Ep 137 Career: The Pros and Cons of Going Out on Your Own

0:00What's going on everybody and welcome into the 137th episode of the Crazy One Podcast. As always, I'm your host, Stephen Gates, and this is the show where we talk about creativity, leadership, design, and a whole bunch of other stuff that matters to creative people. Now, as always, this is always the request. You can lip sync along with me. Do me a favor. If you like the show, tell somebody about it. Send it to a friend. Leave a review. Do something so that what we're talking about here helps other people because it feels like we're in a moment where a lot of people could use some good advice.

0:29And I think along that track That's what I want to do the show about today because I think One of the things I get pretty consistently we've done some other episodes about this Has really been the last three years for me Because I went from i've worked at agencies. I've worked at in-house. I worked at a lot of other places I decided to go out on my own And I am rapidly coming up on the three-year anniversary of that decision So what I wanted to share is basically what's that journey been like? What are the pros? What are some of the cons? And some of the things for me for going through this process and try to share that in case this is something that's of interest to you.

1:09So let's start at the beginning just to give a little bit of background. So for those who don't know, what about three years ago, I got laid off for the third time in my career. And whenever that happened it comes with all of the uncertainty and all of everything else that comes along with that I had hoped that based on the last three experiences that I had learned something or I'd gotten a little bit smarter about it But generally what had happened was I got I got told on Thursday. I was getting laid off I got laid off on Friday and Monday I was gonna reclaim my power and went back out to the internet to let everybody know that I'd been laid off What ensued was about probably a four to five month journey Of what I thought was going to be me documenting like my return to glory and to finding a new job Was me documenting none of that happening and Going through a lot of interviews and a lot of conversations with a lot of people and a lot of companies And not Finding what it was that I wanted right like not finding a good position not finding the salary not finding a lot of things that I think ultimately kind of turned out to be the canary in the coal mine for where the industry is at today.

2:19It was the beginning of the devaluing and sort of contraction of design and a lot of the situation where we see ourselves now. Now, I'd love to be able to tell you that whenever I did that, there was this plan, right? That like I knew that I was going to start my own thing and I was going to go out on my own. And once again, it's this great origin story. and that's not the truth. Because, and I think I can say this now, that I had been in a place of being so institutionalized and so conditioned about what I thought I wanted or what I thought I needed to be happy, that my main plan continued to be that I was going to go back and find a full-time job and that in the meantime, I was just sort of going to freelance to pay the bills.

3:05And as I went through this process and I went through these interviews and became more and more disheartened for what continues to be, and we all need to recognize, is one of the most dehumanizing processes that there are out there. That I think under normal circumstances, it is hard enough. I think when you're creative, it's even harder because you are going through a situation where all you're looking for is some hope. You are looking for some validation that you have made the right decisions in your career. And you're looking for other people to validate that you have talent and that it is a process that is set up to give you almost none of those things.

3:38So I had been doing this freelancing because, look, the idea of going on my own was certainly not something new. I'd had people approach me for years. They've said for years, people had offered me money and other things like that to do it. And I had resisted it every single step of the way. There'd been a litany of different excuses and reasons why I didn't want to do it, shouldn't do it. It was going to be a bad idea. But I think I can say this now. In hindsight, the biggest barrier that I had I think came down to a few things. The first was that I didn't have any idea anymore of what I actually wanted or what I wanted to be happy.

4:15I had gotten to a place where so much of the answer to that question came from a big five or a career ladder or the next job that was offered to me or something like that that I had rationalized that that was what I wanted. Whenever at the end of the day, that was not true. It was affecting my mental health. It was affecting my physical health. It was affecting my marriage as I had turned into somebody that in complete honesty had spent at least five or six years doing no work that I was functionally proud of. I had accomplished things. I had done things. But whenever, and it came to light whenever I was doing a lot of those interviews where they'd say, oh, like show us a project or a design or a strategy you did in the last five years that you were proud of.

4:58And I was having to reach back before five years to be able to get to that. And that was a big eye opener for me. But I think that was what it was, is I didn't know what it was that I wanted. And I think the other thing in that moment was that all I could see was the downside. And I've talked about this in other episodes around really getting to the place of realizing, thanks to my friend Sylvia Baffor and her eternal guidance, which I'll always be thankful of, of just telling me and reminding me that discomfort is the cost of fulfillment, that what I wanted and the things that I wanted were on the other side of all the crap I didn't want to deal with.

5:33So even in light of that, I was doing freelancing. And honestly, I had two clients who came to me and said, look, dumbass, if you would actually just say that you're going to freelance all the time, we would pay you and even put you on retainer. And I kind of went like, wait a minute. So you mean this could be a business or this is something I could do? So there was almost a fear of being happy. There was almost a fear of needing to be dragged kicking and screaming into what has been a huge amount of fun and a real return to me of loving what I do. But this was not, and look, I didn't start this company with any money.

