Stop Hiding Behind ‘Not Ready’ and Learn How to Begin Anyway

The Chase Jarvis LIVE Show

Chase Jarvis

Celebrity, Art, Career, Creativity, Money, Entrepreneurship, Self-improvement, Education, Careers, Writing, Interview, Investment, Influencer, Business, Photography

4.8 • 641 Ratings

🗓️ 16 April 2025

⏱️ 55 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

In this episode, Debbie Millman shares how to begin—even when you feel unready, unqualified, or full of doubt. Debbie is a designer, author, educator, and host of the pioneering podcast Design Matters. She's also the chair of the Masters in Branding program at the School of Visual Arts and editorial director at Print magazine.

We talk about the creative risks Debbie took later in life, why fear and shame shaped her early path, and how she found fulfillment by making deeply personal work—without waiting for permission. From the grief of losing family to the joy of marrying at 57, this is a raw, powerful conversation about love, legacy, and the courage to start—even if you feel like a mess.

Some highlights we explore:

The myth of readiness – Why waiting to feel “good enough” keeps us stuck in place.
Failures that shaped the path – From rejected applications to bad jobs, how struggle created space for clarity.
Creating without permission – Why Debbie’s most meaningful work began when she stopped waiting to be chosen.

Enjoy!

Transcript

Click on a timestamp to play from that location

0:00.0	I think the work that I'm proudest of is work that was completely self-generated.
0:06.6	Work that I wasn't really ever hired to do.
0:10.1	Work that I just did for myself that then over time doing it quite a lot, found an audience.
0:17.5	Like even the podcast, I was paying to do the podcast. And then with this effort with the book,
0:23.6	you know, I didn't start doing these little visual stories
0:25.6	thinking, someday I'm gonna get a book deal with this.
0:28.6	It wasn't it at all.
0:29.6	They were actually very personal, very scrappy efforts
0:33.6	that were truly just done for the sake of my own sort of spark of creativity trying to keep it
0:40.5	alive. This episode is brought to you by My Latest Book, Never Play It Safe. Right now, if you do
0:50.4	not have a copy of my latest book, I want you to listen to what Gary Vaynerchuk
0:55.0	said about my latest book. Building a life you love doesn't happen on accident. It's a process.
1:01.5	Few people know this process like Chase Jarvis does and never play it safe is the roadmap.
1:07.8	Or what Sophia Amaruso said. This book is a powerful compass for embracing risk and
1:13.4	creativity in all the aspects of your life chase shows us how to step out of our comfort zones
1:18.7	and become who we weren't meant to be here's a cool fact all of the best stuff in life is on the
1:26.2	other side of your comfort zone.
1:28.9	And never play it safe is a blueprint.
1:31.2	That's how I designed it.
1:32.0	It's a blueprint to get you there reliably over and over again.
1:36.6	It's not an accident that this was a national bestseller on, I think, four bestselling book lists.
1:42.0	That's because it is a roadmap. It's a blueprint, right? It's going to
	...

Please login to see the full transcript.

Previous episode | Next episode

Disclaimer: The podcast and artwork embedded on this page are from Chase Jarvis, and are the property of its owner and not affiliated with or endorsed by Tapesearch.

Generated transcripts are the property of Chase Jarvis and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.