When to Quit – Lessons from World-Class Entrepreneurs, Investors, Authors, and More (#254)

“Remember: it’s not a failure until you accept defeat.”

-Debbie Millman

I’m very excited to share this episode. It’s our first “roundtable” approach to discussing a single topic. This came about when I asked 5-Bullet Friday subscribers (sign up here if you’re interested) to send me questions, and one that stuck out was: Where’s the line between stubbornly pursuing an idea that isn’t working and the patience and persistence needed to actually make it work? In other words — when should you give up and quit and when should you push on?

Since this is something I myself have struggled with, I came to the conclusion that I should reach out to people who might have a better answer. So, I sent the question to the following entrepreneurs, authors, and innovators:

Their answers are a thorough overview of how to assess your own ideas and opportunities, and determine which ones are worth pursuing. Enjoy!

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

#254: When to Quit - Lessons from World-Class Entrepreneurs, Investors, Authors, and More

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

This podcast is brought to you by Shopify. With the help of Shopify, many readers of my blog — first-time business owners — have ended up making millions of dollars each with their side gigs. Back in 2009, I helped create Shopify’s Build a Business, which is now the world’s largest entrepreneurship competition.

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Listeners to this show can go to shopify.com/tim to sign up for a free, 30-day trial and gain access to video courses that will help you get started — including “How to Quickly Start a Profitable Dropshipping Store” with Corey Ferreira and some goodies from me. Check it out at shopify.com/tim today!

This podcast is also brought to you by 99Designs, the world’s largest marketplace of graphic designers. I have used them for years to create some amazing designs. When your business needs a logo, website design, business card, or anything you can imagine, check out 99Designs.

I used them to rapid prototype the cover for The Tao of Seneca, and I’ve also had them help with display advertising and illustrations. If you want a more personalized approach, I recommend their 1-on-1 service. You get original designs from designers around the world. The best part? You provide your feedback, and then you end up with a product that you’re happy with or your money back. Click this link and get a free $99 upgrade. Give it a test run…

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 Scott Belsky:

Website | Behance | Twitter

  • Connect with Seth Godin:

Website | Twitter

  • Connect with James Altucher:

Website | Twitter

  • Connect with Debbie Millman:

Website | Twitter | Facebook | Instagram | Design Matters Podcast

  • Connect with Adam Robinson:

Website | Twitter

  • Connect with Chase Jarvis

Website | CreativeLive | Twitter | YouTube | Facebook | Instagram 

  • Connect with Rhonda Patrick:

Found My Fitness | Podcast | Twitter | Facebook | Instagram

Show Notes

  • Why Scott Belsky stuck with Behance even when it was going through rough patches. [08:41]
  • Seth Godin thoughts from his bestselling book about quitting. [13:24]
  • James Altucher tells us why you sometimes want to quit when you’re ahead. [19:53]
  • Debbie Millman on pursuing dreams over conforming to the comfortable. [38:58]
  • Adam Robinson ponders the options we all face: to persist, to pivot, or to quit. [47:11]
  • Chase Jarvis on intuition as the most powerful tool we have as humans and the science behind it. [57:12]
  • Rhonda Patrick gives us some insight on why making a counterintuitive choice ended up working in her favor. [1:11:19]

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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42 Replies to “When to Quit – Lessons from World-Class Entrepreneurs, Investors, Authors, and More (#254)”

  1. PHENOMENAL!! This format is the perfect complement to the regular podcast episodes and is exactly the kind of approach I had been hoping we’d get with Tools of Titans. It exemplifies two things Tim does best: find good questions, and ask them of the most qualified people, in order to build a repertoire of the best and most refined thought processes on the planet. In Tim’s regular interviews, we get to be inspired by the stories and personalities of the podcast guests, which is great and highly engaging. But, while inspiring, when it comes to actionable results, it requires more sifting through in order to find the applicable elements you can use in your daily life, and they aren’t always easy to track down in the right context when you need them. In contrast, this format takes one big, pressing question and gives us several angles of approach that feel really tactical and useful to solving problems. This one episode just helped me to answer several questions I’ve been struggling with when it comes to my personal, professional, and humanitarian endeavors. I can foresee a wonderful library of questions that would be an incredible powerhouse to refer to when we find ourselves stuck in any particular rut. PLEASE DO MORE!

    Here are my favorite points and questions that each guest offered to address the question:

    Scott Belsky

    — Is the difficulty you’re running into causing you to question your core assumptions about the project?

    — Knowing all you know now, would you pursue this over again? Or knowing all you know now, would you do something different?

