The Connection Between Creativity, Leadership & Jazz with Josh Linkner
16 Dec 2025 · 26 min
Podcast episode (host Susan Drumm) interviewing Josh Linkner about the intersection of creativity, leadership, and jazz. Linkner frames jazz as a metaphor for modern, adaptive leadership (improvisation, situational awareness, co-creation). He argues creativity is innate and trainable, advocates a growth/experimentation mindset (run many small, cheap tests; "micro-innovations"), normalizes failure (rituals like "F‑Up Fridays"), and offers practical tactics (daily 2-minute creativity ritual; keep a 'to-test' list; "start before you're ready"; "break it to fix it"; "fall in love with the problem, not the solution"). He references his work and resources including his book Big Little Breakthroughs and websites joshlinkner.com and impact11.com.
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Hi, I'm Susan Drumm. And welcome to the Enlightened Executive, where your personal evolution sparks your leadership evolution. Each episode we feature groundbreaking techniques and strategies to help you get the edge in personal and leadership effectiveness. This episode is brought to you by Meritage Leadership. At Meritage, we strengthen teams and empower leaders to achieve high performance. Go to meritageleadership.com to learn more. Today, I am thrilled to introduce Josh Linkner. Josh is a New York Times bestselling author of four books. His experiences in both business and music led him to become one of the world's foremost experts on creativity and innovation. On the business front, he's been the founder and CEO of five tech companies, which created over 10,000 jobs and sold for a combined value of 200 million. And there's more. While proud of his business successes, his roots are in the intriguing world of jazz music. He's been playing guitar in smoky jazz clubs for over 40 years, having studied at the prestigious Berkeley College of Music, and has performed over 1000 concerts around the world. So welcome, Josh. I am so excited to have you on the podcast.
Well, truly a pleasure to be with you. Thank you so much for having me.
Well, of course, there's this amazing intersection that we both love the power of music and we talk about it in our work and write about it. So let's start there. Tell me a little bit about how you took all of the experiences you had in the jazz world and infused that into business lessons and learnings for entrepreneurs and executives.
Yeah. The funny thing is, I started a business at age 20 and I'd never taken a business class. I didn't know anything about business. I knew jazz. And to me, actually, today more than ever, jazz is the perfect metaphor for dynamic leadership and innovation and, of course, entrepreneurship. It's funny, maybe the metaphor in the past was that of a classical conductor, one leader standing in the center of the room, getting everyone to play the notes exactly as Mozart intended hundreds of years ago. But we don't have that luxury anymore. The world is moving too quickly. There's too much volatility. We have to play at our best, and the notes aren't in front of us. And so what? Jazz musicians really do put the musical instruments aside. They adapt the changing conditions. They co create, and they collaborate with other fellow musicians. They invent in real time. They improvise. They use situational awareness and active listening. They bounce back quickly from setbacks and course correct. And so, to me, these are the ideal skills and the ideal skill sets that that's needed in the modern era of business. So I ultimately did take some business classes. But by far the best teacher I've ever had in business is the world of jazz.
Wow, that's amazing. So now, so you started the business and you're applying these same principles or skills that you developed as a jazz musician to being an incredible entrepreneur, obviously scaled these businesses. And now tell me a little bit about when you're speaking about this intersection. What's your key message? What's most important for people to know?
Well, just backing up. I mean, the reason I speak and I love this type of work, is that I really believe deep in my soul that all human beings have dormant creative capacity. Me and you included. We all do. And as human. The research, by the way, is crystal clear that we are all hardwired to be creative. That's like our natural state. Every human. You don't have to play guitar, you don't have to do interpretive dance. We can all be creative in our own ways, but we can all be creative. And then when I look at that fact, and then I also look at the fact that there are so many challenges in the world. Of course there's business challenges, but there's, there's geopolitical challenges, there's public safety challenges, there's environmental challenges, there's, you know, racial problems, there's, there's, you know, wealth inequality. So we got all these problems and we got all this creativity. And if you look at, back at history, creativity has always been the source of progress, from the printing press to penicillin to the Internet and everywhere in between. And so I feel like I'm on a bit of a mission. I feel called to do this work to help people unlock their dormant creative capacity to make the world a better place. And I can't think of, for me anyway, you know, more, more of a noble pursuit. So when I, when I share this with leaders around the world, and I have the great honor, I've done 1300 keynotes over the years to be able to help them think of themselves as an artist. You know, the word artists sounds like, oh, that's really smug. And you should be wearing like a beret. And artists are. You question things, you're willing to challenge conventional wisdom. You, you apply creativity, you work on your craft, you're curious. So I really believe that we can all be artists. And when I help leaders and then subsequently their teams unlock that art, that creativity, I feel deeply, intrinsically re supported. And I just love doing the work. Yeah.
