Ep 150 Creativity: What 10 years of making The Crazy One taught me

0:00So how the actual hell have I been sitting here and talking to myself for 10 years? I'm not sure I know the answer. Where did the time go? How did this happen? I think, I mean, this is always the way that it works, but it's been 10 years of the Crazy One podcast. 149 episodes. I don't it's got to be over what 100 hours of content from the beginning of July 2016 till today just now. That's a long time. And I just wanted to take a minute I guess to I'm not usually one that's big on looking back or doing that sort of thing. But I guess just sort of take a minute and recognize the milestone to stop to think about what have I learned?

0:49Hopefully, what have you learned? What were some of the biggest lessons we all learned along the way over the last 10 years? And to be able to sort of share that out, because again, it's 150 episodes in 10 years. It feels like it's worth 30 minutes. So welcome to the 150th episode of the Crazy One Podcast. As always, I'm your host, Stephen Gates. This is a show where we talk about creativity, leadership, design, and everything that matters to creative people. as always just a little bit of quick housekeeping do me a favor leave a review hit the subscribe button any of those sort of things i think you know if you're looking for a good agency because you're tired of your old one give me a call any of that sort of stuff but it's been 10 years and it's interesting because that's a real unit of time i think it's worth stopping to look honestly, instead of just like the highlight reel, what has been going on?

1:48And it's been, it's been interesting as we've sort of gone through this. So let's maybe go back to the very beginning. So 10 years ago, the first episode was called light bulbs are bullshit, which is born out of, which I think is still just as true today, if not more so born out of my eternal war with the concept of creativity being a light bulb. I hate it then. I hate it even more now. Because why is because it makes what we do look easy, look dismissible, right? Like somehow we all just sit around waiting for lightning to strike and then it all figures itself out. And the argument then was that creativity is a blue collar profession.

2:28It takes work and skill and talent and experience and a lot of those sort of things. And I think that's the interesting thing is that the industry conversation has changed completely in the last decade. That we've gone from doing things like portfolio tips into surviving an in-house culture as that was all the rage to now into AI and how to work with that and some of the existential dread that comes with that. But I think that, you know, sort of episode after episode, I tried to keep the same deal that I felt like I made with you the whole time, that I'm always going to keep it honest. I'm going to share whatever it is I learned along the way to help you.

3:13But also, I think the deal I made with myself was the reason why I did that was it helped push me forward. I couldn't sit on past success. I need to keep thinking of new things and pushing myself and evolving. And that was sort of something I said all along the way was that for me, the show probably helped me maybe more than it helped you because it did some really rare things we'll talk about in a minute. But my deal also was, which is why there's been breaks in the show, I'm willing to put out content when it's worth sharing. I always rejected the idea of doing it on a schedule of doing it every week or every two weeks because then I think you get into the trap of you're putting out content to appease a schedule.

3:54Not because it's good, not because it's useful, not because your audience is going to like it, but because it's a schedule. And I think the last thing that I always did was the show has never had a sponsor. I've never sold ad space because candidly, I just wanted to be able to say whatever it was I wanted to say. I didn't have to worry about sponsors. And honestly, I never went into this even today with the thought of making money. And I know that that's a concept that probably sounds almost laughable now because I started the show, I think honestly, before podcasts were really a big thing, then they became a big thing.

4:28Then COVID hit and they weren't a big thing. Then coming out of COVID, it was all boot camps and, you know, career coaches. And I felt like everybody had a seminar or a book or something they were trying to push and that everybody had an agenda to get your money. Like they were linked to advice. I never, this show was never about that, right? It was never about attracting sponsors. It was never, it was not one of those things. I think in the same way that like over the life of the show, I've never spent a penny to promote it. That it was always that, look, if the content was good enough, it will find its audience.

5:03And I think if anything, the show and doing this thing has been a nice proof of concept for me that some things that I always thought or felt are true. And I don't know this. I think I talked about this maybe once in the life of the show. this goes back to why I actually started doing this. So I don't know what 11 or 12 years ago, I had been actually writing blog posts because I felt like, you know, that serious people are writers. The big flaw with that approach is that I'm a designer by profession and a writer by necessity. Writing is not something that I love, but I did it because I felt like I should.

