The Secrets, Tactics, and Creative Processes of High Performers and Achievers — Debbie Millman (#230)

“No amount of money, no amount of security is ever going to give you the sense that this is the right time.”

– Debbie Millman

This is round two for Debbie Millman, whose first interview on this show quickly became one of the most downloaded episodes of all time (listen to it here).

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.

This time around, Debbie answers the most popular questions submitted by you, the listeners. Topics include:

  • How to turn down stability for opportunity.
  • How Debbie made the leap and continues to try new things.
  • How to outsmart the competition in any job.
  • The future of graphic design.
  • Debbie’s own personal creative process.
  • The most valuable lessons Debbie has learned about designing an ideal life for herself.

Here’s Debbie Millman’s round two. Enjoy!

You can find the transcript of this episode here. Transcripts of all episodes can be found here.

#230: The Secrets, Tactics, and Creative Processes of High Performers and Achievers -- Debbie Millman

Want to hear my first episode with Debbie Millman? — Listen to this episode, where we discuss how to recover from rejection, how to overcome personal crises of faith, class exercises from her most impactful mentors, and much more. (stream below or right-click here to download):

#214: How to Design a Life - Debbie Millman

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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

  • What if, while writing out what life will look like in ten years (Debbie’s exercise from the first episode), multiple potential lives emerge? How do you choose the best one? [06:57]
  • Is there a right time to turn down stability for opportunity? [08:27]
  • How can someone avoid becoming a commodity and stand out in a ruthlessly competitive market? [13:23]
  • The future is not specific to — or barred from — any discipline. [15:14]
  • How can we prevent ourselves from being paralyzed by the act of creation — especially when we feel like our work pales in comparison to the work of others? [15:34]
  • How does Debbie cope with imposter syndrome? [18:03]
  • What’s the one thing you want more than anything that you’re willing to sacrifice everything else to get? [18:40]
  • What is Debbie’s creative process? [20:37]
  • The intentional first impression. [22:23]
  • How does Debbie ensure a healthy balance between work and play? [29:26]
  • Debbie’s favorite visual artists? [33:10]
  • Common threads Debbie has noticed in her interviews with creative high achievers. [33:24]
  • What are the qualities of a good design student? [34:51]
  • Who’s the first person to come to mind when Debbie hears the word “successful?” [35:23]
  • Something Debbie believes that other people think is insane. [36:02]
  • Favorite documentary or movie. [36:32]
  • Morning rituals: her first sixty minutes of the day. [36:59]
  • Obsessions explored on evenings and weekends. [37:31]
  • Best investment of time, money, energy, or other resources. [37:52]
  • Notable quotes Debbie lives by or thinks of often. [38:43]
  • What would Debbie’s billboard say? [39:26]
  • What advice would Debbie give her younger self? [40:43]

People Mentioned

The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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22 Replies to “The Secrets, Tactics, and Creative Processes of High Performers and Achievers — Debbie Millman (#230)”

  1. Tim, what really resonated to me in this podcast was the concept of “multiple callings”. Having been a graphic designer for nearly twenty years now and more recently embarking on a journey in acting (while exploring many other endeavors in-between), I’ve found that the natural evolution of a person’s being is to explore multiple pathways while allowing commonalities between these pathways to form organically. I’ve recently developed the need to blog about my experience in overlapping ambition(s). Guess that’s my triune brain in action eh?

    In other words, I feel it’s perfectly acceptable to do multiple things simultaneously. Usually they end up complimenting one another anyway. Personally I call this process “Inbetweening”. Going back to when I first read the 4-Hour Workweek, Tim I believe you refer to this on the grand scale as “lifestyle design” – using time and mobility to pursue your ambitions in cyclical interests.

    I’m now inspired to write more about this. Thank you for that inspiration.

    1. Hi Rio,

      This is exactly how I would put it. Thank you for sharing and I agree that the natural evolution of a person’s being is to explore multiple pathways…eventually you will filter out your “callings” if not form it into a new calling.

      1. Hi Vincent,

        My pleasure. I always knew that my path in life would not be completely linear but consist of many branches and overlapping pathways. I know now that there are ways to fuse multiple callings into a grander and greater one.

