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.

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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