Leave the Map Behind: Finding Your Way Through Creativity & Uncertainty

Intro: Broadcasting live from the Business RadioX Studios in Atlanta, Georgia. It’s time for High Velocity Radio.

Lee Kantor: Lee Kantor here another episode of High Velocity Radio and this is gonna be a good one. But before we get started, it’s important to recognize our sponsor, Business RadioX. If you’re a business coach who’s tired of being a best kept secret, set up a call with Stone Payton at brookstone.com to unlock your perpetual prospect pipeline. Today on the show, we have Kelly Hudson with Coach Kelly Hudson. Welcome.

Kelly Hudson: Thank you so much, Lee. It’s a pleasure to be here.

Lee Kantor: Well, I am excited to learn about your practice. Tell us about your coaching practice. How are you serving folks?

Kelly Hudson: Sure. So I’m a professional coach and a writer. I got my start just coaching writers and creatives. And then when I got certified as a coach at the Hudson Institute. I also started coaching leaders and nonprofit leaders and people who are in career transitions as well. So what I say about my work is that I help people navigate the space between a promising idea and a meaningful finished work. And that’s true whether someone is writing a book or building a business, navigating a career transition, or just creating a new life chapter. I’m here to help them discover what it is trying to become and then to shape it with intention.

Lee Kantor: So now you mentioned you’re in your backstory. You kind of had a heart for the creatives.

Kelly Hudson: Yes. That’s right. A huge heart for creatives. And I’m a creative myself. And so it’s a, it’s a terrain that I know and love and just love being able to support people as they learn to navigate that terrain.

Lee Kantor: Now, is there like, how are you defining creatives? Is it people that are kind of in the arts, like you mentioned, writing, but people pursuing kind of a career in the arts in some form or fashion.

Kelly Hudson: Well, I’m really glad you asked that because I actually view creativity very broadly. I’m one of those people who will shout it through a megaphone that I think we are all creative and that we are always creating something. So, so far broader than just the arts. And I think at the at the root of it, what we’re really creating is our lives and how we want to navigate our lives, how we want to work, how we want to contribute to the world around us, how we want to be in relationship with other people around us and in relationship with ourselves. All of that requires some amount of creativity.

Lee Kantor: Yeah, something I’m glad you’re talking about it in this manner because I’m with you 100%. I think creativity is much broader than being an artist. Something that struck me, I’ve interviewed lots of people over the years, and somebody told me something that was kind of shocking. And I don’t know if you run into this information yourself, but they said that when a child is super young and they tell them to like draw or paint or something. Everybody kind of embraces it and has fun with it. But even within like the first few grades, they don’t kind of identify themselves as artists. Like they, they decide like, okay, I can do this or I can’t do this. And they’ve kind of self-select out of even seeing themselves kind of in an artistic way. Um, do you, do you agree with that number one? Or do you see that in people as well as that? A lot of people just kind of say, oh, I’m not creative or, you know, that’s they kind of self-select out of creativity as part of how they describe themselves.

Kelly Hudson: Absolutely. I have met so many people in my practice and in the world who say, I’m not creative, I’m not imaginative, I don’t make art. Um, and you’re right, sometimes the self-selected and, and sometimes there’s a story way back there in childhood where somebody told them they weren’t creative or they told them that there wasn’t any value in their creativity. Um, and so we can adopt those stories and limit our ability to be creative just by believing them. But at the same time, I also, I really like to ask people, what language does your creativity speak? Because some, you know, for some people, the creativity speaks in art. It speaks in dance, it speaks in music. But for some people, creativity really speaks in the kitchen, for example, when they’re cooking and they’re playing around with different flavors and spices. Um, I have an aunt who would have sworn for years that she wasn’t creative, but every time she travels, she goes on these huge, epic journeys to places that hardly anybody goes to. And she creates the entire trip day by day. She doesn’t plan anything. She doesn’t have spreadsheets or anything set up for those. Um, so that’s another language of creativity, um, that people speak. I think leadership is one of the most creative Jobs that we can embark on. Because you are creating a culture, you’re creating a team, you’re creating an organization, you’re creating a relationship with your customers or your clients. So all of that I see as being creative work.

Lee Kantor: Yeah, I’m with you. I always say that like entrepreneurs to me are artists because they’re creating something from nothing. Um, and that you have to kind of look at yourself in that manner. In your work. You use a phrase creative wayfinding. What do you mean by that?

