Podcast Summary: Daring Creativity. Daring Forever.
Episode: Dare to Imagine Your Future - Debbie Millman
Host: Radim Malinic
Guest: Debbie Millman (writer, designer, educator, artist, podcast host)
Date: September 29, 2025
Overview
In this engaging episode, Radim Malinic welcomes Debbie Millman, a multifaceted creative, to discuss the power of imagining your future, the role of courage versus confidence, the evolution of creative careers, and her iconic "Ten Year Plan" exercise. They explore how self-doubt, vulnerability, and fear intertwine with creativity, and why daring action—rather than waiting to be chosen—is at the heart of long-lasting creative impact. Throughout, Debbie shares practical wisdom, personal stories, and generous insights into her process as an interviewer, educator, and lifelong learner.
Key Discussion Points & Insights
1. The Ten Year Plan Exercise: Origin and Impact
[04:42–11:17]
- Debbie recounts taking a milestone summer intensive with Milton Glaser in 2005. Glaser’s assignment to write a five-year vision of one’s life, in detailed, day-in-the-life fashion, was transformative for her and many others.
- Debbie's initial essay listed big, audacious goals that seemed out of reach but, to her surprise, most were realized over the subsequent decade.
- She later evolved the exercise into a ten-year plan for her students, emphasizing its power in clarifying desires and intentions.
- The exercise’s "magical" effect is that it both inspires action and lets goals recede into the unconscious mind, only to manifest through ongoing effort and readiness.
Notable Quote:
“I think 13 years later, every single one [goal] came true... I’ve been teaching it ever since, changed it to a Ten Year Plan. And for whatever reason, of all the things that I do, people are mostly always interested in this.” — Debbie [10:30]
2. Life Stages, Self-Acceptance & Fear
[12:53–17:36]
- Debbie shares her reflection on how priorities, openness to experimentation, and self-perception shift with each decade of adulthood.
- Vulnerability in later decades becomes being afraid to look inexperienced or foolish, making it harder to begin new things.
- She distinguishes between the striving for external achievement and inner acceptance, noting age brings greater urgency and, sometimes, greater fear of running out of time.
Notable Quote:
“When we’re 20, we think we will [live forever]. When we’re 40, we hope we will. And when we’re 60, we know we won’t. That’s become the underlying mantra of my life right now.” — Debbie [16:37]
3. Courage vs. Confidence
[17:53–24:03]
- Debbie’s teaching mantra: courage is more important than confidence.
- Confidence comes from successful repetition; courage is necessary at the start when outcome is unknown.
- Human brains are wired to avoid uncertainty (reptilian brain keeps us safe through fear), making first steps hard but necessary.
- The creative journey is fueled by courage and hope, not by the certainty of success.
Notable Quote:
“Confidence only comes after the result. It never comes before. You need to have some faith in your own courage to buoy that courage up, to take that first step.” — Debbie [20:38]
4. Rethinking Failure and Losing
[24:03–27:35]
- The conversation explores that “losing” is trying and not getting the result, but "failing" is only when you give up on yourself.
- Fear is often perceived as a flaw, but Debbie reframes it as an involuntary, protective response.
- The only true creative defeat is abandoning your own journey.
Notable Quote:
“I think that failure—the only real failure—is when you give up on yourself. Everything else is losing or rejection and that’s fine... I never lost a game, I just ran out of time. And I loved that, because that’s a mindset.” — Debbie [25:27]
5. Deep Listening & Interviewing Process
[29:47–38:17]
- Debbie describes her meticulous research process: reading extensively, using podcast transcripts to prepare in-depth, meaningful questions.
- Her goal is to follow where the guest wants to go, building a conversational "billiards table" so each topic can be explored naturally.
- She values criticism and self-improvement, constantly evolving her interview style over 20 years.
Notable Quote:
“People think they’re listening, but really they’re just waiting for somebody else to stop talking until they can start talking again... Seek out criticism because you want to know what people don’t like about your work.” — Debbie [30:16, 31:34]
6. Creating Opportunities & The Importance of Agency
[47:31–51:13]
- Discussing AI’s impact, Debbie compares current anxieties to designers’ initial resistance to computers; AI can’t replace human soul or original thinking.
- Human creativity is rooted deeply in the brain and personal experience—AI is combinatorial, not original.
- Debbie and Radim agree that, as Chris Cornell once said, sometimes you have to "create your own dream band" when the world doesn’t invite you in—that is the true act of daring creativity.
Notable Quote:
“Any creative endeavor... starts in our brains, which AI has yet to master... AI is good at combinatorial creativity, not originality.” — Debbie [46:31]
“A lot of what I’ve created was because I wasn’t readily accepted or invited into the best band in the world… so I had to make my own way, and that was fraught at times and still is, but I’m glad I did it this way.” — Debbie [51:13]
Memorable Quotes & Moments (with Timestamps)
- “I never lost a game, I just ran out of time.” — Debbie quoting a football coach [01:08; 25:46]
- “Humans hate uncertainty, and I hate uncertainty.” — Debbie [13:54]
- “You can’t go into a supermarket and buy a box of confidence.” — Debbie [19:26]
- “Courage and hope—those let you start. Confidence comes later.” — Debbie [20:38]
- “Fear comes before failure. We’re not talking about fear after failure… That’s part of the involuntary behavior I told you about before.” — Debbie [27:35]
- “If it was not for everything you’ve been doing... potentially hundreds of others in this creative sphere wouldn’t be doing the same thing.” — Radim [02:57]
Timestamps for Notable Segments
- Debbie’s Origin Story & Ten Year Plan: [04:42–11:17]
- On Life by Decades & Vulnerability: [12:53–16:44]
- Courage vs Confidence: [17:53–24:03]
- Failure, Losing & Perseverance: [24:03–27:35]
- Interviewing Skills, Deep Listening: [29:47–38:17]
- AI, Creativity, and Creating Opportunities: [45:11–51:13]
Tone & Language
The tone throughout is candid, warm, and reflective, with self-deprecating humor and philosophical candor. Both Radim and Debbie balance vulnerability with practical optimism, encouraging listeners to embrace uncertainty, seek courageous beginnings, and create opportunities rather than wait to be chosen.
Summary
This episode is an inspiring guide for anyone—in any stage of their creative life—who’s ready to act with courage, imagine their future boldly, and build a career or project marked by both vision and generosity. Debbie Millman models the art of showing up, creating meaning from uncertainty, and daring to create your own opportunities. For aspiring creatives and long-time professionals alike, her insights on the power of planning, the reality of fear, and the necessity of soul in creative work are invaluable.