How to Make the Leap to Creative Director

Take It or Leave It Creative Advice

This week, we’ve got ten (yes, 10!!!) questions to tackle. Huge thanks to all of you! I’ll be breaking these into two parts, so if your question isn’t answered this week, don’t worry, I’ll get to it next time. Your paid subscription means a lot, and we’re so grateful to have you here.

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Today, I’ll be answering questions like: How do you become a creative director? How do you turn a side gig into your main gig? How do you decide what to create? How do you increase sales for your product? And how do you integrate your philosophy and hobbies into your content?

Let’s get into it.

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Hey Lé! Love this question. Let’s start with the first part: how do you get over the fear of being seen?

I’ll give you two answers: one for your creative soul and one that’s more cut and dry.

This fear is universal. Even the best of the best feel it. Sharing your work is intimate. It’s hard enough showing the people closest to you, let alone the entire world. But if you want to thrive creatively, putting yourself and your work out there isn’t optional, it’s necessary.

Here’s something I have to remind myself constantly, and I think it’s a good reminder for you too:

It’s okay to take up space.

Actually, scratch that. You must take up space.

Whatever your craft is, whatever you want to say—it deserves to be seen, heard, read, consumed. Stop thinking of your ideas as yours. People like Rick Rubin and Elizabeth Gilbert talk about ideas differently than most. We’re vessels. Inspiration finds us, not the other way around. And when an idea finds you, your job is to bring it to life because if you don’t, it’ll either die or move on to someone else.

There’s something freeing about this. When I approach my work this way, it puts my ego in the back seat and lets the idea drive. That shift is key.

Now, the practical side: you need to practice taking up space. That doesn’t mean you have to stand in the spotlight right away. I spent my twenties doing exactly that—trying to make my personality the work instead of letting the work be the work. It left me burned out, chasing validation, and making stuff I wasn’t proud of.

So when I started Create.Repeat, I did the opposite. I made it faceless. No name, no identity, just the work. I let the message speak for itself. And that shift changed everything.

Maybe try that. Create a faceless account. Use a pen name. Submit your work anonymously. Get used to sharing without making it about you. It worked for me, it might work for you too.

How do you make the leap to Creative Director?

There are two paths: the traditional and the non-traditional.

The traditional is straightforward. You go to an art or advertising school, land an entry-level job at an agency, pick a lane (copywriting or art direction), climb the ladder, jump to another company for a better title, work your way up, land a CD role at a cool startup, rebrand everything, stay two years, then leave to start your own thing.

That’s a great path. But I didn’t take it.

I lucked into becoming a Creative Director, but I was preparing for it my whole life.