Comedian Matt Ruby performs, and creative director Isabel Urbina Peña and illustrator Ping Zhu talk to host Tina Essmaker about their very different paths, working by hand, the value of personal time, and following intuition into opportunity.

Designer Natasha Jen & designer and illustrator Lotta Nieminen talk to host Tina Essmaker about trusting our intuition, living with uncertainty, and embracing accidents along the way.

Designers Dan Blackman and Robyn Kanner talk to host Tina Essmaker about the power of vulnerability, self-initiated projects, and how our priorities shape our work.

Photographer Daniel Seung Lee and writer Jocelyn K. Glei talk to host Tina Essmaker about transitioning well, recognizing burnout, and navigating work and life at a sustainable pace.

Designer Shawna X & photographer Collin Hughes talk to host Tina Essmaker about being in a relationship with each other, how they challenge each other to grow, why it’s okay to be scared, and why we become what we think about.

Artists and illustrators Julia Rothman & Jon Burgerman talk to host Tina Essmaker about knowing your value as an artist, the art of negotiating with clients, and interjecting play into our work routines.

Designer & developer Catt Small and artist & designer Kelli Anderson talk to host Tina Essmaker about their individual paths into design, recognizing our potential, overcoming fear with action, and why the search for creative satisfaction is an ongoing inquiry.

Photographers Meredith Jenks and Alice Gao talk to host Tina Essmaker about the very different paths they took into photography, share their best business advice for aspiring photographers, and reflect on what photography has taught them about the world in which we live.

Designer & writer Amélie Lamont and designer & illustrator, Timothy Goodman, talk to host Tina Essmaker about navigating the expectations of others and ourselves throughout our careers, why our faves are problematic, and finding hope after a challenging year.

Principal Designer at Adobe, Khoi Vinh, and designer & Hello Mr. founder, Ryan Fitzgibbon, talk to host Tina Essmaker about the role of empathy in design, when the political becomes personal, and using art & design to affect social change.

Comedian & Risk! show founder Kevin Allison and entrepreneur & Make Love Not Porn founder Cindy Gallop talk to host Tina Essmaker about their biggest risks, learning to trust ourselves, and what happens when we speak up, take charge of our world, and stop letting others run it. Plus a performance from Kevin Allison!

DJ & producer, Michna, and stylist & author, Stacy London, talk to host Tina Essmaker about how their careers continue to transform, chasing fulfillment rather than success, and why we shouldn’t wait for the perfect opportunity.

Photographer Julia Robbs and artist & designer Aaron Robbs talk to host Tina Essmaker about how their childhoods shaped their beliefs about creativity, why confidence requires time and practice, how they first met, and the power of creative partnerships.

Musician Olga Bell, artist & illustrator Sara Blake, and digital artist Justin Maller talk to host Tina Essmaker about embracing intuition, overcoming the fear of change, and practicing gratitude at every stage of our careers.

Director & filmmaker, Damani Baker, and designer & writer, Frank Chimero talk about why money equals time, rethinking the value of our work, and the risks and rewards of independent making.

Episode Summary: Entrepreneur, activist, and advocate, Anil Dash, and writer and editor, Ashley C. Ford talk about why empathy is a practice, encouraging inclusivity in tech and publishing, and making our time online more meaningful. Plus Prince puns, Kenny Loggins love, and an impromptu round of "Happy Birthday."

Comedian and writer, Aparna Nancherla, and writer, educator, and artist, Debbie Millman, talk about their “Aha!” moments, the magic of connecting with our audiences, and why finding our courage is more important than finding our passion. Plus Debbie reveals her past performance experience!

Multi-disciplinary designer and partner at Pentagram NY, Emily Oberman, and artist and author, Adam J. Kurtz, talk about their respective creative processes, dish on experiences with imposter syndrome, and reveal how fear can be a motivator when we harness our panic.

Iconic street photographer and filmmaker, Cheryl Dunn, and fellow street photographer, Andre D. Wagner, reflect on the power of personal projects, recall their most memorable moments on the street, and reveal why they’ll never be creatively satisfied.

Renowned book cover designer, Chip Kidd, and Brooklyn-based letterer, Jen Mussari, discuss their early years, get real about creative block, and challenge our ideas about failure. Plus Jen surprises Chip with a tale about how he unknowingly influenced her trajectory.