6:07I didn't get any seed capital. I didn't get a loan. I just started. I sat down. I tried to think about what is it that I have to offer? What is it we could do that would be different? And what do I want to bring to the market? And that's where I started and built the business from there. I've deliberately kept it small because for a lot of reasons, right? And if somebody wants to hear all that, I'll do a live or I'll do another show to follow up on that. I don't really think everybody's going to care a lot about the details here, right? But so that was three years ago. And I set off on this journey.

6:40And it's been amazing to me, like I said, of what I resisted for so long has let me fall back in love with design. It has let me fall back in love with my work, of reminding myself how creative I am, of doing work that I am proud of, that all of a sudden I am constantly behind on posting new work or new case studies of the work that we are doing because I'm busy doing the work. But with all of that as the setup, I've tried to sit down and kind of say, okay, look, like what are the pros and cons if you were thinking about doing this as somebody that's gone through it for the last three years. And so let's start with the cons, right?

7:18The cons are never the fun part. The cons are never the, and it's a bummer to end on those. So let's start with what I haven't loved. And I think this, you know, we'll start with one of the things that was one of the other big reasons why I didn't want to do this is that you do have to do a lot of other stuff that is either outside of your comfort zone or are things that are just, they're just not stuff I like to do, Right. Like whenever I think about business insurance or health insurance or 401ks or pacing like paying taxes or chasing invoices or like going out and pitching business or like whatever those are.

7:54I'm pretty sure I went to art school, so I never had to actually do any of those things. But it is a part of it. And I think one of the things I've done well is to recognize what of those things should I do and what of those things should I try to delegate? Whether that's through people that I brought on to help whether it's stuff that my wife does but It is an inevitable part of it that you need to understand Like how do you actually set up an s corp? Or how do you and again? There's a whole episode around the stuff to think about but look you're gonna need to do that And I think there's not going to be a way to be able to escape it That I think you are going to have to go through the process of what I talked about before of getting comfortable With what you want to do and what are you going to offer?

8:38that is going to be different. Because look, I think for this to work, I think for it to be both financially successful and to be something that is worth your time and your effort, you need to build something that you actually enjoy. Because I think that for me has been one of the best parts is like, you know, crazy concepts like having fun again and, you know, working with people that actually respect what I do. Things that had been in short supply, we'll say, before that. But a lot of what it is is I think, And again, there's a whole other episode about this, right? I think for so many people, we just haven't sat down to say, what do I want?

9:15What do I want to do? What makes me happy? And that that can be a really uncomfortable process. Because here's the thing, is that at the end of the day, I think one of the biggest things I struggled with was for every other moment in my career, if it didn't work, if I got laid off, if I changed jobs, there was always somebody else I could point to, right? Oh, the CEO is an idiot. My boss didn't know what they were doing. The company went in the wrong direction. Like something where for whatever level of culpability I had in whatever the problem was that was created, I could sort of move it off and lay part of that on somebody else.

9:53Well, whenever you do your own thing, and I'm very aware of this, if it doesn't work, everybody knows who fucked up. right and I think that there is a lot of vulnerability and I think for a lot of people a lot of sub like subconscious hesitancy and knowing that if this is what I say who I am this is what I say that I want and this is the value what does it say about me if it doesn't work and I think that's a lot of what goes into this is that there is also going to be an inescapable amount of uncertainty that is going to come along with this right you're going to have to pivot You're going to have to evolve.

10:29You're going to have to put something out there maybe before you're ready. But there's a lot of things that whenever you become an entrepreneur, and it's funny, three years later, that is still not a word that I associate with myself. I know I own a business. I know I pay taxes. I know some people call it that. That is not a word that I associate with myself. But you're going to have to act like a business person. And you're going to have to make decisions that are going to be hard and to be able to do some of those things. And I think it has been really good growth for me. But there's a lot of those things that just are not what gets me up and going in the morning.

11:04But I think if you're able to know when you need to ask for help, if you're able to take big problems and make them smaller, and if you're just able to start, to be able to sit down and ask yourself those questions, to think about what are those sort of things that if you have been frustrated with an industry, If you've looked at things and thought that could be smarter, that could be better, we should be doing things differently. That's often the great place and a really good place to be able to start. But again, knowing that it's going to take some level of vulnerability to be able to work through that and to think it through.