5:45and I went along and was sort of doing that and then it started to turn into doing more speaking gigs because people liked some of the content and I remember I was doing one speaking gig in particular so there was one I'd been invited to Graz, Austria so it's a town that's about two hours south of Vienna you fly into Vienna you drive down through the Black Forest uh very really cool town like amazing food didn't see it coming had never heard of the festival the town I think the town's biggest claim to fame is like that's where Arnold Schwarzenegger was from, was in Graz. And I remember I went to do the 15 Seconds Festival because it looked really big and really cool.

6:21And it was, it was all those things, right? For whenever it existed, I continued to say it was like the best festival nobody ever heard of. But the first year was really impactful for me because it was the first time I was doing a lot of sort of canned talks, right? It was sort of the talk that I thought everybody wanted of like a lot of easy advice and sort of very like fortune cookie things out. And I could just, it wasn't the content that I was passionate about. And I could tell it just, it wasn't the sort of talk that I wanted to give anymore. And so I decided that like, look, you know, this, this festival is big, but it's far enough away.

6:58I actually want to take a swing and do something different. So I went into that particular festival and that talk really decided that I want to do something personal. I want to do something honest. I want to do something that sort of broke away from what I was seeing everybody else doing, that it was a risk, but I thought it was one that was worth taking and one I could land because it was just the honesty was something I just felt drawn to. So I went and I did the talk. And the reason why I started the show is what happened after I did the talk. So there was a speaker's reception, sort of like attendee reception afterwards.

7:33That was kind of like a low grade rave at this big warehouse on the outskirts and in Austria. And I'm standing there with a few other speakers that I'd met and people that I knew. And we're just all sort of chatting in this little circle, standing there in the middle of this basically warehouse. And my wife is with me. And for any of you that know my wife or have seen her, like my wife, Whitney is absolutely my better half, love of my life, fierce and true, but she is equally just sort of very direct and honest and human in her approach. And what she was doing was something that I wasn't, was that she was actually watching what was going on in the outskirts of the circle that we were standing in.

8:11And she noticed there was a young man who was standing there who clearly wanted to come to talk to one of us, but sort of either didn't know how to break into the conversation, didn't sort of know how to, you know, kind of come and start the conversation, right? It was very much like this kind of high school dance kind of dynamic. So very much in her way, she walked over and talked to him to a minute and then sort of put her arm around him and brought him over to the circle and brought him up to me and said, you know, look, he really wants to talk to you. Isn't sure how to do it. You know, you two talk.

8:42So I said, okay. So I sort of stepped out of the circle and we're standing there and I'm standing with this young man who's probably, I'm guessing early twenties, mid twenties at his latest maybe. And we're standing there and he starts to cry. It's not the reaction you would sort of expect in a moment like that. It's not the reaction you would want, but he was clearly very, very emotional about something. And so we stood there for a few minutes and he kind of calmed down and he started to talk. And what he was telling me was that he really wanted to be creative. He really wanted to be a designer.

9:16And it's interesting in some of these countries where it's just, it's culturally is, it's different. And I see it in through India and Asia and through parts of Europe where all of his family were accountants and his father was not supportive in any way of him going out to become a designer or become a creative. It almost felt like in the conversation we had that he had come out to his father, like he was gay, where his father had basically disowned him, said if that was a profession that he wanted to follow, that he was not going to support him, he didn't want to talk to him. It was clearly a very different dynamic than what I had really sort of seen or experienced before.

9:59And he was really, understandably, really emotional about this. And he went on to tell me that he had decided that he was going to basically sell most everything he owned to buy a ticket to this festival. and that the outcome of what he found there was really going to determine what he was going to do next. And that if he went there and he could find some people or some group or his tribe that he felt like really aligned with what he was saying, that then he was going to go against his family and just go make it work. But, and I think this was the part that set me down a totally different path that I didn't see coming.

