be an exceptional leader, The Brave Habit here
  • Read Herding Tigers for more tips that’ll help those leading creatives 
  • Creatives can learn how to avoid burnout in Todd’s Accidental Creative book  
  • Listen to more of Todd’s thoughts on the Daily Creative podcast on Spotify 
  • A More Beautiful Question by Warren Burger
  • Visit toddhenry.com to see more of his books and podcast
  • Connect with Todd on LinkedIn

How to embody courageous leadership and unleash your creative bravery with Todd Henry, author and founder of the Daily Creative.

Hello, everyone. Welcome to Question Everything, a podcast all about learning from the successes and the failures of those who dare to, well, question everything. This podcast is part interview, part therapy, and part Price is Right. We have our own game board stacked with questions that'll make even the most successful CMOs totally sweat. I'm your host, Ashley Walter, CMO and partner at Curiosity. On today's episode, I sit down with Todd Henry, author, keynote speaker, and founder of Accidental Creative. Todd uses his authenticity to engage audiences and lead them through whole new ways of thinking about creativity, leadership, and so much more. Today, Todd shares how leaders can be both liked and effective, and why they can't chase both at the same time. Why talented people and client agency readers can be both liked and effective. And finally, why the antidote to imposter syndrome is in fact, self-awareness. Don't hit your snooze button on this episode. Let's get started.

Positioning himself as an arms dealer, which we're totally going to unpack that, for the creative revolution, Todd Henry teaches leaders and organizations how to establish practices that lead to everyday brilliance. He's the author of six books, and he speaks and consults across dozens of 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. Todd, welcome to Question Everything. Oh, I am. So very excited to be here.

Todd Henry explains why it is important to ask good questions: 

Just if nothing else, because of the name, name alone, like that alone is exciting because I love questions. So yeah, very excited for our conversation. I'm so glad you said that. I am a self-identified accidental creative, which I know we'll talk a lot about today. But I read somewhere that you once said that you strongly agree that the future and the present belongs to the curious. And I'm like, this is going to be a great podcast because I've got an agency here of 80 people who believe the exact same thing. Yeah, absolutely. I do believe that very firmly. I just had a conversation the other day, actually, with Warren Berger, who wrote the book, A More Beautiful Question. And we were talking about this dynamic of asking questions.

Some people ask questions, not because they're really curious, not because they want the answer, but because they want to affirm something they already think, which is a very ineffective way to ask questions. The people who ask powerful questions are those who ask questions out of genuine curiosity. And I think they want to move the conversation forward in some way. And I've spent a little bit of time with your agency. And I would have to say, I know that that is part of your ethic, that you want to move the conversation forward, that you're coming not only in name, but in practice, you're coming from a place of curiosity. And so I think that's always an interesting thing for us to consider when we're asking a question.

Am I asking this question because I really want to know the answer? Or am I asking this question because I want to reaffirm something that, I already believe or suspect? The latter is less likely to get you where you want to go. But if you can come from a place of genuine curiosity and ask questions that move the conversation forward, I do believe that the future belongs to you. Oh, I love that. We often will tell clients, you remember the kids who always asked why we hired them. So even in our recruiting and vetting, where we look to see how people ask questions and the kinds of questions that they ask, because I'm with you. I think, the more interesting questions you can ask, the more interesting solution you can get to in the end.

How to embody courageous leadership and unleash your creative bravery with Todd Henry, author and founder of the Daily Creative. 

Absolutely. Well, and I think that the people who ask the best questions get closest to the heart of the matter. They get closest to the metal, as I like to say. And, you know, at some point, unfortunately, I think some people give up. At some point, they feel like, okay, I know enough. I've gone far enough. And they begin to optimize around that knowledge. And unfortunately, that's often the beginning of a slow, gradual death or decline for those people. But those who are willing to keep pushing up the rugged mountain to refuse to settle medias ochris, that's what mediocrity means, medias ochris, halfway up a rugged mountain. For those who continue to push up the rugged mountain, the reward is, I mean, it's a pretty amazing view at the top when you finally get there.

Todd Henry reveals why he rebranded the accidental creative podcast: 

So yeah, keep pushing, keep asking questions. In our world, we'd call that the white space, right? Or the big idea. Like, that's how you get there, is by asking those brave, interesting questions. So tell me, I know you've been really busy. You're traveling a lot. You just wrote a new book. So what's been going on in your world recently? Yeah, I've been I've been traveling a ton, speaking a ton, a lot of events, a lot of organizations, building things out, we just completely rebranded the podcast, the accidental creative podcast, which started in 2005, we just completely re rebranded that as daily creative.