    — Are the sunk costs all that’s keeping you from quitting, because of what you’ve invested?

    Seth Godin

    — It’s a waste of time to repeatedly start things and then quit them in “the dip” (the hard part that makes it worthwhile).

    — It’s important to differentiate between a dip and a cul-de-sac (dead end). Is there forward progress? Are you building assets? If so, it’s more likely to be a dip.

    — Commit to not stopping in the dip and to practice differentiating from dead ends.

    James Altucher

    — Everything has a half-life; if you’ve passed the peak, it may be time to let a project go rather than wait until it ends out of necessity.

    — You may want to quit when things are going OK: For example on a project where nothing is “wrong,” but where it isn’t getting better in proportion to expectations of the market.

    — When you feel you’ve learned everything you can learn can be a good indicator of when to move on.

    — Alternatively, sometimes you’re at the top of a learning curve where every incremental improvement is difficult, but it’s the appreciation of the subtleties that makes it worthwhile in spite of the slowdown.

    Debbie Millman

    — If you feel that you are not capable of achieving your dreams, is it because you are really not capable of achieving them, or because you’re really afraid to put your whole heart in and try?

    — What scares you more: heartbreak, or rejection? What scares you more: resentment, or rejection? What scares you more: regret, or rejection?

    — This is the thing about resistance: If you’re doing what you think you should be doing rather than what you want to do with your whole heart, you are not persisting, you are resisting the truth about who and what you are.

    — If you are doing what it takes to make your heart sing, never, ever give up. Remember, it’s not a failure until you accept defeat.

    Adam Robinson

    — If you don’t get what you want, it’s a sign that either you didn’t want it enough, or you tried to bargain over the price.

    — Obstacles are what you see when you take your eye off the goal.

    — Connect your dream to a mission that is larger than yourself and it can give you the perspective not to quit too soon.

    — Sometimes there are grey areas: You may not need to quit entirely, but you may need to pivot your focus.

    Chase Jarvis

    — Intuition: We are recording billions of data points moment to moment creating an archive of those, which our unconscious mind is drawing upon when we encounter questions to which we don’t have all the answers ready in our working memory.

    — Two questions to ask yourself: 1. Is it working / am I making progress? 2. Do I believe deeply in the mission/vision?

    — Knowing that what we’re working on is the right thing when we are all limited by time is a massive advantage.

    Rhonda Patrick

    — Impact as a criteria: Do you have multiple options to achieve the same goal with different levels of impact? For example, if you value teaching, professorship provides it. But a moderately successful video can reach far more people than a large classroom.

    — Having data to be able to assess the proportionate impact of divergent paths before actually having to make the decision is extremely helpful.

  2. Tim,

    So very helpful as I take a bit of a sabbatical from my business to decide this very issue. Timing could not have been more providential. Dip or coldesac? That was a crucial distinction. And the “smoking your own crack” and cognitive bias was a helpful metaphor.

    Over the next couple months, I may be revisiting this episode as I figure out my next steps.


  3. Had the chance to listen to this as I was driving today, and I absolutely loved this. Thru you, many of us get to tap into the mastermind genius that you have created, and this is yet again a way for that mastermind to present itself in a simple question and multiple ways to answer it. Looking forward to more of these in the future!

  4. The lack of the usual conversational back-and-forth detracted from the episode. I found myself thinking, “I bet Tim would stop to ask X if this were an interview.” Most podcasts I listen to are interviews with the back-and-forth, making them more listenable.

    If Tim is willing to have a 15 minute conversation with each of the guests on the same topic, that would be superior.

  5. A great approach, I would love to hear the question answered from former military commanders, such as Mark Divine, Jocko Willink, or Stan McChrystal as the experience of surviving and leading combat missions dramatically accelerates the processes described. They have had to deal with concepts of mission creep, dips, and dead ends that have life or death consequences. I am listening again, as this may be the most pivotal and thought provoking podcast that speaks to my present situation. -Thanks Tim, you have planted many a seed to sprout into greatness.

    1. Agreed. All of these guests, through no fault of their own, are examples of survivorship bias. The military guys would definately have more perspective on the flip side, quitting at the wrong time, or not quitting fast enough. With deadly potential consequences.

      That said, this was a fantastic episode. I particularly like the concept of quitting when on top or ahead. Most people listening strive to be better, and though we have goals, we rarely contemplate when to quit/pivot from a current pursuit, which gets you in the fabled guided cage.

  6. I’m French People and I really like to learn with your blog. It is very interesting and inspiring ! Thank you so much for this !

