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

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 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…

#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 (stream below or right-click here to download):

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

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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

  • 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]

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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108 Replies to “How to Design a Life — Debbie Millman (#214)”

  1. I hope people also join the conversation in one of the numerous Facebook groups that have been created around Tim and his work.

  2. Thank you Debbie (and Tim.) I relate a lot with her early life and drive. I find it meaningful to hear these stories of healing and personal triumph; not only does it remind me that I’m not alone, but also how strong and expansive the human spirit is. She’s a warrior and her courage should be applauded as much as her many accomplishments.

  3. WOW !!! words alone cannot describe how i feel right now after listening to this podcast. Thank you so much for having her on your show and thanks to Debbie as well for sharing her life story with us. Again, thank you Tim, you are the best !!!

  4. This podcast is absolutely of super value Tim. The way Debbie puts in her “Ten-Year Plan for a Remarkable Life” shifts you into a reflective mode right away.

  5. Tim! I bought your new book to read while backpacking Southeast Asia and it’s way to heavy! I hold you personally responsible for the entire situation because I wouldn’t be here without the 4HWW and I wouldn’t have this stupidly heavy book I don’t want to leave behind if you could just stick to your investing!

    I’m going to need to leave it at a book exchange in Thailand.. any chance you can send me a digital copy so the heartbreak isn’t so real?

  6. Tim, I love your podcast and am willing to read Tools of Titans. It´s the next one waiting for me on my list 🙂

    Congrats for the great work

  7. I found you via another podcast and have begun listening to yours as well as buying Tools of the Titans, which I love! It was the perfect Christmas gift to myself. ありがとうございます

  8. a simpler version of the exercise can be any perfect average sustainable day, without exception or consequences ( e.g. if arm is broken, its not broken, can’t do crystal meth and heli skiing every day)

  9. Why children are able to draw a future life explains psychology theory of Eric Berne. Acording to his theory people unconsciously choose life path at age 6-10 by unconscious decition and later by unconsciously following that decition. Berne explains it in book What Do You Say After You Say Hello.

  10. As an architect and designer, I have great fascination for other creative people’s design process and just overall life design. I can’t believe I’ve never heard of Design Matters ! Might be because I live in France, and the podcast “culture” is not there yet.

    Anyhow, I loved the interview, must be one of my favorites. I was very touched by her sincerity when telling her life story. I related very well to the part where she explained how sensitive she was and how hard it was to take rejection. Inspite of fear, humiliation or shame, everything happens for a reason or at least, there’s always a silver lining if you care to look.

    Also, I did a version of the 10 year-plan a couple of years ago, I should definitely take a look back at it.

    To answer your QOTD, my favorite quote from the interview is : “In order to take that first step, you need courage and that’s much more important than confidence. So for all you who are waiting for that confidence to show up, take that first step in that moment of courage, even it’s abhorrent courage.”

    Off to listen to Design Matters !

  11. 1, “Aberrant moment of courage”

    2, “Don’t accept the first rejection ever – give yourself options”

    3, “Don’t ascribe to malice what can be explained by incompetence or busyness”

    4, “Ambiguity is always perceived negativity”

    I couldn’t choose one Tim, so here are my top four. If you use them as chapter headings you could write a narrative piece of a person on the first part of achieving their first dream.

  12. This is from my blog today…”She is also the survivor of some pretty horrific childhood shit. Debbie very pragmatically states, “I spent the first 18 years of my life in constant terror.” She continues to say that she doesn’t share this part of her life very often (a testament to Tim’s interviewing skills) because she has so much shame.

    Millman now does some work with the Joyful Heart Foundation. (an organization founded by Law and Order SVU’s Mariska Hargitay in response to the cries for help she received from REAL survivors of abuse) She states that her skills as a designer and branding expertise, dovetailed with her personal background, led her to feel as though “her whole life makes sense.”

    TIM’S RESPONSE? (and this is the money, this is MY TAKE AWAY)


    Tim, your interviews are long form, and I catch them when I’m walking, but dayum, you’re GOOD at what you do. . And the content of this podcast is proof of your skills. And maybe even proof that you have a soul. Bwahhahaaa.