And so that's been very exciting. But it's a, it's a lot more effort, because before we would kind of do interviews, and just like topics, things like that. And now it's a more narrative-driven show. So it takes a lot more effort, surprise, surprise, it takes a lot more effort to actually weave a narrative around something than it does just to sort of like, you know, do an interview or, or, you know, sort of edit an interview together. So it's been a lot of fun. But it's also been a tremendous amount of effort, pulling it together. But it's also very exciting. And to your point about asking questions that really began with a question I asked myself several times. And I think it's really  exciting. Months ago, which was, if I were to start over, doing this thing I'm doing right now, would I be doing it the way I'm doing it? And the uncomfortable answer that I came to was, no, I wouldn't, I would be doing things very differently. And then the next logical question is, well, then why are you doing it that way? And so that's what led to a complete reframing and rebranding of the podcast and a complete reworking of really kind of everything I've been doing for the last 18 years sort of got reworked at that point. But it began with a question, you know, an uncomfortable question, but the question nonetheless.

How to embody courageous leadership and unleash your creative bravery with Todd Henry, author and founder of the Daily Creative.

I have been describing it internally as like your Taylor Swift reputation era. Like it's phenomenal what you've done. And I know I've got a question behind one of these numbers, and I don't know which one it is. But I hope we get to unpack that today. Because I think what you did was it's really smart that you took the time to ask yourself that I don't think as leaders, we do that enough. And then you were willing to be honest with yourself, and then do something about it. You know, I think we always fail at one of those steps. And I love that you did that. And you're starting to see like great results. Because of it.

Yeah, it has been really fun to see both new listeners coming on board, but also just some of the listeners that have been around for maybe a decade or more listening to the show who maybe hadn't really listened to some episodes for a while. And now all of a sudden, they're like, what have you done? It's almost like you come home from vacation, and somebody's redecorated your house. And you're like, what happened? Everything is different. It's not the way I left it. And that's kind of been the way it's been for some people who may not have been engaged for a while. But it's a lot of fun. Now to see people completely coming back coming online. That's what I mean, that's kind of what a refresh can do for you.

Right? I mean, same intent, same purpose, same mission for the show. It's just like a complete reinvention of the way that we're doing it to kind of better match where people are where the audience is. Love it. All right. Well, so you kind of know how this works. We've got a game board, my team's going to pull it up for us. And we've got 12 super spicy questions here. You don't know what's behind them. I don't really know what's behind them. But the power is totally in your hands. So we'll start with what's your favorite number? My favorite number is probably seven because the Accidential Creative released on 7/11. And I've had a couple of other books that were released on, you know, multiples of seven. So I guess seven is probably my favorite number since you put it that way. Well, let's start there. How do you feel? Sure. Good. Okay. All right. So you said that as a leader, you can be both liked and effective, but you can't chase both at the same time. So what advice would you have for people pleasing leaders?

Todd Henry gives his advice to those who are looking to please everyone as a leader:

Yeah, this is a really great question.

There's nothing wrong with being liked. There's nothing, obviously nothing wrong with being effective. You just can't chase both at the same time, meaning that sometimes as a leader, you can't chase both at the same time. And I think that's a really good point. You're going to have to do things that people aren't going to like in order to do the thing that is best for the organization. In the end, they may like you for it as well, but in the short term, they may not like you for it. And so it's important you be attached to something bigger than your personal interactions, something bigger than your personal reputation within the organization.

You have to be attached to a mission, a productive passion, a through line for your work that transcends those temporary circumstances. Otherwise, you're always going to do what's most comfortable for you in the moment or what, what, what you're going to do. And so I think that's a good point. You know, makes things easiest for you within the organization. And so my encouragement to people is before you make any, any decision in the organization, understand the outcome that you're driving toward, understand the core reason that you're making this decision to begin with and ask yourself, okay, am I making this decision because of the way it will make me look? Or am I making this decision because I really truly believe this is in the best interest of not only the organization, but our mission and ultimately the people on the team as well. 

It's funny, people love it when paychecks come every two weeks. They love the predictability of that. But whenever you make a decision as a leader to protect the viability of those paychecks that might make them a little bit uncomfortable in the moment, you know, they will suddenly forget how much they like when those paychecks come every two weeks, you know? And so, you know, we have to recognize in ourselves, we have to sort of parse that in ourselves when we're making decisions. Why am I making this decision? Why am I choosing this route? Is it truly because I believe it's the right thing? Or is it because I'm trying to curry favor with someone or I really want to be liked?

How to embody courageous leadership and unleash your creative bravery with Todd Henry, author and founder of the Daily Creative.

In The Brave Habit, I wrote about the importance of having the difficult conversation, of ensuring that you're not shying away from it. This is really difficult for people who thrive on being liked because sometimes when you want to be liked, you might avoid any semblance of conflict. But conflict is natural and healthy. A lack of conflict is natural and healthy. A lack of conflict is not a sign of health in an organization. A lack of conflict is often a sign of a tremendous lack of health because either people don't care enough to fight for what they believe. So they're just kind of like, okay, whatever, you know, whatever you want to do, that's fine. So they don't care, which is not good. That's not healthy. They don't really know what they're doing. And so they don't feel confident enough to argue for something or there's no accountability. They don't even know what they're accountable for. So why would I fight for something? It's not my problem. It's somebody else's problem. There will be conflict in the organization.