Inherent in that concept of growth Mindset versus fixed mindset. A fixed mindset is what I always say, fixed awareness. Right. We have a certain way, like this is how we believe the world is and. And therefore we can't ship. But creativity really involves shifting our perspective and looking at something different. Like you think about Picasso and how he looked at the world, so fundamentally different, and that's what his art was. So noticing the pattern of where you're focused and how you can shift out of that pattern, to me, is the core of creativity and seeing that. So I'm curious to know, in terms of pattern recognition, how do you work with that concept in innovation and unlocking creativity?
Well, first of all, back to the growth mindset. You're exactly right. Many people think that you're either born creative or you're not. Truth is, we all are, frankly. But. But creativity is a skill that can be developed, just like learning to play tennis. It's actually easier to be creative than to play tennis, by the way. So really, that's what I think of it is a muscle, and, you know, to build muscle mass, we need to exercise it a bit. And the same is true with creative output. But the truth is that again, we all can be creative, which is very encouraging. In terms of your question about pattern recognition, your observation is exactly right. Really, all creativity is, is if you can imagine something that is in front of you that you could just think about, oh, this could be something else that you're being creative in that moment. In other words, you're able to project and see the world as what it might be instead of what it already is. And that leap is something that all humans have. It's one of the things that separates us from other mammals, in fact. And it's just a skill that can be cultivated. In terms of pattern recognition, I developed a whole series of techniques over the years that you would apply fresh frameworks to solving problems and seizing opportunities. It actually worked very quickly. Because the good news, again, we're built for this. This is the way we're designed. We just need a little scaffolding, a little support, and that creativity unlocks pretty quickly.
Well, even the framing of the problem to the opportunity. Right. For every problem, there's an incredible opportunity to shift. I mean, people say that when the market goes down, they said, oh, like this is the greatest opportunity to buy or whatever it may be, which is true. But that's true. But like any problem, and I think sometimes people will get stuck in the anxiety of the problem versus thinking, oh, there's something here that could potentially Unlock and create ripple effects that benefit you in ways that you don't, you don't even realize. So can we actually, I mean, this is a crazy mindset, but celebrate the problem because this is an opportunity for us to apply our creativity.
Well, it's funny that you say that. You know, having done a lot of research over the years, as well as my own experiences, the best innovators, the best leaders, the best creative people, they really do look at failure differently. You know, we're taught in school that failure is the worst thing ever and mistakes should be avoided at all costs. The truth is that first of all, if we're not ever making any mistakes, we're not going fast enough like that. We're just playing it small. Second of all, if we want real innovation and breakthroughs and success, we're going to have to tolerate some stumbles along the way. That's just part of the process. I mean, if you think about any innovation laboratory, imagine, you know, Pfizer inventing a drug therapy. It's not like they have 100% batting average, like 1% maybe, if they're lucky. Which means that there's lots of sort of failed experiments that allow us to get to, to the good ones. So the most effective people and leaders don't look at failure as humiliating or something you should be ashamed of. It's more like, okay, what can I learn from this and how can I pivot and ultimately prevail? You know, a couple funny things. One of the person I interviewed in my most recent book, which is called Big Little Breakthroughs, How Small Everyday Innovations Drive Oversized Results. Wildly successful entrepreneur. He was telling me about a practice that he does. So every Friday he and his entire team do something called F Up Fridays. They say the whole word, I'm just being polite. But F up Fridays, they have a big brown bag lunch. And one by one, every team member in the company has to stand up and proudly share what they effed up that week and what they learned from it. Inevitably someone they get to didn't F something up that week and they're like, well, why not? What are you going to try next week? And just think for a minute, think about the implication of that zero cost ritual. The implication is that aren't everybody in our company is an innovator, that we expect you to challenge the rules, we expect you to take responsible risks, we have your back when you stumble. We expect that that's part of the process. And so whether you embrace a ritual like that or something of your own, the notion is that if you get people in the right setting where they feel safe, creativity really flourishes. It turns out that the single biggest blocker of creativity is not natural talent. It's fear. Simply put, fear and creativity cannot coexist. So what I help leaders do is say, let's remove the fear. Let's create the conditions that are safe, like Fridays. And creativity will blossom naturally because that truly is a part of who we inherently are.
