Ep 140 Keynote: 'Bet on Yourself" BeMore Festival 2025

In this episode of The Crazy One, Stephen Gates shares the lessons learned from his journey of leaving corporate America to start his own agency. With over 20 years of experience across industries, Stephen dives deep into the tough decisions that led him to bet on himself. He talks about embracing the fear of failure, navigating imposter syndrome, and overcoming the challenges of creative work in a corporate culture that doesn’t always value it. Whether you’re considering going out on your own, struggling with self-doubt, or just looking for a way to reconnect with your creative passions, Stephen’s story offers valuable insights and actionable advice to help you take the next step in your career. Tune in for a candid conversation about the challenges and rewards of betting on yourself and turning your passion into your profession.

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Transcript

What's going on? Good to see everybody. Just so you know. So I'll have the chat up during the whole thing. When we were going through and doing this talk. These are always interactive. So if there's a question you want to ask, anything you want to do, introduce yourself. Stop me. You say, what the hell. Go into that more detail, anything like that.

Feel free to do that. So we're together for the next. What is it, 40 minutes? 45 minutes or so. So what I want to do is probably talk for about 30 or 35 minutes and then be able to just open it up to questions. But like I said, feel free to make it interactive. Anything like that as we go through it.

So let me share my deck and we can jump in. How's everybody doing? I mean, you showed up for my session, so I'm guessing you, you know, at least know my name. So my name is Steve Gates. I've been a designer since forever. I was one of the original, like, co-founders and one of the original mentors on the ATP list.

So I've been here from the beginning. I think I presented it every one of these things that's ever gone on. And it's been interesting. Right. And I think it's been it's been really interesting. So I think today what I wanted to do was, like I said, just give you a little bit of background about me and then kind of talk about why we're all here and, and, you know, again, kind of what's going on.

Just for context. Right. So my experience has been I've worked in agencies, I worked at Corporate America, I've worked at huge companies, I worked at unicorn startups like envision, like, you name it. I've had teams of like, you know, two people up to 500 people and everything in between. So I did that for a really, really long time.

I've gone to pay designers since I was 12, up until about three years ago. Like, I've done tons of stuff. Most people know me for my work in branding and digital and that sort of stuff. That's Tim Cook with some of my work from Apple. I thank you, Jennifer. I've had the Crazy One podcast for about eight years now, which has been just a fascinating exploration.

I think in kind of everything that I've learned along my career, a lot of the stuff I feel like people should talk about and don't, and just a lot of things like that. But that's been a passion project of mine for a long time. And three years ago, I basically talked about and started to do what was the why we're all here, right?

I, I got laid off for the third time. I was completely frustrated and sick of sort of what was going on. I didn't really understand how unhappy I was. And so three years ago decided to take the leap and went out on my own. So I started a very small, there's three of us agency called crazy.

Whenever I started it, it was just me. And I've had a incredible kind of three year ride. So, you know, we really are very small, independent, based in here in Pittsburgh, Pennsylvania. But we work with clients all over the world. And a lot of what it was for me was just wanting to bet on myself. Right. And I think it was a really interesting inflection moment.

Three years ago, I decided to leave New York City and move to Pittsburgh, and a lot of people told me I was crazy and I just couldn't bring myself to go back to corporate America again. And everybody told me I was crazy. And so it just felt like between the podcast and this, that was the perfect name for an agency.

And so we've been able to do a lot of really cool stuff over that time. But I guess that's kind of what I want to share today is what did I learn along that journey? But I think also, you know, the number one question I've gotten asked over the last 2 or 3 years, one is how do I find a new job?

And two is I'm thinking about going out on my own. What do I need to do? So I think that's what I tried to call together in this talk is, I think, one, what are the things that I've learned? What are the things that I discovered when some of the things I've learned the hard way? And also what are the most common questions that people ask me week in and week out?

I do three sessions every single week on ADP list. And so again, this is probably the number two topic that comes up because and look, I think it's understandable. The industry is in maybe one of the weirdest moments I've ever seen. And I think that there's a lot of people that are frustrated and looking for something new. I think that, you know, we have seen any time there's an economic downturn or economic uncertainty, design, marketing, creativity, engineering, a lot of these things tend to be the first thing that they take a hit.

I think that that hit is a little bit bigger this time because there's a lot of companies who don't necessarily understand AI, who are thinking that it's a magic bullet and are finding out that maybe it's not the magic bullet that they thought. But I just think, you know, we've seen the big Fang companies, the Googles, the apples that were always thought to be untouchable and stable have been laying people off.

Right. So I just think there's a lot of people that just have hit a moment. I think coming out of Covid and so many other things are just like, look, this isn't it. And look, because I think, you know, for me, this was the biggest thing is I just felt like I'd spent way too many years of my career working to keep my job instead of doing my job.

And that, you know, one of the biggest things that I had realized was that I had become far more of, I don't know what a politician and an interventionist and a therapist than I was a creative or a strategist, or I needed the things that I loved. Right. And I think that also a lot of people have found out the hard way that creativity and corporate culture don't generally like to coexist because, you know, one really likes certainty and predictability and creativity.

It, you know, prioritizes trust and risk taking in a lot of things like that. Right. So I think that there's definitely a place where I was seeing some of my friends who have been willing to quit to nothing in this economy, then keep going where they're at. And and so this is sort of a line that this is not my line, but it's one that I keep coming back to.

And I just think like at some point, you can't blame a clown for being a clown, but you have to ask yourself why you keep going back to the circus. And I think that was it for me, right? I had had just an actual breaking point where I think, you know, my health, my my physical health, my mental health, a lot of things where I was just like, I can't go back to another broken company.

That's going to say what, you know, this stuff that they want and then not be willing to follow through on it and look. And I think that at the end of the day, you know, a lot of what this journey has been for me has been a journey of reflection, of trying to figure out what do I want to do, what do I think that I have to offer and look, and I think whenever I step back and look at myself objectively, I'm not the most creative person in the world.

I'm not the best designer in the world. I'm sure there are some people out there who would tell you, I'm not the best leader in the world, right? I think I'm better than average, but I think that whenever I kind of look at it, what my superpower has been is just my ability to bet on myself or let it fly, right.

