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If Not Now, When?

with Chase Jarvis and Debbie Millman

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Class duration: 0h 55m

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About The Class

There's a common misconception that artists have a monopoly on creativity… But the very act of making waves - no matter the career - is a creative one. The Chase Jarvis LIVE Show is an exploration of creativity, self-discovery, entrepreneurship, hard-earned lessons, and so much more. Chase sits down with the world's top creators, entrepreneurs, and thought leaders and unpacks actionable, valuable insights to help you live your dreams in career, hobby, and life.


I absolutely love Debbie’s openness, vulnerability, and wisdom and I’m super grateful to share it with all of you. If you’re a fan of folks like Brené Brown, Gretchen Rubin or Elle Luna, then this one is for you– and if you like what you hear, check out Debbie’s class on CreativeLive.

  • She says that “confidence is overrated.” This is something I know a lot of you struggle with and I love how she talks about this. Confidence is created by repeatedly doing something, and if you’ve never done something before how could you have confidence? Confidence – in her view – is the easy part. It’s finding the courage to do the thing when you DON’T have confidence that is the gamechanger.
  • The importance of teaching: why Milton Glaser said it’s the most important thing he ever did and why Debbie has always made it a big focus in her own career– because as she says when she teaches, the students teach HER
  • Why even hyper-achieving legends struggle with feelings of unworthiness and what the levers are for coping with it. This is a nearly universal thing that’s very rarely talked about, and it’s super important that you put your own mechanism in place to keep it from sabotaging your success


Debbie Millman is currently the Editorial and Creative Director of Print Magazine, but she has an insane track record going back decades: she’s the author of 6 books including “How To Think Like A Great Graphic Designer,” a prolific design writer in outlets like NYT, Fast Company, and Design Observer, chairs the Masters In Branding program at SVA (co-founded with Steven Heller), and hosts a long-running podcast called “design matters” which has done 265 episodes over 10 years with legends and icons like Michael Beirut, Stephen Heller, Chip Kidd, Massimo Vignelli, Isaac Mizrahi and Malcolm Gladwell. And that’s just the biggest headlines – there’s a ton more I’m leaving out, and I feel terrible about it but we’d literally be here all day if I listed all the amazing stuff she’s done. The bottom line is, if you look up “badass designer” in the dictionary, you’re definitely going to find Debbie’s picture there.

Lesson Plan

  1. 01

    If Not Now, When? with Debbie Millman


Meet Your Experts

Chase Jarvis

Chase Jarvis is a well known photographer and entrepreneur. As a photographic master, he is regularly cited as one of the most influential photographers of the past decade, having won numerous awards from Prix de la Photographie de Paris, The Addys, The Lions, Digiday, The Advertising Photographers of America, and The International Photography Awards among many others. ... read more

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Debbie Millman

Named “one of the most influential designers working today” by Graphic Design USA, Debbie Millman is also an author, educator, brand strategist and host of the podcast Design Matters. As the founder and host of Design Matters, the first and longest running podcast about design, Millman has interviewed more than 250 design luminaries and cultural commentators, including Massimo Vignelli, Milton Glaser, Malcolm Gladwell, Dan Pink, Barbara Kruger, Seth Godin and more. In the 11 years since its inception, the show has garnered over a million download per year, a Cooper Hewitt National Design Award and—most recently—iTunes designated it one of the best podcasts of 2015. ... read more

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