Christina walks us through her path from a childhood spent training as a ballerina to a last-minute pivot into art school, and how she’s found her way back to ballet as an adult, just for the joy of it. We get into the reality of freelancing for the last 8 years: the moment she quit a full-time job for a one-month freelance gig, the ebbs and flows that never fully go away, and how her slow seasons have actually led to some of her biggest projects. 

In this episode, we dig into the full story: how Freddi went from finishing a master’s thesis in type design to co-founding a startup with no business experience and what it really takes to go from concept to product. We also get deep into the neuroscience side of things: synesthesia, aphantasia, the Ira Glass gap, and how understanding different brains perceive the world shaped Freddi’s research from the very beginning.

She’s been a fine art major, a print designer, a Barbie packaging designer at Mattel, a surface pattern designer, an art licensing exhibitor, and, for the past 10 years, an artist coach.

In this episode, we sit with Jeanetta Gonzales, Ilana’s first art licensing mentor, for a conversation that goes way beyond business strategy. We’re talking about the long, winding road of building a creative career, what it was actually like to exhibit at art licensing trade shows, and why the seeds you plant at a show might not sprout for years.

Jeanetta also shares all about her brand new book series, Free Pass, four illustrated coupon books published with Chronicle that are essentially permission slips for creatives, workers, resters, and parents. The creativity book was born directly out of her coaching work after she noticed that the moment she gave an artist the green light, everything changed.

In this episode, we’re joined by illustrator, letterer, and YouTuber Chris Piascik for a wide-ranging conversation about building a creative career without a grid master plan and why showing up consistently can change everything. 

Chris shares how a daily challenge that started as a way to reconnect with drawing quietly became the foundation of his entire career. We talk about what it means to play the long game as a creative, how personal work can naturally lead to apid opportunities, and why focusing on making matters more than chasing the perfect strategy. 

In this episode, we sit down with designer Josh Jevons to discuss what it actually looks like to build a sustainable creative career without burning out, cold-pitching nonstop, or doing everything yourself. We also get into real-world outreach strategies, including walking trade shows, pitching without being salesy, and why face-to-face connections still matter. Along the way, we talk packaging, brand strategy, work-life balance, and designing systems that allow you to grow without burning out.

In this episode, we sit down with illustrator, designer, and jill of all trades Marisol Ortega for a conversation that’s equal parts honest, hilarious, and deeply relatable for anyone navigating a creative career.

Marisol talks about leaving full-time work (again!) to return to freelance life, why office-centric culture doesn’t support the way many creatives actually think and work, and how being a parent shaped her career decisions. We dig into the reality of juggling big-name clients, managing energy, working with a rep, and building a sustainable freelance practice that doesn’t drain your soul.

In this episode, we’re joined by a very special guest, Rebecca Shostak, co-founder of Flodesk and lifelong designer-turned-entrepreneur. This conversation is packed with insights into how creativity, design thinking, and intentional decision-making can shape not just a project but an entire company. We also go deep into AI, the fears, the opportunities, and what it looks like to use it as a tool that supports creativity rather than replaces it. 

What does it look like running your own design studio that works with names like Rosie Huntington-Whiteley and Kourtney Kardashian? In this episode, we sit down with Amber Asay of Nice People to discuss the winding path that led her from scrapbooking experiments and show choirs to launching a successful design agency and a creative podcast.

We’re joined by the wonderfully optimistic and multi-talented hand lettering artist & muralist, Lisa Quine, someone who has done everything from lettering murals for pro sports teams to designing custom hairbrushes for celebrities (Fergie included). We talk about her unique creative journey, how optimism fuels her freelance career, and how her Cleveland roots helped shape a dream path she never could’ve planned.