And how you deal with that conflict is everything, really. That's what's going to determine the health of the organization. And that's really, it really comes down to being liked versus being effective. You know, that means sometimes you'll have to say things that other people won't like, or do things they won't like, that will create a more effective environment for everyone in the organization. So there's just a couple of thoughts on it. Yeah, that's great advice. A good friend of mine, and she was on this podcast before Robin once told me that you only give feedback to the people you like. And that stuck with me so much because I'm like, why do we as leaders hold feedback back? Or why are we intimidated to give it? And if you just kind of reframe it a little bit, I think it gives you kind of that freedom to really say the things that are going to potentially even change the career trajectory of a human. I mean, it certainly has mine in my history when a leader has been brave enough to share. I also really appreciate how you're saying it's not, one or the other, and that you can bring both into an organization. And I think that it's important. We can't rest all the way in one camp or the other, but it's almost like this pendulum a little bit, right? Like you're always on the teeter-totter, but you got to be able to be fluid on both.

Yeah, absolutely. Well, and that's, that's the nature of leadership, right? You know, you're, you're wrestling with uncertainty every single day. I mean, if things were certain, then bravery would not be required. It's the uncertainty that demands bravery of us. And so, yeah, you're exactly right. It is going to be a fluid, um, you know, cultures are not static. Organizations are not static. You don't figure something out and then just set the thermostat and that's the way it is for the rest of your existence. Um, so I think that's what a lot of leaders struggle with. You know, I think people have a difficult time dealing with the complexity of human needs and psychology. And then, oh yeah, by the way, we still have to get the work done as well. In the midst of all this, you know, because that's kind of why we're here. Um, and so they default to one or the other, they default to, I'm going to be the kind of leader who is just known for getting the work done, or I'm going to be known as the kind of leader who, whose team just loves them.

And we're all just here to grow together and have a great culture. I mean, it's never quite that dramatic, but you do find leaders who sort of err one in one direction or the other, because they don't like the ambiguity, the tension of trying to maintain a healthy culture, an open culture, a communicative culture. And so, you know, I think that's, I think that's a very important part of being a leader. about leadership is that you have to have a very effective culture while also knowing that you have to kind of get more done with less because that's the nature of most organizations.

How to embody courageous leadership and unleash your creative bravery with Todd Henry, author and founder of the Daily Creative. 

Todd Henry offers his take on fear-based leadership:

It's that tension that takes a lot of leaders out of the game. I think. I got to ask if you've ever, um, or like your, your perspective on this, but I once had a leader. Um, I would, I would say a very ineffective leader. Tell me when I asked, so what's your leadership style and trying to get to know him. He said, um, I believe people are best led by fear. And have you come across that in any of your learnings and your teaching? Um, a fear-based leadership and is it effective? Is it a good way to go?

Well, first of all, I've never heard anybody, um, articulate that, but I've encountered some people who have led that way. I think that there are some situations, some cultures in which that kind of motivational strategy can be effective. For example, we're going into battle together and some of us are going to die. And so I'm going to lead you in a way that's going to be effective. If you're not going to be effective, you're going to be a great leader, but if you're will, you know, help you understand the true stakes and consequences of what we're about to do. Yeah. Um, but when we're in the business world. A creative industry. Absolutely not the creative industries. Absolutely not. I mean, I think that isn't, that is frankly, a manipulative way to lead.

Because essentially what you're doing is you're motivating by, motivating by fear essentially says I'm going to motivate people by promising them to take something away from them if they fail, right? Versus let me show you how much more is possible for you if you succeed. You're focusing on the failure instead of focusing on the success. Success. You're focusing on the punishment instead of the vision. And I cannot for the life of me see how that could be an effective form of motivation. Yeah. Maybe in the short run, maybe you can squeeze a little bit more out of somebody in the short run, but they certainly aren't going to admire you for it. And they're certainly not going to go the extra mile for you.

They'll do whatever they have to do to avoid punishment, but they're not going to extend themselves beyond that to try to help you accomplish something you hadn't even thought of. Whereas when you're motivating by, ambition and vision, when you're motivating people with an eye toward the infinite game, not just the finite game, in the words of James Kars, popularized by Simon Sinek, you know, where we play the infinite game, which is there's something bigger here that we're all doing that transcends just whether or not we won that client or we won that account. There's something bigger here that we're trying to do to keep ourselves in the game and to try to make the game bigger for everyone.

It's just a much more effective way to develop a culture and to lead an organization. And if you look at it, all of the most, the most effective organizations in the world are about something more than just, did we win this account or did we succeed on this project? Now, those things are important. They're important metrics for us, right? To pay attention to, but that's not the ultimate thing we're doing here. Those things are getting us towards something that we're, that we're ultimately trying to accomplish together. Love that. I wish I would have known you. I would have called you. And unpacked that as my therapist to get through that time in my life. So that's great. All right, let's go back to the board.

