A lot of creatives are feeling it right now: the market shifting, projects slowing down, the fear of asking “wait… is it just me?” causing a spiral into the anxiety void.

This week, we're thrilled to get to talk to one of our heroes, Dan Kuhlken of DKNG. We'll dig into what it actually looks like to stay sharp (and sane) through years of creating, risk-taking, and what it's critical to let go of to move forward.

We go way behind the curtain into the technical Illustrator work, the screen-printing mindset, and the less-glamorous reality of running a two-person studio that has to keep the lights on.

We also talk about insecurity (yes, even legends struggle with it). the real kind. The “99 kind comments, 1 brutal comment, and now I’m questioning my whole identity” kind.

Here are some of the most tasty nuggets to listen for:

• How Dan built a non-destructive letterpress tool in Illustrator using graphic styles + the appearance panel (and, yes, you can own it).
• “Gatekeeping is a choice” and why sharing process usually makes everyone better (don't hide your secret sauce, it ends up working against you).
• Dan’s take on insecurities, including envy and jealousy, and how to turn them into an energy drink for your creative soul (instead of letting it eat you alive).
• Why halftones/textures exist, and why Dan thinks design is as much about construction as looks.
• The delegation dilemma. What happens when growth starts requiring skills you didn’t need to build the thing in the first place.
• [Bonus Story] The Flight of the Conchords poster moment and the surreal full-circle “pinch me” of musicians collecting your work.

If you’re an illustrator/designer trying to stay good through changing seasons or you’re deep in the “how do I make this look human?” Illustrator rabbit hole, hit that play button!

And if you want more of the behind-the-scenes thinking like this, the Creative Slash newsletter is linked in the show notes. Get our five-part “Off the Record” email series. It's FREE and packed with the operating systems, philosophies, and tools that top creatives recommend.

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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