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

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