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June 10, 2024 • 2hr 7min
#795 - Ryan Holiday - 11 Harsh Stoic Truths To Improve Your Life
Modern Wisdom
Ryan Holiday is a bestselling author, marketer, and one of the world's foremost experts on ancient Stoic philosophy. In this wide-ranging conversation, Holiday discusses key insights from Stoicism and how to apply this timeless wisdom to modern life. He covers topics like success, decision-making, ethics, parenting, and the proper understanding of Stoic principles.
Host Chris Williamson explores Holiday's perspective on everything from the dangers of talking about projects prematurely to the importance of defining success on your own terms. They delve into Holiday's writing process, his views on competition and self-belief, and how to maintain integrity in a world full of temptations and shortcuts.
#795 - Ryan Holiday - 11 Harsh Stoic Truths To Improve Your Life
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Key Takeaways
- Don't talk about projects you're working on before finishing them - Talking prematurely can reduce motivation and give a false sense of accomplishment
- Competition is for losers - focus on running your own race - Define success on your own terms rather than comparing yourself to others
- Self-belief is overrated - generate evidence instead - Build confidence through accomplishments rather than blind faith in yourself
- Big life decisions are rarely simple "f**k yes or no" choices - Major life changes often involve uncertainty and risk
- If something makes you a worse person, it's not true success - Success should improve your character, not compromise it
- Be quiet, work hard, and stay healthy - sanity sets you apart more than ambition or skill
- Stop wanting things to be easy and prepare for them to be hard - Embracing difficulty builds character and resilience
- Justice is about doing the right thing right now - Focus on making ethical choices in your daily life and actions
- Transparency and accountability help maintain integrity - Being open about your actions keeps you honest
- Stoicism is about mastering yourself to help others, not just self-improvement - The philosophy should lead to positive engagement with the world
Introduction
Ryan Holiday is a bestselling author, marketer, and one of the world's foremost experts on ancient Stoic philosophy. In this wide-ranging conversation, Holiday discusses key insights from Stoicism and how to apply this timeless wisdom to modern life. He covers topics like success, decision-making, ethics, parenting, and the proper understanding of Stoic principles.
Host Chris Williamson explores Holiday's perspective on everything from the dangers of talking about projects prematurely to the importance of defining success on your own terms. They delve into Holiday's writing process, his views on competition and self-belief, and how to maintain integrity in a world full of temptations and shortcuts.
Topics Discussed
The Dangers of Talking About Projects Prematurely (02:00)
Holiday explains why he has a rule against discussing projects he's working on before they're finished:
- Talking prematurely can give a false sense of accomplishment
- It uses up motivation that should be directed towards actually doing the work
- There's value in working on something privately without external validation
- Waiting to talk about projects until they're nearly done preserves the drive to complete them
As Holiday puts it: "You don't want to take that [sense of accomplishment] on credit. You want to earn it."
Competition is for Losers - Run Your Own Race (07:30)
Holiday discusses the idea that competition often leads to suboptimal outcomes:
- Focusing on beating others means success is out of your control
- It's better to define success on your own terms
- Running your own race allows you to set higher, more meaningful standards
- Going where there's less competition creates more opportunity for success
He notes: "If you only run races where winning is up to you, you'll always win."
Self-Belief vs. Evidence (31:30)
Holiday argues that self-belief is overrated compared to generating real evidence of your capabilities:
- Blind faith in yourself isn't as valuable as concrete accomplishments
- Focus on building a track record you can point to
- Confidence should come from past successes, not just positive thinking
- Understanding your limitations is as important as believing in your strengths
He states: "I don't believe in myself. I have evidence."
Big Decisions Are Rarely Simple (13:12)
Holiday pushes back on the idea that major life decisions should always feel like an obvious "f**k yes or no":
- Truly life-changing choices often involve uncertainty and risk
- Being 100% certain about a big decision may indicate willful ignorance of potential downsides
- Some of the best choices in life start with only 51-60% certainty
- The conviction often comes later, after you've committed to the path
He reflects: "I would love to say in retrospect that I knew all the big risks that I took in my life were going to pay off, but if I did, I guess they wouldn't have been risks."