Eight years ago, if you objectively looked at the world and said, look, does the world need another podcast from like an executive white guy who thinks he's got like the inside track on something, the answer would have been no, probably still is no. Today, right? But I think that in a lot of cases, you know, my career is what it has been because I have made moves and done things and were willing to bet on myself in ways that a lot of other people don't.

Right. And this is the thing I tell people all the time. Nobody and I mean nobody would tell you that my career path would be a good idea, that I started in adverts, that I went into hospitality, then I went into finance, that I went to like a SAS startup, then, you know, then I went into wellness, then I started my own thing.

I've cut across industries, I've cut across executional like it's just recruiters look at me and they're like, what? But but that's my thing, right? Is that nobody would look at that and say, that's going to work out well. And I think that's a lot of it. The theme for me here is that like to remember and we'll come back to this.

Right. Like success is a concept that only exists in hindsight. There's been so many innovative things that I've done in my career that whenever I was doing it, I thought I was going to get fired like nobody supported it. And then after it worked, everybody knew it all along, right? So it was like, shut up needed. But I think that's the thing, right?

Is today I just want to try to help share some of these things because I think, you know, look, if if you are at a place where you're showing up to this talk or attending this conference during whatever it is, these are the questions you're asking yourself of saying, look, something probably needs to change. I'm just either not sure what that is or I'm not sure where to start now.

Probably about a year ago, I did what's probably a fairly nuts and bolts episode of the podcast, which is episode 128. The QR code will take you there. That is an episode that is much more of the nuts and bolts about. Should you form an S-corp or a C Corp, or, you know, an LLC? Or how do you think about getting insurance or right, like there's because there is some just basic blocking and tackling, there's some financial benefits.

There are some things that you're going to want to get in place before you actually set out and do this for legal reasons, for cost reasons, for tax reasons, for a lot of things. So that I don't want to do kind of the nuts and bolts stuff today because that just you can kind of get that stuff anywhere.

But that episode is there to be able to help with that. Right. But look, I think that betting on yourself can take a lot of different forms. I'm not simply saying that everybody needs to out on their own. I'm not saying that everybody needs to build their own product. I'm not saying right. I think betting on yourself can take a lot of different forms.

And I've always been a big proponent of this, and I think a lot of people get personal brand confused with betting on yourself when I talk about this. Right? Because whenever I talk about the importance and I've talked about it for over a decade, the importance of having a personal brand, that does not mean having a logo. That does not mean like, you know, you necessarily have to have a tagline.

Do you need those things? Yes. But for me, a personal brand is saying, who am I? What do I want? What am I good at? What makes me different? And that that is something. Whether that can help you in your current job, it can help you in your next job. It can help you if you want to go out on your own, it can help you.

If you want to do your own startup. Right? Like I think that you have to have that level of clarity because, you know, I think this is often the thing is that people just aren't sure what it is they want. I think, you know, having this sort of clarity really helps to, to help fight imposter syndrome. It is a difficult journey that we will talk about.

But I think that ability to be clear on what it is you want and not have your career dictated by a big five or a career ladder or those sort of things where for so many people that I talked to, their career has been covered by whatever the next rung was on the ladder, whether they sort of wanted it or not, and that a lot of that leads to the frustration that leads to the thing of like, okay, look, what do I do?

I think that it also just frees you up to be more creative because you can genuinely exist is who you are. And I think for me, I have tattoos on both forearms that are dedicated to my mental health journey into making peace with myself. That's why I'm here. So the crazy ones tattooed on my right arm, not because it's an Apple fanboy tattoo, but because of the moment I started to authentically show up as who I was was the moment my career took off.

Because showing up as who I thought everybody wanted me to be was absolutely freaking exhausting. And it just it took too much out of me. But I think that that's the thing that we need to recognize, right? I think there's going to be a lot of rah rah content today, and this is going to be great, and this is going to be wonderful.

And shouldn't you go do this? But at the same time, I think I've got to recognize that, like believing in yourself is often one of the hardest and most rebellious acts there is, because I think for most companies that are out there, right, like they often will tend to prioritize compliance over creativity or leadership. If you want to go out on your own.

That's one of the things that I definitely had to grapple with, right? Because in every other point in my career, if I change jobs, if I did something different, I could blame a dumb CEO. I could blame the board of directors. I can blame a bad boss. I could blame like there was some reason why it didn't work out and I moved on to the next thing.

Whatever you got on your own, whatever you bet on yourself. The other part of that is like, if it doesn't work, everybody knows who's who screwed up. And that can be in credibly vulnerable and really anxiety inducing. So I think it's just something to recognize that, like, this is not going to be all sunshine and rainbows, that it is going to really like, ask for you to be honest with yourself at a lot of different points.

Because, look, the reality is, most people at most companies float around with the status quo because it's just easier, right? It's easier to be the employee that they want you to be, to act in the way that you want to be, to smile at the stuff that drives you crazy, to write, to do all that stuff, taking a position, saying, this is who I am, this is what I believe.

This is what I want to build. You plant a flag, right? Which means you're sort of taking a position and now people can support it. They can judge it, they can shoot at it, they can make fun of it. And but that's sort of the thing in all of this. But I think while there is that risk, that's also where the brilliance in this comes.

Right. And I think that's the thing is that there are so many fears and barriers. There's always going to be a reason why not to do it right, that it's too sunny today, it's too rainy today, it's Wednesday. It's like, you know, somebody did write me back. Somebody didn't write me back. Right? Like those are always going to be there.

And you can rationalize that to the end of the world. But I want to go through what I think are basically like, here are the five most common problems and barriers that I hear from people, and how I've tried to work through those. I think the first is just the basic one of you don't know what you want.

It sounds really simple, but I think for me this was one of the hardest things that I did after I got laid off and started to contemplate going out on my own was just the basic question of like, look, the realization that there is such a huge difference in building the career that I want versus the one that the industry has given me, and that most of the time what I have wanted.

Like I said before, has been built on a company's big five or a career ladder or what my boss said I should work on, or there was always a reference point of success will look like what something has been defined. And now all of a sudden, I think, and this is one of the most paralyzing things for a lot of people.

It's like, Holy crap, what do I actually want to do? What actually makes me happy? What? And it's just and it's not being dictated by another corporate structure or something else like that. And so I think that is often one of the hardest parts, because, you know, it's like, okay, great, what do I want? And I think that a lot of this for me was sitting down and asking myself what sound like some really simple questions, but can have really complicated answers, right?