10:37because he'd said if he didn't, he was so distraught. He was so lost. He was so uncertain of what to do. He had decided that the other reason why he sold everything was that at the end of the festival, if he didn't find his people, if he didn't find somebody that he felt like gave him some hope that he'd made plans to go to a bridge outside of town and he was going to kill himself. I was I think understandably speechless I hadn't had a conversation like this before I wasn't sure what the right reaction should have been that I think obviously I've had a lot of experience with my father and things like that that I'll talk about more in a minute so I like I understand how difficult it can be but I had never understood being creative in this sort of terms or this sort of stakes.

11:31And he went on to tell me that the talk I'd given, this first time I'd given something that was really personal and really honest, and I really shared what I had been going through, was the first time he felt like he heard somebody he could relate to. That all the rest of them were so polished and so overproduced that he felt like it was just an impossible standard that he couldn't attain. And I still talk to him today. And actually, I've ended up over the course of the show, So there's probably about five or six people that I've had very similar conversations with, and I keep in touch with all of them for obvious reasons.

12:06But I remember flying back from that festival and sitting on the plane, and it just, it rocked me to my core. Because I just sat there thinking that I have a message, I have a voice, I have something that can have an impact. And clearly sitting there trying to write about it or write blog articles or whatever it was, that wasn't going to be the way to get it done. And so I landed back home in New York, and it was the third week in June. And I really just sort of said, because look, empirically, when I thought about it, the world didn't need another podcast. The world didn't need another white guy who thought he knew better than everybody else to share something.

12:46But I just couldn't get that kid out of my head. And I felt like the need for clarity, for honesty, for authenticity was so needed then that I had to do something differently. And so that's the real story of why the show started was because in that moment, I felt like I have good material, I have these articles. And that's what the first couple episodes were, right? It was just sort of regurgitations of talks and articles before I found my footing and I found my voice. but I think that that's the part for me where as we start to look back it really set the foundation for and I think doing the show is only validated for all of us that a few things are true and they're still true today I think one more than anything is that authenticity humanity realness cuts through it cuts through the noise and especially the time now right I feel like there's more noise and bullshit on LinkedIn and everywhere else than there ever has been.

13:47There's more conjecture on what's going on than there's ever been. But if you show up, whether it's in a job search, whether it's in your job, whether it's in creating content, whatever it is you do, I've always felt that if you showed up as your authentic self and you really put out stuff that you really felt and really shared, that you'll find your audience. And I think I learned that, And that was sort of reinforced along the way because I'm always big on going out and studying with other people who do what I do. And along the journey, one of the times I sat down with a comedian who is that's what he does for his profession.

14:22And I was always really interested around how do you write jokes? What was your process? How do you know what works? And he told me something that very much aligned with that. where he said, Steve, the biggest laughs I get are always from the things that are the most honest, the most embarrassing, the most human. That always gets the biggest laugh because it's almost like attention release. And I always thought that makes a lot of sense because I think even in a lot of doing something like this, the best episodes have been the most human. There have been episodes that I've done around gender bias and like a lot of the share the mic shows after the murder of George Floyd, where I'm like, I'm going, there's a decent chance I may end my career.

15:02But that's always the interesting thing is that, like I said, I think if you show up with authenticity, if you recognize that we all have a story to share, because I think that's the other part of this. And I think I've had to come to grips with this in through doing the talks and doing the show is that a lot of what I talk about, I don't really, I'm not really sure why it needs to be a talk or it needs to be a podcast. Because a lot of the things to me feel very obvious. They feel like, oh, you look at that situation, you look at that problem, that feels like that should be the solution. But I think for all of us, not just me, it's a trick, right?

15:46That we think it is obvious, but whenever I stand on stage or I make a show and I say the thing, I see people write it down. They take photos of the slide. They share the show. So your story and your authenticity probably isn't as obvious as you think it is, that I think there's a lot of power and a lot of support and a lot of community in what that is. And that's always been my argument. Has been believing in yourself, standing up for yourself, understanding your brand, which is not a logo or a color or a website. Your brand, as in what do you stand for, is critically important. Because I think that's the other thing that I've realized over the past 10 years is while a lot does change, a lot still stays the same.