    [Moderator: link removed]

  13. Hey Tim, I saw your pilot episode of gym cribs with Kelley Starrett and thought it was fantastic! I am biased however… having earned my MS in Kinesiology, working as a strength and conditioning coach with the Baltimore Orioles and being a local gym owner. My name is Trevor Howell and I live just down the road from you In Pebble Beach, California. Anyway, I have a beautiful home garage gym including a washer and dryer! Haha. Joking aside, if you would like to film another episode and you think my credentials and proximity are appealing then let me know! I also have access to some very cool flywheel technologies that you, the great tinkerer/explorer might be interested in.


    Trevor Howell

  14. Remarkable interview. Debbie is so honest about success and rejection. Love her idea of imagining life in ten years and reading it every year.

  15. Another great interview! Formula One style learning as usual! Tim, will you be contributing to the fight of Opiate addiction? Your approach towards learning and breaking subjects down could be a huge benifit to this epidemic. I encourge you to look at the dichotomy between use and medicinal treatments. Thanks bro!

  16. I wanted to have her instructions for the 10 year plan for a remarkable life written down so I transcribed them and figured other people would like the instructions as well:

    “It is Winter 2027. What does your life look like? What are you doing? Where are you living? Who are you living with? Do you have pets? What kind of house are you in? Is it an apartment are you in the city are you in the country? What does your furniture look like? What is your bed like? What are your sheets like? What kind of clothes do you wear? What kind of hair do you have? Tell me about your pets, tell me about your significant other, do you have children? do you have a car? Do you have a boat? Talk about your career? What do you want? What are you reading? What are you making? What excites you? What is your health like? Write this one day ten years from now. So one day in the winter of 2027, what does your whole day look like? Start from the minute you wake up, brush your teeth, have your coffee or tea, all the way through until minute you tuck yourself in at night. What is that day like for you? Dream big, dream without any fear. Write it all down. You don’t have to share it with anyone other than yourself. Put your whole heart into it. Write like there is no tomorrow; write like your life depends on it because it does. And then read it, once a year, and see what happens.”

      1. Frank Kern taught me this exercise years ago…I’m sure he got from someone else. Start by describing the perfect day….because the perfect day leads to the perfect wrk, day, month, year, decade, century.

    1. Outstanding! The way Debbie sets up the exercise is really powerful. Thanks for transcribing the instructions.

  17. I was very impressed with the 10 yr plan essay and brought tear to my eyes. I am 74 and will do this exercise and wish that I had someone to advise me when I was younger. Tim you are my favorite interviewer and I have purchased 2 of your 4 books, the 4 hr body and Tools are so usedful to people of any age. THanks for what you are doing.

  18. This episode was wonderful throughout, but I was most struck with how candid she was about her childhood assaults. As a male who has gone through similar traumas, I applaud you for working to help the foundations targeting preventing these sorts of abuses from happening, but especially focus on helping to rebuild the lives of the victims. You are truly an inspiration! I totally understand the feelings of being alone due to the abuse, and have been in therapy to focus on those feelings in myself. Thank you for sharing yourself with the podcast, and know that you have been a tremendous force for good in the world!

  19. My 10 year plan has 9 full pages of what I like a day to look like in the future. Amazing exercise. Only when we apply what we learn will we see a difference in our lives. Absolutely loved this interview. Big fan of the podcast and thank you for your service!

  20. Thank you, Tim and Debbie for sharing such incredible wisdom. Had goosebumps listening to her stories… Keep up the amazing work.

  21. Perhaps one of my all time favorite podcasts because Debbie shared timeless life lessons that often reaffirm how life happens for us and not to us. We might hold grudges or resent certain situations, but if we choose, they can serve as beautiful gifts to be opened in the future. Thank you Tim and Debbie.

