Ep 131 Career: What's stopping you from going out on your own?!?

After 13 months away, the mic is back on—and we’re starting exactly where too many of us are stuck. In this raw and real return, Stephen unpacks the one conversation that’s been rising to the surface in every mentoring session, DMs, and late-night career spirals: Should I start my own thing? But the real question hiding underneath? Why can’t I bet on myself?This episode isn’t about logos, color palettes, or pitch decks—it’s about confronting the fear, vulnerability, and truth at the heart of every creative career pivot.

Whether you’re debating a freelance leap, building your own agency, or just trying to reclaim your voice in your next job, this one’s a mirror check.

What you’ll learn in this episode:

• Why most people ask the wrong questions about starting their own thing
• The emotional weight of discovering your personal brand
• How industry trauma erodes creative identity and confidence
• The difference between choosing your path vs. accepting what you’re given
• Why betting on yourself is terrifying—and totally worth it

Because there’s no “right time” to bet on yourself. There’s just now.

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Transcript

What's going on, everybody? Welcome into the 131st episode of the Crazy One podcast. And as always, this is the share we talk about creativity, leadership, design, and a whole bunch of other stuff that affect creative people. Now, as always, look it. If you like the content, let me know if there's other stuff you want me to talk about.

Let me know if you like the whatever platform you're listening to this on. Leave a review. It helps people know that after 13 months away, we're actually back. So a lot of those sort of things and this is the new format, right? We're going to do a little bit more shorter, a little bit more focused. Right. Trying to condense it down a little bit more into a little bit more bite sized content.

And today what I want to talk about is because I think over the last two years, I still do free mentoring every single week on the amazing design People list. It's still a huge thing that I love and believe in. I love having those one on one conversations, meeting different creatives. And as I look back really over the last two years, two and a half years, one question clearly rises to the top.

And I think that's for so many of you. You are thinking about struggling with debating arm wrestling. Look, I'm not happy with where I'm at. I'm not happy in my job. Should I go start my own thing? I think, you know, a lot of people come to me because they've seen that I did that. I started my agency crazy.

And, you know, look, how's that going? What have I learned? What was the process? And the thing is, that's really interesting with all of these conversations is whenever people come to me, the vast majority of the time, they ask me the wrong questions. I think they're extremely understandable questions. But at the end of the day, they're sort of circling around the real issue.

And that's what I'm gonna talk about today, because for most people it's like, well, look, you know, what should the logo be? Or what should the colors be? Or what should I call it? Or like, what should my pitch deck look like? Nobody cares. Right? Sorry, sorry. But at the end of the day, call it whatever the hell you want.

Make it look like whatever you want. We'll talk about sort of what the agency stands for in another episode. But so many people are like, look, I can't pull the trigger on it. I don't know why. I can't figure out how to make this more differentiated. I don't know why. And I think, you know, the the real heart of this issue comes out of is, I think in this moment, for so many of us, it's the first time maybe ever, maybe just in a really long time where we've had to confront the question of who are we?

What makes us different? Why is anybody going to care about this? And I think that's it's why so many people struggle to create their personal brand. It's why so many people don't have an about section on their portfolio. It's why so many people have such generic descriptions of themselves that can apply to literally anybody who is doing what you are doing.

And because, you know, for too many of us, we move through the industry, taking what it will give us. The next step in our career is based on what is the next step in the career ladder at our company, or what our boss tells us we should work on, or what are those sort of things? And we've almost lost touch with who we are.

What makes us different? What do we want? I mean, God forbid even just what makes us happy. I mean, that's been an interview question of mine for years, and it's still shocking the number of people who just don't have a clue. But usually that's what's stopping you. Or somebody you know, or whatever that is. Like, that's what's stopping you, because there is probably not going to be a more vulnerable, more emotional and more difficult moment than sitting down and saying, what do I want?

Not what do I think the industry wants me to be, because that's you and your rawest form. That's you and your most vulnerable form of saying, this is what makes me different. This is what I want to do. This is what I want to work on. This is what values to me. This is what makes me happy, right?

Happy. Do it. Do you remember what that is? Do any of us remember what that is? Because I think for so many people right now, like I saw a stat the other day of like 80% of people or something crazy like that hate their job, right? Another one's even crazier. Like 20% of people are actively trying to sabotage their employer, because I think that's what we've seen, right?

