Artist Danny Gregory ’82 Evangelizes for Cultivating Creativity

Artist and author Danny Gregory ’82 appreciated the creative opportunities that came with being an undergraduate. He acted in plays, wrote for The Daily Princetonian, and studied literature, history, and politics. But by the time he reached Princeton, he’d set aside his childhood fascination with drawing and shelved the idea of a creative livelihood. It seemed impractical.

“I remember when I applied to Princeton I wrote an essay which was about why expressing myself in words was better than expressing myself in pictures,” Gregory said. “That was my application essay. It’s sort of ironic.”

In the last 15 years, Gregory has published more than a dozen books, including illustrated journals that tell stories about his life or guide other artists on their creative paths. And with co-founder Koosje Koene, he’s created Sketchbook Skool, an online art school where a faculty of about 50 illustrators have taught drawing to some 50,000 students around the world.

Gregory’s path as an artist was influenced by a life-altering tragedy. Before his sketching renaissance, he had built a career in advertising, starting as a copywriter and working his way up to creative director. All that changed abruptly when Gregory’s wife, Patti, was run over by a subway train and paralyzed from the waist down. With an infant son to care for and a jarring change in his life path, Gregory found solace in his sketchbook.

“I went through a period of kind of looking for meaning and searching for a fresh understanding of the world because I really had my whole worldview shaken by this experience,” he said. “And I found my way to drawing as a meditative act. I started to draw the things in my life, the things around me, in a way to just to reconnect and to live in the present.”

His journals led to published books (including Everyday Matters, a memoir about the year following Patti’s accident), and Gregory began teaching workshops for illustrators while building an online community of friends and colleagues — first by blogging about his art and later by sharing his work and his thoughts about creativity on social media.

“I’d discovered this kind of magical effect that it had on me and I wanted to share it with people,” he said. “I wanted other people to know, ‘You can do this.’ … I wanted to evangelize.”

Eventually, a few years after his wife passed away, Gregory left advertising to create Sketchbook Skool. His current book project, inspired by the school, is titled How To Draw Without Talent. He has a new creativity-themed podcast, “Art for All,” and is looking forward to the first SketchKon, an in-person gathering of the virtual community of illustrators and students that will be held in Pasadena, Calif., this November.

Gregory’s instructional books are filled with inspiration, tips, and a healthy dose of encouragement, with messages about overcoming the “blocks” that keep people from creativity (or, to borrow from the subtitle of his book on The Creative License, “giving yourself permission to be the artist you truly are”).

For Gregory, there is a larger purpose for cultivating creativity. “I think it’s more important now than ever because we are in a time of such incredible change,” he said. “Allowing yourself to think creatively means that you can respond to change and you aren’t stuck in a certain way of doing things. If you think creatively, you are willing to create new solutions.”