Okay. Let's do, we'll do number, we'll just stay in the, in the row there. We'll do number three. Okay.

How to embody courageous leadership and unleash your creative bravery with Todd Henry, author and founder of the Daily Creative. 

Todd Henry explains how professionals can manage imposter syndrome: 

I love the psychology on how people pick their numbers. Okay. So you've spoken a lot about self-awareness versus imposter syndrome. And so I want to hear you talk a little bit about the difference and why it's important for leaders to really understand the nuances between the two. They're kind of rooted in the same thing in a lot of ways. A lack of self-awareness and imposter syndrome. There are people who would rather live with perceived invulnerability than actually test their limits and discover they have some. So they would rather pretend like I'm invulnerable, but they never take chances because they don't want to test that theory and find out that they actually have some limits.

And I think so imposter syndrome, but the root of it is this belief that everybody else has it figured out. I'm the only one who, who doesn't know what I'm doing. Everybody else knows the answer. Somehow they have the cheat code and I don't have it. And so here I am trying to figure it out. That's really at the root of it. What imposter syndrome is. It's a belief that I'm overmatched. Um, ironically, the key to overcoming imposter syndrome is self-awareness. It's recognizing your limits. It's testing your limits. It's putting yourself through the rigors and recognizing, Hey, I may not be the smartest person in the room, but it's okay. I can, I can figure things out because I've done it before. Yeah. I have, I have succeeded in small ways.

I've taken small steps of bravery, small, I've made small, small acts of bravery, small leaps into the unknown in the past. And I've succeeded some that failed some, but I'm still here. I'm still alive. I'm still kicking. I'm in the game. Um, and so the, the key to overcoming imposter syndrome is reminding yourself of those small wins in the past, even if it's unlike anything you've done before, I've stepped on stage in front of in the room, 10,000 people, and 400,000 people watching remotely at like locations, right? Like that's probably the biggest, what is definitely the biggest venue I've ever been in is, is 400,000 people at once.

It's not fundamentally different from speaking in front of 500 people or one hundred people or 50 people. When it comes down to the technical nature of like what I do, the only thing that's different is the psychology, right? Where I'm thinking like, Oh, an ex-president was just on or the next person has sold, you know, 17 million copies of their book or something. Um, it's the psychology of it, right? My job is just to remind myself, listen, I've, I've done this a thousand times before in different arenas, different arenas, differing, you know, levels of audiences, but you know, all I have to do is step on stage and do what I do because I know I've done this before. That's how we begin to combat imposter syndrome.

Imposter syndrome wants to tell me, who are you? Who do you think you are? You know, an ex-president just spoke and now you've got this person who sold 17 million copies. You own as well, 17 million copies of your book. People don't know who you are. Like they don't know who you, I mean, compared to those people, I just have to remind myself, I know what I'm capable of. I've done it before. I may not be perfectly suited to the situation, but I'll figure it out. I'll figure it out. And so I think that's really self-awareness is the antidote, I think, to imposter syndrome in so many ways, because it's just a reminder to yourself that you're more capable than you think you are. It's so true.

And I think that comparison can be like the death of our psychology, right? And after I read this, the way you described self-awareness versus imposter syndrome, I kind of reflected on my own life in my own career, and I have wrongly called it imposter syndrome in many scenarios. And so now even like if I find myself in a meeting or an opportunity where I'm feeling like that, I'll even just jot down in my notebook, okay, here's a couple of reasons why I'm in this room. I need to remind myself that I actually do belong here. And my voice is important. My opinion is important and people want to hear it. And so I do appreciate that. Yeah.

And one other thing I will say, because it's interesting that imposter syndrome was actually coined specifically and specifically targeted toward women in the workplace originally. And many people don't know that now it's just sort of this broadly adopted term, right? But the women who actually developed and coined this phrase were researching women in the workplace. And we're asking questions about why is it specifically that women often come into situations and they feel like overmatched or whatever, which I find actually really interesting. But specific to that, I think that it's very important that we not confuse confidence with competence. That is a common, 

How to embody courageous leadership and unleash your creative bravery with Todd Henry, author and founder of the Daily Creative.

uh, conflation in the marketplace, right? Where somebody comes into a room and because of the extreme amount of confidence they exude, we assume, well, that person knows exactly what they're doing. Yeah. Uh, or that person must've done this 50 times before. And I'm the only one in the room who's never done this before. Not the case, not the case at all. As a matter of fact, often when you peel back the layers, that person is like, they have no clue what they're doing, right? In some cases they just come across as so unbelievably confident. And so, you know, I think in our minds, psychologically, we're wired to conflate confidence with competence. And we just need to make sure that we don't allow that to happen. And the ironic thing is, and it's funny because you look at some of the research too, about how this works. Sometimes when you begin to project more confidence, you actually begin to feel more confidence or competence, right? Like you actually begin to feel competence as you project confidence. And so, I mean, it's a little, sort of psychological trick, but I think we just have to be careful. We have to be really careful not to conflate those two things. And just to recognize that everybody, I mean, I've met people and worked with people who are like household name type people. And every one of them, if you really hold them aside, every one of them feels like maybe I'm overmatched here. Maybe I don't belong in the room, right? At some point, everybody feels that way because it's such a relative thing. And so you've said to be very careful not to conflate those two things. Yes. So I have to ask, do you have a power pose?