        Debbie had a quote, “Everything worthwhile takes a long time.” Well, not just a long time but a lifetime. The flames of your dream’s passion never die out so do whatever you need to feed and fuel them as you evolve.

  2. This was one of maybe two episodes that I have ever immediately listened to a second time right after the first. Fantastic episode! My favorite quote is the same one highlighted in the show notes: “No amount of money, no amount of security is ever going to give you the sense that this is the right time.” Even if she had spent the entire 40 minutes repeating just that sentence alone, it would have been worth the listen. Thanks again to both Debbie and Tim for this wonderful Round 2! PS – it was nice to hear one of Tim’s high-achieving guests whose morning routine consists of getting their coffee and taking the dogs out to pee. Glad to know I’m not the only one. 😉

    1. Yeah. Love this episode but can’t think of a guest and sponsor more diametrically opposed. Seems odd. Oh well, can’t complain, it’s quality free content!

  3. Another powerful episode to remind that our most important decisions, energy and motivations are spiritual, clear and from deep within rather than external. An attitude and stamina, more than a tactic or trick to “success” (or, more simply, living well).

    All if we can keep at bay the nibbling of fear.

  4. Please could you try and get someone from the Metal band Tool on, they are all world class musicians and I feel they would be a great fit for this podcast.

  5. Dear Tim,

    I am a drunk panda right now.

    You recently asked which cities you should go to on a tour. I would encourage you to come to London.

    I don’t say this as a Londoner, with the tubes and the fumes and the over-cooked beef. I say this as a Scotsman living in London, a different breed of haggis, a man free of venereal disease and with the childlike excitement of life not yet sucked from my very marrow. Coming from a land of noveau cuisine like the battered mars bar and cheese on chips, I stand before you and implore you, Tim, Timmy Tim Tam o Shanter (look up the poem) why not pay a visit to our fair shores? Come drop some wisdom pearls on the people of London.

    In return, I pledge (as a Scotsman living here), to bagpipe outside your event. Such melodic and beautiful tones you won’t have heard, Tim. People will come from far and wide to ask ‘who makes this great music?’ and like the disturbingly pied piper tale, citizens of the world will follow me into your event. After the event, we will go for a whisky and I will teach you the way of the Scotsman

    I only send one such an invitation every century so hoping you accept.

    Slangevar and thank you for your advice thus far.

    Kind regards,

    E. Peebles

  6. Debbie Millman is a gem. Thanks for the second show, Tim! My favorite part of the show was when she talked about confidence being overrated and that having courage moves you forward. That’s given me the inspiration to embark on a new discipline that I have been holding back on because I’ve lacked the courage. Debbie really hit home when she talked about her best quote, “Everything worthwhile takes a long time”. Anything too easy isn’t challenging-time is a great teacher!

  7. For anyone who might have wanted to do the “Intentional First Impression” Exercise, here is an edited transcript:

    The intentional first impression. [22:23]

    How do I want to be perceived?

    What is that first perception?

    Write two paragraphs.

    The first is what you believe your first impression is, how you show up and what people perceive about you.

    The second is what you want your first impression to be.

    This culminates in writing a statement about what you project today and what you project tomorrow.

    For example, I might write: “today I am shy and recessive; tomorrow I’ll be more Curious and Engaging.”

    This Debbie calls this the “Intentional First Impression”

    We should be able to determine how we come across in a much more ownable and decisive way. Don’t leave it up to others to determine who you are or how you show up think about how you do this, if you actually create a conscious plan to be you on your best day when you show up, then you will be able to show up that way.

    It’s not about manipulation; it’s about intention.

    I also asked my students to determine the three-word combination that could only describe them.

    This should be an accurate and deep expression of Who You Are.

    The three words should be reflective of your full self, not just your best self.

    So the word should be cognizant of your strengths as well as what you might perceive as your weaknesses – but I find that your perceived weaknesses actually give us an opportunity to peer into a part of yourself that is really meaningful, if we dig deep enough.