Like just for me, what do I need to be happy? What are the conditions that I have discovered through my work that lead to me doing great work? And then what are the conditions that I know don't lead to great work? Right. And I think just that thing of daring to be happy, like, it sounds so simple, but I think that's the thing.

I've been happier the last three years that I have been in the last 10 or 15, but it it's an act of will to almost be happy and to bet on yourself. And I think that's a lot of what it is. Where do you want to go build a product, whether we want to go out on your own no matter what that is.

Right? I think a lot of it for me is sort of like, great, if you have that experience, something has brought you to this moment. So either like, what would you do differently if you had the ability to do it? Like, what does the world need that only you can provide? Because I think that's the thing for most people.

I'm like, well, like what? What are you really passionate about? And again, most people immediately, if you go to great detail and tell me what that is and get really fired up about it, and that's really great, but it's like, great. Those are the foundations and the things, if you're going to go do this like it needs to be passionate, it needs to be different because that's often what I think, you know, happens in so many of these cases is we tend to get caught up in busywork because so many people, when they come in, to me, it's like we look at my logo, we look at my company name, or you look at like

these screens for my app design and all this other stuff that quite honestly, look, I'm not saying it doesn't matter, but it is such in the back seat. Like if you want to go start your own company, nobody's really going to give a shit what you call it, right? What they're going to care about is they're going to buy into you, or they're going to buy in what you are offering or why is it different?

Or why can it get me results? Or and then again, that's this is where most people in the world get a visual identity and a brand confused. That is where some of these questions around what are those are so important. Right. And I think that and look and I think Tony you're right is that, you know, for so many of us, we can just get caught in this loop of just what about what about what about what about because that's that's what we're trained to do as a profession.

Right? Like find the problem, fix the problem, find the insight, do whatever that is. And especially and I think we're going to we're really going to talk about this in a minute. Right. Because I think for so many of us, these are all the tools that we have. But when we turn it on ourselves, we get stuck right where it's like, you give us a client or somebody else.

I can coach them. I can do all that sort of stuff. I look at myself and it's like, what the hell? But like for me, I sort of came to four realizations whenever I want to start crazy. One is that I wanted a small team and I did not want a lot of clients. I'm actually and again, it's one of those things I am vocally anti scale people all the time.

What do you get? Have 20 people. What are you going to have an office just this side of never. Right. That is not what I'm interested in. I'm interested in actually going through and doing the work and being hands on. I don't want to. I'm not looking for an exit. I'm not looking for. Right. Like, what I want to be able to do is to be able to spend time.

I just want to do cool shit with cool people, right? Like that's really just all it kind of boils down to for me is that I'm not looking like what I want to do is to get paid what I think I'm worth and do it with the right people. That, and again, I think a lot of my work, what it really is, is that I prioritize trust and relationships.

That is the foundation of any great work. And I have to laugh that so many people like, whenever I have prioritized these things, I'm doing maybe some of the best work of my career right now. And people are like, well, how did you do it? And it's like, well, gee, isn't it interesting that I went through and I prioritize that I'm doing the work again.

I'm prioritizing what I need to be successful and then good work followed, right? I'm embracing the mess. Like I said before, my career to most people has been a mess. But what I love right now is that I'm just embracing as many diverse problems as we can. I'm designing an I, an app, a brand, a restaurant, right? Like it is just nothing necessarily makes sense.

And I love it because like, again, I just we want great problems. What form those take. We'll take it all on. And I think a lot of it for me is also like, look, I want to do stuff that I care about. I move back to Pittsburgh because this is where I'm from. This is a town that I deeply love.

It is a town that needs more design, leadership. So for me, whenever I built my company, it was also the ability to say, I want to have an impact. So I will only hire and work with people who are from Pittsburgh. I want to bring clients like Metallica to young designers from community college to let them work on this stuff.

I want to be able to, like, use the directors of photography and the videographers who are here. I want to build up my community. I want to invest in those things. But these are the four things that I really cared about. And again, being very strong and clear on this is what I want to build that on. But a lot of what this is, is I think in a lot of cases it's like, great, where do I start?

Because and I think, Tony, it's what you said before, right. Like you can just start going in loops and there's just that, like it's got to be perfect or it's not good enough or whatever it is. The first thing I will tell you is like, look, I think setting goals and deadlines treat yourself like a product or a project or a brand and put together a schedule of like, when am I going to have this stuff done?

Because one of the things I've embraced in my career and in my leadership style is that, like panic can be a great catalyst for creativity. But I think the other thing with this is that, you know, for me, I also know for me that I need accountability because it is infinitely easy for me to be able to disappoint myself that like I said before, I'm going to have this positioning figure it out.

And you know what? I didn't get enough sleep. I got too much sleep. It's too sunny. It's too rainy. I'm not going to. I can rationalize the reasons why I'm not going to do it from now until the end of time, right? I easily and I can just keep going in loops and not do that. If I have somebody else who holds me accountable, why?

Maybe easy for me to let myself down. I will crawl through broken glass from new Jersey to not let somebody else down. Right? So I think a lot of what it is, is putting that accountability in there to be able to say, okay, look, you know, I know that whenever it comes to me doing this, for me, that is harder.

So put some accountability in there. But I think the other thing that we need to address for so many people that I talked to, right, is to say, if you know, for me to do whatever it is I want to do, I have to have it all figured out. I need to understand what all is going to happen.

And right. And I think that's the thing, most people won't make a change. They won't do it in their career. They won't do it on going out on their own or whatever that is, because they think they have to have it all figured out. And to me, that always is a little bit funny. And I think this is one of those moments when we talk about, like our skills, when we turn them on ourselves, they all seem to short circuit, right?

Because what I tell people in leadership, what I tell people in this position, right, is that you don't need a plan, right? What? You're sorry. What you need is a plan, not the answer. Because the funny part is, is that whenever you think about it, your life and your career, these are just design problems. And I think that is the way that I've started to think about so much of this is that whenever I go into a designer or creative problem, I don't have the answers.

I have a plan that I want to go out, and I want to be able to research this sort of thing. I want to investigate this. I want to go into that. I want to get myself the grace of going through the process on a deadline. But I think that for so many of us, we're kind of paralyzed because it's like, well, I don't know what's going to happen when I get to step four.

