Steven Estrella.

What happens when the work you make for yourself catches the attention of the NBA? Steven Estrella joins Howard to talk about finding his visual voice, rebuilding creative momentum after moving to Toronto, and learning to trust the things he loves making.

Steven traces his path from a creative family in the Philippines and a fine arts education to photography, video, and digital illustration. He opens up about the uncertainty of immigration, the periods when creativity had to take a back seat, and how a supportive community helped him find his footing again.

They explore how Steven’s style evolved from carefully rendered realism into expressive characters, distorted anatomy, and wide-angle compositions inspired by skateboarding. Steven explains why sharing that work has helped attract clients who want his particular perspective—and why he no longer tries to lock himself into one style forever.

Steven shares how he applied to the NBA’s creator program with just a few days to spare, adding a basketball illustration to a portfolio full of skateboarding pieces. He walks through working directly with a creative director, moving from sketches to color and finished artwork, and the freedom he found within the briefs. He also explains how his Celtics illustration led to a later coloring-book commission, and how personal projects can help start conversations with dream clients.

The conversation gets practical with Steven’s simple iPad workflow: drawing in Adobe Fresco, using built-in brushes, and finishing in Photoshop. They also unpack his 36 Days of Type experiments, turning human poses into letters and discovering how a limited palette and a playful challenge could push his work forward.

At the heart of it all is a shift away from making art for approval. Steven reflects on taking pressure off the process, following his curiosity, and building a creative life around work he actually enjoys.