The Daily Stoic - BONUS | 8 Life Lessons Ryan Holiday Learned The Hard Way
Episode Date: August 26, 2025Life lessons aren’t handed to us, they’re earned the hard way. In this bonus episode, Ryan shares the eight truths he had to learn through failure, patience, and time🎥 You can watch t...his episode on Ryan Holiday’s YouTube Channel: https://www.youtube.com/watch?v=T7yEl4mpQt8📚 Sign up for Ryan’s free monthly reading list newsletter: https://ryanholiday.net/the-reading-list/📖 Preorder the final book in Ryan Holiday's The Stoic Virtues Series: "Wisdom Takes Work": https://store.dailystoic.com/pages/wisdom-takes-work🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast🎥 Watch top moments from The Daily Stoic Podcast on YouTube: https://www.youtube.com/@dailystoicpodcast✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us: Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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Welcome to the Daily Stoic Podcast, where each day we bring you a stoic-inspired meditation
designed to help you find strength and insight and wisdom into everyday life.
Each one of these episodes is based on the 2,000-year-old philosophy that has guided some of
history's greatest men and women help you learn from them.
to follow in their example, and to start your day off with a little dose of courage and discipline
and justice and wisdom. For more, visitdailystoic.com.
I think about the things that in my 20s, I was so intense about. I cared so intensely about.
I'm like, what? Right? I could have been more patient. I could have been calmer. I could have
realized that the thing you're thinking about is never as important as you think it is.
Another one is don't say maybe when what you really want to do is say no, right? Don't say I'll
think about it. Don't say, I'll try. If you can't do it, if you don't want to do it, just say no.
As they say, no is a complete sentence. You don't owe anyone anything and you certainly don't
owe them an explanation. Number three, I should just always listen to my wife. Every big business
mistake I have made, my wife told me beforehand, that's a really bad idea. You got to learn
whose judgment to trust. You've got to learn who knows you better than you know yourself.
And you've got to be able to trust and defer. You can't fix internal issues with external
accomplishments. Hitting number one in the New York Times, so is selling millions of books,
making money, doing all the things I've done. You know what it feels like? Doesn't really feel like
anything. Do you think it's going to be this big cathartic relief? It's going to change things. It's
going to undo things. It never does. You can't fix internals with externals. If you think professionals are
expensive, try hiring an amateur, right? I've tried to get around hiring. I've tried to do stuff
myself. It always ends up costing you. But I would say there's a caveat to this. Sometimes just because
someone or something is expensive just because they're an expert, does it mean they actually know what
they're talking about and you can rack up very large bills and not actually move the ball forward
in any way. Anger always makes stuff worse. I don't think I've ever lost my temper and then afterward
thought, I'm so glad I did that. I'm so proud of myself. It's not how it goes. You always
regret getting upset. Just like I was saying, you look back at the things you used to care so much
about and you're like, why was that such a big deal? Character is fate, as they would say. I don't know
why I expect it to be different than it was the time before.
I don't know why I'm surprised
when people have already told me who they are.
You gotta look at the core of who they are
what makes them tick,
because that's what you're gonna get from them.
The last one is that it always takes longer
than you expect, even when you take that into account.
My first book came out in 2012.
I don't think I hit the New York Times of Settlest
until 2016 or 2017.
I'd started my first website in 2005 or 2006.
If you had told me at the time that that's how long it would take, I don't think I would have believed you, and I don't think I could have handled it.
It always takes longer than you think it's going to take.
Take that into account, then double it, and be ready for it to take even longer.
I read a lot. It's sort of my job. You can't write without reading.
But for almost 15 years now, once a month, I send out an email with my favorite book recommendations for that month.
Books that I've been reading, books that I've been going through, books that changed my life, that inspired me.
but I think connect to what's happening in the world,
and you could sign up right now at ryanholyde.net slash reading list.