I don't. Are you talking about Amy Cuddy? Are you talking about the research? Yeah. Yeah. I don't. I don't actually. I probably, I should, but I don't have one. Oh yeah. You should. Next time when you're, when you have a fit 500,000-person arena, you go in the bathroom power or wherever you are in the hallway, power pose for two minutes. You'll have all the confidence in the world. Right. Right. All right. Let's do it. All right. Let's do number four. Okay. We'll just, we'll go, we'll go to the right. Okay. Let's see here. Okay. Okay. What do business leaders misunderstand most about creatives? What empathy-building strategies can leaders use to build harmony across departments and avoid the dreaded creative burnout? It's such a great question.

How to embody courageous leadership and unleash your creative bravery with Todd Henry, author and founder of the Daily Creative.

Todd Henry reveals the two primary things creatives need from their leader:

There are two primary things that talented people need from you as a leader. And I'll say talented because I think that we're creative can sometimes be a little bit misleading. People think, well, I'm not a creative. I don't oil paint or I don't, you know, make music. I'm not a creative. I'm not a creative. I'm not a creative. I'm not a creative. I'm not an artist. Yeah. Right. But if you, but if you solve problems, you're creative. I mean, that's the nature of creativity. And so I think one thing that, that leaders misunderstand about talented people is that they need, they primarily need two things from them.

Stability, which is clarity of process, clarity of expectations, and clarity of relationship. They need to know that the ground rules aren't going to change halfway through the game, because that can be very frustrating for people who are doing complex creative work to, to not only deal with the complexity and ambiguity of the game, but also to deal with the complexity and ambiguity of the work. But then to have somebody come in and say, that thing we said we were going to do now, we're going to do it a different way. So can you go back and redo the thing that you just did? Okay, fine. So they need stability, but they also need challenge. They need to be pushed. They want to try new things. They want to experiment. They want to risk. They want to venture into new territory. They want to grow themselves and their skillset.

I think one of the things leaders misunderstand on that front is they think talented people just want complete freedom, all challenge, just give me all challenge all the time. And I just want complete freedom. And I just want complete freedom. And I just want complete freedom. And I just want complete freedom. Don't tell me what to do. Don't give me any boundaries. Just let me do my thing. It's not true that the most not maybe immature, talented people want that. But most professionals need stability, they need boundaries, they need clarity, what we're aiming for is bounded autonomy, freedom within limits. What they want you to do is give them some limits or some boundaries within which to work, but then let them do their thing.

Don't control them, lead them by influence, not by control. That's what they need. And so I think this is a fundamental misunderstanding. A lot of leaders have them think that they need to come in and basically like work with them closely and prove that they're close to the team by working with them closely, which really equates to control of their work. Or I just need to let them go and do their thing and just trust it's going to end up in a good place. Well, no, that doesn't work either. Bounded autonomy is what talented people need from them. And so I think that's probably the biggest piece of it. Now, people who have come up through the ranks where they've been technicians in an organization. So let's say that you're a designer who then becomes like an art director, a design director, and you become creative director, people who have sort of moved up through the ranks as a technician, and now they're leading other people. Often, they want to step in and teach and tell people how to do the thing that they used to do, they want to do the work of the team.

And they think that by doing that, they're going to be able to do the work of the team. They're bringing themselves closer to the people on the team, what they're actually doing is proving to the team that it's more important to you that this is right than that you let me come up with the solution, right? And so they see themselves, they almost see the leader that is aligning more with the client or with the organization than with their desire to actually do the work.

And so you start to lose people if you control them, if you instill too much stability.

How to embody courageous leadership and unleash your creative bravery with Todd Henry, author and founder of the Daily Creative.

Similarly, if you instill too much challenge, without freedom or without boundaries, then you're going to lose them as well because they'll feel like they're being challenged without the corresponding level of infrastructure to support them. And they'll get angry and frustrated and start seeking better horizons. And a lot of agencies end up in the space where they're overly challenged, and under-stabilized because they're taking on too much without the right level of boundary or stability to support it. So that's really what we have to do is figure out for our team members, what level of stability and challenge do, they need in order to thrive, and then constantly be tweaking the dials, you know, if we're over-challenged, but under-stabilized, great, what can I do to help instill a little bit of stability, a little bit of process, a little bit of predictability to bring them back into that healthy place? Or if they're under-challenged, maybe they're feeling stuck, because we're doing repetitive work over and over and over again. How do I instill some challenge in the team so that we get back to that sort of healthy place that we need to be? And do you think it's a team mentality? Or is this individual by individual?

