Leo Babauta on Zen Habits, Antifragility, Contentment, and Unschooling (#488)

Illustration via 99designs

I learned that none of the urges that I thought I needed to act on were actually commands.

— Leo Babauta

Leo Babauta (@zen_habits) is a bestselling author and the founder of Zen Habits, a website dedicated to finding simplicity and mindfulness in the daily chaos of our lives. Zen Habits has more than two million readers, and Time magazine has named it one of their “Top 25 Blogs” and “Top 50 Websites.” He is also a student of Zen and on a mission to help the world open through uncertainty training.

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#488: Leo Babauta on Zen Habits, Antifragility, Contentment, and Unschooling


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What was your favorite quote or lesson from this episode? Please let me know in the comments.


Want to learn more about metta (loving-kindness) meditation? Listen in on my conversation with Sharon Salzberg, the world-renowned teacher who wrote a book on the subject. We discuss self-compassion as a secret ingredient, mental frameworks, defusing anger, doing the good that’s in front of you, and much more.

#277: Sharon Salzberg, World-Renowned Meditation Teacher



  • Connect with Leo Babauta:

Zen Habits | Twitter | Facebook


  • Rewinding the clock, Leo shows us what his life was like in Guam circa 2005 and shares the catalyst that sparked the big life changes he’s made between then and now. [06:54]
  • After trying to quit smoking seven times before, what made Leo’s eighth attempt stick? [12:15]
  • Why the inevitable dip we experience when forming a habit is potentially the most important part of making it stick — if we absorb what it has to teach us in the moment rather than allowing it to derail our efforts. [15:40]
  • Embracing the suck, putting mindfulness to work for us when the going gets tough, and the thought processes that led to Leo and his family of eight to move from Guam to San Francisco in 2010 — from a place of comfort surrounded by extended family to a somewhat jarring and alien landscape where they didn’t really know anyone. [17:56]
  • When Leo started Zen Habits in January of 2007, how did he manage to expand its popularity from an audience of one (his wife) to thousands — and eventually millions — in a relatively short period of time? [25:42]
  • In hindsight, what other forays into the productivity space and experimental tactics really helped launch Zen Habits into the blogging stratosphere between 2007 and 2009? What made Leo’s work stand out from the competition in this crowded arena? [31:47]
  • What would Leo suggest to someone trying to simplify their life — especially during the anxiety-driving uncertainties of 2020? [38:10]
  • How can we get better at saying no to overcommitments that unnecessarily complicate our lives? [40:37]
  • What are some of the rules, constraints, and forms of accountability that Leo has found powerfully effective in his own life? [43:39]
  • What resources would Leo recommend to someone curious about Zen Buddhism, what are some commonly mistaken preconceptions people have about it, and how has the practice been helpful to Leo in his own life? [45:06]
  • What are the bodhisattva precepts, what vows has Leo considered taking, and what has motivated him to take them? And in spite of some surface similarities, how do these precepts differ from the 10 commandments most Westerners will find familiar? [48:23]
  • How have Leo and his wife managed to homeschool — or, more accurately, unschool — six children, why did they choose this over other options for education, and what does unschooling look like? [53:06]
  • Is unschooling an ideal preparation for potential entrepreneurs? Does it perhaps underprepare someone seeking to continue their education at a traditional university? [59:53]
  • Resources Leo recommends for people who would like to learn more about homeschooling and unschooling along with common pitfalls and best practices? [1:02:47]
  • What changes in life habits or new beliefs have had the greatest impact on Leo’s contentment, and what do they look like in practice? [1:03:40]
  • Resources for people who want to delve further into metta (loving-kindness) meditation. [1:09:53]
  • What compelled Leo to go through nine months of masculine practice training with John Wineland, and what did he take away from the experience? [1:11:16]
  • A practical daily exercise Leo learned during this time, and some of his most surprising results. [1:14:32]
  • Why this pandemic presents a unique opportunity to train ourselves to cope with uncertainty and anxiety, and how Leo proposes we can put this into practice. [1:17:07]
  • Some bad news and good news from a Tibetan Buddhist master that might help you surf the chaos accompanied by less fear. [1:22:23]
  • Parting thoughts. [1:24:46]