Wow. So I love what you're saying about how fear can't exist with creativity because inherent is taking the risk that you need to take because you don't know your creativity is creating something new. So you don't really know. And we don't have certainty there. And we're always. What I see leaders always trying to strive for certainty. That's just not going to be there. So can you learn to embrace that piece? That's uncomfortable. And this story is powerful because you also think about. It sounds like, you know, not only just being open and honest about your failures, but truly celebrating them in a way that it sounds like there's almost a competition who can f up the big yesterday.
Right. It's so true. And, you know, furthermore, people think that trying something new is risky. And the one thing I've Learned now in 34 years in business is that too often we tend to overestimate the risk of trying something new, but we underestimate the risk of standing still. And the real risk of doing nothing is far greater than most people think. We have this false belief that doing nothing, just following the rules, that's safe. That is hardly safe. That is one of the riskiest things that we can do. You know what that looks like? Oldsmobile and Pan Am airlines. That's not a safe approach. So I think a more pragmatic approach is to say, look, the world's changing. We need to change as people, as leaders, as businesses. And then how can we de risk change as opposed to taking on the gigantic risk of stagnation?
Yeah, right, Right. And so how do we de risk change?
The good news is there's a very simple antidote, and the antidote is experimentation. Most people think of innovation or creativity. Like you come up with some cool idea in the shower, and then you roll it out everywhere. Very high risk tolerance. And we often think of innovators as these guns ablaze and swing to the fences, take these moonshots. My most recent book, I spent over a thousand hours trying to understand how do the most innovative people think and act. And So I interviewed CEOs and billionaires and celebrity entrepreneurs and Grammy Award winning musicians. And what I learned is they do the exact opposite of what you think. Instead of these wild risks, they cultivate small baby innovations, like micro innovations on a high frequency basis. And another way to say that is they run a lot of experiments. So instead of taking an idea and just being wildly risky, you're better off coming up with lots of ideas, little baby ones, and then test them cheap and fast. Like 15 bucks in 20 minutes. Cheap and fast. If that little experiment shows promise, don't go crazy, just double the size of the experiment. If it doesn't show promise, dump it quick and move on. And I think a really important idea is that if we are all running experiments all the time, let's say three or four times a week, you're running a little experiment and most will fail. That's okay, get rid of it. When something shows a little promise, get a little bit more into it. And so what that does is by the time you actually get to effectuating real change, you've taken 90% of the risk off the table. And so change innovation. Creativity does not need to be this overwhelming, scary, difficult thing. We can just take all the risk right out off the table through a series of small experiments.
Can you give some examples of what a small experiment might look like?