  22. Hi Timothy – I just sent you an email on linked in (not business related but I didn’t want to post it on here – too embarrassing!)! Hopefully you make some time to read it! Enjoy the weekend. Moni B

  23. Thank You Tim !

    What would you suggest / advise for someone ( like me ) who lack imagination and are living by default , in going through the 5 year or 10’year excercise ?


  24. I was skeptical about the opening comment (“this may be most important podcast episode you ever listen to”) until I got 3/4 of the way through the interview. Nothing resonated until she described that exercise. I’m doing it now. I think it can be life-changing. It’s not a new concept (you yourself prescribe something similar in 4HWW) but for some reason the way she described me has given me the fire to REALLY do it and take it seriously this time. Thank you for another delightful episode – there truly is something to take away from every one.

      1. I’m 1hr 11minutes into it and still wondering “so where’s the ‘most important ever’ part coming. So I should listen to the rest of it?

      2. I just listened to the “10 year plan for a remarkable life” which starts at 1:33:51. In fact, I just started the sentence “It’s Monday in January 2027 and I woke up at 5am to go to the gym.” I like where this is going already.

  25. Strangely enough, my lesson was listening to her voice. It was warm, and drew you in, which one would not have expected from a NYer that was dealing with trauma and abuse. Instead of walls, she welcomes; I see that as a triumph in human spirit. Other lesson was the “where” you live. I don’t think that gets enough attention when people design their lives, and for some people it is the most important thing. For some, it is not. Good interview, I will have to go back and listen to her podcast now.

  26. Phenomenal conclusion to the podcast. This was the first time I had heard of Debbie Millman and Tim’s edification of her set the bar very high and it didn’t seem like it was going to get there until BAM! The 10 year exercise and Debbie’s decision making agony landed like a ton of bricks. Afterwards I listened to Tim on Debbie’s podcast and the two conversations combined make an extremely impactful whole. Tim’s tireless work and the insights from Tony Robbins, Ramit Sethi and Kamal Ravikant have kept me going when all I wanted to do is just throw in the ultimate towel.

    Thank you Tim!

  27. Wonderful podcast. Debbie’s experiences with rejection (or perceived rejection) rang true, particularly from my younger days. What Tim shared also seemed familiar. Good to know I’m not the only one and continue to learn to pause and reconsider. Thanks to Alex H for writing out the 10 year plan. I’ll certainly try it.

  28. Thank you so much for this one guys!

    I love you both!

    “Dream BIG.

    Dream without any fear.

    Put your whole heart into it.

    Write, like there is no tomorrow.

    Write, like your life depends on it.

    It does.

    Write and see what happens.

    It’s MAGIC.”

    I’m so fascinated and inspired by Debbie’s journey!

    I moved to Manhattan, NYC, from Siberia 6 months ago.

    Went through hell and now magic starts happening.

    I just felt I got to be there.

    That was my life path.

    I had to make it happen.

    That was my goal.

    This place making me more me and It’s only beginning…

    December 31st 2016.

    I wrote down EXACTLY what I want to happen now.

    Fitness/spokes model

    Online health business

    My own health products…

    My own show…

    And I am on my way…:) IT’s MAGIC!

    Thank you Debbie and Tim! Thank you SO MUCH!

  29. I’m happy to hear about Debbie’s success. It was very refreshing to listen to her honesty. I too jumped around after I (also) graduated from college in 1983. I’m on the West Coast but I can relate to a lot of her story. I too was always into being creative, and realize I still live my life that way, no formula wanted. I’m a bit too defiant to give up on my success story, even though I still goof up. Thanks, Tim, for your enlightening interviews and for showcasing some great people.

  30. I actually found that intensely uncomfortable to listen to, but fascinating and engrossing, non the less.

    Interesting point about how feeling that rejection is final, and the end of the story.

    I wonder how that idea develops in the mind?

    Well worth listening all the way, for the 10 year plan bit towards the end.

  31. There have been 3 Tim Ferriss podcasts that have had a profound, lasting impact on my life.

    #1 – Sebastian Hunger.

    #2 – Jamie Foxx.

    #3 – This one! Debbie Millman.

