ABOUT THIS EPISODE
Most creatives have heard the advice a hundred times. Pick a lane. Niche down. Be known for one thing.
But what happens when the thing you're known for is just you? Doodles one day, glossy dimensional lettering the next, hot pink whenever the brief allows it, and a pencil hair clip you designed because you wanted one to exist.
In this episode, we talk with Jess Goldsmith, the Brooklyn-raised lettering artist and illustrator behind Chick of All Trade and the founder of Women of Type. On the surface, it's a conversation about clients, pricing, and portfolios. Underneath, it's about deciding how you want to work, then holding the line, whether that means walking away from a Super Bowl job or asking a client to tell you the budget.
It's part pricing masterclass, part cheese debate, and part Bob Lazar rabbit hole we didn't plan to fall into.
In this episode, we talk about:
- Why your portfolio works like a menu and how showing work you hated doing is the fastest way to get hired for more of it.
- Walking away from a Super Bowl job, including the five-figure project Jess turned down, and what she did with the idea afterward.
- Why she tells friends exactly what she got paid especially after a friend landed a job she'd quoted at $10K and did it for $2,000.
- "You are the niche" and why the worst advice Jess and her friends ever got was to niche down, even when your many styles start to look like one person.
- Business cards nobody throws away from pretzel snack bags to a spinning-wheel-of-death plush with an NFC chip in its hand to a crayon-box matchbook for Adobe MAX.
Whether you're still building a portfolio or you've been freelancing for twenty years, this one reminds you that the work you choose to show, and the jobs you choose to turn down, shape the career you end up with. Also, the cottage cheese has to be four percent. Jess was very clear about that.
ABOUT THE CREATIVE
Jess Goldsmith is a Brooklyn-raised, NYC-based illustrator, lettering artist, and creative entrepreneur who works under the name Chick of All Trade. Her work is color-drenched, often pink, and moves freely between styles. She's a Webby Award winner, an Adobe ambassador, and an Adobe MAX speaker.
She's also the founder of Women of Type, a community that uplifts and amplifies women and nonbinary type and lettering artists, and the creator of the self-published Women of Type book, featuring work from around 130 artists worldwide.
Her newest project, Soft Skool, is a six-week program that helps creatives build the soft skills that turn talent into a paying career. It's open to everyone, and the next cohort is planned for January.
Website
https://www.chickofalltrade.com
Instagram
https://www.instagram.com/chickofalltrade
Women of Type
https://womenoftype.com
Women of Type on Instagram
https://www.instagram.com/womenoftype
Soft Skool on Instagram
https://www.instagram.com/softskool
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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.
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.
Credits
Audio/video editing: Clara Wright
Cover art: Brad Woodard
Intro animation: Seth Austin
Intro music: “Snakes and Fire” (Instrumental) by Pär Hagström