11:38But I think, you know, all in all for me, that's really what the biggest cons have been is just a lot of the day-to-day business stuff of books and those sort of things. And I think that for me, those have become so much more tolerable of those sort of things because of all of the pros and because of what I get to do. And the most interesting part for me in looking back at all of this comes down to one really simple moment. And it's the first moment of every day. Because what I realized was for far too long, I would wake up in the morning. I would start to sort of think about the day. I'd start to try to figure out what do I need to do?

12:19What are the meetings I need to be in? What do I need to do or deliver or talk to or like whatever that was? And what I realized was that moment for so long was a moment when I just was trying to figure out how to survive the day. What were the meetings I had to be in? What were the ones I could skip? What were the ones I could be off camera? What are the ones where I could do something else? And I've even talked about that in relationship to this show, right? I realized how much of this show was born out of and was driven by that moment of not feeling heard, not feeling creative, not feeling like I had much value.

12:54And so I would come here and talk to myself and record it and put it out into the world as a way to displace that energy. And that whenever I was doing things I love, how just, again, that was a bit of why the show fell by the wayside because I just didn't have that energy anymore. but now instead of that moment of trying to survive the day Now I wake up and I get to think about the cool stuff. I get to work on I get to think about doing work that I love again I get to think about so many of these other things and look forward to the day And it's just such a different thing And I know that for so many people in the face of what's going on in the world and the economy and politics and other things like that You know the last couple years have been really hard, but I think the thing that I have found is to be honest, I found more financial success last year than I have at any other point in my career.

13:44And again, I think that it was, and look, it was validating to be able to show up and to say we could do things differently and to be able to kind of lean on this sort of stuff and to be able to have it work. Now, I'll be curious to say if I do this show in six months or another year as things around us continue to burn, will that be the case? We'll find out. But look, I've got faith that no matter what it is, I have faith that I can figure it out. But it's fundamental things, right? I'm doing work that I'm proud of again. I'm having fun again. I'm leaning into the glorious mess that is creativity of leaning into uncertainty and new problems and, you know, what felt like it had been this liability of I'm somebody that can go from working on a business problem to working on strategy to working on execution that, you know, on a lot of different problems.

14:32So many people in corporate life are like, hey, stop doing that. Like, just pick one lane. And I'm like, no, I like all the lanes. I want all the things. And I think, you know, so that's why right now I'm designing an app and I'm designing a brand and we're doing an AI and I'm doing an event and I'm designing a restaurant. And like, I just, I love celebrating coming back to just getting like a really good problem. And I'm not going to sit here and say like, look, it hasn't been easy. It's been a massive amount of work because I think honestly that financial success last year came with too high of a toll.

15:02That I was working seven days a week and I was out of control. And on the one hand, I will say that like, look, for me, working 40, 50, 60, 70 hours a week is a lot. But I can also tell you that, man, does that time hit different when you're doing something you love. Man, does it hit different when you're not trying to survive it, but you're really leaning into what it is you're doing and that that work doesn't necessarily feel like work. And that seeing that doing things differently, seeing to lean into trusting my gut has worked, to getting back to partnering with people. They're just like, look, that's my whole goal is I just want to do cool shit with cool people, right?

15:41I want to take on problems that I care about. I want to make other people's problems my own. And at the end of the day, I really want to prioritize my time, my creativity, and my happiness. Now, I have to recognize that a big part of that is possible because of where I am in my career or because of the career I've built and things like that, that has allowed for a lot of that to happen. But I also don't think that diminishes the risk or the work or a lot of those sort of things because, look, I'm somebody that always believed in people. I'm always believing that things could be different. I'm always believing that we could work different, that creative could be more empowered, that we could do those things differently.

16:20And the last three years has very much been a celebration of that. But there's also been a lot of moments where I've definitely been reminded of, how do I phrase this? I've definitely been reminded of the way people can behave whenever money, power, and ego get involved, and that nothing is immune to that. And there's still those moments where no matter how hard you work or how hard you try or how good the work is, that those things will still get in the way, So I think it hasn't been able to solve all the universe's issues. But look, I still really believe that if you're able to take the experience you have, however much that is, if you're able to be able to say, look, things can be different, that I have a unique set of skills, all the stuff that I've talked about for the last eight years on this show.

17:09right if you're able to base what you want to do in that there is still a lot of work and a lot of demand for what that is because I think we're at a time where results are at a premium honesty is at a premium that for a lot of people the ability to to show up and say look I have an opinion I have some experience to be able to deliver this I can be able to help you with that I sincerely want to do that and I'm not just going to sell you a bunch of BS or make a bunch of noise, there's still a real market for that. But that's the thing. For me, I haven't, I mean, it's been at least 10, maybe 15 years since I've been this happy.

