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.
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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
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