In this episode, we talk with illustrator Shea O’Connor about building a creative career that grows through personal work, community, and consistency over time. She shares how she approaches social media as a place to explore ideas and connect with people while building work that attracts the right opportunities.

We get into how she balances personal projects with client work and how that balance shapes her creative direction and business, plus a lot more, including:

• “One for me, one for them.” How balancing passion projects with strategic work actually fuels growth
• Why social media works best when you treat it like a portfolio and not a popularity contest
• Building an engaged audience instead of chasing bigger numbers
• Creating work that attracts licensing deals, agents, and brand partnerships
• Why people can feel when you are trying too hard and how to avoid it

Shea also talks about how her priorities have shifted as her career has grown. She focuses less on doing everything and more on doing the right things well. She shares how she is thinking about licensing and passive income as a way to grow without trading more time for money.

If you have ever felt stuck between making what you love and making what sells, this conversation offers a clear and honest look at how those two things can support each other.

Join the Creative Slash Newsletter and Get the 5-Part “Off the Record” email series FREE

Click here to get the five-part “Off the Record” email series

Note: If you're looking for hard-earned advice, resources from top creatives, and the products they can't live without, you're going to love this.

Brad Woodard

Brad is an illustrator and designer behind Brave the Woods, a full-service studio working with clients like PBS Kids, Ford, Target, and USPS. His bold, playful style and heart-led storytelling shine through everything from brand campaigns to children’s books.

View Brave the Woods

Dustin Lee

Dustin is the founder of RetroSupply, a shop for retro-inspired brushes, textures, and digital tools used by tens of thousands of creatives from indie artists to major studios. He shares what it’s really like to run a creative business while keeping it small, weird, and intentional.

View RetroSupply

Credits

Audio/video editing: Clara Wright
Cover art: Brad Woodard
Intro animation: Seth Austin
Intro music: “Snakes and Fire” (Instrumental) by Pär Hagström

In this episode, we talk with illustrator Rob Zilla, whose work spans pro sports teams, major brands, and a career built on discipline, adaptability, and doing the work (whether anyone’s watching or not).

No shortcuts, no chasing trends. Just years of sharpening skills, building systems, and finding creative parallels in unexpected places (like sports, teaching, and even rejection).

We talk to Rob about building a creative career that actually lasts, plus a lot more, including:

• Drills build skills. Why the boring reps are the real difference-maker for creatives
• Rejection is fuel. How to turn setbacks, limitations, and even spite into momentum
• Credit is currency. Why visibility matters just as much as the paycheck
• AI as a tool (not a crutch). Using it to communicate ideas without losing your edge
• Business over talent. Why knowing contracts and money matters more than perfect technique

Later in the episode, we get into creative careers in the real world. We're talking contracts, net terms, getting paid, and why young artists should think twice about how they position themselves from day one.

If you’ve ever felt stuck chasing clients, frustrated by the system, or unsure how to turn your skills into something sustainable, this conversation offers a grounded (and honest) perspective on what actually works.

Join the Creative Slash Newsletter and Get the 5-Part “Off the Record” email series FREE

Click here to get the five-part “Off the Record” email series

Note: If you're looking for hard-earned advice, resources from top creatives, and the products they can't live without, you're going to love this.

Brad Woodard

Brad is an illustrator and designer behind Brave the Woods, a full-service studio working with clients like PBS Kids, Ford, Target, and USPS. His bold, playful style and heart-led storytelling shine through everything from brand campaigns to children’s books.

View Brave the Woods

Dustin Lee

Dustin is the founder of RetroSupply, a shop for retro-inspired brushes, textures, and digital tools used by tens of thousands of creatives from indie artists to major studios. He shares what it’s really like to run a creative business while keeping it small, weird, and intentional.

View RetroSupply

Credits

Audio/video editing: Clara Wright
Cover art: Brad Woodard
Intro animation: Seth Austin
Intro music: “Snakes and Fire” (Instrumental) by Pär Hagström

In this episode, we talk with illustrator and toy designer Chris Lee (AKA The Beast is Back), who built his career mostly through word of mouth and steady visibility.

No cold emailing campaign, no hard sell, just years of getting better at what he does, following what genuinely interested him, and putting the work out where people could find it.

We talk to Chris about making great work that you stand behind, plus tons more, including:

• His early obsession with toys, aquariums, and tiny made-up worlds turned into a real career.
• Advice people love to give creatives, especially "just make what you love," and where that starts to fall apart.
• Protecting the work you care about while still paying the bills.

Later in the episode, we talk about physical products and why so many people want to skip straight to mass production. Chris explains why starting small usually makes more sense, both creatively and financially.

If you've been doing all the usual things and still feel stuck chasing work, or you're trying to figure out how a personal obsession turns into a career, this conversation offers a different way to think about it.

It's honest, practical, and a lot less polished than the usual creative-career advice, which is probably why it lands.

Enjoy the episode, and if you love toys, nostalgia, and design, be sure to follow Chris Lee on Instagram.

Join the Creative Slash Newsletter and Get the 5-Part “Off the Record” email series FREE

Click here to get the five-part “Off the Record” email series

Note: If you're looking for hard-earned advice, resources from top creatives, and the products they can't live without, you're going to love this.

Brad Woodard

Brad is an illustrator and designer behind Brave the Woods, a full-service studio working with clients like PBS Kids, Ford, Target, and USPS. His bold, playful style and heart-led storytelling shine through everything from brand campaigns to children’s books.

View Brave the Woods

Dustin Lee

Dustin is the founder of RetroSupply, a shop for retro-inspired brushes, textures, and digital tools used by tens of thousands of creatives from indie artists to major studios. He shares what it’s really like to run a creative business while keeping it small, weird, and intentional.

View RetroSupply

Credits

Audio/video editing: Clara Wright
Cover art: Brad Woodard
Intro animation: Seth Austin
Intro music: “Snakes and Fire” (Instrumental) by Pär Hagström