10 Lessons That Will Make or Break Your Creative Career
What You’ll Learn in this video
- How to build a long-term creative career without burning out
- The biggest creative mistakes I made (so you don’t have to)
- How to define your vision for life — and adjust when it changes
- The difference between being “multi-passionate” and being scattered
- Why everyone is just making it up as they go
Hi, I’m Justin, your brand and marketing coach. I help artists, creators, and thought leaders turn “someday” projects into real projects and small businesses.
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How do I know if my idea is good enough to launch?
The short answer: you don’t. And that’s the point.
The lesson I keep learning is that no matter how much you plan, things will always turn out different than you expected. Which is why it’s actually better to give yourself less time to plan—so you can test, learn, and reset faster.
The Trouble With “Fail Forward”
I’ve always hated the phrase “fail forward.” Because here’s the truth: I’m a Black man in a country that doesn’t give people like me the same room to fail. My whole life I’ve felt I had to be twice as good just to get the same opportunities.
So I studied hard. I worked hard. I did everything “right.” And it paid off in my career as a creative director.
But entrepreneurship? That’s a whole different ballgame.
Entrepreneurship = Experiments
I once had a conversation with my friend Chris Guillebeau, and he helped me see this clearly:
Entrepreneurship is just a series of experiments.
Failure isn’t the enemy—it’s a gift. Every test teaches you something new. And when you start thinking about your ideas as rough drafts or tiny experiments, it becomes so much easier to separate your self-worth from the outcome of any single launch.
That’s a blessing for the perfectionist in me who still shows up now and then. Because if an idea doesn’t land, it’s not me that failed—it’s just that idea. And I can relaunch it over and over until I get it right.
What Really Might Be “Off”
Most of the time, it’s not even the idea itself that’s the problem. It could be:
- The audience
- The messaging
- The positioning
Those are all things you can change.
From Home Runs to Base Hits
For a long time, I thought I had to hit a home run every single time. But now I know the real goal is just to get to the next base. And if I strike out? That’s fine too. Tomorrow, or next week, or next month—I’ll step up to the plate again.
Because every swing is another chance to learn.
So, how do you know if your idea is good enough to launch?
You don’t. You just launch it anyway.
How do I post consistently without burning out?
The only way to post consistently without burning out is to build a system that actually works for your unique brain.
Here’s the truth: you might have to experiment with a few approaches before you land on the one that sticks. But once you do, everything feels lighter.
My System (The Simple Version)
In 2019, I made a promise to myself: send out a weekly email every single week, no matter what. That one decision changed everything.
Over time, the format evolved, but here’s what works for me today:
- One pep talk
- Five memes
- Three things that made me happy this week
This structure works because:
- It gives me freedom to cover lots of different topics (I’m multipassionate, so I need variety).
- It’s repeatable—like muscle memory for my creativity.
Repurposing Is the Secret
Here’s where it gets even easier. Once I’ve written the email, I break it apart and reimagine it for Instagram and Threads.
- A pep talk becomes a carousel or text post.
- A meme works exactly as-is.
- My “three happy things” become a thread or story series.
The magic is in the recycling. I’m not reinventing the wheel each week—I’m just remixing.
Why It Works Long-Term
The cycle becomes self-sustaining:
- Newsletter → Social posts
- Social posts → New ideas for the newsletter
It’s a back-and-forth that keeps me planting seeds, cultivating ideas, and reaping creative rewards—without burning out.
The bottom line: Consistency doesn’t come from discipline. It comes from designing a system that plays to your strengths and then letting that system carry you forward.
You made it to the bottom-of-the-email club.
Hit reply and tell me your favorite podcast—your notes remind me this is a conversation, not a monologue.
Got a question for a future issue? Send it my way. I’m here to share everything I know about personal branding, career growth, content, and marketing. Put my seven years as a creative director to work.
How do I figure out what I want to be known for?
The truth is—you already know this answer. You might just need to peel back a few layers to uncover it. Here’s a process to help you get there
1. Look at Your Career
Make a list of everything you’ve done professionally that you’re incredibly proud of. Don’t overthink—just write down the moments, projects, and milestones that felt meaningful.
2. Look at Your Personal Life
Now do the same thing with your personal life.
- What do you enjoy consuming content about?
- What hobbies or personal projects have lit you up?
- Where do you lose track of time?
3. Revisit Your Past Selves
Sometimes clarity comes from remembering who you were in earlier chapters:
- In college, what were you obsessed with?
- In high school, what did you love?
- In elementary school, what could you not get enough of?
4. Make Connections
Write everything down on notecards or sticky notes and spread them out. See what themes connect. Which words, ideas, or experiences repeat?
My Example
Here’s what this exercise looks like for me:
- Career: I worked in advertising, did communications for an arts high school, and handled marketing and design for a museum.
- Personal Life: I love nostalgia, long walks, and using neuroscience to better understand myself.
- Projects: I launched a culture magazine in New Orleans, cofounded a creative entrepreneurs’ conference, wrote a book about my mental health journey, and make illustrations and memes about daily life.
When I put all this together, I start to see a theme: mental health, creativity, and the pursuit of joy.
Those became my three content pillars and a loose idea of what I want to be known for.
Do the Work
Finally—don’t just think about it. Write, draw, speak, record, design…whatever your creative form is. The only way to discover what you truly want to be known for is to practice, create, and let the patterns reveal themselves.
The point isn’t to have a perfect one-sentence brand right away. It’s to start noticing the threads of who you already are, and then follow them until they lead you to clarity.
take a breath
Inhale.
That’s all you have to do right now.
No need to figure it all out.
No need to cross another thing off the to-do list.
Just breathe in.
Exhale.
Let your shoulders drop.
Let the tension melt.
Let go of the need to prove yourself.
This moment is the only one that’s real.
Not the stories spinning in your mind.
Not the past tugging at your sleeve.
Not the future that doesn’t even exist yet.
Just this inhale.
And this exhale.
You’re safe here.
You’re enough here.
You’re allowed to just be
here.
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