And it's like, well, okay, if you're designing this, how would you do that? It's like, oh, well, then I go through step one, two and three. I'd learned a bunch of stuff and I get to step four. Then I'd have a good insight. It's like, great, why aren't you going to do that here? It's like, I don't know.

But I think that's the thing is, if we start to think about these problems and start to think about what we want to build as a design problem and utilize our skills through that lens, right. And I think that, you know, definitely is a way to be able to approach it. But I think that, you know, that's the thing is that to be able to do this, a lot of what it comes down to is being afraid to be different or being afraid to say the word I right now, as somebody who's been in leadership, the word AI is extremely difficult for me because like, it's always been about we.

This is why, for me, whenever you're a leader, quitting is one of the most wrenching things in the world. Because you have come in, you've built a team, you work with other people, you have done things for the week. Quitting is an AI statement, right? I am going out on my own. I am doing something different. I am leaving you behind.

And so I think that that's often it's anxiety inducing to be able to do that. But again, I think for so many people this is the problem. This is why people don't get promoted. This is why career is flatline. That and look, I think that's the problem. And especially in the job hunt, especially if you're thinking about going on your own.

Right. Like nobody's ever going to promote or hire generic talent. And I think that is one of the number one biggest problems I see with the founders that I work with, with the people that I mentor, with, the people that I try to help get jobs, is that I think it is such an exact. And look, it is a very understandable thing that your brain goes, Holy shit, I've got bills to pay.

There's things that I need to do. We need to appeal to everybody like it's this is the same sort of thing where I'm like, okay, I've got to appeal to everybody. I can't miss out on anything. But again, if we look at that like a design problem in design, if you appeal to everybody, you appeal to nobody. And so again, you like that ability to stand out, to say, this is why I am different.

This is what I do to be loud about what that is, is the way. And that's why I said, those are the people this this is why stupid people are successful. Like honest to God. This is why stupid people are successful because they're loud. Because they own who they are. They're going to jump off the roof. And if they smash or but on their body, then they'll heal and go run up and jump off in a different direction.

But I think for again for. So for those of us who are empathetic, for those of us who are thoughtful, for those of us who are creative, we tend to be, you know, one of those people that definitely just we tend to hesitate more and so, again, I think that for a lot of this and again, this has been my probably crusade, I guess, for the last 10 or 15 years is that, look, we function in an industry and we function in a society that will want to make you believe that your differences are a weakness.

Right? For so many corporations that I've gone into or worked with or even in my career. Right. There's an ideal employee, there's an ideal sort of way of doing things, and anything that falls outside of that box is either meant to be kept quiet or not utilized, or do a lot of those sort of things right, and again, I think that was literally what I called my entire platform, the crazy one, because I truly believe that believing in yourself is an act of will, and it requires you to be a little bit mentally off, because I think it's it's easier to just go along with what they want you to be.

But I think for me, that is the thing that I will preach until the day that I die. Is that what whatever your background is, whatever your education is, whatever your upbringing is, whatever your experience is, whether you've been in this industry your whole life or one day, right? You're bringing a different perspective and a different way of looking things into your work that sets you apart so that if you are going to go out into do any of these things, the one thing in the world, you cannot be as generic.

But I ask people all the time, who's your favorite painter? Who's your favorite musician? Who's your favorite band? Right. Like whatever that is, whoever it is did not get where they are by being like everybody else. And so we have to recognize that there's a tension to want to blend in, to try to appeal to everybody, but then also recognize that whenever we do that, you're going to appeal to nobody.

And the way that I get a lot of people to start doing that is I'll say, look, because, you know, for me, whenever I sit down and try to say what makes me different, it is this mental war between what I write down is this who I actually am? Or is this who I aspirationally think I am? Like, is this real?

Or am I lying to myself? And one of the best exercises I'll do is I'll go out to my friends and ask them to describe the impact that I make, or what they think makes me different. In three individual words I don't need war and peace. I don't need a big explanation. But what I'm going to do is I, as you start to ask people to be able to send those to you, you can get a mural, get a mural like something, start to write it down and you'll see they start to cluster together.

And the reason why I think this is important is because it starts to give you a real sense of how do people see you? Because I also recognize I'm always going to be my own biggest blind spot, right? The way that I think I influence the world is not always the way it actually happens, and that I need to be able to get some of this, and I need to be able to get some level of confidence that whenever I say, this is what makes me different, that's that's actually based in something.

Because if not, then I go in circles for forever. The other biggest thing that I have found is that I have worked in corporate America for too long or business for too long, and that there seems to be this immovable filter between my brain and my keyboard whenever I try to write this stuff down. Now, I've long said that I'm a designer by profession and a writer by necessity, but I have spent hours sitting down to write down what do I want?

What makes me happy? How do I position the business? What am I going to do? And at the end of it, I am shocked that I've written so many words that say absolutely nothing. And because it just it goes to this like Santa sanitization filter or something in my brain where it just turns something that I feel very strong about and makes it sound so generic.

And the trick that I've learned to this is that it is the typing part of this that is screwing me up. So one of the best things that I will do is actually open a Google doc, open a word doc, open, you know, obsidian, whatever it is you use. And I turn on dictation and start to talk. Because what I find is that the content tends to be much more compelling.

It has to be much more sharper, much more in the tone that I like to be able to do those sort of things, and it is much more human and authentic. Don't take the easy route of going to ChatGPT and asking it to tell you what who you are, because again, like if you look at that stuff long enough, you start to see how it all blends together.

But I think that it's just that simple idea for me of changing the form factor of how I interact and create that content has made a massive, massive difference in how it connects with people. And again, like, I think what Tony had said, right. Like it's a different version of kind of journaling and it's a good habit to be able to get into.

But that's the one thing that I think you have to do, no matter what it is you want to be able to do. And like I said, if you want to stay in your current job, get a new one, go build a product, go out on your own. It is. How are you memorable? Because, you know, I see portfolios every single week.

I see startup pitches and everything else. And I go back to when I was in art school. Right. And it was a bit of a different time, but I always go back to I had one professor whenever I took an advertising class, who would do the same thing as you would post all the ads up on, kind of like a corkboard.

