Derek Sivers is an author, a TED speaker, a businessman, a musician, and one of my favorite thinkers on the planet. During our conversation, Derek talks about pursuing mastery, having enough, what success means to him, how he thinks about money, having and raising a kid, and more.

Derek's book Hell Yeah or No is one of my all-time favorites, and his essays have had a huge influence on my life. I love Derek's originality, his enthusiasm for life and ideas, and most importantly, his generosity, kindness, and friendliness.

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00:00 Intro

00:32 Written off from an early age

02:40 How Derek knew he wanted to be a musician

08:50 Transitioning from a musician to a businessman

15:40 Having enough

22:28 Money

28:15 The importance of quiet, journaling and solitude

40:45 Freedom and children

54:48 Giving away $22 million

01:03:52 Lifestyle creep

01:08:34 Why Derek chooses freedom

01:11:14 Envy and maintaining minimalism

01:19:25 Success

01:21:21 Quotes from Derek's essays

01:26:02 Dan's New Zealand story

01:35:06 Small actions can have big consequences

01:37:23 Reach out to Derek: https://sive.rs/contact