John Zeratsky was a designer in the tech industry has worked with hundreds of startups in his time at Google Ventures. He’s also obsessed with redesigning time and thinking about what matters in life. Earlier this year he just got back from 18 months living on his boat "Pineapple" with his wife sailing around Central America, which he wrote about in an article titled “What quitting my job to sail around central america taught me about fulfillment.”

In this conversation we talk about:

Growing up in a small lake community
His love of sailing growing up
Why him and his wife change their mind on taking the trip in 2015
Rethinking convenience and comfort
What comforts are worth paying for
Belonging and community
How his relationship with money has changed
How him and his wife are structuring their life to work how they want
The one change that helps people be less addicted to their phones

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What living on a boat for 18 months can teach you about work & life (John Zeratsky)

The Pathless Path with Paul Millerd