And he would walk up and he'd put his thumb over the logo and he would say, if you can't see the logo, can you tell me who this is for? And it is amazing to me that so many of the businesses and portfolios and things that I see, if I did just that, if I put my thumb over their logo on the screen, that it really, you know, is one of those things where it's like that intro sentence could apply to everybody in the industry.

And so again, I think that ability to do that really is just something different. Now. The other thing that honestly, for me and I think this is probably gonna be a little bit more relevant if you're further on in your career, but it's just not anything that I ever hear people talk about is, you know, look, first, I want to be honest because I think for so many people it's like, oh, I always knew I was going to do this.

Oh, I always knew that I was like, this was going to be brilliant. This was my plan all along. Me going out on my own was not my plan all along, right? I got dragged backwards into this because I never wanted to start my own agency. Right? That was just not I didn't want to have to deal with, you know, health insurance and 401 KS and like, in going out and pitching new business and doing all that sort of stuff.

But I think if I was really honest with myself, the biggest thing for me was that I thought about going out on my own all I could see is what I could lose. I could lose my reputation. I could drag my wife in, like our livelihood into something else. I could, and I think that was the part of it for me.

Was that I could only see the downside, and I really struggled to find the upside. I think part of this again, as a creative brain, you're just you're really good at finding the problems. But I think that, you know, for me it was a real struggle. And it was honestly until I was sort of I'd gone out, I'd interviewed, I'd done all this stuff.

And I think, you know, I just I couldn't find a company I would work for. Everybody was Lowballing me. It wasn't working out. This was documented in front of millions of people on LinkedIn, where I thought I was going to go out and this was going to be this triumphant like, you know, return to the market and find a new job.

And it was a spectacular face plant. And I had to pivot. And I think that was the thing for me was that it really was going through and kind of saying like, look, one, I need to surround myself with other people who think in a more positive way. I need to be able to bring in context. I need to what I would describe as like a personal board of advisors.

And in general, I always recommend three people on your board of advisors. I think you need one person who will just tell you the hard, unvarnished truth. Like somebody who's just going to tell you what it is. I think you need somebody who can be a mentor, who is doing what it is you want to do that can advise that.

And then I think you just you need a hype man, right? You need somebody that is just energy. And like, it's good to be able to help keeping you going in those moments when you're down. But I think you've got to be able to start to get a support system in place, because that is often one of these kind of the if the first barrier is figuring out what I want to do, the second barrier is then how do I not basically go into isolation whenever I do it?

And to lose all context of how am I doing? And imposter syndrome sets in and a whole bunch of other stuff, and I think this is a quote that somebody who is on my personal board of directors gave me. That is something I think about every single day, because whenever I was in that moment. Her name is Sylvia Baffour.

If you don't know who she is, please go check her out. She's a incredible, incredible emotional intelligence expert. She'd been charged with Maya Angelou for 14 years. She's an amazing book and I dare you to care. But she's kind of my own personal Yoda. And what I did was I was sort of going through all these reasons why I didn't want to do it, and where I was and how frustrated I was and why this wasn't working.

And poor me, and she just has this way of cutting through all of it. And she said, Steve, look, I need you to think about right. Like discomfort is the cost of fulfillment and that what it is you want and what is you're unhappy with and what you want to get to is on the other side, that it really is one of those kind of things where like, you've got to push through.

And so for Karen. Yeah. So you want somebody that I think is going to just tell you the truth. Right. So an advisor is a little bit different. I think you want somebody that is just going to is not going to be asked you. Right. I think two is that you want a mentor. So not just somebody in the industry, but somebody who's really willing to work with you and invest in what that is.

And then the third one is that kind of high emotional energy person. Because like I said, I think it's just those a little bit of differences where like, there are times I need to go to somebody who's just going to tell me the truth. But I think the other part of this is that for a lot of people, a lot of where I think that they struggle really comes back to under to imposter syndrome.

And do you really understand what that is? And I think I've spent a long time really studying imposter syndrome to understand that there are five types that we all struggle with. Anybody who tells you they don't is lying full stop right. And I think, you know, honestly, in a lot of ways, that's why I try to give some of these talks where even in the last few years, in some ways, I want to destroy my brand because, you know, whatever.

I was going through my search and started my own thing. There was this concept that like, oh, I could work anywhere I wanted to, and I just it's such a toxic construct that I think at some point you're not subject to those sort of things, and it's just not the truth. But quickly, I think I just want to run through there are five types of imposters that again, I've got, you know, podcast episodes and other stuff to go into more depth.

The first one is the perfectionist, right? It's just what it sounds like. These are people who set incredibly high goals, want everything to be perfect. They tend to really struggle whenever they're creatives, because we work in an industry where two plus two is not four, it's burnt Sienna. And so there's not a right answer to what we do.

But I think that it's one of those things where like, look, if I'm not getting it perfect, I there's a designer who works for me right now and that's what I'm working through with her. Is that like she almost sees me giving her feedback as a negative, right. Like, why is it just not right the first time? And so again, I think that's something, you know, to be one of those things that definitely comes up, I think a super man or a super woman, right.

Like, these are people that are convinced that they're phony, is working alongside real people. These people are easy to spot. They're the ones that they're done at 4:00. They don't leave till six because they feel like, you know, they've got to work harder and harder to measure up. And that it isn't about the impact, it's about the time you invest people who feel like they're natural geniuses.

Right. These are usually the gold star kids whenever they were younger. But it's like, look, if I if I don't if I don't understand this the first time, then I kind of feel ashamed of it. I think that there's a ton of creatives right now that are struggling with natural genius when it comes to AI, because I think for a lot of them, it's more systems thinking.

It's a different way of working. It's more about curation. It's a lot of those sort of things. And I think like if they can't go in and just create the way that they always have, they're struggling. An individualist, right. And I think this is the person who thinks they can do everything on their own. And I and this is probably one of the biggest ones, is we talk about going out on your own or doing those things is that they feel like if they have to ask for help, that all of a sudden it's calling them out as a phony, right?

That's why everybody on LinkedIn is like calling good looking and well-educated and super smart and successful. And none of that's true. And I think that the expert. Right. And I think that there's a lot of people that, you know, this usually comes from people who sort of just hoard knowledge. You can never know enough. You can never take enough training, you can never know enough, you could never know enough apps.

