These Are All The Ways Ryan Holiday Feels Poorer Than He Is
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May 25, 2025
Ryan Holiday discusses the paradox of feeling stressed despite financial success. He delves into the multifaceted nature of wealth, emphasizing time, social connections, and mental well-being. Nostalgic reflections highlight the importance of meaningful experiences over material richness. The conversation encourages listeners to prioritize freedom and fulfillment, challenging conventional views on happiness. With practical insights from Stoic philosophy, it's a compelling reminder that true wealth may lie beyond just financial assets.
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question_answer ANECDOTE
Success Brings Seasons of Unbalance
Ryan Holiday shares how career success hasn't prevented seasons of unbalance and tunnel vision.
His social relationships often suffer the most during these intense work periods.
insights INSIGHT
Money Doesn’t Equal True Wealth
Financial wealth doesn't guarantee feeling rich; many billionaires lack social or mental wealth.
True poverty can exist despite riches, rooted in insecurities and poor relationships.
insights INSIGHT
Anxiety Costs True Wealth
Ryan Holiday experiences anxiety mostly from needing control and things going well.
This anxiety creates feelings of powerlessness and detracts from living fully.
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This book rejects the notion that money is the only type of wealth and instead offers a blueprint to build a life around five types of wealth. After three years of research, personal experimentation, and thousands of interviews, Sahil Bloom provides practical steps and actionable insights to help readers prioritize energy-creating tasks, build deeper social bonds, engage their purpose, maximize health and vitality, and achieve financial independence. The book aims to help readers make better decisions and design the life they have always dreamed of.
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In today’s episode, Ryan opens up about how despite his career success and net worth, he still struggles with anxiety and stress, not so much about the state of the world but about the constant pressure for things to go right.
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