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Episode 85

Channeling Anxiety For Creative Genius with Reddit’s Brand Ambassador

Will Cady
Global Brand Ambassador &
Former Head of Creative Strategy at Reddit

Will Cady, Reddit’s Global Brand Ambassador, joins us to discuss the relationship between anxiety and creativity.

“There’s a connection between anxiety and ideas. It’s a human energy—these emotions, these feelings that we have—that is fodder for a story, that is kindling for fire, that is the very raw material of creativity.”

He shares practical advice on transforming anxious feelings into creative fuel and highlights the importance of managing emotions to enhance creativity. We also explore how artificial intelligence is changing the creative workforce and why Will believes AI is best used to complement, not replace, human creativity.

“With the advent of the AI, we’re discerning the difference between creativity and work. And there’s a lot of work that we do that pretends to be creativity. And there’s a lot of creativity that is hiding inside of work.”

Learn how to turn your deepest anxieties into artistic expression and navigate the evolving world of creative professions.

Topics On This Episode:

  • Anxiety and creativity
  • Creativity and AI
  • Coaching and tools
  • Writing and journalism
  • AI’s impact on the workforce
  • The future of creativity
  • Resources and communities

Watch the Live Recording

Full Episode Transcripts

Tessa Burg: Hello and welcome to another episode of Leader Generation, brought to you by Mod Op. I’m your host, Tessa Burg, and today I am joined by Will Cady. He is the global brand ambassador at Reddit. And we are going to explore the topic of the state of creativity in a world of Gen AI. Will, thank you so much for being our guest today.

Will Cady: Here we are, let’s talk about it. Let’s talk about creativity, let’s talk about AI, let’s see what else comes up.

Tessa Burg: Yes. Before we got on the line, we were sharing our experience about the solar eclipse. And I will say it definitely calmed me down, remembering that moment that we, everyone stopped, took a deep breath and really soaked in like a miracle that was happening in the universe. So, thank you, because I think, you know, with so much changing and so much going on, it’s easy to get swept up and stressed and just trying to sort through everything right in front of us.

Will Cady: It’s literally a very grounding experience going outside, touching grass, and looking up.

Tessa Burg: Yes. So let’s get into this topic and help others not freak out when it comes to AI. Tell us a little bit about your background ’cause you’ve had just an incredible career and journey, and then what’s your perspective on where we’re at right now in creative?

Will Cady: I think we can tell that story backwards a little bit. So I just re-released a book, hardcover came out in October, audiobook came out the day of the eclipse, actually April 8th. And the opening statement of that book is “Anxiety is creativity ready to be transmuted.” And I arrived at that statement from a few different paths that are represented in the subtitle of the book, it’s called, “Which Way is North? A Creative Compass for Makers, Marketers, and Mystics”. So those three words, maker, marketer, mystic, they represent my background. Yeah, I grew up in a household with a father who was Rinzai Zen Buddhist monk, and I was a professional musician for about 15 years and have been a marketer for about 20 years. Built the creative strategy agency in-house at Reddit called Karma Lab. And each of those threads brought me to the same point of remembering the human element and what it is to be human. And it was really 2020 that it came together when there was just an abundance of anxiety everywhere, you know, individually, collectively, that I started to realize the connection between anxiety and ideas, that it’s a human energy that there are these emotions, these feelings that we have that are fodder for a story, that are kindling for fire, that are the very raw material of creativity itself if you have that relationship with it. So how not to freak out, I suppose my approach has been to freak out, go into the freakiness and then see what’s coming up for you, what is the freakiness trying to tell you, and how can you facilitate the expression of the story? Because that’s always, in my opinion, where the most interesting stuff is hiding.

Tessa Burg: I love that statement because I think when we get anxious, we wanna immediately turn away from it or try and figure out how to get out of it as opposed to lean in and explore it. When you’re coaching people and helping them kind of come to that piece, are there any tools or processes or ways that they can do that productively or effectively?