You could never do those sort of things that if you don't have the answer to everything that you sort of feel like you're you don't you're kind of a knowledgeable. And I think this definitely feeds into if you're in, you know, in a unicorn role, this is a huge part of what that is. But here's the thing that I've discovered and kind of want to share with everybody as you go through this, that there's a lot of parts of, you know, what we talked about in those five verses of imposter syndrome that make you great, that you continue to learn and keep, keep pushing forward to doing these sort of things, to be able to

continue to evolve. Right. That is what is going to make you great. And so the you know, the idea for me has never been to eliminate imposter syndrome. It has always been to keep it in balance, that if I keep it in a healthy proportion, that that allows me to continue to push and do the things are going to make me great.

But if it gets out of balance, then it paralyzes mean it stops me from doing what I need to do. But I think there's just, again, sort of two final thoughts I'll leave you with. And then we can get to the to the Q&A. Right. And this is one of the things that I mentioned before, but I think is really worth repeating, is that that is definitely one of the things that I've learned in my career is like, success is a concept that only exists in hindsight, that the number of times that I've done something or, you know, you think about what it is you want to do.

There's always going to be skeptics, detractors, reasons why not to do it again. That's why I you know, I've got I'm so attached to the word crazy because I think at a certain point you have to jump and bet on yourself to say that, look, I have the skills or I have the ability or I'm stubborn enough or whatever it is, because it's only after it works.

And everybody knew, right? Like whenever I left advertising to go to start hotels for three years, three years, all of my friends and everybody in the industry kept saying, where are you going in house? That's where you end your career. That's so dumb. You're not going to do real work. Why are you doing all that stuff? Like you work in a hotel company?

That's stupid. And as soon as our work showed up in the first Apple commercial, all those same people in the know, if I was hiring and I think, you know, it is one of those things, that definitely it's just like I said, when you're going through it, it doesn't feel like successful. And you look back, you're like, that was great.

But I think this is my thing is that for so many of us, like, this is the chance to do what you wanted to do, to take a risk, to do something else. Like, you can always pivot. You can always go back to a job, you can do something else. Like, even for me, like you can try like keep the job that you have.

Start setting up your business. Try finding a few freelance clients, get it set up to the place like it doesn't have to be this big dramatic moment, but this is your time and your ability to go out and to sort of exist loudly in the world, to make that mark, to do the thing, to build whatever it is, to contribute what you think you have.

And that's the thing for me, is that one, I've had more fun in the last three years than I had in a very long time. And the other reality is, to be honest, last year was the most financially successful year I've ever had in my entire career, and it was just about getting to move back to my hometown that I love to leave New York behind, to be able to bet on myself.

Now the world continues to try to lose its mind, and we'll see how that keeps going. But I think this is the sort of stuff to think about. And so, look, I think also for me, I'm I'm here to be able to help. Right? I think, you know, I like I said, I do mentoring three times a week on ADP live.

That's my personal email address where you can reach out to me and ask me questions. I do coaching, I will, I coach founders, I work on like up and coming products. Right? Like there's tons of this sort of stuff. So that's anything that is of any interest. Those are all the different ways that you can get Ahold of me.

I'll leave that up for a second. And then I think we can go over and start to jump into the Q amp. A.

Exist, loudly. I love that, Stephen. Thank you so much for this amazing session. Big fan of your podcast, by the way. So I was just having too much fun in the chat with everyone over here. I love the energy. Let's quickly head over to the Q&A session. First one with a lot of upvotes is any thoughts about how you can slip those imposter syndrome traits into power?

Like how can you harness perfectionism? Or in individualism in the right way with the right boundaries?

It's a really good question. I wish there was a one size fits all answer. Right. I think this is why we're going to write self-help books and books on creativity and everything until the world ends, because in a lot of ways, that's why I don't tend to say what works for me, because I, I tend to find that a lot of cases, it's like giving somebody like yesterday's winning lottery numbers.

I think there's there's more details that I have in the podcast and some of those sort of shows, because again, I think, like with perfectionism, what I'll have a lot of people do there is actually start sharing your work before you're ready. Right. Like that. Shared it to either share it in a more rough form where you're just doing writing or a sketch instead of a full blown design.

Right? Like you start to train yourself because usually perfectionism comes with two problems. One is that you share too late and that too you're usually too heavily invested in outside validation to think that you're good. So like I said, for me one the easy one start to share either in a rougher form or sooner than you're comfortable and also again start to look at how can you balance that feedback that if you think it's good and everybody else doesn't, that maybe you have a good idea that it's just badly presented, or it's not a reason to be able to just sort of give up on it, that you can, again, kind of just reframe some of those things.

Oh, you're on mute.

Speaker 2
My bad. Thank you for that solution.

Speaker 1
And I was like, oh crap. What happened?

Speaker 2
Yeah. And the next question is from Raoul. So he says, thank you, Stephen, earlier you mentioned you prefer to keep your team lean rather than scale with a lot of employees. I'm curious, who did you consider your first essential hire, and at what point did you know it was time to bring that person on?

Speaker 1
Yeah, so it's a really good question. So for me, the first year it was just me, because I was just, look, I don't want to carry the overhead of an office or a lot of other stuff. I'm getting this up off the ground. So I have y there's me and two other full time employees. I there are people that I use on contract or things like that pass that.

Speaker 1
But my first hire was a head of operations, because one of the things that I also try to work on is knowing what I'm good at, but also knowing what I'm not good at and like I'm not, can I do calendars? Can I do budgets? Can I set up weekly status meetings? Can I do all those things? Absolutely.

Speaker 1
Should I know? Because that's the trap I was in when I was in corporate America. So I think most people would be like, oh, you hired a designer or a creative? No. My first hire was an operations, a woman who runs all of our operations because I'm like, look, that that was the first thing that I needed was I needed that structure.

Speaker 1
And again, like, I am determined to focus on what matters, right? Like for me, it's staying on, staying creative, staying on strategy and again, understanding where to start to offload some of those other things. I mean, technically, I think my wife was my second hire because she does the books. But again, I think like it wasn't the last hire in my wife.

Speaker 1
I guess technically is employee, but she's not on payroll. But then again, so my designer was actually the last hire I made.

Speaker 2
Lovely. I actually have the same question, so thanks for asking that. And the next question on stage is from Diego. How would you structure a scalable service model for a mid-sized design agency that balances creative integrity with operational efficiency across time zones? And how would you price innovation network versus commoditized services?

