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Published Oct 31, 2019

271: Ryan Holiday | Stillness Is the Key

Bestselling author Ryan Holiday delves into the art of thoughtful decision-making, the power of self-improvement, and finding success through stillness, offering profound insights on evaluating opportunities, balancing growth with criticism, and achieving contentment despite the pressures of ambition.
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  • Opportunities

    shares his experiences with weighing significant life and career opportunities. He recounts a moment when he was offered a high-ranking position in the Trump administration, which required him to move to DC and put his assets in a blind trust. Despite the allure of the role, Ryan realized it contradicted his values and lifestyle preferences, illustrating the importance of thoroughly evaluating opportunities before making decisions 1.

    It's really hard to be like, "This is my thing. This is what I'm doing. And to have the patience and the discipline to go to actually weigh the opportunities or the options against whatever that rubric is, and people just don't do that."

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    He emphasizes the difficulty of saying no to money, sharing a personal anecdote about turning down a lucrative consulting offer because it conflicted with his desired lifestyle 2.

       

    Life Choices

    Making informed life choices requires careful consideration and a willingness to challenge societal norms. discusses the importance of testing inclinations and thinking long-term, drawing from Stoic philosophy to guide decision-making 3. He shares his own experiences of leaving college and a corporate career to pursue writing, highlighting the value of taking calculated risks and the freedom that comes with it 4.

    When I decided I was going to walk away from a very good, lucrative corporate track to be a writer, I was able to go like, "Oh, I can always just go back."

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    adds that the best time to make significant decisions is often when it feels most inconvenient, as it forces deeper reflection on one's true desires 4.

       

    Quality Reps

    The quality of experiences, or 'reps,' is crucial in skill development and achieving goals. argues that simply quitting a job to pursue a passion without a solid foundation can be detrimental, emphasizing the importance of building a parallel track before making a leap 5.

    It's about the quality of the reps and not just making sure that you've screwed yourself over so that you have to do it full-time.

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    reflects on his journey in podcasting, noting that it took years of practice and dedication to hone his interviewing skills, underscoring the value of persistence and gradual improvement 6.

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