Deep Questions with Cal Newport

IN-DEPTH: The Art of Non-Conformity (w/ Chris Guillebeau)

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Jun 12, 2025
Chris Guillebeau, author of 'Time Anxiety' and founder of the World Domination Summit, shares insights on redefining our relationship with time. He reminisces about the early days of blogging and contrasts it with today’s social media dynamics. The conversation touches on navigating creativity in a segmented digital landscape and the psychological aspects of productivity. Guillebeau emphasizes the importance of managing time anxiety while pursuing passions, advocating for simple, lifestyle-centric planning.
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ANECDOTE

Chris's Blogging Genesis

  • Chris Guillebeau entered the blog world with a professional site anchored in his quest to visit every country. - He leveraged existing communities and link sharing to grow his presence in the early 2000s blogging era.
INSIGHT

Close-knit Early Blog Community

  • Early 2000s blogging connected a smaller, more intimate group, making it easier to know and elevate peers. - This closeness fostered unique community energy unseen in today's fragmented social media landscape.
INSIGHT

Books as Enduring Medium

  • Books provide a lasting, deep medium that captures years of thinking and crystallizes knowledge. - They also offer financial opportunities that occasional online formats like blogs lack, despite changing media landscapes.
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