Sure. Well, by the way, I'll just quickly say that I do this type of thinking not just in my business, but also in my family. You know, give yourself as a creative person. You don't have to be one way at home and one way at work. You're the same person. It's more like work life integration. So I have seven year old twins, they're terrible eaters, they don't like going to sleep. So I'm always trying like new things. Here's a little trick to get them to eat better. Here's a little thing that you know to go to sleep better. So the reason I start with that is that it doesn't have to be like this big scary, like genius level thing. It's just trying lots of little maneuvers. But in a business standpoint, let's say you have a new idea, like, hey, I wonder how I could improve my close rate if I'm a professional salesperson. And you might say, okay, I'm gonna try this one thing and roll it out everywhere and I hope it makes my year. That's overwhelming. Don't do that. Just say, okay, what are five little ideas I could try? Maybe I flip the order of my sales presentation and so try it. Once on a Tuesday afternoon with one client, see how it feels. You have to close the deal. If. If your client scowls at you, don't do that again. If the client's like, awesome, where do I sign? You're like, oh, that's that. That experiment kind of worked. Maybe I'll try it on a second day. And so the point I'm making here is these experiments don't need to be like, hey, I've invented the fifth dimension of the universe. They could be very teeny little things. And just the more you try stuff, you get into this experimentation, mindset, the risk goes away, and the creativity blossoms.
Great, great. What are ways that or other ways that you help people find and unleash their own creativity?
Well, I really helped explore the mindsets, habits, and tactics that will help them be successful. I'm a very pragmatic, like, get stuff done kind of guy. I'm from Detroit. So it's like, like, let's get that scrappiness. You know, I don't want to analyze something in an ivory Tower for 80 years. Like, let's go out and do it. And so I've developed a series of mindsets over the years that are really the core mindsets and beliefs of creative leaders, creative people. And so I often, in a keynote, will walk them through some of those mindsets and help them understand, you know, a new way of thinking. And then underneath each of those mindsets, of course, I have various tactics that people can employ, but I'll just share one, couple quick examples. Yeah. One mindset that I just love, and it's sort of not just mine, but really proven, is called start before you're ready. And too often, when we see an opportunity or a challenge, instead of going for it, we just like, pause or waiting for a perfect plan or ideal conditions. Thing is, there's a real risk in waiting is that we might lose the opportunity altogether. And so the best leaders, best innovators, they just get started even if they can't see the finish line. And then they sort of bob and weave and they course correct. They adapt the changing conditions. They sort of find their way in route. And so that. That's one example. Another one that I love is I call it break it to fix it. And I'm sure you've heard that phrase, Susan, if it ain't broke, don't fix it. By the way, who came up with that advice? That's terrible advice. Do you want your doctor doing that? Do you want your airline pilot? Wait until something's broken? That's bonkers. So I think we owe it to ourselves and colleagues and customers and communities to do the opposite, which is, even if something appears to be working fine, let's examine it, let's deconstruct it, put it under the microscope and see if there's ways to upgrade it. It's the notion of always being in a flow of upgrading, like proactively breaking it to fix it rather than wait until something is actually broken.
Yeah.
And so, you know, those are just a couple examples. They're counterintuitive, they're easy to remember. But when you start embracing these mindsets and seeing them come to life through rich stories, it starts to shift the way you think about it. And my goal, really, if I to zoom out, is say that instead of people thinking of creativity as something that you do, is start to think of creativity as something that you are. And so it's really embracing a way of thinking about your role in the world and how you walk through life and who you are as much as what you do.
Yes. And I also think there's sometimes this sunk cost belief, like we've already put a lot of effort and time and research behind something, so being able to then switch to something else gets people stopped from the innovation. How do you help people like that? You know, like, I've already invested so much in this and it's not working out, but I don't want to let it go.
Yeah, that's a common problem, actually. It's a good point. One of the other principles that I wrote about in my most recent book was this notion. Fall in love with the problem, not the solution. And I see entrepreneurs make this mistake, they come up with some idea and they're so committed to, like their idea or their technology or whatever, as opposed to the problem they're trying to solve. If you anchor your commitment to the problem rather than a particular solution, you're indifferent on how you solve it. You just want to solve it the best possible way. And if you're. You're really committed to the problem, that's where your focal point lies. You're willing to let go of one approach in favor of a better approach, and you're willing to look at it from a lot of different lenses as opposed to falling in love with your particular solution. Then you become tunnel vision and you're thinking about sunk costs and all the things that you just described. So it's more. It's more of a shift of saying, what's the problem I'm trying to fix and how can I remain open minded and fluid and flexible. I'm committed to solving that the problem the best, most efficient, most effective way possible and I don't even care how I solve it. That's a healthier approach than being locked into a particular approach and being unwilling to change.