16:30That over 10 years, there's a lot of episodes that have remained the number one download because they're topics that still work. People still struggle with imposter syndrome and how to lead and how to do a lot of the things that I've talked about that I've struggled with over the course of the show. Now, I think there are parts of that that are just, I've come to understand that they are evergreen. I'll be honest, there are other parts that are wildly frustrating. That there's a lot of talks that I have and episodes that I've done around corporate culture and creativity and things like that that are just as popular today as they were 10 years ago.

17:03That is frustrating. The fact like, I would hope that that content would age really badly, that we would learn and move on and to do those sort of things. But I don't know. I think there's some things we learn and some things we don't. But I think in all of that, right, in thinking about authenticity and sharing your story, I think one of the best things that the show taught me, and I think one of the things that none of us do enough of, is the importance of finding time to focus and recognize that your creativity, your process, your approach, it's a tool, it's an instrument. And again, I think that's something to me that's been so valuable, is that the show forced me to create time to think about my process, to think about topics, to reflect on why I do things, to not just sort of hurdle headlong into the abyss.

17:54But that I think that every episode that I did where I tried to share some advice or some insight, what doubled for me as something that was sort of like a working session in real time, too. that it gave me this structured time that was recurring, that was time to reflect. And again, I think that it's just, I think more and more people don't take that time to build it into their career. They just sort of jump from fire to fire. And I would be one of them, and I only got it because I forced myself to show up to a mic every week or so for 10 years until it became something that was more embedded in who I am.

18:32and again I think it's just something to think about about are you making time to do that do you understand are you really showing up as your authentic self or not because if you're not it is exhausting and I think I only recognize that after I decided to step away and change some of my priorities around that but I think that's the other thing that I've really learned and I know mentioned that a little bit before is that I think one of the things to me that I hope the show has done is to get people to recognize that more people are having the problems that you're having than you realize. That, you know, again, the number of episodes I've done on imposter syndrome, on like the value of design, on, right, like all of those sort of things are recurring that I think they're all things that we struggle with, but we buy into this myth that there's a right way to do it, that there's a right way to go about this.

19:24And I joke with people all the time whenever I do mentoring that like, look, nobody would tell you my career path was a good idea because it's not. It wasn't. It only was after it happened the same way that only after I opened my own studio, only after I launched the show, only after I've done it and it worked, then all of a sudden did everybody go, oh, no, we always knew it was going to be a success. Like, no, no, I remember the conversations. No, you didn't. Right. But I think there's also that being the person that just speaks the thing, right? That says it out loud that, you know, whether that's for your team, for your company, for your community, like whatever that is to be able to be the person that actually shows up and says the thing that gives other people permission to be that way.

20:09And I think whether that's from an emotional standpoint, whether it's from a creative standpoint, I still argue that everybody's creative. Most just everybody forgot that. I think that that's the part of it is the journey. And I think that was probably the next thing that I really sort of thought about is, you know, 10 years is a decent chunk of time. And I think back to who I was, the sort of work that I was doing whenever I started this, I'm nowhere near the same person that I am today. And I think that for a lot of us, we can, we really pressure ourselves sort of at every moment or every step in the journey to have everything figured out.

20:46And I think that's maybe one of the things with the show that I've really tried to lean into sometimes in spectacular fashion is a willingness to demonstrate hopefully that I don't have everything figured out that I've been laid off three times that I've shared that journey that I tried looking for a job and hoping it was going to be this big success just to face plant and have it not work out and have to come out with a backup plan but but again I think that it's just allowing yourself the grace that whatever your plan was doesn't need to be what your plan is. Because it's interesting that I think that's the thing I've realized in my career journey and the journey of making content and everything else.

21:25Nobody really remembers that plan but you. Nobody's disappointed by it but you. Nobody knows it went off track but you. That if you're doing it and you're happy, which often leads to then being successful, it's interesting how those things have changed. But also just the recognition that I think that it's just what's around you is going to change too. And I think that's a lot of what it is. When I think about sort of what's changed underneath me and around me that, you know, look, I went from the highs of being featured in 10 Apple keynotes and like doing incredibly cool work to the lows of being laid off three times to the industry changing to seeing us devalued, then in-house and wildly valued.

