Leo Babauta on Zen Habits, Antifragility, Contentment, and Unschooling | The Tim Ferriss Show

Tim Ferriss interviews Leo Babauta about how, around 2005 in Guam, he was overweight, a smoker, deeply in debt, and feeling like a failure, then changed everything one habit at a time over roughly a year. Leo explains the mechanics of lasting habit change, including meaningful external reasons, social accountability, separating the urge from the action, and planning for 'the dip.' The conversation covers the early explosive growth of Zen Habits in 2007, the surprise success of writing about simplicity, and how Leo applies simplicity to commitments and anxiety. They go deep on Zen Buddhism and the Bodhisattva precepts, loving-kindness (metta) meditation and self-compassion, the masculine/feminine polarity work he trained in with John Wineland, and unschooling his children. Leo closes with practices for staying present with uncertainty and anxiety during a turbulent time.

• Leo's rock-bottom moment was breaking open his kids' piggy bank to put milk and cereal on the table because he couldn't afford food for his family.
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• After failing to quit smoking seven times, the eighth attempt succeeded because he made a meaningful promise to his wife and daughter rather than only to himself.
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• He learned to separate the urge from the action, realizing smoking urges were just feelings in the body that rise, peak, and pass rather than commands he had to obey.
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• He discovered every habit hits a 'dip' that feels like getting punched in the face, and that planning and rehearsing for it beforehand keeps it from ending the habit.
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• The unexpected key to Zen Habits standing out was simplicity; while many blogged about productivity and motivation, applying a simplicity lens to everything became his differentiator.
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• Leo's wife quit her teaching job to homeschool the kids, and the family later abandoned structured homeschooling entirely in favor of unschooling.
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• His daily decision practice, learned from John Wineland, is to drop into wide-open consciousness and ask 'What is life calling me to do?', which surfaces the most important (not most urgent) thing.
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• Leo's core teaching is that habitual responses to uncertainty (smoking, Netflix, Amazon, procrastination) are automatic, but you can train to drop into the body and stay curious with the anxiety instead.
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• Leo had to quit smoking partly because his wife, pregnant at the time, would resume after giving birth, and because his kids were far more likely to smoke if he did.
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• Within about a year of starting to change, Leo lost 30 pounds and ran a marathon at the end of 2006.
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• The interview was recorded in late September 2020, during the pandemic, election season, racial protests, and West Coast wildfires.
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• When the family moved from Guam to San Francisco in 2010, they sold everything and relocated with just a backpack each, and the kids had never seen a homeless person or anyone using drugs before.
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• Zen Habits launched in January 2007, the same year Tim Ferriss released The 4-Hour Workweek, and the two met online that year.
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• At his peak hustle, Leo was producing roughly 15 to 20 blog posts a week across his own site, five paid freelance blogs, and guest posts.
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• Tim credits getting his Geek to Freak muscle-building post onto the front page of Digg as a major early inflection point for his own blog.
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• Leo's kids once threw him a birthday party celebrating him as a 'super dad' superhero, fulfilling his goal of being an example who left his comfort zone.
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• In 2018 Leo did a 9-month program with John Wineland, a disciple of David Deida, doing masculine/feminine polarity and leadership practices.
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• Leo cites a Chogyam Trungpa quote: 'The bad news is that you're falling through the air with no parachute. The good news is there's no ground below.'
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