Will Cady: It’s about getting to a place of recognition and recognition is a very charged word in the mystical space. You know, there’s a great work called the “Recognition Sutras” by, there’s a translation by an author named Christopher Wallace, and it’s like this old kind of dusty scroll from the Shaivists, like 100s of years ago. And the whole concept there is about recognition of what is happening in your field of experience. The opening scene of my book is when I was sitting down with the Zen master who taught my father, and he was teaching me that behind an emotion, like fear is awareness. And that path of Rinzai Zen is about just being aware, not saying, “I am afraid”, but there is fear, right? Noticing that there’s something in your field and that it presents as information. Everything that I generally do when I’m coaching people is to help them get to that point of awareness. I’ll add another one, which is from the musical background, one of the greatest things that master musicians do is they turn any sound in the room into music. And that’s a little esoteric, a little hard to describe, but, you know, literally if somebody kind of, let’s say they dropped their phone in a jam session and it hit, you know, like a piece of metal and it made like a little clang, like a great musician would be like, “Do that again. Keep doing that, keep doing that, keep doing that.” So I’ll do that in conversation with people that I’m coaching. Something will come up, they’ll say a word or some kind of weird memory might pop up and they’ll bring it into conversation. And especially with branding exercises, a lot of times people will just say something like, “Wait, that thing that you just said, let’s make music with that.” Right. Then from like a meditation coaching standpoint, it’s about helping people to drop into their breath, to just center and get to a place where they notice every sound, every feeling, it’s all information. And from a marking standpoint, it’s really like looking at all of the feeds, everything that’s happening in culture, in media, on TVs and radio, on, you know, social media, and anything just that you notice that’s a little bit different that has that kind of charge, especially if it makes you actually a little bit anxious, picking that up, recognizing it and realizing that there’s a story here that wants to be told, there’s music that wants to be made, there’s something that’s coming into your field for you to be aware of and create with. Everything that I do helps people to cultivate that precise skillset, recognition.

Tessa Burg: I love that. So if we think about recognition in this state of Generative AI, you know, I don’t have the opportunity, I wish I had more opportunities to interact with the creative team. We have some awesome creatives, writers and designers and UX/UI people at our company, but I do hear comments that sometimes make me stop and think and be like, “That’s an interesting perspective” and the one I hear the most is, well, you know, “I was gonna tell my kid to be a writer, or I used to be a writer, or I think I’m gonna do this in design”, but now is a bad time to do that, now you would never say go into writing. And I always get curious and like that, and maybe it’s naive, but I don’t think that’s accurate. I think writing is a amazing skill and something that we will always need, but if I were a writer, that could definitely be a moment of anxiety and stress for me. So how do creative folks, how are they taking that right now and how are they going from recognition to what do I do next to continue my creative journey?

Will Cady: Well, first off, I totally agree with you. I don’t think it’s naive, I think it’s a wise perspective that you have, and that’s a great example because with something like writing and a lot of creativity in the face of the anxiety wrought by AI is we’re actually boiling down what it is that is creative at the center of it in the first place. Because we’re in this phase with the advent of the AI and our reaction to it of discerning the difference between creativity and work. And there’s a lot of work that we do that pretends to be creativity.

Tessa Burg: Hmm.