22:12And then that going away and the rise of AI, none of us could have predicted any of that. And I think that that's the thing is that, you know, that's what led me to I took two hiatuses from the show because I lost my voice. I lost my way in what that was. I felt like I wasn't sure I had anything to say anymore. I felt deeply broken and lost at more than one point over the last decade. and it i think that that's where the the show is maybe added some pressure or a different thing because i think whenever you allegedly show up as somebody who can give other people advice and you don't know what to do with your own career it's kind of like this atomic imposter syndrome that shows up but i think we all go through that moment right where we're supposed to have it together we're supposed to to do those sort of things and i think a lot of it for me was i also have to acknowledge that probably what was the biggest discovery along this journey was the one that came from what was episode 108.

23:11I still remember it. And that was in 2020 when my father passed. And I think that the run up to whether he knew he was sick or not, but just we had conversations in 2019 and 2020 that he and I had never had before. That, you know, 108 was an episode that I did to try to honor his life, to honor what he taught me, the career that, you know, had been handed down. But it also was the recognition through those that I do think I have a bit of a different perspective that I have, I am somebody that has been able to see almost all of the arc of a creative career of somebody that, you know, growing up with my dad, who is, you know, working, who owned an agency, who did a lot of those sort of things, was very much in his prime to then sort of struggling with relevancy, getting laid off, doing freelancing, sort of fading away, fighting and then kind of accepting the lack of relevancy, I guess, in his work.

24:07And I think that it was something along the way when I started the show that I didn't see, and it hit me like a freight train along the way, was in 2019. I remember I was standing in the backyard of the house I grew up in, and we were standing out there at the grill cooking dinner. And all of a sudden, he turned to me and he said, you know, if I'd have known you whenever I was still working as a creative, I had a completely different career. And it never occurred to me that the reason why I'm creating the show, I'm trying to help all of you was because in a lot of ways I was trying to save him.

24:40He was my first boss. He was my first creative director. He was my dad, right? Like, and again, I think a lot of it was that I really have seen the very tangible damage that imposter syndrome does, that the fight for relevancy does, that what happens over the arc of your career as you start to come down the backside of what that looks like and you know what do you want that to be but I think that you know for me that was a lot of what I discovered along the way was actually starting to do this and create the content with one idea of why I was doing it only to discover it was a wildly different reason and has sort of continued that because his again I know that the unspoken hypothesis he had was that he wasn't very talented that, you know, again, he had a lot of ideas that he didn't think anybody wanted.

25:29It was clear as day to me that after he passed and I cleaned out his studio, finding the postcards that were never sent, the promotional flyers for his work in addressed envelopes with stamps that were never sent, that where he'd let the imposter syndrome win. And I know that for me, it's why I get so incredibly fired up about this stuff, because I've seen the impact to one of the people I've loved the most in my life. And again, I can't imagine that on the scale of I know, you know, whatever it is, the 150 countries where people listen to the show, what that is like spread across an entire world.

26:09And it has been right. And I think I've tried to share that journey. I think that a lot of what's been interesting to me has been also I've long believed. right and I think this goes back to the authenticity point that how you show up matters how you work matters how you treat people matters now I've certainly had more than a few moments where I have done things I'm not proud of treat people in ways that I regret and other things along the way but I've always felt like that was important I think that maybe that's like the Pittsburgher in me because Pittsburgh is very sort of blue collar. You do what you say, very, you know, direct, hardworking.

26:51You show up, you know, what you say means something. I think it's why I left New York to come back here because it's just that that's just sort of who I am. And it's been interesting because I think it's sort of in the episode 128 through 137, a lot of that was sort of talking about, you know, leaving the system of sort of leaving corporate culture, leaving agency life, trying to build my own thing with crazy as my agency. But I think that a lot of it for me, that whenever I've talked about it, I haven't talked about it as a sales pitch, but I think that the show, even my agency, that there is something different.

27:25I don't know what, I don't know if it's normal or not. I see, again, this is the problem whenever I sit here and talk to myself is that you can take this a lot of different ways. But I think a lot of this for me has been like sort of my thesis on that these things are important and that they do matter, having them play out. Because I think starting my own agency, you're talking about a lot of stuff. It wasn't because it was a business story. It was because to me, I wanted to prove that if you did things honestly and you made content for the right reason, people, you'd find an audience and people would care.