So it's experienced in team, but it's an individual-by-individual thing. So each person needs something different from you. One person might be, hey, just wind me up and point me in the direction and check in with me every so often. And I'll just that that's all the stability they need, you know, just like point me in the direction and give me the resources and I'll go. Other people might need daily check-ins with you to make sure that they're doing things the right way that they're on the right course. And you need to be able to provide what they need in order for them to have the level of stability that they need. There comes a point where you might need to help them grow beyond that maybe it becomes a little too needy or a little too.

Like it's time to cut the umbilical cord, right? Like you're fine, you're good. Just go to your thing. But you need to provide the level of stability and challenge that each person on your team needs from you in order to thrive. We're always we do a lot of one on one. So we do a lot of one one-on-one coaching with our teams here at Curiosity. This seems like a really great one conversation topic to have once a month or, you know, throughout throughout a project to really understand where that person sits. You said bounded autonomy. And I absolutely love that phrase. I think it works not only managing your teams, but managing agencies. So a lot of our listeners are brand managers, CMOs who have to manage an agency and get the most out of them too. And I imagine having some of these conversations would set you up for even more success there.

Oh, yeah, unquestionably. Absolutely. Because if you have talented people on your team, why would you want to do either of those things? Why would you want to overly control them? In that case, you're not really getting out of them what you hired them for, which is their talent, their brilliance, or their perspective, their experiences. Or why would you want to set them free, but not give them any kind of directed guidance? Because that's primarily your job as a leader, your job isn't to do the work, your job is to lead the work, right? And so, you know, yeah, absolutely. I mean, this is applicable to any time you're doing complex, problem-solving work, which certainly in the, you know, the brand world, I mean, that is, that is the definition of complex, you know, uncertain work. These principles apply just like they would in any kind of creative field. Awesome. All right, let's go back to the board.

How to embody courageous leadership and unleash your creative bravery with Todd Henry, author and founder of the Daily Creative.

Todd Henry provides details on his morning routine and why it is so important: 

Ah, boy, let's go with, we'll do number 11. I did lucky number seven, we'll do lucky number 11. Love that. Okay. So you once referred to the snooze button as the devil. I have been told you have an incredible morning routine. So I'm hoping you will teach me your ways. What does a morning look like for Todd Henry? And how does it set you up for success for the day and even the week? Okay, so I want to be really clear before I share my morning routine. I don't believe there is a morning routine that works for everyone. And I read the morning routine, these people all the time. I was even featured in a book about morning routines. I forget what it was called. But I was featured in this book about it. 

There are people who will shame you with their morning routine. Like if you're not out of bed by 4:30, if you haven't run a 5k by 5:15, and eaten three hard-boiled eggs, and then done a cold plunge, and then you while you're reading Cicero or something, and then you get up and you know, I don't believe that that's true. And I think that there are some people who like, hey, if you get a, like Winston Churchill, who basically worked from bed all morning while he was drinking mimosas and whatever, like, I don't think it's going to be the same for everyone, you have to figure out your optimized routine. For me, what has worked really well is getting up earlier than I would prefer. Mostly because it gets my day off on a good foot.

Lots of coffee, because I love coffee and spending an hour in the morning studying and thinking. And studying and thinking and filling my mind with valuable stimulus from other people, people who have gone before me who are far wiser than I am. And this is by the way, been for 20-something years I've been doing this. And then spending some time thinking and writing. And sometimes that thinking just looks like me sitting there and spacing out. And then I'll just write down anything that comes to mind.

But also journaling and writing about what I've just been studying or what's going on in my world and trying to get ahead of whatever the day might bring. So some of my best ideas, have come from just sitting in the quiet of the morning with no email, no pings, no interviews to do, no travel to do, no, you know, emails to respond to, just sitting there and just allowing my mind to wander wherever it might go. And it's amazing when you create space for yourself to be human again, to reclaim that part of your humanity, it's amazing what sometimes comes to the surface. So really, I think morning routines, what routines do is they disrupt, they disrupt the status quo, the status quo for humans is I'm going to do the most comfortable thing, the thing that feels best to me, which is typically hit the snooze button, sleep in, drag myself out of bed, rush into work, right?

Yeah, that's what's most comfortable. Routines disrupt that they force us to do something that might be outside of the norm, a little bit less comfortable, they carve out space in our life. And that's what my morning routine does. It carves space in which I am guaranteed, at least to have a little bit of time to think in my life, which is a really rare thing these days. I've often said my best ideas come in a shower. And that's why, right? Because it's quiet, you're not doing anything, you're not thinking. So very similar vibe. But I think that's really good advice for folks is, you know, once you get to work, it's, it's super chaotic. And even when I get home, I have three kids, everything's very busy. But carving out some of that alone time to sit and think and refuel, I imagine much of what you're reading and writing is just fuel for you. And I think that's really good advice. 

