Featuring: Jessica Hische, Studioworks In episode 145, I sit down with Jessica Hische—a world-renowned lettering artist, New York Times bestselling author, and one of the most thoughtful creative voices of our generation. And full transparency: I’ve been a huge fan of Jessica’s work for a long time. Her ability to pair obsessive craft with clarity, intention, and humanity has influenced how I think about creative work for years. This conversation goes far beyond tactics or tools. We dig into what it really means to answer a creative calling—and then protect it. Jessica shares how she’s built a career that honors her instincts, values her time, and stays deeply connected to her craft, without burning out or selling out. We talk about the choices she’s made to stay true to her creative voice, even when external pressure—clients, platforms, trends, or scale—could easily pull things off course. We also explore the less romantic but absolutely essential side of creative freedom: boundaries, systems, pricing, and self-advocacy. Jessica opens up about how she’s learned to put structure around her work not as a constraint, but as a way to preserve joy, sustainability, and long-term creative integrity. Whether it’s choosing the right projects, saying no without guilt, or building tools that support creatives instead of exploiting them, her through-line is clear: creativity thrives when it’s respected. For agency owners and creative leaders, this episode is a powerful reminder that building a business—or a career—on your own terms isn’t about sacrificing ambition. It’s about defining success for yourself, staying grounded in your craft, and making intentional choices that allow your work, and your life, to evolve together. This one felt special to record—and I think it’ll resonate deeply with anyone trying to build something meaningful, creatively and personally. Key Bytes • Why answering a creative calling is an ongoing commitment, not a one-time decision • How staying true to your craft doesn’t require self-sacrifice • The role boundaries and structure play in long-term creative freedom • Why defining success for yourself is the real creative advantage • How creatives can grow without burning out or losing their voice Chapters 00:00 Following a creative calling 06:40 Staying true to your craft over time 14:10 Defining success on your own terms 22:35 Boundaries, pricing, and protecting creative energy 31:20 Structure as a support, not a constraint 40:05 Evolving creatively without losing yourself 48:30 Advice for creatives building sustainable careers Jessica Hische is a lettering artist and New York Times Best-selling author based in Oakland, California. She specializes in typographical work for logos, film, books, and other commercial applications. Her clients include Wes Anderson, The United States Postal Service, Target, Hallmark, and Penguin Books and her work has been featured again and again in design and illustration annuals both in the US and internationally. She’s been named a Print Magazine New Visual Artist (20 under 30), one of Forbes 30 under 30 in Art and Design, an ADC Young Gun, a “Person to Watch” by GD USA, and an Adweek “Creative 100”. She's also the co-founder of Studioworks, invoicing software for creatives by creatives. Contact Jessica on their website, Threads, and Instagram, and learn about Studioworks here.
