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

Show notes

What’s going on, everybody?

Welcome into the 131st episode of The Crazy One Podcast. As always, this is the show where we talk about creativity, leadership, design—and all the other things that matter to creative people.

If you’re enjoying the show, let me know. If there’s something you want me to talk about, let me know that too. And if you’re listening on Apple, Spotify, or anywhere else—drop a review. It helps other people know that yes, after 13 months away, we’re back.

We’re in a new format now: shorter, more focused, more bite-sized. And today, I want to talk about one of the most common conversations I’ve had over the past two and a half years:

“I’m not happy in my job—should I start my own thing?”

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The Wrong Questions

Every week, I do free mentoring on the Amazing Design People List. And that question comes up all the time. People know I started my own agency—CRZY—and they want to know how I did it, what I learned, and what they should do.

But here’s the thing:

Most people are asking the wrong questions.

They ask:

• What should I call it?

• What should my logo look like?

• What colors should I use?

• How do I design the pitch deck?

 

None of that matters.

Sorry—but it doesn’t.

The real issue? They’re stuck. And they don’t know why.

They don’t know how to make themselves—or their work—feel truly different. They’re afraid to pull the trigger, but can’t explain why.

And it’s because they’re avoiding the deeper, scarier question:

“Who am I? What makes me different? And why would anyone care?”

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We’ve Lost Ourselves

That question is vulnerable. It’s emotional. And for many of us, it’s the first time we’ve ever been asked to answer it.

That’s why:

• So many portfolios have no “About Me” section.

• So many bios sound like generic LinkedIn templates.

• So many creatives struggle to articulate what makes them special.

 

Because we’ve spent our careers being shaped by other people:

• Promotions decided by company ladders.

• Opportunities dictated by bosses.

• Identity wrapped up in job titles.

 

We’ve been living in a constant state of “on the way to something else.”

And the result?

We’ve lost touch with ourselves.

We’ve lost the ability to say, “This is who I am. This is what I want. This is what makes me happy.”

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Betting on Yourself

That’s the real block.

There is never a “right time” to start your own thing. Just like there’s never magically two weeks on your calendar for vacation.

The scariest part of all of this is not the risk. It’s the decision to believe in yourself.

When I decided to leave New York and move to Pittsburgh, I was terrified.

People had opinions—lots of them. Some loved it. Some treated it like I’d been banished to some sitcom punchline of a city.

But you know what? I’m happier here than I’ve ever been.

Still, even with that move, starting my own studio was the real block. Because all I could focus on was what I might lose. Not what I might gain.

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Getting Dragged Into Happiness

Let me be clear:

There’s no romantic founder origin story here. I didn’t march out of a boardroom and shout “I’m starting my own agency!”

I got dragged into it.

Kicking. Screaming. Reluctantly.

I was still job-hunting. I had two terrible lowball offers. I didn’t feel like myself. I couldn’t show work I was proud of. I’d spent years as a creative politician instead of a creative leader. And yeah—I was damaged.

And then two clients came along and said:

“Hey dummy, if you just do this full-time, we’ll put you on retainer.”

That was the start of CRZY. Not a bold vision. Not a business plan. Just two people who believed in me when I didn’t believe in myself.

Even then—I had to force myself to be happy. I had to push through years of corporate trauma that convinced me I deserved to feel disposable. That being overlooked, dehumanized, and underpaid was normal.

It’s not.

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You’re Not Struggling with Your Brand. You’re Struggling with You.

If you’re stuck trying to name your studio, pick a color palette, or write a brand statement—chances are, that’s not the real issue.

That’s just busywork to distract yourself from the truth.

You don’t need a brand book.

You need to believe in yourself again.

And yes—it’s terrifying.

It means sitting down and asking:

• What do I actually want?

• What makes me happy?

• What am I really good at?

• What do I want to be known for?

 

These are simple questions—but the answers aren’t. They take reflection, honesty, and sometimes a little pain.

So talk to people. Ask your friends, your family, your mentors:

• What do you think I’m great at?

• What do you think I should be doing?

• Would you bet on me?

 

Because we’re all our own biggest blind spots.

And too many of us are still trying to “earn” the validation we never got from our last employer.

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Make a Choice

This doesn’t mean you have to go start your own agency. You don’t.

But even if you’re going back in-house or to another agency, you need to go back on your terms.

There’s a massive difference between:

• Taking whatever the industry gives you

  vs.

• Moving forward based on what you want.

 

History doesn’t remember well-behaved people.

And companies don’t want to hire generic talent.

Being different is your superpower. It’s not a liability.

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Final Thoughts

This is the truth I’ve landed on:

The only thing holding you back—is you.

• You stopped believing in yourself.

• You gave too much power to people who didn’t deserve it.

• You’ve forgotten what it means to want something for yourself.

 

But that can change. And it starts now.

Ask the hard questions.

Be vulnerable.

Be real.

And if you’ve been wrestling with all of this—you’re not alone.

Let me know what you’ve been going through.

Reach out. Comment. DM me. I want to hear your story.

Because even though we’re starting this show back up from zero, I know we’re building something honest. Something real. Something crazy.

And hey—as always—Stay crazy.

Tagged as:
building a brand career growth career independence creative career creative mentorship entrepreneurial journey finding career fulfillment industry norms launching an agency personal brand self-belief starting a business Stephen Gates podcast