Wow, I love it. How does someone fall in love with the problem? Like what a mindset shift there is. What do you recommend? How does someone know that they're more oriented on the problem, let's say, than their own solution?
If you're a physician and you're like, hey, I'm really good at this one procedure and darn it, I'm only going to do this procedure the way I want to because I love this procedure, you don't want to go to that position. If on the other end, that physician says, I'm committed to curing heart disease and I'm going to use the most modern and effective tools and I'm willing to embrace new possibilities to have better outcomes, that's the person you want to see. And I think it's the same mindset for us in business, even in life, you know, if you're committed to raising healthy, productive kids. It's not like I'm committed to one particular educational approach. You're committed to the outcome, you're committed to the problem, and then you remain sort of neutral and fluid on the manner in which you solve that problem.
How do you get more cognizant of what the potential problems are? And I mentioned this because I'm thinking about, as my listeners are know, I'm deep in the enneagram and I'm thinking about my, my own type here is type 7, which tends to look at all the positivity and not as much of the problem. And so I think sometimes, you know, when you say inspect it or keep your eye out for where the problem could be, I think is a good one. But I'm guessing that there's also additional things that one can do to identify what the challenges are in a more, you know, concise way.
Yeah. And just to be clear that this is not being like problem oriented even. I'm one of the most biggest optimists I know. I think I'm always seeing the bright side and everything, but it's more about choosing a problem that you feel committed to solving something that's important. And so the problem I'm trying to solve is how do I get 7 billion people to unlock creative capacity? Now, if that solution is a book, awesome. If it's a keynote, great. If it's a podcast with you. Awesome. I don't care how the problem is solved. I'm trying to solve that problem. It doesn't mean I'm wallowing in problems. I'm not like, on the hunt for problems. I've identified something that I feel called to work on, and then I'm willing to solve that in any way possible. In your case, as you work with incredible leaders around the world, you have such an amazing impact on people. You're committed. I'm just paraphrasing. Let's say you're committed to helping leaders become the best versions of themselves.
Yeah.
And if the enneagram one day is replaced with something else, you'd be like, yeah, that's cool, whatever. But I just want to help those leaders be the best versions of themselves. And so I don't think. Again, just to be clear, it's not like you sit around looking for problems and being negative. The opposite. It's committing your life's work to something that you care about and that matters to you and then being flexible and how you go after that solution as opposed to over indexing on a particular way.
Yeah, I couldn't agree more. Because what I've seen is the best leaders commit to a meaningful mission that I say is outside themselves. So many times I see leaders are actually working for trying to make themselves whole. Right. You know, ego, identity, self image. I want to be respected. I want to be, you know, admired. I want to feel safe. Right. All these things are really about protecting, but it's still from a place of fear and protecting themselves, where when you get committed to something outside yourself. Right. Then you're not worried about you anymore. You're just about that mission. Right. And so what you're talking about is very much this. It's like get committed to a mission that has meaning for you and then you're always excited.
Could have said about it. We're saying the exact same thing, you know. Furthermore, when you. When you end. I've seen my experience when I see leaders chasing more selfish pursuits as opposed to more noble pursuits. So if the selfish pursuit is I want to make more money, I want to get a corner office, I want people to respect me. Not only is that taxing and uninspiring, and it actually rarely works. Like the people that chase money rarely find money. On the other hand, if you're chasing purpose and impact and helping and service, the money and those other accolades ironically encounter intuitively come as a byproduct. It's like that follows a noble intent that doesn't lead. And when you chase it, when you chase the greedy thing, you rarely get it, but you chase the noble thing. The stuff the greedy person wants actually comes as a byproduct.