  7. @timferriss

    – I loved James Altucher talking about quitting while on top like Jerry Seinfeld, and when you run out of creativity or vision.

    – I also loved the comment about opportunity costs.

    – Tying your pursuit to a bigger cause than yourself.

    – What do you fear more: Regret or Rejection?

    – Perhaps instead of quitting you should pivot: become a coach instead of giving up professional athlete dream.

    I recently decided to discontinue my Olympic dream of competing in the 2020 Tokyo, Japan Olympics in the Pole Vault. Falling in the air after jumping very high is something I love and it excites me more than anything in my life.

    I have been stagnant (like James talked about) for years. I’ve been persisting and I don’t want to pass up huge opportunity costs to grow myself professionally. I know that I would not be happy to only have my wife support the both of us while I train for the Olympics… I like to provide. I know that by pivoting now, I can funnel my passions into business and provide my future kids with the chance to train very young and coach them if that is something that they love.

    I’ll be listening to this again soon. Thanks for the great post.

    And remember, NEVER QUIT!

    Unless it’s






    Or there’s something better out there for you!

    – Drew

  8. It would be cool to hear an episode about “what the listeners learned”

    That is, asking your listeners what they have taken away from the lessons/strategies/ideas provided by you and your guests. How listeners implemented lessons in their lives and what difference that has made.

  9. Tim,

    Thanks so much for this episode. The timing for me was uncanny. The experience, as well as advice, that each guest shared was helpful to me. Thanks again for the work you do.

  10. Love everything you showcase on your podcast. I love 5 bullet Friday,also. I am I corporate sales & I love

    sales & selling. My question I would like to ask you,

    as an experienced sales executive 20+ yrs dealing

    with executives from Fortune 500 companies, how do you motivate younger sales executives to share the

    vision to success I have experienced?

  11. Fascinating! Thank you. A great reminder that the fear of failure is often the greatest obstacle to success.

  12. Debbie’s portion was sorely needed today. It even stopped streaming for about 10 seconds at a particularly paramount part, as if the universe was demanding me to think about the preceeding sentence. I listened to it three times in a row and was in tears on the way home. Thank you, Debbie….

  13. Tim, this podcast was just awesome. Each of the participants spoke to a particular part of me and at the end I felt a bit down for having let myself turn 56 years old without following my true passion.

    I re-accept my role as a teller of stories that are simple and moving and lasting. I need to get to it.

    Thank you.

  14. Thanks, not sure I like the audio format in the latest podcast as much. I personally like hearing a conversation more and I like hearing your input and questions too. But that’s just me. I do have a question. Not that you have time for my question. I get that. If I never hear from you, I understand… I’ve been writing now, for small but growing number of horse riding enthusiast. I’m a trainer/teacher and I love to write short inspirational articles. Lately I’ve been getting more people sharing my stuff. It’s great. But the not so great part is, I’m also getting more criticism from new people who either don’t like what I say or the way I say it. I get more good than bad so I feel I shouldn’t be so sensitive. But I am. How do you deal with criticism? How do you read a negative comment and then go about your day without the constant reminder that someone thinks you suck? I get over it. I’m not depressed about it, but it does carry weight for longer than I want it to. What are your or your colleague’s tricks for dealing with criticism? How do you manage comments in the social world or on your site? Do you delete them? Do you respond to them? Shit, that was more than one question. Sorry. and thanks for doing what you do.

  15. Great format. A question I would like in a future episode – How do you exercise your intuition muscles? I am a business owner but rarely get the “gut feeling.” Any ideas on how to improve this ability would be appreciated.

  16. If we are talking “world class” can we have folks from some other parts of the world and people of color; have given you the benefit of the doubt so many times but now it’s just getting old. Check out Bozoma Saint John @badassboz, I’m sure she can get give you a whole host of folks to check out. You’re getting stale, expand your horizon and get out of your comfort zone!

  17. I noticed that the last few podcasts were recorded in MTL. I live there but was in Tokyo the past few weeks. Is there any chance you’re still kicking around the lilypad? If so, I’d love to shake your hand. If not, it’s the fault of the FHWW. Without which I may not have traveled to Japan for almost 2 months this year. I’m a comic book writer and VO actor which allows me the freedom to move about willy nilly. If meeting you is not in the cards at this time that’s cool. However, this year I traveled to France, LA, Florida, and Tokyo. I’m down to meet you anywhere you happen to be in the world. I don’t want anything, just the chance to say thanks in person. (Which as I write it sounds like I’m an assassin of some kind. Tony says “Thanks.”) Barring that, thanks for everything! Your books, shows, and podcast are a continued inspiration to me.