    Thank you Debbie, for being so open and candid! Tim – superb interviewing skills with this one (as always; x10 with this one). You did a fantastic job listening, delving deeper, and respecting Debbie when she brought up deep topics.

    The 10 Year Plan for a Remarkable Life is BRILLIANT – I will be writing my essay tonight.

    Tim, please do an Episode 2 with Debbie. This was beyond fantastic; I take my hat off to both of you!

  32. Perhaps one of my all time favorite podcasts because Debbie shared timeless life lessons that often reaffirm how life happens for us and not to us. We might hold grudges or resent certain situations, but if we choose, they can serve as beautiful gifts to be opened in the future. Thank you Tim and Debbie.

  33. Hi Tim !

    I got the best gift for my birthday after weeks of depression and feeling the lowest low for the first time ever in my life. Gift was finding your podcast…..(also my first podcast). I picked episode # 210. I immediately felt my life was and could be more than what I was thinking it to be. Since then I have got books (Rumi, Ernest Hemmingway, Tool Of Titans, 4HourWorkWeek, 4 Hour Body(audible)), started my morning pages, meditating and found myself being a whole new person. I got myself out of the dump that I found myself in and came out stronger. I continue listening to your podcasts and discovering myself to be capable of so much more, feeling wiser, stronger and courageous with each podcast. I am excited to see how I shape myself in the next couple of months with all these tools that I have gathered from your podcast. It amazing how through your work you have helped many like me by steering us towards such wonderful treasures of wisdom and saved us …or given us a new life.

    Thank you

  34. Tim – excellent interview! I had the honor of interviewing debbie as the first episode of my show as well. If you’re planning on a round two, there might be some bits you’d enjoy digging into:

  35. She seems like a very likable person. But your best ever podcast episode? I’m 1 hour and 10 minutes into it. So maybe it gets better.

    1. It’s definitely not the “best” for everyone, but for those dealing with similar issues or traumas, I would wager so.

      1. Totally agree and validated by the many comments.

        I just listened to the “10 year plan for a remarkable life”. In fact, I just started the sentence “It’s Monday in January 2027 and I woke up at 5am to go to the gym.” I like where this is going already.

        When are you coming to San Diego?

      2. Kudos to you, Tim, for making Debbie feel so comfortable to open up. It reminded me of your strategies for podcasting as explained in Tools of Titans.

        Thanks for everything. You are a constant inspiration for me!

        PS: The book has several references to Argentina (mate, Malbec, Borges) which shows you still have us in your mind. Need to come back here ASAP!

      3. was definitely best for me! I felt like it’s my story with a happy ending (especially Manhattan part) 🙂 gave me more inspiration.

  36. Tim, thank you sooooo much for this episode! As a female and as a graphic designer who graduated the same year as Debbie, I could really relate. She’s such a great speaker, so articulate, so easy to listen to. Loved listening to her journey, the lessons she imparted. It’s refreshing to hear someone other than a health or workout fanatic. That drawing she made as an eight year old? That is amazing!!!!!

  37. A punch in the nose of profundity here, thank you so much Debbie. And, so apt for early into January 🙂

    I started journalling daily since before Christmas during annual review (finally, thank Tim) and the exercise is scheduled for my longer sit next weekend. I hope to let you both know how the magic turned out in 5 years time!

    I most valued the discussion around the one most important thing – and Tim’s interjection on how we tend to underestimate “the where”:

    “humans tend to put why at the top, what somewhere lower and the where as an after thought. But the where is much more critical than we give it credit for and you can start there…the geography defines who we’re surrounded by all the time…”.

    For the ocean (surfing) and its eclectic searching soul, I left London from San Francisco six years ago and that decision explains much…

    Part II please!

  38. Wow. Thank you so much to both of you for this episode. Debbie – what wonderful insight, delivered with such sincerity and authenticity. Your description of the 10 Year Plan for a Remarkable Life was so much more powerful in audio format. It would not have moved me the way it did if I had read it in print. You really sold it.