Yeah, absolutely. Yeah, no question. And by the way, also, it's not just the morning routine. But I tend to, in the middle of the day, typically, I'll take a little bit of time in the middle of the day, and I'll go for a walk, or I'll go for a run, or I'll do something that sort of, again, pattern disrupts, it sort of creates a cleansing of the palate from my morning to my afternoon activities, because usually my morning activities are creative work. So I tend to try to get most of my creative work done when I'm not traveling. And then the afternoon tends to be reserved for meetings or client calls or other things.

And so it's nice to have that kind of cleansing of the palate. But again, it's a pattern disruptor. And so if you start thinking about routines, not as, oh, I need to, I need to do this, because if I do these sequence of things, I'm going to be successful in my life. No, all it's doing is just it's a container, it's creating space in your life within which good things can happen. And they don't always happen, but they'll happen more often. Often than not, if you carve out that space consistently, Gretchen Rubin said, what you do every day matters more than what you do once in a while. And I think that's true. That means that you do it every day. And some days, you're going to have these profound breakthroughs. And some days, it's going to be like, okay, I did the thing, you know, nothing really happened. But if you do it consistently enough, you're going to see over time, you're going to see that the water level is going to rise. And occasionally, you're gonna have these big breakthroughs that all of my books, all the ideas for my books have come in, at some point in the morning, when I'm sitting there doing nothing, and I have this like, ah, moment, right? Where dots connect. Yeah. We don't create space for dots to connect in our life, because we're so busy. We're bouncing from thing to thing. We expect great ideas to happen into cracks and crevices. And that's what routines do for us. They carve out space for great things to happen. Consistency is key. That's great. All right, let's go back to the game board. I think we have time for two more. Maybe. We'll see. All right, let's go. Let's do number 10. 

How to embody courageous leadership and unleash your creative bravery with Todd Henry, author and founder of the Daily Creative.

Okay, so we heard, I'm so glad you picked this one. So we heard that you were a singer in a country band. So we have to know, how did you go from country singer to the incredible Todd Henry creative leader that you are today? And I know you've opened some amazing acts like the Dixie Chicks. Did I get that right?

Todd Henry explains his journey from starting as a country singer to becoming who he is today:

It's true. Yeah, it is true. Okay. So I went to Miami University. I studied marketing at Miami. I did, too. And from the time I was young, I was playing music. I loved music. It was kind of part of my life. And I put myself partially through school performing. So I would like leave on the weekends and go play like county fairs and festivals and do all these kinds of things. And so I thought, Hey, I'm going to, I'm going to try to make a run at this. I'm just, to see if I can I can do this and this is like early mid-90s it's like mid-90s right um and so I was splitting my time partially between Cincinnati and Nashville at the time I moved to Cincinnati after school like you do if you go to Miami it's either Cincinnati or Chicago I moved to Cincinnati um and was spending about half my time in Nashville half my time in Cincinnati and you're right I mean I got the chance to tour and open for a ton of amazing acts and Dixie Chicks, Toby Keith, Kenny Chesney we did some shows with Vince gill or a show with vince gill we did a show with a bunch of shows with a band called Diamond Rio who was like at the time like kind of big, I had a bunch of interest in Nashville from folks there and so it was really fun like really had a chance to kind of do some fun things um but as these stories often go was making absolutely no money doing it right so like I was technically making a living playing music but it was one of those like okay can I sustain this for the rest of my life and so I again as these stories often go I met a girl um she was in Cincinnati and I started asking like okay music business gainful employment marrying an amazing woman I can have two of the three I can't have all three right um so I chose gainful employment marrying an amazing woman I ended up through circumstances some friends ended up getting a job as a creative director leading a small team of people um that team over time grew I ended up becoming um uh in the midst of that started asking some questions about you know like how do people in my situation how did they come up with great ideas I was meeting with some great creative directors at some of the bigger firms in Cincinnati where we're based um and started in the midst of that a podcast called the accidental creative 2005 was when I started the podcast and that sort of then led me to um a couple of years later started having articles on my own and I started writing articles on my own and I started writing articles on my own written about the show in some major magazines and then started getting invited to speak at companies and all this stuff so I was it was kind of a crazy um crazy season a crazy transition but then in 2009 got offered the book deal for the accidental creative and that was kind of when I realized all right I think I need to this is probably the time for me to make my exit and start my company so since 2009 really I've been doing this full-time now I guess 15 years um traveling and teaching and speaking and I've been doing this for a long time and I've been doing workshops and writing books and podcasting and all the all the fun stuff I do now I love that but yeah that was kind of the transition was as often these stories go it was like met a girl realized that I don't think I probably want to be raising a family like from across the country you know like still on the road trying to make it as a singer but what's fun is like some of the people I was writing songs with back then and performing with and all of that like they've gone on to just have these amazing careers in Nashville so it's kind of fun to get to see like kind of do their thing uh from afar and I get to do my thing you know the thing I'm doing now which is a lot of fun um and I still have a lot of friends in the business so that's kind of the story i know it's kind of a weird story but that's kind of the story I imagine you were like really scratching that creative itch as a country singer that you have translated into what you're doing now and you being on stage and you're getting comfortable opening for some of those acts has set you up to be so successful in what you're doing today oh my goodness a hundred percent because when you're the opening act nobody came to see you nobody is there thinking like oh finally thank goodness this person I've never heard of before is going to come on and play songs I've never heard before right um like they're they paid money to go see the main act and so I had to figure out ways to win people over like I had to tell clever stories or find ways of like like I played piano was kind of like my main instrument was like my main primal instrument and so like we would play Jerry Lee Lewis songs right and I would like jump up and down the piano play it with my feet like do all this crazy stuff to like get the crowd riled up because it was like the only way I could keep people's attention was by doing that because like we're the opening act and so got this really great reputation as a performer but to your point like it's not that different from what I'm doing now like I used to get in a metal tube with a bunch of sweaty guys and go up and down the stage and I'd be like oh my god I'm gonna be like and play music and now like I drive to the airport and they fly me into a city and I get up on a stage and I present and it feels very much the same in execution it's just it pays a little better first of all what I'm doing now um but second of all like it's kind of the same thing at the root of it I'm trying to have an impact on people I'm trying to influence people in some way whether that's through music and entertaining them or by teaching them something that they can go and apply in their life and make their life and their work better and I'm trying to influence people in some way it's kind of the same thing that drives me as drove me back then um so yeah it's been an interesting transition with some interesting through lines right to your point about the creative thing like the being creative on demand thing like working with songwriters having to write songs and you know figure out like how to make something work when you're collaborating with a bunch of people all of whom might have different interests and now you're trying to write a song together like it's that was a really interesting experiment early on that taught me a lot about the creative process I love that too because I think a lot of our

