by

Tim Ferriss

How to Design a Life — Debbie Millman (#214)

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debbie millman

“Hard decisions are only hard when you’re in the process of making them.” — Debbie Millman

For some of you, this may be the most important podcast episode you ever listen to. I don’t say that lightly.

It has nothing to do with me and everything to do with my guest, who walks us through gripping stories, tactical details, humor, pain, and emotional redemption. We cover some sensitive and extremely important ground.  Thank you, Debbie.

Graphic Design USA has named Debbie Millman (@debbiemillman) “one of the most influential designers working today.” She is also the founder and host of Design Matters, the world’s first and longest-running podcast about design, where she’s interviewed nearly 300 design luminaries and cultural commentators including Massimo Vignelli and Milton Glaser.

Debbie’s done it all. Her artwork has been exhibited around the world. She’s designed everything from wrapping paper to beach towels, greeting cards to playing cards, notebooks to t-shirts, and Star Wars merchandise to global Burger King rebrands.

Debbie is the President Emeritus of AIGA (one of only five women to hold the position in the organization’s one-hundred-year history), the editorial and creative director of Print magazine, and the author of six books.  In 2009, Debbie co-founded (with Steven Heller) the world’s first masters program in branding at the School of Visual Arts in New York City, which has received international acclaim.

We cover a lot in this discussion: how to recover from rejection, how to overcome personal crises of faith, class exercises from her most impactful mentors, and much more.

Please enjoy (and reflect on) this wide-ranging conversation with Debbie Millman…

Listen to the episode on Apple Podcasts, Spotify, or wherever you get your podcasts. You can find the transcript of this episode here. Transcripts of all episodes can be found here.

#214: How to Design a Life – Debbie Millman

Want to hear another episode with an influential podcaster? Listen to my interview with Stephen J. Dubner. In this episode, we discuss how to grow a podcast, the President’s actual influence over the economy, how virtual reality might affect education, and much, much more:

#199: Stephen Dubner — The Art of Storytelling and Facing Malcolm Gladwell in a Fist Fight

This episode is brought to you by FreshBooks. I’ve been talking about FreshBooks—an all-in-one invoicing + payments + accounting solution—for years now. Many entrepreneurs, as well as the contractors and freelancers that I work with, use it all the time. Head over to FreshBooks.com/Tim to get 90% off your FreshBooks subscription for 4 months.

This episode is brought to you by Wealthfront! Wealthfront is a financial services platform that offers services to help you save and invest your money. Right now, your cash can earn 3.30% APY—that’s the Annual Percentage Yield—with the Wealthfront Cash Account from its network of program banks. That’s 8 times more interest than a typical savings account at a bank, according to FDIC.gov as of 05/18/2026 (Wealthfront’s 3.30% APY vs. 0.38% average savings rate). Right now, for a limited time, Wealthfront is offering new clients that use my sign-up link an additional 0.75% boost over the base rate for three months, meaning you can get up to 4.05% APY, limited to a $150,000 balance. Terms & Conditions apply. Visit Wealthfront.com/Tim to get started. 

The Cash Account, which is not a deposit account, is offered by Wealthfront Brokerage LLC (“Wealthfront Brokerage”), member FINRA/SIPC. Wealthfront Brokerage is not a bank. The 3.30% Base APY on cash deposits is as of January 30, 2026, is representative, subject to change, and requires no minimum balance. Wealthfront Brokerage sweeps cash balances to Program Banks, where it earns the variable base APY. The Direct Deposit Plus Investing Program from Wealthfront Advisers LLC and Wealthfront Brokerage LLC provides eligible clients a 0.25% APY increase above the base APY on eligible Cash Account balances (up to an overall boosted rate of 4.30% for a limited time when including the three month 0.75% APY boost for new Cash Account clients) when you direct deposit $1,000/month plus maintain a funded investing account. Wealthfront may change or end the program at any time and determine eligibility at its discretion. Terms and conditions apply. Full details for both promotions at wealthfront.com/promo-terms.

Tim Ferriss, who is not a client, receives cash compensation from Wealthfront Brokerage LLC for advertising and holds a non-controlling equity interest in the corporate parent of Wealthfront Brokerage LLC, which creates an incentive that results in a conflict of interest. Tim expresses his own opinions and Wealthfront does not endorse, sponsor, or promote them. This ad may not reflect the experience of other Cash Account clients, and similar outcomes are not guaranteed. Investment advisory services are provided by Wealthfront Advisers LLC, an SEC-registered investment adviser. Securities investments: not bank deposits, not bank-guaranteed or FDIC-insured, and may lose value. See full disclosures here. 

QUESTION(S) OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.

Scroll below for links and show notes…

Selected Links from the Episode

  • Connect with Debbie Millman:

Twitter | Website | Facebook | Instagram | Design Matters Podcast

Show Notes

  • As someone who has such a diverse tapestry of backgrounds, how does Debbie describe what she does to someone she meets for the first time? [07:14]
  • How a rediscovered childhood drawing predicted Debbie’s future. [09:13]
  • Debbie never set out to become a designer. [14:47]
  • On being thwarted by (and recovering from) initial rejection. [21:59]
  • What would Debbie say to her college self after her first big rejection? [26:38]
  • Empathy for those who reject us vs. feeling slighted by them. [30:53]
  • How did a lifelong desire to live in Manhattan figure into Debbie’s pursuit of happiness and influence what she does today? [36:54]
  • Debbie talks frankly about a history of abuse, and how it guided her desire for self-sufficiency and her work with NO MORE and the Joyful Heart Foundation. [44:34]
  • On coping with the aftermath of abuse and feeling profoundly alone because the ordeal seems “so surreal, and unnatural, and punishing.” [51:18]
  • Debbie tells us what it was like to be called a “corporate clown” and a “she-devil.” [57:57]
  • The lowest point becomes the catalyst: the journey from she-devil to godmother. [1:14:21]
  • Brochures can change the world. [1:18:07]
  • The origins of Debbie’s Design Matters podcast, and how it’s changed over the course of twelve years. [1:24:08]
  • Debbie explains the impact of Milton Glaser on the world of design and her life. [1:28:03]
  • Debbie shares “Your Ten-Year Plan for a Remarkable Life” exercise she modified from Milton Glaser and teaches in her classes. [1:33:51]
  • “Hard decisions are only hard when you’re in the process of making them.” [1:40:00]
  • Design Matters episodes Debbie recommends for people who might not know much about design. [1:49:50]

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