Kelly Hudson: Yeah. So creative wayfinding is descriptive of a, I call it a philosophy of practice. And what I mean by that is it’s a way of thinking. It’s a mental model and it’s also actionable. There are practices, there are ways to implement these thoughts into your work and your life. And I first developed creative wayfinding through my coaching work with writers. Um, So create a wayfinding borrows a metaphor from the ancient practice of Polynesian wayfinding. And way, way back in the day, traditional wayfinders would help guide these transoceanic journeys. And they didn’t have any maps. They didn’t have any instruments, no GPS or compass or sextant or anything like that. So how did they navigate these vast oceans? They paid very, very close attention to the information that was available to them. They looked up at the stars and oriented to the stars in the sky. They would gauge the currents and feel the ways that their currents would change, or the swell would change. And of course, they would pay attention to the weather patterns as well. Now, what was key about the earliest wayfinders is that they set out on these journeys, and they didn’t know what they would find. They went out to discover what was beyond the horizon, and they knew that getting lost was an inevitable part of the journey. There would be fog that would block out the view of the skies for days, or these great storms would come through and the the boat would spin off course. So orienting and navigating for the traditional wayfinders weren’t static states, but they were dynamic, continual practices of attention.

Kelly Hudson: And I think creativity works this way too. In. When we set out to create a book, say, we think we’re supposed to know what we’re making before we make it. But the most interesting and impactful creative work also involves discovery. We set out to find something that we can’t entirely see, and even when we feel lost or we get lost, we keep going. And then as I continued to coach leaders and professionals, I saw that life works this way too. And we all know that certainty is elusive, and yet we spend this enormous amount of time and energy seeking it out. We want to know what’s the right book to write, what should I write, or what career should I follow? What path should I get on? What’s my five year plan? Or I mean, in the words of Mary Oliver, what is it that I want to do with my one wild and precious life. So wayfinding really just asks, what if we approach not only creativity, but our lives and our work with a wayfinders curiosity and attention? So instead of needing to know exactly where we’re going and how we’ll get there before we even begin. How do we learn to navigate through uncertainty with curiosity and attention and imagination? And of course, some amount of trust? And what I find is that in answering these types of questions, we learn how to become someone who knows how to find their way even when they’re lost.

Lee Kantor: One of my favorite books is by Ryan Holiday. The Obstacle is the Way. Um, where he talks about, um, obstacles aren’t there necessarily to stop you or to sabotage you or, you know, part of life is fairness or unfairness. It’s just part of the journey. So you, when you’re on a journey, you have to learn how to get around or under through the things that are in front of you.

Kelly Hudson: Yes, exactly. Exactly. And, and those things may not be easy. They oftentimes aren’t easy. If it were easy, it wouldn’t be a journey. Um, what would be easy would just be never leaving the shore. By which I mean never setting off for that horizon, never embarking on a journey of discovery. Um, just staying where things are safe and familiar and certain and known. Um, but of course that’s an ideal. We can’t actually do that because the world is continually changing and we are continually changing.

Lee Kantor: Now what? And the clients that you work with, what is kind of the problem that they’re having right before they call you? What, like, what are some of the signs or signals that, hey, maybe I need to get fresh eyes on this and maybe I should call, uh, Coach Kelly. What? What’s going on in their lives that are kind of maybe a, you know, a flashing red light that says, hey, you might need some help here.

Kelly Hudson: Usually, I would say most of my clients who come to me, whether they’re writers and creatives or whether they’re leaders or, or entrepreneurs, most of them have had some kind of an idea. They have some sort of a spark or an inkling of what they want to do. And maybe they even maybe they’ve even started, maybe they’ve sort of left the shore. Um, but pretty quickly they get lost, which is of course inevitable, right? As I just said. So they feel a little bit lost and they’re not sure how to get unlost. Um, and what’s interesting to me is that a lot of people who first reach out to me are hoping that I can just give them a map and show them the way out. And of course, there isn’t a map. You make the path by walking. Um, and so my job really is to join them on that journey and to show them that when they are lost, that that’s a part of it, and that that’s where the richest possibility can actually happen, because that’s where a work can really change and become something entirely unexpected.

Lee Kantor: Now is that I mean, are you kind of a you’re part of their Wayfinder team? Uh, in telling them maybe, hey, look at that store over there. That’s an interesting store. Or the current seems to be shifting. What do you think of that? Like, is that kind of your role in this?