How to embody courageous leadership and unleash your creative bravery with Todd Henry, author and founder of the Daily Creative. 

people have side passions and side hustles and you know call it whatever you want and i think giving some space for those things to happen can translate into better leadership better work output etc so yeah I love the through line and thinking how we connect those passions to what we're doing every day for sure for sure yeah and by the way also your life is a portfolio of passions anybody who thinks that your life can your job can contain the sum total of your creative engagement is is is wrong they're they're fooling you if they tell you that you know your job can never contain the sum total nor should it contain the sum total of your creative engagement you should have some things you're doing outside of work that fuel you that feed you and allow you to express yourself in ways that your job never can contain because at the heart of it you're a creative professional there are two parts to that creative yay we get to make things professional sometimes I have to make things I don't necessarily love because that's what the client wants or that's what the organization wants that's what the market wants right like I have to do things sometimes I don't love but that's the professional part of creative professional the creative part cannot be contained by your job so make sure you have something in your portfolio that's fueling your creativity outside of your work cindy gallop just gave me some advice and she said everybody talks about passion but what I want you to do is to find the thing that gives you rage and go solve that I was like yes okay yeah yeah yeah compassionate anger compassionate anger, not just anger but it's also compassionate anger it's not just anger, it's not compassionate – meaning suffer with passion the root of the word passion means to suffer so compassionate anger means I'm suffering with someone else meaning I identify something and it makes me so full of compassionate anger that I need to go solve that problem yes right that's where a lot of the best ideas come from and I think that's probably what cindy was getting at yes well what a good way to wrap i am so grateful for your time but before I let you go I've got a dot fun this or that if your game sure okay so this is

How to embody courageous leadership and unleash your creative bravery with Todd Henry, author and founder of the Daily Creative

rapid fire first thing that comes to mind we want to know a little bit more about Todd Henry here we go all right guitar or piano oh man that's like hard to uh you know quiet weekend at home or adventure abroad quiet weekend at home writing in the morning or at night a.m speaking at a university or at a conference uh at a conference because of the multiplied impact I think love that and then hosting a podcast or being a guest? Oh boy, that's tough too. Um, probably being a guest because I'm always surprised by the questions people ask. Well, we are so grateful you were a guest with us today. Uh, how, what's the best way for folks listening to reach out to you and, and hear more about you?

So toddhenry.com is my website. You can find all my books there, my speaking, my everything else I do. The podcast is called Daily Creative. Um, we're on a little bit of a hiatus until May the first week of May we're starting season two, and we'll have 13 fresh episodes. Um, but it's, but all the old episodes are still there and are available to you wherever you get your podcasts. Awesome. We'll make sure that we link to all of that in the show notes. Thank you so much, Todd. This is great. Thank you. It was a lot of fun.

BIO

Todd Henry

Positioning himself as an “arms dealer for the creative revolution”, Todd Henry teaches leaders and organizations how to establish practices that lead to everyday brilliance. He is the author of six books (The Accidental Creative, Die Empty, Louder Than Words, Herding Tigers, The Motivation Code, Daily Creative) which have been translated into more than a dozen languages, and he speaks and consults across dozens of industries on creativity, leadership, and passion for work.

With more than eighteen million downloads, his podcast Daily Creative offers weekly tips for how to stay brave, focused, and brilliant.

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