We've all been reminded of how disposable we are. People, the big Fang companies, the Googles, the apples, the Amazons, and also they were immune to it. You're not. I've talked for the better part of a decade around either you know how disposable you are, or you work long enough to find that out, right? Whenever money and power get involved, you see the worst part of people almost every time.

And this is that moment where I think for most people, that's what they're afraid of. That's what's holding them back, because there's never going to be a right. It's like going on vacation, right? You never look at your calendar go, oh, look, there's two weeks where I've got nothing to do. I should go on vacation. That that's what this moment is.

There's never going to be a right moment to bet on yourself. And I think that, for me, was probably the most eye opening, heart wrenching, disheartening, empowering moment. Whenever I thought about the fact that I wanted to leave New York to move to Pittsburgh, and for so many people, whenever you still say Pittsburgh, some people go, oh, that's really cool.

I love that town. And a lot of people still think it's like some bad 80s comedy where you're going to get like sent there whenever you don't behave well. And that's B.S., right? Yeah. I am so much happier living here. It is just unbelievable. But doing that was such a mental block for me, right? Going out on my own was such a mental block for me because all I could see is what I could lose.

I couldn't see what I could gain. Being happy, honestly, was an act of will, because I'd spent so many years living in my corporate trauma, convincing myself that what I was going through, the way that I was being dehumanized, the way that I was being overlooked, the way that I was being put down was okay. Right? It was okay.

The fact that I'm disposable, I understand that right. And I think even honestly, this show probably helped me deal with some of that because I felt like I had some part of a voice, even if it wasn't where I worked. And so when it came to the moment to say, I want to leave New York, I want to start my own studio, I want to again go out on my own.

I want to bet on myself. That moment was so tough for me because I realized the only thing that was stopping me was me believing in myself that I could leave New York and it wouldn't end my career. I could go out on my own, and I could still make this work, that I could have more to gain than I would to lose.

And it's a tough moment, right when you have to look in the mirror and just go, what the hell have I turned like? When did this happen? How did how would I live in this body every minute of every day that I'm awake, right? Like, how did I get to this point where I lost touch with me and became this derivative version of myself?

And I think that's what I that's what I hear from so many of you. And I think that's what you're struggling with, is the, you know, a lot of those questions around kind of what does the industry want me to be? Well, again, I still come back to write like history doesn't remember well behaved people and companies don't want to hire generic talent.

And I think it's the realization that the only thing that's holding you back is you, is the willingness to bet on yourself, to bet on your happiness, to say, in this moment, look, I'm going to jump. I don't know that I've got the answer, don't know that I've got everything figured out, but I'm willing to bet on myself and I'm willing to figure it out.

Then I'm going to sit down for the first time in either too long, maybe ever. Let's say, what do I want to do? What do I think I'm good at? What makes me happy? They're very simple questions, and it's amazing. I think whenever you sit down to start to think about that, how hard the answers are, right? They don't come easily, they don't come quickly.

And I think a lot of cases, there's a lot of self-reflection, there's a lot of guilt, there's a lot of other things that come with it around. Just because I think, look, the job search, starting your own thing, it's hard. It's dehumanizing. It can be humiliating because all that it is is just really the search for validation. Hire me.

So I feel like my career choices have been the right ones. Hire me. So I feel like I am useful and talented again. Hire me so that again you can validate who I am. So none of those are understatements, right? That's really what's going on here. I think we like to couch it in sort of other things. But this is why, for so many of you that I talk to you like even just putting that green open to work ring on LinkedIn is so hard because it feels like a scarlet letter even laid off, right?

How can you not take it personally? They kept these people and they got rid of me. How do you not take that personally? But I think it's the time for if you're starting to ask that question, if you have that inkling, that's some part of you screaming that you need to bet on yourself again. Now, that doesn't mean that you have to go start your own thing, right?

I think even if you're going to go back into in-house or back into an agency or back into whatever it is, right, you need to go back into it saying, look, this is what I want because there is such a profound difference in moving through your career saying, this is what I want and this is what I want to be, versus your career being taking what the industry will give you.

I think that's been a theme in this show, right? Is that too many of us just take whatever we're given, we become whatever we think, and we rationalize happiness out of it. But coping mechanisms aren't like that, aren't sustainable. And then we get into a problem. But but that's I think for most people, what that hang up really is my willing to be happy.

