Derek Sivers is an author of philosophy and entrepreneurship, known for his surprising quotable insights and pithy succinct writing style. Formerly a musician, programmer, TED speaker, and circus clown, he sold his first company, CD Baby, for $22 million and gave all the money to charity. Derek Sivers contributed a chapter to Tim Ferris’ bestseller Tribe of Mentors. He has written a range of popular books including Anything You Want, Hell Yeah or No and most recently How to Live: 27 Conflicting Answers and One Weird Conclusion. Of Derek Sivers’ book, How to Live, author Mark Manson said ‘always brilliant and succinct, I guarantee you have not read a book like this before’. What makes the book so unique is that each chapter in the book disagrees with the next, creating a philosophy of conflicting philosophies. Please enjoy our interview with Derek Sivers.

You seem to have your fingers in a lot of pies, how do you describe your occupation?

The pies are in my past. When you first encounter someone, you get their whole history at once, which makes them seem super-impressive. But really it can be like one thing they did 20 years ago, another thing they did 10 years ago, and something last year.

Never compare your inside to someone else’s outside.

These days, I’m just writing my pop-philosophical books, which is why we’re talking.

Talk us through a typical day for you…

Wake up naturally, no alarm, usually around 5 am. I don’t know why I wake up so early.

I write for hours before turning on the internet and seeing what’s up with the rest of the world.  This is my best productivity hack.  Drain your output before taking inputs.

I take care of my wife, and play with my kid for many hours a day, doing whatever he wants.

About an hour emailing with strangers who email me.  A couple of hours programming the tools I use to run my life.

Then I turn off the internet and all devices for the rest of the night.  Read.  Sex.  Sleep.

reasons and persons - Derek Sivers interviewWhat are you reading at the moment and what made you want to read it?

Reasons and Persons by Derek Parfit, because I’m getting more and more interested in philosophy, and I heard this is an important work I should know.

Are you a page folder or a bookmarker?

I use my pen as a bookmark.  I underline a lot while reading.  See my notes here.

When did you fall in love with reading?

I don’t love reading.  I love learning.  So far, reading is the most efficient way for me to learn.  If I found a better way, I might switch to that.

Can you talk us through your research process when preparing for a new book?

Oh, no, I don’t do that.  It’s important to shine a spotlight on one idea at a time.  So I post ideas on my site – one at a time.  Only later do I bundle them up into a cohesive book.  One idea per chapter.

If you could gift yourself books at age 16 and age 25 – what would they be and why?

Awaken the Giant Within by Tony Robbins.  I read it at 19 and it changed the way I see the world forever.  If you read it now, you may find its references dated, and you may cringe at his motivational speaker approach.  But damn, its core teachings are so profound for living a great life.

the war of art - Derek Sivers interviewWar of Art by Steven Pressfield – ideally his mini-series on this subject, including “Do the Work” and “Turning Pro”.  At 25, I was a professional musician and needed this message of doing the necessary creative work.

For someone starting out in your career, which three books would you make required reading and why?

1. War of Art by Steven Pressfield
2. On Writing Well by William Zinsser
3. Story by Robert McKee

You’ve had multiple very successful books published, is there one you’re most proud of and why?

How to Live: 27 Conflicting Answers and One Weird Conclusion, my newest.  It’s the culmination of everything I’ve learned in my life, but I edited the 1300-page rough draft down to 112 pages. It’s a powerfully succinct read.  It’s the greatest thing I’ve ever created.

What’s the best book you’ve read in the last 6 months?

Essays and Aphorisms by Arthur Schopenhauer.

What two pieces of advice would you give a young aspiring writer?

Edit ruthlessly.  Be as succinct as possible.  The unnecessary words dilute your message.

awaken the giant within - Derek Sivers interviewPost your ideas one at a time online, sharing them widely.  Get the echolocation of public response for each idea before burying it on page 213 of a book.

What is the book that you feel has had the single biggest impact on your life? What impact did it have?

Awaken the Giant Within by Tony Robbins.  It teaches that “I can’t help the way I feel” is a myth, that you can make your mental associations whatever you want them to be.

Which book sat on your shelf are you most excited about reading next and why?

Critique of Pure Reason by Immanuel Kant.  The other philosophers I read refer to it as the work that changed everything.

If you’d like to learn more about Derek Sivers, be sure to check out his website and follow him on Twitter.

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