Kelly Hudson: Yes, yes, I think I think that’s part of my role. Um, I had a coach, I worked with a coach once who described, I love this description. She said that she joins a client and they’re going to take a journey. She’s going to be at their side. They get to choose what direction they’re going, but she has a flashlight and she can shine that flashlight around to help them a make that choice so that, you know, they know that there are three forks in the road and they get to choose which one they take. And then she gets to shine that light on things that they might not otherwise see. And that’s really what my work is.

Lee Kantor: So it’s kind of a Sherpa, but kind of a you’re letting the client lead, but you’re there with a flashlight.

Kelly Hudson: Always. Yes. Sorry. Always. Because only the client can know what is right for them. Only the client can know what their work needs or wants to become, and who they need to become in order to bring the work into the world. Um, so I’m never here to tell somebody this is what you need to do next. Here’s a plan. Go forward and do it. I’m here to ask them questions that help them clarify their own direction.

Lee Kantor: Now, is there any advice you could give somebody who might be struggling, whether they’re at a plateau or maybe they feel like they’re backsliding, or they just feel like, you know, the world’s not fair. Um, is there any kind of low hanging fruit advice that you can help somebody kind of work through something that’s in front of them right now?

Kelly Hudson: Absolutely. So I have lots of advice and it’s kind of funny because as a coach, I’m supposed to sort of refrain from giving advice. Um, and so I think of them more as sort of prompts to help shift the quality of your attention and to help you think more expansively about what’s possible. Um, so usually when somebody is stuck, it’s because they don’t have much of a sense of possibility. If they had a sense of possibility, they wouldn’t feel stuck. Um, so what, what I’ve devised under the umbrella of creative wayfinding are five practices. Um, and they’re not linear. We kind of cycle through these at different stages in the journey. But wherever you are in on the journey, these five practices, you can look at them and they serve as a sort of spark to help you open up to what else is possible.

Lee Kantor: So do you can you share them?

Kelly Hudson: I can, of course. Yeah. So and feel free to interrupt me if you want to talk more about any of these five practices.

Lee Kantor: Well, first of all, I’ll go through them and then we can expand upon some of them.

Kelly Hudson: Okay. Yeah. So the first practice is start where you are. Um, and by that I just mean you don’t have to wait until you have the perfect idea or enough confidence or enough time or a complete map from here to there. Uh, you don’t even have to know that there’s a there there. Your circumstances right now and who you are right now, those are your starting coordinates. And everything that follows is going to run parallel to your journey. The second one is follow the energy. And I know I’m a Californian and we can sound a little bit woo woo when we talk about energy. Um, but what I mean by that is just pay attention to what feels alive and what you’re curious about. Um, where do you find momentum or fascination or where do you find friction or discomfort? Because energy doesn’t necessarily equate to being easy. Sometimes energy is found in the thing that we’re avoiding or the thing that we don’t want to write about or think about. The third one is ask the unanswerable questions. Um, so the most potent questions that we ask ourselves aren’t problems to solve. They’re openings to exploration. And wayfinding isn’t about finding answers. As I said, getting lost is a critical and inevitable part of wayfinding. So I want people to ask the questions that get them lost. Um, there’s a big difference, for example, between asking what job should I take and asking what kind of work makes me feel alive or what, what do I want to contribute? Uh, who do I need to be to move forward in the way that I want? Or what am I making of my work in my life? So to deepen the questions down to the marrow, the fourth practice is create generously.

Kelly Hudson: I love this one. Um, and the great words of Brenda Ueland, she said, writing is not a performance, it’s a generosity. And I think that’s true of all creativity. And this is where our work becomes relational. Create generously asks you to consider what you are giving. For writers, it’s about the gift you want to give the reader. Uh. For a leader, it’s about how you want to create space for others to do more or become more. And for any human being, it really is saying, how are we in relationship with ourselves, with our work and with the people around us? And how can we be more generous with that work? And the fifth one is my favorite. It’s unlimit the imagination. So, so often we jump to what’s realistic. Uh, but this practice asks us to live in the imagination, in the imagination, for a little bit longer. And the reason is that possibility is a creative function of the imagination. So the more time we can spend in our imagination, the more possibilities we can create.

Lee Kantor: Now.

Kelly Hudson: Oh. Go ahead.

Lee Kantor: Well, in, uh, I think it was one of the early ones you mentioned the importance of, of kind of leaning into being lost. How do you kind of coach your, the people who are leaders and especially executive leaders, um, when it comes to being this vulnerable around the inevitability of being lost at some point when they’re at least in the, in terms of the organization or the team, or maybe only in their own mind that they’re supposed to have some of these answers and they’re, they’re being hired, or maybe they rationalize that they’re not supposed to be lost. I’m supposed to know some things because I’m the leader. Um, so how did they, how do you kind of help them work through that? Uh, which sounds paradoxical.

