Radical Candor: Communication at Work
Radical Candor: Communication at Work
Kim Scott, Jason Rosoff & Amy Sandler
Finding One More Molecule of Hope with Debbie Millman 7 | 20
50 minutes Posted May 14, 2025 at 7:00 am.
) Introduction
) Starting Design Matters
) From Maker to Manager
) Communicating with Impact
) Feedback & Growth
) Confidence Through Repetition
) A Gardener’s Beginning
) Learning to Ask for Help
) Hope Over Shame
) Processing Emotions
) Fulfillment in the Process
) Control & Chaos
) Harvesting and Sharing
) Something to Plant
) Conclusion
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50:06
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Show notes
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:
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Amy introduces guest Debbie Millman, designer, author, and host of Design Matters.
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How Debbie started the podcast to reconnect with creative purpose.
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The tough transition from doing creative work to leading others.
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Why how you show up matters as much as what you say.
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Learning to receive criticism and evolve from it.
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Why confidence comes after doing — not before.
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How one creative experiment led to Love Letter to a Garden.
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A turning point in accepting guidance and sharing vulnerability.
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Choosing to keep going — one molecule of hope at a time.
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The value of feeling your feelings, not rushing past them.
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Why lasting joy is found in the act of creating, not accolades.
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Using design and gardening as ways to find agency.
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Turning garden bounty into nourishment and love.
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Debbie’s parting wisdom: plant something—and let go.
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