17:49It's been, and I think that's not just based on the financial results. I think it's just getting back to work that I care about again, feeling like I have some control over my destiny, that getting rid of that uncertainty that if some board of directors or some executive just randomly decides that they want to hire a consultant or go in another direction or do whatever it is, that everything I've done, everything I've built, all of that can just go away in a flash. And that that, even if it sat in the back of my mind, took a real toll. And it was a toll I was tired of. It was a toll, I was tired of knowing how disposable I could be.

18:30And I think that's something we've seen over the last few years is that realization has rolled through a lot of the big fang companies, the Googles, the Yahoos, the Apples, the Metas. A lot of people who thought they were immune to that because tech was always immune to that. And, you know, again, we're a family, which is a myth in business. And you saw it roll through that. And we've seen it where, again, what was the next safest segment, right, was government. Well, now we're seeing that, you know, burn and, you know, get completely upended. it's a moment of a lot of uncertainty like I think that's for me the last several years I keep thinking at some point we're gonna hit the bottom at some point we're gonna right like stop seeing great talent get laid off at some point we're gonna recognize that but look I think it's a moment where the industry for design and creativity is in a moment of contraction I think we're seeing this because of business and AI and a lot of other stuff but I also see it as a moment of opportunity.

19:22And look, I think at the end of the day, even if this fell flat on its face, even if this was something that didn't work, just the fact that I was willing, I was willing, I guess, to bet on myself, to be able to build it from the ground up, to be able to grind to what that is, to be able to say, look, this is what I want to do. And just to try. Because I think I'd lost too much of myself along the way, right? It's part of the reason why I left New York City. It's part of the reason why I did a lot of the decisions I made was just, you know, look, I'm tired of being who everybody else kind of thought I should be or something.

20:01But as I said, like, look, I'm not going to sit here and say it's been easy. I'm not going to say that I've always had the answers. I'm in a moment right now where, look, you know, we had two clients that were in the liquor business who have gotten, you know, kind of destroyed and their retainers have ended and I'm about to have to go out and find new business and see if this model keeps working and there's a huge amount of uncertainty and imposter syndrome and that sort of stuff that's there and this is kind of feeding that fear of mine of like hey what what if this all goes to hell what if I can't pay my bills what like what am I going to do to my wife and my family and everything else but at the end of the day I think it's just I know if I can bet on myself and to be you know to to pivot and to do whatever I need to do I'll find a way through and that that way through is not tied to like if if I succeed on the reason why and if I fail on the reason why and I think falling back in love with that that this isn't you know based on some executive or decision or layoff or whatever right that you know and I sort of joke like you know this isn't the days where like if I was on the USS stupid and it sank that I was going to be able to just you know kind of go down with the ship or get dragged down it's like look now I've got my own little boat and I can sort of row away if things go sideways and can kind of control where the boat goes.

21:14But for me, it's been worth it. I know it's, you know, like I said, I know because of my brand, a lot of other things like that, my story is not typical. But I think that I've seen it with enough other people that I have talked to. I've seen it with enough other friends who have done similar things of them finding that same realization. And it took two, three, four, six months to be able to get there or to get it off the ground or to go grind or whatever it was but they found a way through and i think there's just there's a moment where i think a lot of people are just really tired they're just tired and i think they want to be able to try to bet on themselves so hopefully this helps like i said let me know i mean leave it in the comments or wherever you read this or reach out to me or something like that if we want to talk about this more if you want me to do a live you know q a about this if there's more detail you want about any of this stuff.

22:06Again, there's some older episodes that go into like how to start setting things up. If you're looking for that, go back to that. You know, again, if you're looking at I'm not sure where to start. I did an episode on, again, that problem where there's a lot of people just don't know what it is they want. But just think about it, right? Because I think if you made it this far in this episode, there's a reason why. There's some part of you that's calling out to that. There's some part of you that is interested in this. There's some part of you that, I don't know what you're too tired, too frustrated, too done to just, you know, you're tired of the same old script over and over again.

22:40You still care about your talent or you want to still make an impact. And if you do think about it, right? And like I said, really think about what it is you want. Because I think if you were able to lean into that, you're going to find that differentiator. And again, over a lot of my career, I think if you really do that, you'll find the audience, you'll find the clients, you'll find those sorts of things. I think it's whenever you try to make it generic or make it what other people want. Those are the moments where you get into trouble and you feel like you're spinning your wheels or you just, you keep playing a broken game.

23:09But anyway, that's a show for another time. But like I said, hopefully this was somewhat helpful or a little bit of perspective. Let me know either way. Happy to dig into more, happy to dig in less. But like I said, don't, betting on yourself is a pretty smart bet, I think, most of the time. So hope this helped um again let me know and as always stay crazy