Kelly Hudson: It does sound paradoxical. Yeah. And, and part of the trouble, I think, is that the, the idea that a leader needs to have all the answers that a leader needs to be the expert in the room is sort of an outdated model of leadership. Um, this is a model of leadership that really fit the world when it was more predictable, when there was more certainty. Um, and nowadays leaders are facing extraordinary levels of change and disruption on a near daily basis. So even if you don’t think you are lost, even if you have the answer today, that could change tomorrow. So part of my work with these leaders is, first of all, getting more comfortable with the uncomfortable feeling of being lost. And what that really means is dissecting those stories. Well, I’m not supposed to be lost. I’m supposed to have all the answers. I’m supposed to know what’s coming next. I have to steward this organization into the future. And what happens when we admit that we’re lost? This is really interesting to me when we can admit that we’re lost. It invites other people to. To participate in the process. It invites other people to bring their imaginations and their creativity and their expertise into the conversation so that what we build moving forward is bigger than any one person could build alone. And that’s what can happen when you’re willing to accept and embrace not knowing.

Lee Kantor: Now, is there a story you can share that maybe illustrates how you work with, uh, an individual or a team when it comes to unlocking this kind of creativity in their work or in themselves. Uh, don’t name the individual or the company, but maybe share the challenge they came to you with and how you were able to help them get to a new level.

Kelly Hudson: Absolutely. Yeah. So I have been coaching a nonprofit leader, um, for we’re just wrapping up. So I’ve been coaching her for about a year. And when she came to me there, a social sector nonprofit who are facing a lot of budget cuts and government constraints. Um, and she was worried about steering this organization that’s been in place for over 30 years now into the future and staying alive and continuing to serve the people that they serve. And she initially came to me and said that when she feels like her team looks to her for answers, she is almost always able to give them those answers. Now, her trouble is that she feels inauthentic in the answers that she’s giving them, because the truth is that she doesn’t know she feels lost. But instead of saying this to her team, she comes up with answers that sound good, that satisfy their urge for answers. Um, but that don’t actually serve as real, true answers to the problem that she is facing for herself because she doesn’t know how to answer those problems. So the first thing that we worked on was her sense of authenticity and what it means to be authentic. Her team rated her as extremely authentic. She did the leadership circle profile. Authenticity was her highest rating from her team, and it was her lowest rating that she gave herself. So we really had to explore what that meant for her. What does it mean that you’re not showing up as authentic in your own eyes, but your team thinks that you are. And what that boiled down to was that she felt that she wasn’t being authentic because she wasn’t able to share the messiness and the struggles and the challenges that she was encountering as a leader.

Kelly Hudson: She had to perform as though everything was fine, as though she had it all figured out. Now, this put a ton of stress on her. And of course, her team kept coming back to her to ask her more and more questions. Um, because things kept changing and she kept performing that it was fine, but it wasn’t fine and she didn’t feel fine. So to first uncover the roots of that inauthenticity and where that feeling was coming from for her. And then slowly, through small experiments, she would practice being more vulnerable with her team. She would practice saying, I’m not sure when they would ask a question that felt hard or saying, I have a few thoughts about that, but what do you think? So she started outsourcing the ideas to her team. She started reflecting the questions back to them and just listening to what they said. Now she was scared that her team was just going to stare at her and kind of blink, like, hey, what are you? What do you mean you don’t know? But in fact, to a tee, every single one of them jumped at the chance to be a part of that conversation. And some of them had some really good ideas. And it wasn’t about good or bad ideas even. It was about opening up the exploration so that it was beyond the frame of her own brain, and so that she could think without that pressure, to have to perform as though everything was fine. She could think in a collaborative way with the people that are on that journey with her.

Lee Kantor: And it’s amazing that when you kind of lean into that, I mean, you were kind of teaching her to be a coach. Those are some of the skills of a good coach is asking more questions rather than providing the answers.

Kelly Hudson: Absolutely, absolutely. And I think it’s really important to do because sometimes when we provide the answer, we jump over the entire creative process of, of building something that wasn’t there before. If you have the answer, then you’re not creating something, you’re repeating something you know.

Lee Kantor: Right? And you’re never even entertaining the opportunity to just get even something tangential that could be impactful down the road. You’re kind of shutting down any other type of insights because you have the answer. So they don’t want to share anything. They think because you have the answer.

