The Tim Ferriss Show: Derek Sivers Reloaded – On Success Habits and Billionaires with Perfect Abs

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Tim’s first interview with Derek

What do you do?

  • “I’ve heard that Stewart Brand gives a different answer every time he is asked,” a good challenge
  • I like saying “I don’t know,” “I’ve never thought about it before.” This helps derail the routine of a boring conversation (it’s like finding someone who doesn’t know their name)
  • Derren Brown: On confusing people and opening them to suggestions of what is happening

First person that comes to mind as successful?

  • The first answer to any question isn’t much fun, it’s just automatic
    • Thinking Fast and Slow: Instant unconscious automatic response (System 1) and Slower, rationale conscious thinking (System 2)
      • Derek is more interested in the latter, slower thinking
      • For those areas where automatic response is useful, first take the time to slowly come up with that response

[Derek Sivers] Who is the 3rd most successful person that comes to mind and why are they more successful than the first?

    • 1st: Richard Branson
    • 2nd: Tim Ferriss?
    • 3rd: I can’t answer without knowing a person’s aims, because that is how to evaluate if they were successful at it

What are the most common misconceptions about You?

  • I feel pretty understood
  • Better to think about the goal of writing to avoid being misunderstood vs. being understood

Morning Rituals?

  • I don’t have them, there is nothing I do every day outside of eating/writing
  • I get really focused [obsessed?] on 1 thing at a time for a period of time (e.g. hardcore coding project, hiking in New Zealand, reading books outside, work on big keynote speech)
    • CD Baby started like this, just lasted a lot longer than most projects
  • My nature doesn’t allow me to focus on my top 3 things at the same time
    • Knowing this, I can plan accordingly

World Class At, That People Don’t Know About?

  • I have the world’s longest attention span (it is happily rubbing off on my son)
  • I don’t meditate/yoga, my daily life is my form of meditation

[Sam, Stockholm Sweden] Status of the Do List Project?

  • I have about 120 directives that need some explanation and each will get a 1 page spotlight
    • Sign-up to be notified at or email [email protected]
    • Once they are all up, I’ll link to the full set with links to the detailed lists
    • Last step to put them into a book

[Tobin, Bolder Colorado] What are a few directives for sharing thoughts online in an authentic way, particularly for introverts?

  • Everyone is scared to share publicly, but online is easier than on stage
  • Recommended Book: Show Your Work, Austin Kleon
  • 4 Directives:
    • Teach whatever you’ve learned immediately after learning it, while you still remember what is like not to know it
    • Share your work online, if it isn’t online, it doesn’t exist
    • Share the process, people want to see how the sausage gets made
    • Release your creation after you’ve already moved onto your next project, so when you get feedback it won’t feel as personal/direct

[Ayman, Morocco] Why in hell did you become a programmer?

  • Necessity, the best reason to learn anything
  • If you want to start programming, you need a serious problem you want to solve
  • Now I just love it for its own sake, to sit alone and just make things

[Tobin, Bolder Colorado] Directives for creating relationships with people who hold interesting world views?

[Dave, Kalamazoo Michigan] Does success in business need to be more complicated than coming up with ideas to help other people succeed?

  • Things are both Simple vs. Complicated, and Easy vs. Hard
    • We treat things we like as “simple” and things we don’t as “complicated”
    • Simple might not seem easy
    • Success in business can be simple: Just find a need that people are willing to pay for and fill it (but that still isn’t easy)
    • Notice things when complications are holding you back and look to simplify, but then look at the results and recognize when they might benefit from more complexity
  • Shut off all the junk business advice out there and just get started
    • “If information were the answer, we’d all be billionaires with perfect abs”

[Matt, Toronto Canada] How has knowing your [Myers Briggs] type (INTG) affected your life and played a role in an important decision?

  • Not much, It’s just shorthand for my preferences
  • Myers Briggs is like 16 little clubs, like Harry Potter houses, and allow us look seek out those who are also in our club – we tend to get along well
  • I found when I stopped going against my introvert nature and shaped my life around it, I became very happy
    • Work alone, avoid big group things and have good 1:1 time with other people

[Tobin, Boulder Colorado] What should someone ask to determine their own utopia?

  • Ask yourself if your idea is in theory or in practice?
    • There are so many things that seem great in theory, but are not
  • Do little tests, try a few months of the life you think you want, but leave an exit plan to go back
  • Stumbling on Happiness, Daniel Gilbert
    • Talk to people who are where you think you want to be, ask them for Pros/Cons

[James, Ireland] How do you define success, what habits matter most for success?

  • A lot of fame/fortune is luck, but people with it are actually miserable/horrible
  • Success: Master yourself and help others
  • Habits:
    1. Managing your state and emotional actions/reactions
    2. Know what people need in general and you need in particular
    3. People skills
    4. Focus, learn, practice and apply what you learn

[James, New Zealand] If you instantly lost all your money/resources/etc. and were not recognizable, what you do to become successful?

  • If you take everything from me, I’d still be successful because I know how to be happy, considerate, useful and how to learn
  • Having millions gives you a nice sense of security, but I don’t use it on a daily basis
  • What actually makes me happy:
    1. A nice quiet place to live alone
    2. Working laptop, internet, books
    3. Money for food
    4. Good health
    5. 2 good friends
  • Specific Actions:
    1. Find any job
    2. Find an old laptop, install Linux
    3. Teacup/tea
    4. Get back to reading, learning, writing, thinking and sharing what I’ve learned
    5. If you want to make money, pick any online program that has been proven to help you pick a business and optimize it (not the get rich quick ones), just actually follow-through

Something you believe, but other people think is insane?

  • Alcohol and olives taste bad
  • I don’t like the smell of coffee (have never tasted it)
  • All audiobooks should be read/recorded by people from Iceland, best accent
  • Would be wonderful to move to a new country every 6 months for the rest of my life
  • You shouldn’t start a business unless people are asking you to
  • I’m below average (deliberate to compensate for our tendency to think we’re above average)
  • The movie Scott Pilgrim is a masterpiece
  • Music and people don’t mix: Music should be appreciated alone without seeing/knowing the musicians, or with other people around
  • It is unwise to prioritize Lifestyle Design, dangerously self-centered and you should be focusing on being useful to others
  • Loyalty to others is silly, we should try be disloyal and only be loyal to the rare thing we can’t be disloyal to
  • It is good to feel smug, it means you are proud of yourself, which means you’re living according to your beliefs
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