    Tim – This is your best episode yet. Please keep this up. You really have something here.

  39. Brilliant podcast! Thanks Tim and Debbie, the 10-Year Plan was one my takes from this interview, I’ve recently working on that but this has expanded my perspective. Fantastic interview, thanks Debbie for being open about the life experiences you shared.

    Hugs from Australia

  40. OHMYGOSH!! I know I already posted my favorite take away: “We’re NOT alone!!”

    I also determined to do the Life writing exercise, TODAY. Historically, I have had trouble completing such activities, as I just had no vision, no hope, and didn’t dare to DREAM BIG. (that’s changing!!)

    So, today, this happened. LOL. Words are powerful. I’m sorry it’s long form, but dayum…sometimes I just have to tell the story!!

    FOUR YEARS AGO, dyslexia was NOT on my radar. I was a traditional classroom teacher in a 4th and 5th grade English Language Arts class. My journey to become a dyslexia therapist would not even be a thought in my mind or heart for 2.5 more years. (I am currently completing a post-grad 2 year program to become a certified academic language and dyslexia therapist. This program EATS MY LUNCH, but that’s another post)

    Today, THIS interaction popped up in my Facebook page memories:

    January 16, 2013.


    Walt Disney had dyslexia, which I had NO CLUE about at the time. I just knew that I loved fairy tales (still do) and that reading and writing them brought joy, imagination, and hope to both myself and my students.

    Be careful what you say. Words are POWERFUL. What are the stories we tell ourselves? Are we too fat? Too female? Too weak? Too drunk? Too poor? Too depressed? Too MUCH? Change your words, change your story, write your own fairy tale. YOU. DO. YOU. And I’m going to keep on doing me. As challenging as that has historically proven to be!

    Here’s to all the Walt’s in the world. And to Fairy Tales.

  41. Hi Tim. I thoroughly enjoyed listening to this podcast with Debbie. I was touched by her many challenges. She is a most resilient and courageous person. I learned a lot from listening to her and, while I’m 69-years old (and still doing the work I love), I will write out a day in my life 5-years hence. (At my age I don’t want to press with 10-years. There’s an old saying, “When (wo)man plans God laughs. Haha.) Here’s wishing you and Debbie much joy, success and good health in the many years to come. Peace and abundant blessings, Richard

  42. For me, your best interview so far Tim. Thank you Tim and thank you Debbie. I’ve done the 10 year exercise before but, from the starting point of ‘if money was no object’ Debbie’s starting point of ‘if you could do anything you wanted without any fear of failure’ is such a better place to start.

  43. Hi Tim, I would really appreciate if you could make a small audio of the thought exercise (remarkable life) in the same fashion you did with Tony Robbins gratitude exercise. I believe other people would find value in it as well. What do you think?

    All the best!

  44. Great episode, thank you both! I got so much out of it, and at a very challenging and, dare I say, critical point in my life.

    Weirdly, serendipitously, unexpectedly, I am in a middle of making big, critical decisions that I keep putting off; when all I really want is to travel the Dalmatian coast (I speak the language but my cat doesn’t) and have a go at a six month mini retirement project. So I did the obvious thing and bought Tools of the Titans. Wonderful stuff.

  45. Truthfully, when Debbie describes the Ten Year Plan, there’s a bit of podcast magic there. It just brings you into a meditative and reflective state.

    Thanks Guys!

  46. When I first started this episode I wanted to end it after 5 minutes. Not because it was bad but probably because I was not really listening. Today it started up automatically where it left off and WOW I am glad I continued to listen.

    One of the best interviews I have heard to date, specifically with regards of how rejection lead to major shift in Debbie´s life.

    I will be using the 10 year essay with my team as well.