Speaker 1
Yeah, so both are really good questions. My model is a little bit different because I think, you know, a lot of it for me was like in terms of our services, I, I actually I'm not terribly interested in doing a ton of project work that what happens is our clients actually buy our time because again, if I'm trust, if I'm prioritizing trust and prioritizing relationships, what I like to be able to do is to say, look, we're going to come in here and work on this problem or we're going to work on whatever this is.

Speaker 1
More than likely we're not going to be able to know all the details of what that is before we get in and do the work. So we have a certain amount of hours and that they can then decide and we can pivot and sort of understand how do we want to use that. So for me that tends to run more on a blended model that's a little bit kind of cutting across some of the more innovative work versus commoditized work.

Speaker 1
In general, although if I am doing project work, like the, the innovation work tends to go at about 3 to 5 acts on an hourly rate over the commoditized work, because for me, the reason why I'm pricing it that way, the same way if I'm doing personal coaching, it's like 200 an hour. If I'm doing leadership coaching for a big company, it's 1000 an hour because it's not about the time, it's about the impact.

Speaker 1
And I think that's where a lot of people get tripped up where it's like, oh, but this is just an hour, okay. One, I hate the word just. And two, it's not about the time. Like again, there's an old joke about like a plumber comes in and you pay him $500 an hour and he walks in, he turns one screw and it fixes the problem.

Speaker 1
And the guy goes, why did I just pay you $500 to be able to turn a five cent screw? And he said, because of the 30 years of experience, I have to know which screw to turn. Right. So I think that a lot of it is for me is that I tend to price more on impact than necessarily because and I think it really is.

Speaker 1
You use the right word of commoditized is my value, and our value is in the strategic thinking of what that is. That's why clients are going to stay with us. That's why they're going to come to us to begin with, especially now. Right. Like everybody that's in that commoditized layer is just getting ravaged by AI. So that's why I've never and even now my opinion is on AI that, you know, you're gonna have creatives and a lot of copycats and that you want to start to move or reposition what you offer in that commoditized category, because that is just going through massive disruption.

Speaker 2
Wow, that was awesome. Thank you so much. And thanks for the question, Diego. Now there's another interesting one from Capella. He says, can you go back to the ask which we observations about use site for a site because he wants to screenshot.

Speaker 1
Yeah, I can yeah. And so look what it is is that it's a, it's a simple thing of just you go out, go to your friends, go to your loved ones, go to people that you work with or people you trust or to do whatever that is. And all that you want to do is just to be able to say, look, what I want you to do is whenever you think about me personally, professionally, whatever that is.

Speaker 1
Right? Like what makes me different or if it's in a work context, what did you think I was good at? And I don't want war and peace. I don't want a big explanation. I want three separate words, not three words in a sentence. I want three separate words. So if it's creative, disruptive, you know, innovative, honest, you know, quirky, weird, like whatever that is.

Speaker 1
And so that's the first part is you go out partially because when you just ask for somebody for three words, it's like, come on, like everybody, it's this is going to take you like five minutes tops. So nobody can give you an excuse. They're not going to do it. But then what I do is you start to collect that, do it with sticky notes, stick it on a mural, do whatever that is, because you're going to start to see that they start to cluster, right?

Speaker 1
Okay. Here's a whole area that's around creativity. Here's a whole area around like my ability to be honest. Right. Like here. And those are the ones I usually get right is that it's like strategic, creative and painfully honest. But I think that that way you can start to cluster those together to be able to sort of see where the heat is.

Speaker 1
And again, you may get some outliers that are really interesting that you want to follow up on, but I think whatever you have, that is a basis. Now when you go back and you write that content around yourself, this is for your resume, for whatever it is you want to do. You don't feel like you're just spitballing. It's the same reason why whenever I talk about my leadership, I'll bring in my Clifton Strengthsfinder or my 16 personalities or right, like I'll bring in some data to try to be able to use that as a foundation.

Speaker 1
So it just doesn't sound like I watched a bunch of Ted talks, and I'm kind of talking out of my neck.

Speaker 2
So then I'm curious, the last time you asked a friend about, you know, what were the three different things about you? What did you hear?

Speaker 1
I so I, I'm sort of a little masochistic with that. I usually do it about every 6 to 12 months. There actually there's two things that I do. One is that I, I do that on a fairly regular basis because I do like to constantly just reevaluate what's working and what do I need to burn down and fix.

Speaker 1
And then the other thing that I do is I actually keep a happy file because I think in a lot of cases like that, there are some times when it's hard to remember what you are good at when things aren't working. So remember positive emails or positive reviews or comments that I've gotten like some of the reviews from ADP list, right?

Speaker 1
Like I'll just kind of put them off to the side. But yeah, the three that I always get are I think I've been getting happy a lot lately, which has been, funny, which I think that had disappeared for quite a while. But usually, like, creative is, you know, kind of outside of the box. That sort of stuff is a big one.

Speaker 1
Honest is always a big one, because I think I'm just somebody told me once I have the pathological inability to not talk about a hard topic. And then that idea of a sort of strategic right, that right brain, left brain kind of a thing, those tend to be the ones that I get the most lovely.

Speaker 2
And I think there are a couple of chats about how great, mentorship with you is. I think some of your mentees are here joining us, so some of them deserve to go on your happy side tonight.

Speaker 1
No, that's I mean, like I said, I think that's like, I'm like, look, if I can share what that is or shorten somebody else's journey, it's always incredibly humbling to see. And thank you for everybody that that said that.

Speaker 2
Amazing amazing. So next question on stage. This is from role. Again. Can you tell us about how you got your very first client for crazy? I love to hear what that was like for you.

Speaker 1
So the interesting part was so my first two clients actually were I had just I was like, I was at that point still convinced I needed a full time job. That's what I wanted to go out and do. And I just said, hey, I'm going to just I'm available for freelance or those sort of things, like if you guys are like, if anybody's interested.

Speaker 1
And so I had two freelance clients. One was, Cemesto Hotels, which was an old coworker of mine from Starwood, and two is actually Metallica, who's a long time kind of freelance client of mine. And they both came to me and said, and this is actually why I started the agency. They came to me and they're like, you know what, dumb ass?