Absolutely. We have this phrase we call, they're called senior commitments and senior more in terms of like, you know, senior debt. They rise to the surface. So if you're more focused on looking good, being right, being in control, these things like when you go after them, they're not bad things. Looking good is, yeah, we, you know, being right, being in control, all of those things or belonging, they're good things. But when you pursue them as your pursuit, you'll find that they'll actually be elusive to you. And everyone else can see it. They don't actually come out and say, I'm yeah, I'm really about looking good. They may not even see it themselves, but underneath it, that's the voice that's driving them. Right. And so if you can quell that. And actually that stuff comes as a byproduct when you're doing a meaningful mission. It's you are looking good. Like you are being included. You are, you know, working towards something that's right and good. So it's just, you can't go after those directly. You, they're elusive. So what's one thing that leaders can do tomorrow to help bolster their creativity? We've talked about some, but so I want to add, just add some additional tips and tricks for people if I may.
I'd love to share too. Yeah, so I, every, every morning I do a two minute creativity ritual. It's like jumping jacks, your creativity, it's super easy. Try it for 30 days. You'll, you'll be blown away. Just do it. 30 days, check it out. First minute, I just absorb the creativity of others. I might listen to some music on YouTube, stare at a painting, read a poem out loud. You know, all that kind of stuff I'm doing is like absorbing others creativity. It's like priming the pump. The next one minute again, it's only one more minute. I choose an unrelated problem, something that I have no personal stake in. So as you know, I live in Detroit. Traffic in Atlanta doesn't. I don't have a personal stake in that outcome. And so for one minute I try. I don't say, how can I solve traffic in Atlanta? Because when we try to solve a problem with a silver bullet, we rarely do. I would say instead, in the next 60 seconds, how many small little teeny ideas can I develop that Might improve traffic in Atlanta and I'll see if I can come up with 30 of them. You do this with the lane and none of it doesn't matter. I'm not, I'm not so much concerned about the output. I'm more just getting my creativity going and I'm trying to look at things from different angles. It's jumping jacks for your creativity. Each day choose a new problem. How can I speed up the TSA lines at the airport? How can I make the check in process at a doctor's office more effective, unrelated to you? And you do that for 30 days, you will be blown away. Your creativity will just leap forward. Because what's happening is that you're not really learning a new skill. You're unlocking an existing part of who you are. So that's one, one trick, the other one, and this is so effective and so easy. I know every one of us has a to do list. My suggestion, keep a second list. Keep a to test list. So as you mentioned, experimentation, mindset, the best leaders are the best experimenters. The best innovators are the best experimenters. The best artists are the best experimenters. So if you just keep a running list, anytime an idea pops in your head, big, small, little, stupid, silly, goofy, doesn't matter, don't judge it at all. Just stick it on the list. Here's the thing, the mere existence of the list will boost your creativity because it keeps it top of mind. Like, oh, I'm an experimenter, I'm always testing stuff. And then you know, once a week say, hey, what are the three or four things I'm going to test this week? And the more people are just thinking about the notion of experimenting, the more your creativity will you experience really powerful.
I mean, I think the fundamental mindset that we each have, creativity. I've heard, heard leaders say I'm not that creative. Oh, I don't have that creative piece. And your whole mindset shift is, yes, you do. You just have decided you don't. But the reality is you actually do. So where can people learn more about you and your work?
Well, thanks so much. You know, it's really been a pleasure with you, hanging out with you and I just have so much admiration for your work in this podcast. But if anyone wants to get in touch with me, I'm pretty easy. It's just joshlinkner.com J O S H L I N k n e r.com and you mentioned the work that we're doing at Impact11. We're helping thought leaders build it, build and scale their practices. And you can check that out@impact11.com it's just the word impact and the word11.com.
And it's a fantastic group. I am a member of it and thank you for creating such an incredible community for other speakers to connect and learn and grow from. So appreciate your time here. Josh thank you. And if you love this episode, you're not going to want to miss my interview with Frankie Russo, another Impact 11 member and a serial tech entrepreneur with a proven track record for using authenticity and purpose to foster innovation. Let's all lead the way. Hope you enjoyed today's episode, and I'd like to point you to the next important step. Hit the subscribe button to get notified when we release new content. I'll see you on the next episode of the Enlightened Executive.
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