    Thank you,


  47. I was very taken with the section about the 10 year plan and had started to write it. By chance I then heard Duncan Trussell’s interview with Jordan Peterson – about half way into that they talk about Peterson’s self-authoring program which seems to me like a much expanded version of what Debbie is talking about with added benefit of sections that explore your past and present to help to free you of psychological obstacles that are hindering you realising your plan. The Peterson interview is well worth listening to (he would be a great guest on Tim’s podcast) and also explore his website:

  48. Beautiful monologue by Debbie Millman. Sweet. Smart. Honest.

    She talks about healing, about shifting her negative inner voice to a positive one. When her inner negative voice whispers doubts and insecurities, she voices them out loud. ” I was trying to be sexy but that didn’t work.”

    Debbie might not have healed everything she needs to heal but she imposes the discipline of honesty on herself. Very few people openly share with others when they feel inadequate. Constantly striving to be truthful with oneself and others is the only true healing. The journey to process our shadow self and ‘heal’ never ends, there is one layer of shadow-self after another. The braver you are, the more honesty you can withstand. Debbie is a champ.

    I think the more spiritually evolved we are as human beings, the funnier we naturally become because pure honesty is hilarious. Debbie made me laugh so much. Her saying something and doing the opposite, being insecure, being overly self-aware, all of it is funny. We are all insecure, incoherent, and scared. Serious people are always the most scared and insecure ones and as they use seriousness to try n hide it. If you’ve got little to hide, you’re naturally funny.

    Thanks to Debbie and thanks to you.

  49. I did the exercise as a 5 year exercise I am not of college age anymore. I have been on a runner’s high ever. A copy of the link to my shrink, a copy of the link to my wife, and copies of the link out to a few friends.

    I highly suggest doing a list at the end of the exercise. It provided a ton of clarity for me while the prose was from the heart. I found writing as I looped back Debbie’s instructions was really helpful. Her voice, particularly during the instruction of “write like your life depends on it….because it does” gave the exercise additional meaning.

    Absolutely fantastic stuff! I will be returning to my list weekly and look forward to re-reading the prose next year.

    Much appreciated Tim! Looking forward to the inevitable part 2 with Debbie.

  50. Wow! I went through Debbie’s exercise and wrote (what looks like an essay) on “My Remarkable Life” in 2027. What a powerful exercise! I feel goose bumps with excitement and was left with a confidence that my dreams really will be my reality. I look forward to reviewing this annually.

    Tim – I am new to your blog and podcasts, but after just a few months of listening and reading The Four Hour Workweek, you have me hooked. (My husband has been following you for years now, and went to your latest live podcast in NYC, but I have been missing out all of these years, and kicking myself for not listening to you sooner.)

    I had a question for you or any others who read this post. (It’s not directly tied to Debbie’s podcast, but I was not sure how frequently the blog comments were read on prior posts that may be more applicable.)

    I have decided to open an e-commerce store and would like to find a mentor or coach who could assist me with some questions on the initial set-up. (I have done a lot of research myself, however I am almost bordering on too much research, and want some assistance in drawing me back in.) I have come across many self-declared “experts” in the field, but I’d like to work with someone who comes recommended, rather than just picking someone blindly(especially since some charge $1,000+). Are there any coaches or mentors that you would suggest?

    Thank you in advance,


  51. Hi Tim, excellent podcast! Ms. Millman mentions being in a long term psychoanalytic psychotherapy – I wonder how many of your other Titans are as well? I am a psychoanalyst & know the (slow, inexorable & deep healing) power of this practice. You yourself might be interested in psychoanalysis as subject for study. It is a very deep & very storied “life hack” method. Keep up the excellent work Tim!! Regards!!

  52. Tim, I have been an avid listener of this podcast for the last two and half years, but this episode brought tears to my eyes and so much inspiration. I started my career in graphic design and buried myself in my work at a young age to escape a similar upbringing. Just want you to know this podcast at least made a huge impact on one of your listeners, thanks for doing what you do!

  53. Im happy you dare to speak up. It tears up long buried childhood pains and abuse. But it’s needed. I can’t speak up as the person abusing me was my father and it would break my mother’s heart. I never had pro counseling on the issue. I think it’s time to reach out for help now, 26 years later. As I was hoping I’d forget it or the horror would go but it never did… So there is help out there. Thanks for sharing it.