Will Cady: And there’s a lot of creativity that is hiding inside of work. You know, you practice or you do your daily journaling and when you’re in the grind, in the toil, in the sweat, sometimes that’s where a make ideas pop out, right? That’s a creative process. But I would argue that, oof, my sixth revision of a presentation and the copy that I’m writing in that, or all of the different, you know, I’ve got like 64 different headlines that I want to ab test on. Spending time on that stuff, a lot of that I don’t believe is creativity, I believe it’s work. The challenge is how do we as writers, as creators evolve our profession, how we get paid in the direction of where this is going? I do think that we’re getting what we want ultimately, which is to be more human, to be more creative, to focus on those things that are truly unique to the human experience, and taking away a lot of the stuff that I don’t think we really like to do. I don’t think we really like to like spend time focusing on ad specs, right? That’s important, but that’s not where we wanna spend our time, we wanna spend our time on the story that’s going into what’s inside of those ad specs. But it requires an evolution. And so writing, you look at the state of journalism online as an example, and you see that a lot of difficult changes happening where a lot of these companies that have built themselves on clickbait candidly, are the ones that are having the most challenges and having to make the most cuts. And that’s because they’ve built around something that is easy for AI to do. But the companies that have built around, like in-depth investigation, the journey that is a part of journalism, like really thoughtful writing, asking good questions, that can’t be replaced because somebody has to experience it. That to me requires deep, deep training to be a writer. So I’m a huge believer in liberal arts degrees because it’s just not about confusing the means from the ends. Right, the skillset of writing, of actually, I guess knowing how to write in cursive what it, that’s what it was before, knowing how to type on a keyboard, knowing how to structure a sentence and the different formats of articles or emails or whatever, that’s not the writing, the writing is in knowing how to wrestle with an idea, to have an experience or to have a journey and to come up with something interesting to say, to recognize where the story is. That is a deeply, deeply human thing, and it’s not math, it’s not science, it’s not technology, it’s art. And I think we’re about to have an amazing future for anybody with a liberal arts degree where it’s gonna be more valued than it has at any point in our lifetimes. From that basis of having the training to find something interesting, to express something interesting, or something even more simple to having fluency in aesthetic, in styles, genres, so that you can more effectively tell an AI what to do. Gimme a little bit more cubism in this image, right? Or I want this to be more of an impressionistic piece. That stuff that requires an education in the humanities to know how to prompt a machine to give you something according to the human elements that you want to paint with.

Tessa Burg: Yeah, and I’ve seen that firsthand, like when we talked about prompt engineering and it being extension of your expertise and background. When I do prompt engineering to create a visual or to improve the design, the output is and has been in tests lower quality than when the designers do prompt engineering because they know how to instruct and coach and ask the right questions to get to a higher quality, more immersive output, where that’s just not, you know, that’s not where my background is. But then if you flip it, one thing that I’ve found extremely helpful is when I’m wrestling with an idea, but the idea is more technical or in code. And if I can’t find out why something isn’t working the way I wanted it, or if I feel like I’m missing something, I have used ChatGPT to give me additional perspective. Like, you’re a developer, you’re trying to get this to execute, to deliver on this solution, what’s missing? What’s wrong here? And that’s been, but I know how to ask those questions where a designer probably wouldn’t have the experience to go the other way. And so I don’t know if that’s a good example, but I have seen where, I cannot seem to get an image out as good as our designers. And this does happen, like presentations where someone’s like, “Hey, can you make some slides for this?” And I’m like, “Well, sure.”

Will Cady: Those are great use cases. Yeah, so there’s zero to one creativity if you’re trying to make a film, it’ll be really nice to have some help with the storyboarding and just be able to do that extremely fast. Right. There’s also getting help stepping outside of your biases, because as a human, as a creator, it’s your job to have biases. You’re supposed to have taste, you’re supposed to make choices. And that is the strength of great artists, not what they do, but what they don’t do, what they choose. But that also becomes a limitation. And so AI is a great tool for helping you zero to one, test an idea, express an idea in its most basic, so that you can then, you know, refine it and, or just giving you something completely outside of your domain of bias and surprising you with randomness or surprising you with something that you would never even think of. And then you get to react to, in both cases, it’s the reaction, the human reaction.

Tessa Burg: Yeah, I agree. We’re talking a lot about the positives of what creators can do with gen AI, how important the human element is. But there’s another side to this human element, which is a lot of business leaders think that gen AI means they need less of it, and they want to cut back staff. And there have been layoffs and people have said, “Oh, we’re using AI and so we don’t need these people anymore.” And people has encompassed everything from knowledge workers who are doing like customer support, but also writers and creative designers have been impacted. Charging toward this less people more output, is that the right charge or what is your perspective on that sort of linear thought?