I'm willing to bet on myself. Am I willing to say, okay, look, you know, I am different. And that's a superpower, not a weakness, because I think for a lot of people that are having these conversations, you've been told probably a little bit too much that standing out the doing things differently, that questioning the status quo. Right. These are all weaknesses in corporate culture.

This is why creativity in corporate culture, you know, we just don't really get along because what we do just inherently tries to do different things. And I also have to be honest here, right. Like there's not some big origin story here around me starting my own agency. I got dragged into it kicking and screaming. Yeah. Like I very publicly on LinkedIn and everywhere else said, look, I'm going to go look for this job.

I'm going to do this. I talked to 100 companies, did all this sort of stuff, you know, got two lowball offers. And that was kind of it. I got to be honest, I think that part of that was because I couldn't show work I was proud of. I wasn't proud of myself. I wasn't in a good headspace to go into those interviews.

I was damaged from being laid off from the third time I was damaged, from 5 or 6 years of not doing any work that I was proud of, and I had to come to grips with that, that I was, you know, a big part of why that did not work out, that it's easy to say it's the industry and whatever else, but I needed on my part of that to that, I had just crafted a career and a body of work coming through that point.

That was just B.S. it wasn't me. And that's I mean, man, you want talk about atomic imposter syndrome, do a show for seven years talking and giving people advice on their careers, then have that realization. Holy crap. But I think that's the part of it, right? Was that for me? I was still looking for that full time job.

I was just said, look, I'm going to do freelance. I'm not going to do my own. I don't want to take the risk. I don't want to. And I just honestly had, you know, two clients who are like, yo, dumb ass. You know, if you said you're gonna do this full time, we'll just put you on retainer and pay you because we love your work.

And it's kind of like, wait a minute. So this wasn't like, this was some part of some great plan, or I'm like, I'm going to go out on my own. Like, even I had to get dragged into being happy. Right? And that's such a weird thing to say. But I am like, it's not that there aren't like their struggles I'm very much reminded of.

So again, an agency how disposed of you are. People are assholes and in shocking new ways. But I'm so much happier than ever I was. I'm happy for where I live. I'm happier in my marriage. I'm happier. I have more friends than I've ever had, like so much of it. But all I could see was the negative. I could see what I could lose.

All I had to come to grips and make peace with my journey. And that's the moment, right? I think that's what so many of us are going through, where it's not that you're struggling to what to name your agency or what the brand colors should be, right? That's just busywork where you're distracting yourself from the real question. But I think that's what you need to do talk to family, talk to significant others, talk to, you know, coworkers that you trust or ex coworkers or whatever that is to say, okay, look, what do you think makes me great?

What do you think I'm really good at? What do you think I should be doing? Should I do this? You know, get an outside perspective. We're all our own biggest blind spots. But I think just having that vulnerability and having that conversation and realize that's what's really at the heart of this, because I think once you're willing to start asking those questions, once I think you start to look at it through that lens of saying, like, when did I stop believing in myself?

When did I give other people this much power? How do I want to change that? You become a healthier version of yourself. You become better no matter what. Like I said, no matter where you want to go with your career, you become better for it. But I think that's the key question. That time after time after time, whenever I say, look, that's what you're dealing with, you watch it just sort of wash over people with that mix of surprise, a little bit of horror, a little bit of like, okay, this is going to be more work than I thought it was going to be.

But I think that's the moment because that's what I always think, you know, reel is going to cut through. Authentic is going to cut through. Honest is going to cut through, especially at a time now where there's more noise than ever. But that's the sort of thing you need to be able to think about. So just like I said, think about what do you want out of your career?

Not how do I just simply rationalize what I'm given? Because when you're able to do that, it's such a massive, massive unlock. And so let me know what you think right now if you've been going through similar things. What, am I just out on an island here? Am I the one who's just sort of like going out and doing my own thing, you know?

Have you been struggling with something similar to a lot of this? But let me know, because I think I'm definitely I'm interested to hear from more of you. I'm interested to hear other stories around what this is. And like I said, I appreciate we're starting the show back up from zero. We're going to take it in a little bit more different direction, a little bit shorter, things like that.

But let me know. And hey, as always, stay crazy.