True Success Shouldn't Make You a Worse Person (42:11)
Holiday emphasizes that real success should improve your character, not compromise it:
- If achieving something makes you bitter, frustrated, or damages relationships, it's not true success
- Be clear about what you want your life to look like day-to-day
- Don't chase status or money at the expense of becoming a better person
- Success should expand your capacity for kindness and positive impact
He advises: "Being really clear with yourself about what success looks like is really important, because if you start to get it, it becomes this rocket ship that you're riding on, and you are not going to have the control then of it."
Sanity and Consistency Matter More Than Raw Ambition (31:39)
Holiday shares his most popular tweet about what really sets people apart:
- Being quiet, working hard, and staying healthy is more valuable than pure ambition
- Consistency and reliability are underrated qualities
- Avoiding drama and maintaining your sanity gives you an edge
- Focus on doing good work steadily rather than chasing attention
The tweet reads: "Be quiet, work hard, and stay healthy. It's not ambition or skill that is going to set you apart, but sanity."
Prepare for Things to Be Hard (57:03)
Holiday discusses the importance of embracing difficulty rather than wishing for an easy path:
- Expecting everything to go smoothly sets you up for disappointment
- There's value in struggle and overcoming obstacles
- Preparing for challenges makes you more resilient
- The right amount of difficulty builds character and skills
He advises: "Stop wanting things to be easy and prepare for them to be hard."
Justice is About Doing the Right Thing Right Now (1:13:26)
Holiday explains his view on the Stoic virtue of justice:
- Justice isn't just about big philosophical questions, but everyday ethical choices
- Focus on doing the right thing in your immediate sphere of influence
- Small acts of integrity compound over time
- Don't wait to be ethical - practice justice in your daily life and work
He emphasizes: "Justice to me is all about not, you know, should we provide weapons to Ukraine or not...Again, all of this is extremely important and part of the virtue of justice, but it starts with these sort of fundamental decisions that we make as individuals over the things that we have the most control."
Transparency and Accountability (1:39:09)
Holiday shares an anecdote about a Roman politician who made his house more visible to keep himself accountable:
- Being open about your actions helps maintain integrity
- External accountability can reinforce good behavior
- Transparency laws benefit both consumers and ethical businesses
- Consider how your choices would look if made public
He notes: "We should be wary of the things that allow us to create a distinction between who we are in public and who we are in private."
The True Purpose of Stoicism (1:56:49)
Holiday discusses his role in popularizing Stoicism and how he views its proper application:
- Stoicism isn't just about personal improvement, but engaging positively with the world
- The goal should be mastering yourself to help others, not just for your own benefit
- Be wary of using Stoic ideas to justify selfish or unethical behavior
- True Stoicism involves taking responsibility and trying to make a positive difference
He emphasizes: "Stoicism is a philosophy that gets involved, that gets engaged, that tries to make a positive difference again, not always by becoming a senator or something, but by how you choose to run your business, how you choose to run your life, how you choose to show up and do things for your family, for your community, for your neighbor who's struggling."
Conclusion
This wide-ranging conversation with Ryan Holiday offers a wealth of insights on how to apply Stoic wisdom to modern life. Key themes include the importance of defining success on your own terms, building real evidence of your capabilities rather than relying on blind self-belief, and focusing on making ethical choices in your immediate sphere of influence.
Holiday emphasizes that true success should make you a better person and contribute positively to the world around you. He warns against using Stoic ideas merely for personal gain or to justify unethical behavior. Instead, he advocates for a version of Stoicism that involves taking responsibility, engaging with the world's challenges, and striving to make a positive difference through your actions and choices.
Ultimately, Holiday's perspective offers a roadmap for living with greater integrity, resilience, and purpose in a complex world. By focusing on doing the right thing right now, embracing difficulty as a path to growth, and maintaining transparency in our actions, we can cultivate the virtues that lead to a life well-lived.