Speaker 1
Like, if you would actually say you want to do this for a living, like we put you on retainer. And it was like, oh, wait a minute, like that, this could actually work. But I think that's been, you know, so for me, that's how it started. I think my story is not normal. It is why I do believe in community.

Speaker 1
It's why I believe in creativity. It's why I believe in giving back. In the over three years I've run the agency, 100% of my work has always come on referral that it's people who know my reputation and people who, again, have worked with me or done those sort of things. I think we're at an inflection point now, and I'm probably gonna need to figure out if I need a business development pipeline, but, it really just started that organically.

Speaker 1
And the funny part was actually, I had the agency for six months and didn't tell anybody because when I got laid off from my last job, I always check the fine print on a severance agreement. And it actually said if I started my own thing or if I got another job, they were going to cut off my severance.

Speaker 1
So I didn't actually announce crazy until I was sure the last severance check had cleared.

Speaker 2
Wow. Okay, there. Here's, a follow up question to that. So, Gerald, thank you for a great talk. And he says this might be a dumb question, but tell us about that moment when you finally made that big risky move and thought, okay, I'm going to do it. What or who triggered you and what were you doing at that time?

Speaker 1
And look, and I think a lot of it, this journey for me has been the journey back to these sort of moments happening all the time. Right? I think the first big moment for me that led to the tattoos and everything else was the work that I showed with Apple, because I realized I spent so long in my career apologizing for being demanding, or apologizing for being honest, or trying to fit in with everybody else, or trying to slow down the way that I worked, or make my ideas smaller and more palatable for people.

Speaker 1
And it just I struggled with it so much. And then all of a sudden when I went to Apple, all of those things is what made me successful and got me in ten keynotes. And I know that's a very like it sounds like a humble brag kind of thing. There's not a way I know to tell that story without saying it right.

Speaker 1
But I sort of realized it was like, wait, maybe I'm not the problem, maybe everybody else is. And I think that sort of started me on this journey of like, why don't I believe in myself? Why don't I? So again, I think that was the first moment. I think whenever I started this agency, there was another moment of when I decided to leave New York to come back, to go out on my own.

Speaker 1
I realized that what I was so afraid of was betting on myself. And look at if you had a podcast at that point for 6 or 7 years trying to tell people career advice and you don't know how to take your own advice, right? Like that's a tough moment. But I think that for me, I've never regretted in any of those moments.

Speaker 1
Right. And starting the show and starting my own thing and moving between industry, it's like I've never regretted the risk that I took. I only regretted the risks that I didn't. And I think that so for me, that that's where I don't know that there was necessarily one moment I think there was a series of me kind of saying, you know, why am I not willing to bet on myself?

Speaker 1
Like, what? How did I get back to here? That I had to admit to myself how unhappy I really was and the damage that had done? I think, again, I'd stop that, put the show on hiatus for a year because I realized that the show was born out of so much frustration and unused creativity in my day job, that it was hard for me to see it in a positive way for a while.

Speaker 1
Right? But I think that's my thing is, like in my career, it's a very long answer to a very short question, but it's also very weird. Like, no matter how much research I do, no matter how much data I look at, no matter how much like I always, I'm very diligent in how I do things, but at some point it just comes down to trusting my gut and just jumping right.

Speaker 1
And and I think that's why I said that's why I think I've developed into my superpower is just my willingness to go. And I tell people this all the time, right. I really try to embrace the fact that there's a difference between crazy and stupid, and I always want to be crazy that I everything I do is for a reason, that there is a thought behind it, that there's an intention and a strategy, even if it is not apparent at that moment.

Speaker 1
That stupid is just like, oh, just jump in, who knows? Right? So I think for me, it's finding those moments where I am unhappy or where I just like, look, something needs to change. And then just saying, look, based on what I know, I think this is the right way or the industry to go into and to make that jump.

Speaker 1
And like I said, it's only now when you look back that people go, oh, sure, like that worked out. You're here in the moment. Nobody was like, yeah, that's a good that's what I said. At one point I went three years where everybody's like, you're an idiot.

Speaker 2
Now difference between crazy and stupid. That was awesome. Well, we've got one more question to take. So this one is again from Kapil. He asked during your journey, how do you distinguish between this and think to success from this is evidence this might never be successful.

Speaker 1
I think a lot of what it is, is just putting it out there. Right. Because I think that, you know, the where I started with the agency was much more I thought this was going to be more consulting or doing more coaching or doing like some of those sort of things. And I thought it was like, okay, look, I'm gonna do more talks and do things like that.

Speaker 1
And the market sort of quickly told me that it's like, that's not really what we're as interested in as interested is like having you come in to help solve a problem. And I think that's what it is, is I think, like for me, that's why I always go back to when people are like, move fast and break things or fail fast or whatever it is.

Speaker 1
I always hate that, right? Because to me, like when something fails, that means it's gotten to the point where it can't recover, right? Like, for me, failure is just learning. You didn't listen to. And I think if you go into it with this idea that because in many cases you're not going to get it right the first time, right that it might look and you're going to have to pivot.

Speaker 1
I can't tell you how many times I've had to kind of pivot the business. I'm, you know, again, I'm going to need to do it now. So. Right. Like, that's the thing is it's I for me, it's always been looking about it and saying, okay, look, I'm going to take the risk. I'm going to figure out how do I tune it, how do I I've done that with my career, I've done that with the show.

Speaker 1
I've done that with the agency. Right. So I think that it was the best way I would know to be able to answer this is I think you need to go into things with strong beliefs that are loosely held, that you have a very clear sense of what it is that you want to do. I think you need to figure out which one of those are immovable object.

Speaker 1
So this is what I think it needs to be. And then what are the ones that I am flexible on and I can try doing in different ways. Again, think about it like a design problem, that if you are designing something that doesn't work the first time, you don't go, okay, I'm going to go be an accountant. You just say, okay, look, I need to come with this or a different angle or think about it a different way.

Speaker 1
So again, I think that that would sort of be my way is don't always think about things and kind of it's a success or failure sort of a thing.

Speaker 2
So. Well that was awesome. Thank you so much, Stephen, for answering all the questions and for just the awesome session that you just delivered. The crowd had a lot of fun and so did I. But yes, we have reached the end the end of the segment. And, we look forward to seeing you guys hop over to other sections that are happening now.

Speaker 2
Thank you so much.

Speaker 1
Thanks so much. And see everybody later.