Will Cady: I think there’s a lot of mistakes being made there. You know, we can’t deny that there’s a lot of business leaders that are being opportunistic to cut their costs so that they can optically look better on their P&L. And you know, I love what Scott Galloway says, calling this corporate ozempic basically, it’s like, oh wow, we have like a fast, easy way to trim down. And I think the consequences of that remain to be seen. So, but it’s case by case. I’ll acknowledge that as well too. And that said, it’s also a very interesting time. Let’s say you are a creator that is on the wrong end of that equation, and you have lost your job because your business leader has decided that they wanna take the opportunity to trim down the staff in your organization. This is also a time where you can be more entrepreneurial than ever because you are also the beneficiary of these tools. And so if there is a vision that you have, a grand idea, it has never been more possible to build that, to go zero to one, to put together a pitch deck or to create some AI agents that help you with some of the operational tasks that you might not be as good at, or so many of the different elements to just kind of make your vision a reality. So we’re in this process of change, I think, and there’s a lot of talk out there in terms of like, what will be the first billion dollar company run by one person? So there’s an expectation that that’s going to come up. I don’t know, so I’m a creative person, I have no, like coding ability. I don’t know how to program, my technological skills are very weak. And for my entire career, I would never have considered myself a candidate to be somebody like that. But now, rather than having to be a programmer or a developer, you can be a creative and be that one person who launches a billion dollar business. And that’s a high watermark, I think that there’s a lot of different watermarks beneath that. I think that creating an operation for yourself as a contractor, as a consultant, where you are making a steady six figures and you know, you’ve got an operation that allows you to be the master of your own schedule, I think that that’s available for people too. And we’re going through this change where there’s a lot of talent that is getting kind of ground in the mill and being let go because it’s value isn’t being recognized. And if anybody here is listening that has been on the receiving end of that equation, like I hope they feel empowered that you have a value that you can start to give back to yourself and build with yourself. You have time now, and this is a moment where for the next, let’s say two to five years, some absolutely enormous and impactful and strong businesses are going to be built that we haven’t seen before, structured in ways we haven’t seen before. And you as an artist have an invitation to be a part of that in a way that you haven’t been invited to the dance before.

Tessa Burg: Yeah, and I think it’s still true that greatness comes out of pain. And I think some of, yeah, those businesses we haven’t seen before are going to come from a story like the one you just described, that someone’s value was taken away from them. They were seen as not valuable. And a lot of it is, is not because of AI and ML, like you said, it’s opportunistic, they’re just saying that so it sounds really good in the board call. But regardless, that’s how you feel. And like you were saying before, almost recognize that lean into that anxiety and there’s more there that can be explored and do something that’s never been done before with the very tools that they said replaced you.

Will Cady: Yeah, people love an underdog story, people love a story that begins with someone with remarkable talent who was taken in for granted, and that is happening all over the world right now. So there are people while we’re having this conversation that are building exactly what we’re describing.

Tessa Burg: Yes, and I’m very excited to see that and I’m excited to see, you know, it happened on the other side. I’ve heard comments where people are like, “Well”, well, I think Sam Altman said this himself, or I don’t wanna misquote so I won’t say it was Sam, but somebody in AI, one of the founders of the LLM movement said, “You won’t need to know code anymore.” And I fundamentally disagree with that because it’s similar to a writing process, how you create something that works, operates and executes, that itself is a process that helps you unpack and solve problems and it’s entire, that is very human, that we will continue to wanna solve big issues, that we’ll want to make things better. And if you have those processes and tool sets or the understanding of how it works, then it just won’t be rich enough. Right. And I don’t think that will lead to the billion dollar business. Can you make a small little game or a small little app or a webpage? Sure. But is that a solution to a bigger problem? Is that a business? No.