    PS: Will be Taking the JLPT this December in TO! Again, thanks to your example.

  18. This is easily one of the most valuable episodes I’ve listened to. Loved the format! I thought it was awesome to hear such a high-calibre group weigh in with different angles on the same question—I think it brought a level of depth to this topic that would not have been possible with just a solo guest. Possibly the coolest part was just being able to step back and reflect on all the different responses and weave together the combined, overarching message for myself. It was pretty sick, brah!

  19. I know its a great podcast when i stop to take notes.

    This was just the perfect information at just the perfect time. I was on the road to quitting (in that dip) but after hearing this podcast it’s clear that the goal is still valuable and the work is still worth doing.

    Thank you very much Tim for positively affecting one humans trajectory.

  20. Hey Tim, Let me start by saying, You,re one of my ( Favorite ! ) Mentors. I,m a huge fan of your first ( Book – 4 -Hour Work Week ) I purchased the Audio – Book and, listen to it regularly. I,m an Entrepreneur ! and, my focus is ( Building Multiple Streams ! ) of Income. I loved this Podcast ! Its one of your best. I listened to the whole thing. 4- favorite – Speakers for me were ( Debbie Milmer ) ( Adam Robinson ) ( Seth Godin ) ( Chase Jarvis )…..Keep up the great work , Tim !!!……………Donnie I Henderson

  21. Like the roundtable format but think it could have used a final comment at the end to the it all together.

  22. Hi Tim!

    Your podcast has had a profound, wonderfully enriching impact on my life for years. THANK YOU more than I could ever say.

    I’m an artist, designer, and seamstress. If you ever need an amazing costume or something more serious it would be an honor to make you something as a gift. (Travis Brewer, ninja, can vouch for me being a real person with skills.)

    I loved the Animal video in the last 5 Bullet Friday to help decompress from stress. [Moderator: link and some text removed.]

    Great episode (and timing for me personally). I think my favorite quote would have to be Debbie’s: “If you’re doing what you think you should be doing rather than what you want to do with your whole heart… you are resisting the truth about who and what you are.” Especially loved Adam’s response too.

  23. As always, love listening to your podcasts and read your blogs. read this one and the RDF Eye Contact one today… Your blog is like my daily dose.. 🙂

  24. Hi Tim,

    Absolutely loving all of it! The blog, the podcast and now finally reading Four Hour Work Week.

    BUT, it appears the Comfort Challenge on page 93 – getting phone numbers of the opposite sex, only applies to straight people?… hmmm…

  25. Found it very helpful, thank you. I have been pursuing a dream for 10+ years now, and its pushed my limits. Here is my bit, I believe its your attachment to something more interesting, something higher than what you are currently pursuing is what really detaches you. Found some good examples of this principle in the podcast.

  26. Hi! I never commented a podcast episode before. And I listened to all of them!

    I just listened to a third of the episode, but I already love it. I don’t know if it will help me, yet. But the idea is great, far better than the other “summaries” of past episodes.

    I hope there will be other similar round tables.

    Thank you!

  27. Echoing, “great podcast.” Main takeaway for me here is to be aware of the “sunken cost” phallacy. If on re-examining your vision and what you want to achieve no longer corresponds to what you are doing, no matter how much you have invested in your project, it may well be time to quit.

    Second takeaway is laying to rest the notion that “winners never quit.”

    Thanks Tim as always for the work you do.

    Carl Kruse

  28. This was an important question to cover. I actually listened to this episode twice. The question itself seems so counter intuitive to what we should be think I about that we may not see its importance. My question I would like to have answered is this. What do you do when you can’t unplug? I’m at that point in the Four Hour Work Week that suggests unplugging for a week and only reading fiction and listening to music. But the podcasts and non-fiction books (Tools of Titans included since I started that before the Four Hour Work Week) seem to give me focus when I’m having a difficult day.

  29. Sir , last question , can you send to my email a notice for time and work , and how do i use translator no anyone can see it 😀

  30. Like the format. “The failure of the opportunities we have as humans to pursue the things that we love as joy.” Chase Jarvis stuck with me.

  31. Man…. Why do all the “high performers” have to constantly act like puffer fish self promoting their products etc … shows how insecure everyone really is …. What I learned from this episode is that nobody really knows when to quit and when to persist and to some extent fate plays a big part in things. If we can all just admit that instead of pretending like we have answers then that honesty would be really welcomed