  54. Tim, I have not finished listening to the episode; and I don’t want it to end. Thanks so much for having her; and thanks to Debbie for sharing so much. This one will probably be one of those that I want to back and listen often. She’s amazing, and my heart is broken for everything she went through. Looking forward to finish listening to it. Really, THANK YOU

  55. Debbie Millman – for 2 days I have been teaching my 4 classes to write their “My 10 Year Plan for a Remarkable Life”. Very remarkable, inspirational, and invigorating. Students quiet, talking about the task, questions, then “wow, I love this”, “can I take it home and work on it?”, and others stumbling, finding their way today. Thank YOU! I Love this picture! of you and Mrs. Obama. I was posting this on FB, but we are not friends there.

  56. Fantastic interview. I wonder if Tim and Debbie think the “10 year plan excercise” can also work magically for those of us who are not student age, I. e. at the beginning of their professional lives, but rather in the middle of their lives or at some sort of crossroads. Does it make sense to “dream big” if it’s not all out in front of you any more? Thanks for what you are sharing with all of us!

  57. Hi Tim. Thanks for a great episode.

    And thanks for probing her on the specifics of her practices. Particularly the 10 year plan exercise.

    And great call leaving the interview at that – on a good rep! Cheers!

  58. I absolutely loved this episode. My favorite pice besides the “remarkable life essay” is when she talks about rejection. “Don’t accept the first rejection ever”. She is amazing, she really has master a life designing and the way she communicates it is so touching and real. Great episode!

  59. Tim, after hearing you and Debbie’s conversation about Manhattan living and re-reading PG’s essay about Cities and Ambition from your rec via 5 bullet Friday, I immediately thought of a book exploring the same topic that I read last year and thought I’d recommend (although it’s likely you’ve already read!). It’s called “Geography of Genius”, by Eric Weiner. Aside from that, I’d also like to thank you for your body of work and the transparency with which you pursue Truth. Coming across your work as a Freshman in college sparked my own interest in continual personal evolution and truth-seeking and an intellectual curiosity that I don’t think I would have had the courage to explore so early and at such depths without your work. Keep up the good living man!

  60. In regards to your chosen quote at the top. That’s the worst quote I’ve ever read. You can’t more blatantly state the absolute obvious better than that.

  61. Great episode! Debbie mentioned a book at 1:11:40 called Cool Girl. I can’t find it! Does anyone know which book she’s talking about?

  62. Thanks for taking the time to record this. I really like Debbie’s distinction between courage (doing something the first time) and confidence (which comes from doing something repeatedly). I think this distinction alone can help people to feel as if they can take on something new.

  63. Thank you thank you! My mind is blown – this episode gets better and better and better as it goes on. Is it possible to get a transcript? My bf is hard of hearing and I would love for everyone I know to be able to access this amazingness, especially him! Thank you, again.

  64. I’d love to see an interview with Dr. Carol Dweck! This episode was fabulous, and based on the conversations you both had around bouncing back from challenging feedback I think you’d love her work. Plus I know her book has been mentioned by other guests.

  65. Hi Tim and readers,

    I completely understand that you may have other priorities and may not be able to respond to this, so thanks either way.

    First, I hope you and your family are well and safe. I am writing the “10-yr plan for a remarkable life” essay but stuck on professional aspirations. Do you have any tips that may help me? So far, I tried/am trying the following:

    – List things I enjoy and not enjoy doing in my personal life and current profession (Scientist)
    – Thinking of alternate careers (e.g., designer, blogger) and checking the same (what I might enjoy/not enjoy)

    If you need more info (e.g., draft of aforementioned exercises) to help me, please let me know.

    Also, is there a recommended time limit to complete the essay? I am guessing sooner is better but is 1 year too long?

    Best regards,


  66. Hi Tim

    I have been listening to your podcasts since last month.I have devoured 5 already . These are so damn helpful and are unfolding avenues for me

    I m from india, the land of karma. The good work you are doing will come as blessings mulrifold

    Debbie Millman was a phenomenal interview

    Thank you