Will Cady: I remember that quote, I remember the discourse around it. I think your point is very important. It’s an important countering to what I’m expressing as well, because while I do believe that there’s an opportunity for people with humanities and liberal arts degrees to take those skills and build off of them. The counterpoint to that that came up when that quote was being discussed was that if you don’t know how these things work, you’re losing some agency. And the idea of like, you don’t have to learn how to code anymore is misleading, because that basically puts you at a level where you’re always gonna be a customer of somebody else’s platform and service, and you’re not actually able to really work with the soil itself. Right. And knowing how to code is that, it’s getting down to the bottom of something and it gives you more control, it gives you more power. It’s gonna be hard for everybody to do that. There’s gonna be different, I think levels of how we work with these AI tools and I think that a lot is going to be possible with the resources that most people are given by some of these companies. But that’s like that million versus billion versus trillion dollar opportunity, right? If you want to get something really that takes you to the moon, you’re gonna have to know how to code.

Tessa Burg: Yeah, yeah. And even if you don’t go all the way, or a full developer, like you said, it gives you more agency, but it also prevents you from being led down the wrong path. Like just knowing what questions to ask and what to look for can be really powerful, and we have seen this, I mean, AI and ML is accelerating it, but we’ve seen this with other technologies that have come out where companies will make big statements and promises and sell things to marketers or creative folks or people who don’t understand exactly how the platform was built. And then they get into it and it’s totally underwhelming. And all that happens is problems don’t get fixed, they just keep getting told different things until you finally call in your own tech team. But it’s like, you can avoid that cycle if you have time and space, especially to learn some new skills. Maybe you don’t have to master them, but learn them enough to know what questions to ask ’cause in this state we’re at now, just like the beginning of all other technologies, there’s gonna be some bad actors and there’s gonna be a lot of overpromising, a lot of overhype. And it will serve everyone best if they know what questions to ask and where to start so that they don’t really get led astray.

Will Cady: It’s literacy.

Tessa Burg: Hmm. Yes. We talk about literacy a lot at our company and just having that shared understanding and just going deep enough that we get what it is, the impact, the value, and then the dangers and where we need to kind of put up guardrails to be secure and compliant. And that’s probably good for everything.

Will Cady: I think so.

Tessa Burg: So Will, where do we go from here? What do you see coming as the next big wave of opportunity for creators?

Will Cady: Well, I think we’re still in this change wave where we talked about that, the tide is going out before it comes back in. And I would expect 2025 will probably be the cycle where we’re gonna really see some of those first wave founders and luminaries that are these characters that we’re talking about. And they could be 16, they could be 60, we don’t know who the, like they could be anybody. And I think ready for a new founder archetype to step onto the world stage and bring their ideas to bear. So I think that that’s going to be next. And we’re going to see, we’re gonna learn collectively what that path is going to be, what kind of leaders they’re going to be and represent in the conversation. So I’m keeping my eye on that. And in the meantime, as the technology evolves, I do think that we are due, I don’t think there’s much we can do to avoid it, but I think that we’re going to end up as consumers, not as creators learning about this hyper personalized video content in particular.

Tessa Burg: Hmm.

Will Cady: Like some version of like a Netflix meets TikTok, but everything you see is an AI generated video customized to your algorithm. I think we’re gonna see that and we’re going to have to have the experience to separate the wheat from the chaff from it, because I’m allergic to it, I have to admit, like that’s a really scary thing to me. But there’s gonna be something in there that’s valuable and we’ll have to go through that process of figuring out, right, what is this bringing it up for us? Like what do we keep? What do we throw away?

Tessa Burg: Yeah. Yeah, and I think, you know, that’s normal and there will be anxiety, but I like what we’ve touched on in this interview on how to channel that anxiety and get back to that state of recognition so that you can be productive with those feelings, emotions, and thoughts that you have around that process.

Will Cady:  Mm-hmm, mm-hmm. So my bellwethers are, I mean, entertainment is great for that. Like the stories that we tell ourselves and how we tell these stories, that trickles down into all of the other different categories. You know, the music, you know, sports, news, right? The way that our culture shifts, one of its starting points is music and film.

