Finding One More Molecule of Hope with Debbie Millman 7 | 20

Radical Candor: Communication at Work

Radical Candor

Business, Management, Careers

4.7 • 729 Ratings

🗓️ 14 May 2025

⏱️ 49 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

Growth sounds beautiful—until you’re knee-deep in failure, self-doubt, and a garden full of dead plants. Amy gets real with Debbie Millman—design legend, branding expert, and accidental gardener—to unpack the not-so-glamorous side of creativity, leadership, and learning to suck at something new. Debbie shares how screwing up (repeatedly) can actually make you better at just about everything and why success can kill your spark, how confidence actually works (spoiler: it’s not magic), and what gardening taught her about patience, failure, and asking for help. Her new book Love Letter to a Garden isn’t just about flowers—it’s about finding hope in the mess and meaning in the mistakes. Oh, and her wife, Roxane Gay, included a killer tomato sauce recipe. If you’ve ever felt stuck, scared, or unsure where to begin, this is your reminder to grab a shovel and just plant something already. Get all of the show notes at ⁠⁠RadicalCandor.com/podcast⁠⁠. Episode Links: ⁠⁠Transcript⁠⁠ ⁠Debbie Millman Debbie Millman: Creativity, Leadership And The Courage To Tend | Radical Candor Design Matters Love Letter to a Garden Connect: ⁠⁠Website⁠⁠ ⁠⁠Instagram⁠⁠ ⁠⁠TikTok⁠⁠ ⁠⁠LinkedIn⁠⁠ ⁠⁠YouTube⁠⁠ ⁠Bluesky⁠ Chapters: (00:00:00) Introduction Amy introduces guest Debbie Millman, designer, author, and host of Design Matters. (00:04:05) Starting Design Matters How Debbie started the podcast to reconnect with creative purpose. (00:07:17) From Maker to Manager The tough transition from doing creative work to leading others. (00:09:28) Communicating with Impact Why how you show up matters as much as what you say. (00:12:00) Feedback & Growth Learning to receive criticism and evolve from it. (00:16:48) Confidence Through Repetition Why confidence comes after doing — not before. (00:19:05) A Gardener’s Beginning How one creative experiment led to Love Letter to a Garden. (00:24:54) Learning to Ask for Help A turning point in accepting guidance and sharing vulnerability. (00:27:51) Hope Over Shame Choosing to keep going — one molecule of hope at a time. (00:31:20) Processing Emotions The value of feeling your feelings, not rushing past them. (00:34:40) Fulfillment in the Process Why lasting joy is found in the act of creating, not accolades. (00:38:06) Control & Chaos Using design and gardening as ways to find agency. (00:41:11) Harvesting and Sharing Turning garden bounty into nourishment and love. (00:42:55) Something to Plant Debbie’s parting wisdom: plant something—and let go. (00:45:54) Conclusion Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	Got a business problem? There's a TED Talk for that. Stay updated on everything business, on TED Business, a podcast hosted by Columbia Business School Professor Modupe Akanola. Every week she'll introduce you to leaders with unique insights on work, answering questions like, how do four-day work weeks work? Do Will a Machine ever take my job?
0:25.0	Get some surprising answers on TED Business wherever you listen to podcasts.
0:28.1	Hey, I'm Dr. Maya Shunker.
0:31.2	I host a podcast called A Slight Change of Plans that combines behavioral science and storytelling to help us navigate the big changes in our lives.
0:36.7	I get so choked up because I feel like your show and the conversations are what the world needs,
0:44.5	encouraging, empowering counter programming that acts like a lighthouse when the world feels dark.
0:52.3	Listen to a slight change of plans wherever you get your podcasts.
0:59.8	Hello, everyone.
1:01.6	I am Amy Sandler, principal coach and podcast host at Radical Kander.
1:06.5	Today, in addition to these headphones, I am wearing another hat, that of aspiring gardener.
1:12.7	And by aspiring, I mean I've got a fake tree in my office that doesn't need any water.
1:17.4	So I'm counting that as a win.
1:19.1	We are really here today to talk about growth, not just of plants, but really of creativity, of courage, of connection.
1:27.0	And I could not be more excited, more honored to welcome Debbie Millman to this conversation.
1:33.8	Debbie has been named one of the most creative people in business by Fast Company.
1:40.2	She is a designer, an author, illustrator, educator, a brand expert, also an executive fellow at Harvard Business School.
1:49.0	And you might know her as host of the incredible Design Matters podcast, which has been 20 years running.
1:57.7	Debbie's got her newest book, and let me pull this up here, love letter to a garden. And it is
2:05.1	exactly that. It is part memoir, part creative manifesto. It is chock full of wisdom about what it really
2:13.7	means to tend to the things that people that we love. So we're going to talk about gardening,
2:18.5	creativity, failure, leadership. Maybe there will even be some gardening horror stories. Welcome to
2:25.8	everyone listening and welcome to Debbie Milman. Debbie, welcome. Thank you, Amy. It's really lovely to be
	...

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