Kelly Hudson: Exactly. And that’s where, like in this leader’s case, her ability to be more vulnerable invited her team to also be more vulnerable. So it also invited her team to be able to say, I don’t know, or I’m not sure what’s going to happen with this. Um, and to all learn together to be able to sit in that uncomfortable space of not knowing, of not having the certainty of a particular outcome.

Lee Kantor: And at the heart of this, though, there has to be a high level of trust. And I think that’s where a lot of the organizations kind of break down there. Isn’t that level of trust to be vulnerable there. There’s a fear of a repercussion if you say you don’t know or you or you at least think there’s going to be something negative going to happen if you express this level of vulnerability.

Kelly Hudson: Absolutely, absolutely. And that’s that’s sort of the double edged sword of imagination, right? So so when, when we say like, if a person says, I don’t have an imagination. Well, think about all the ways that you imagine that, for example, being vulnerable is a risk. All the costs that might happen if you’re vulnerable, your team might turn on you. You might be seen as incompetent, you might lose your job. You might not have any respect or credibility as a leader anymore. All of those things your imagination is running in the background and preventing you from actually trying, preventing you from running a small experiment. Whereas if you flip that sort of imagination and you use it for possibility instead, you might think, well, what if I say I can’t predict the future, but I think that I have a solid direction for us to move in, and I want your feedback on that. So it’s not quite the same as saying, I don’t know, but it is inviting participation into the conversation.

Lee Kantor: And it’s inviting a culture of experimentation. And I think that that’s extremely important that you can’t just think there’s one way to do anything, and everything should be an experiment, and it has to kind of earn its way as the way we do things.

Kelly Hudson: Mhm. Absolutely. I think it’s so funny because we are I’ve been called a know it all in my life. I have a bit of a know it all about me. Um, but knowledge is actually such a limitation on us because when we think we know something, we’re unwilling to, we’re unwilling to consider anything else. Um, and what we’re facing in our, in our current business climate today demands that we do not know. It demands that we wonder. Instead, it demands that we ask, demands that we’re humble because there is so much more that we don’t know than that we do know. And so what I want my clients to do, and what I want to do in my own life, is to play in the sandbox of not knowing and to seek out not knowing, to find what we don’t know, and to follow that thread until it becomes something new and something exciting.

Lee Kantor: Yeah. And especially with the AI kind of revolution that’s happening now, everybody has access to all the information and all all the smartest experts. So like, just your knowledge isn’t enough anymore. Like you have to be creative and connect dots and, and mix and match and things. It can’t just be knowing things. That’s not enough anymore.

Kelly Hudson: No, it’s not enough anymore. And what, what still and will always differentiate human beings from AI is our ability to. To ask questions from a place like almost from an existential place, um, to bring our emotions and our feelings and our epic dreams and our imagination and our fears into the conversations that we’re having into the ideas that we’re building. And that is so much more than information.

Lee Kantor: Right? It’s leaning into the humanity of sometimes being irrational or impulsive or, you know, doing something that isn’t kind of by the book. That’s, that’s where the, the great inventions happen. That’s where the breakthroughs happen is on the edges or beyond the edges, not on the direct path.

Kelly Hudson: Exactly, exactly. Yeah. We have to just leave the map behind and say, I’m forging my own path now, and it’s going to be long and challenging. I’m going to have to really push, but I’m going to find a new path as I’m walking it. And what I see out there is going to be something that nobody else has seen before. And, and once you find that thing, then you can switch from being a wayfinder to a cartographer to a cartographer. So that’s when you can say, now I’m going to lead other people here to this terrain that I’ve now learned and navigated.

Lee Kantor: Good stuff. Well, congratulations on all the success. If somebody wants to learn more about what you got going on or get on your calendar. What is the website? What is the best way to connect?

Kelly Hudson: Yep. So I’m at www.coachkellyhudson.com. Um, and I also have a creative wayfinding newsletter. You can link to it from my website. And in that newsletter, I send out twice a month or so. Just thoughts about the creative wayfinding journey, um, and some reflections and prompts and practices that you can try in your own, in your own writing or in your own life and work.

Lee Kantor: Good stuff. Well, thank you so much for sharing your story today, doing such important work. And we appreciate you.

Kelly Hudson: Great. Thank you so much, Lee. It was a delight to talk with you.

Lee Kantor: All right, this is Lee Kantor. We’ll see you all next time on High Velocity Radio.