    For example, I had a student that identified that one of her words of the three was know-it-all. I asked her to deconstruct why she was like that and she identified that she came across as a know-it-all because she was really insecure about being smart. She wanted to be perceived as smart. What that meant was that she needed to be perceived as smart and didn’t just accept the fact that she was smart, that harbored a suspicion that she wasn’t smart enough. That she wasn’t as smart as people around her. Coming across as a “know-it-all” she was compensating for this deep-seated fear that she wasn’t smart enough.

    Just knowing that, facing that feeling that she wasn’t smart enough allowed her to really understand whether or not that was valid and she wasn’t coming then out of aggression or manipulation. She was understanding that her need to do that was really trying to cover up a feeling that may or may not be accurate and if it wasn’t accurate, why would she need to do that?

    If it was accurate, what you need to be doing that would allow her to feel or be smarter and improving that would help her stop having to compensate for something that may or may not be accurate.

    So think about what those three words can be. There should be some tension in those three words. Ultimately that unique combination, if you really do this successfully should be something that only could be used to describe you. But part of that is being able to identify some of the things that you are afraid of others knowing about. So spend some time with this exercise, first been some time thinking about what your intentional first impression is and then spend some time thinking about what are the three words that only could be used to describe you, taking into account that some of what you perceived to be weaknesses are areas that are available to you to consider more honestly and become stronger around.

    1. “If it was accurate, what you need to be doing that would allow her to feel or be smarter and improving that would help her stop having to compensate for something that may or may not be accurate.”

      I find this part confusing. Can you please clarify for a non English speaker?

      Many thanks. And thanks Tim for the excellent podcast.

  8. Hey Tim,

    My name is Steven Shoemaker. I work at WeWork Domain in North Austin. You were recently in our downtown Congress building during SXSW and I rushed over there but didn’t get a chance to meet you. I just wanted to say that I am a huge fan of yours and I’m loving tools of titans. I interact with a lot of business owners and I recommend that book to anyone who will listen. No reply necessary, just wanted to let you know your work is appreciated.



  9. Design a life – Design a day

    Tim (and co), I loved your pod with Ms. Millman, and I appreciate you bringing her back to outline writing out a life. Thank you. Thanks to Ms. Millman. In putting forth what I want my days to look like in 10 years, I am looking to optimize my days now.

    I have about a 30 min block in my day where I want to insert some intense cardio workouts. Time is limited to 30 min. Any suggestions for exercises, or direction for resources in prior podcasts, the 4HWW, 4HBody, 4HChef? Ferriss community – thoughts?

  10. Awesome podcast Tim! Hats off to Debbie! I have learned a lot especially now that I am getting torn between “callings”. I think following these callings is a filtering process, that by trying all these callings, will lead you to what you will eventually do for the rest of your life. It could be one of them or a combination of all of them.

  11. “I start out with a desire to make something”… “And I have a vision for what that is. Sometimes that vision happens really fast, and it comes when I have been marinating, germinating, and thinking and thinking and thinking, and sometimes it comes really slow after doing exactly those same things and feeling really helpless that I’m never going to come up with an idea. The one thing that I can suggest is that if you are stuck, take a walk. Walking really helps me generate ideas. The more I walk the more ideas I have. So in terms of approach, think about what you want. Think about what it is that you want to make. Think about the end game. What does the vision of that look like, and then either start doodling, start drawing, start making, start sketching, start pulling your hair out. (*laughs*) Whatever it takes to get that process started, and then keep going until you feel like you have something worthwhile. That might take an hour. That might take a day. That might take a year. That might take a lifetime. But I think that if you enjoy the process of making, the fact that you don’t have a result makes it somewhat easier. But I say ‘somewhat’ because I think that the whole idea of making anything in the first place takes a great deal of courage.” -Debbie Millman

  12. Debbie, you mention that one of your philosophies is to say YES to everything. I have often heard many other people say that too many people actually don’t say NO enough. Even on one of Tim’s previous podcasts, with Derek Sivers, one of the big takeaways was “Hell yes, or no!” ( How do you think about saying yes to lots of opportunities but also guarding your time?

  13. Debbie – You have no idea how much your message and comments in the podcast meant, really hit home at a time that I needed boosting. Thank YOU!

  14. I wonder what people like Post Malone do, what is their creative process and do they workout etc. etc. ?