Tessa Burg: Yes. So this has been a very enlightening conversation. Thanks so much, Will for being our guest. I feel like we could keep going like, but we are at time. Before we leave, I want everyone to know the title of the book is “Which Way Is North”. So if you’re ready to sort of start this journey or just prepare yourself, maybe you’re excited about where things are going, you wanna find that center, definitely check it out. Are there any other resources Will, that you would recommend for creators in this time of Gen AI?

Will Cady: Hmm. So yeah, “Which Way is North” is available as an audio book. There’s a lot of meditation in there. There’s my original music, so of course I would point people towards that. My website is will-cady, c-a-d-y.com. And I have some meditations on there as well that are designed to help people with creativity to turn that anxiety into creativity, so you can kind of dive a little bit deeper into that. So, I guess I’m pointing the finger at myself here, but those are my projects that I created to help as best as I know how.

Tessa Burg: I love these as resources and solutions as opposed to like pointing to some training you should take in data science or Coursera, you know. So it’s really different than what, and not saying that those aren’t important, but I think I have loved this conversation, it’s grounding, it’s the best place to start is with yourself and your strength and your value and your inner beauty. And that is truly where this next wave of businesses and the way we solve problems is gonna come from.

Will Cady: It’s true. And you know what else is really useful? Reddit.

Tessa Burg: Yes. It is. I love the communities on Reddit. Anytime I have a question, that’s where I go first.

Will Cady: So I’ll point people that direction too.

Tessa Burg: Yeah. Yeah, and you’ll probably find your folks there. Whatever creative space you’re in, there’s a community on Reddit that is talking about the challenges and issues right now.

Will Cady: Yeah, whatever it is, you know, if it’s a division pro and spatial computing, or if it’s to AI, find the community and you’ll find people that are exploring every nook and cranny of it and are collectively more brilliant than any individual could be. So always keep an eye on the subreddit that is built around whatever it is you’re building for.

Tessa Burg: Yeah. What I find most enjoyable about Reddit is the lack of like AI in it, it’s true like human to human speak, and you get like the authentic truth about whatever is actually going on. So like for example, I follow the NWSL Reddit communities because in Cleveland we’re trying to get a women’s professional team and it’s hard to peek behind the curtain as to like, what is this decision criteria? What are the dynamics in the.

Will Cady: Yeah, yeah.

Tessa Burg: Man, you, I don’t know where these people are located in Reddit, but you can really get great insight, information and connect with people who share your passion and curiosities so quickly. So yeah, it’s been a space that has always been inspiring for me and like the technical communities are fantastic.

Will Cady:  They are, yeah. So I mean, deeply insightful people, great discussions. And of course go to Reddit.

Tessa Burg: Well, Will thank you so much for being a guest today and I’m excited to catch up with you in like, you know, six months to a year. It’s gonna be interesting to track progress in the creative space, see who these entrepreneurs are ’cause I agree, it’s gonna be happening sooner rather than later.

Will Cady: We’ll see, we’ll check in and we’ll see what’s changed and we’ll see what’s the same too. That’ll be interesting too.

Tessa Burg: Yeah, no, that’s true. All right. And if you wanna hear more episodes of Leader Generation, you can visit us at Mod Op, m-o-d-o-p.com and click on “Podcast”. Or you can find Leader Generation on any of the podcast channels, wherever, whichever one is your favorite. And until next time, thanks for listening.

Will Cady

Global Brand Ambassador &
Former Head of Creative Strategy at Reddit
Will Cady from Reddit

Will Cady has walked a path from zen monasteries and touring rock bands into his current role as the Global Brand Ambassador at Reddit, where he also serves as the company’s weekly meditation guide and tarot reader. On his path, Will studied deeply with virtuoso musicians, mystical healers and boundary-breaking entrepreneurs to develop a uniquely potent practice for cultivating creative vision. This practice is at the core of how he builds, leads and advises teams of creators today. Be sure to follow Will on LinkedIn, Instagram and X. Plus, check out his book, Which Way Is North: A Creative Compass for Makers, Marketers, and Mystics, available on Amazon.