The Daily Stoic - This Is The Secret To Dealing With People | Ask Daily Stoic
Episode Date: September 4, 2025The Stoics understood that the boundary between "me" and "you" is thinner than we realize. 📚 The Four Stoic Virtues: Justice, Temperance, Wisdom, Courage, are timeless keys to living ...your best life. The Daily Stoic is releasing a limited collector’s edition set of all four books signed and numbered, with a title page identifying these books as part of the only printing of this series. PLUS we're including one of the notecards Ryan used while writing the series. Pre-order the Limited Edition Stoic Virtues Series Today! | https://store.dailystoic.com/pages/stoic-virtues👉 Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content coming soon: dailystoic.com/premium🎟️ Come see Ryan Holiday LIVE in Austin, Texas on September 17! | https://www.dailystoiclive.com/🎙️ 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.
you might get the impression that Marcus Aurelius didn't particularly like people.
He writes about how they frustrate, annoy and disappoint us, how they fall short, how they fail us,
even how they stab us in the back.
Not just sometimes, but often.
In the morning, Marcus says in book two of meditations,
remind yourself that the people I deal with today will be meddling, ungrateful, arrogant,
dishonest, jealous, and surly.
Yet he adds that we can't let this drag us down.
shouldn't let these people implicate us in their ugliness.
Instead of being pessimistic, he was trying to help us avoid being caught off guard by the flaws of
others, to not allow our emotions to be triggered, especially emotions like anger or hatred.
And then, of course, there is the most critical part of this exercise,
actually putting yourself in other people's shoes to understand why they are acting this way.
Even Marcus Aurelius's idea that the obstacle is the way isn't.
about accomplishing grand heroic feats.
Rather, he's talking about dealing with difficult people,
how each challenging interaction with someone,
especially a jerk,
is actually an opportunity to practice virtue.
It's easy to connect with someone who's just like you.
But developing empathy for those we don't naturally understand or even like,
caring about them and acting in a way that's mutually beneficial,
this requires hard work and real virtue.
And not just one virtue,
but each of the stoic virtues. Empathy demands courage, engaging with someone or something you don't
like or is unfamiliar to you. It also requires discipline to keep your emotions in check,
requires justice to genuinely care about other people as much as yourself, and then wisdom
to explore different perspectives and transform that information into understanding. And the idea is
that the more difficult the person, the more difficult the situation, the more virtue is
required. And the greater the virtue is when you apply it. That's what I've been thinking a lot
these last six years as I've worked on this Stoic Virtue series, that each person is a chance
to practice courage, to practice discipline, to practice justice. And then most recently,
it's a chance to practice or obtain wisdom. That's the final.
book in the series, Wisdom Takes Work, which is out in October of this year. And actually, we have
a limited collector set of all four books signed and numbered. It's a limited run of just 1,500 of
these. We are almost out of them. If you wanted to grab one, I'll link to that in today's show
notes right now, but you can grab them at daily stoic.com slash stoic virtues. Get this plus a bunch
of other awesome bonuses. That's what it's all about. So if you haven't read, Courage is calling. This
discipline is destiny, right thing right now. And of course, I know you have it, what wisdom takes
work. This is a way for you get all four books signed and numbered by me in a limited edition
set, daily stoic.com slash stoic virtues to check it out.
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Hey, it's Ryan. Welcome to another episode of the Daily Stoic.
Stoic podcast. Here we are on a Thursday. I went for a long walk yesterday, trying to work through
what I want to talk about in two weeks. I'm doing my talk here in August. If you want to come see me,
you can grab tickets at daily stoiclive.com. I'll link to that in today's show notes. It's at the
Westlake Performing Art Center. That's going to be fun. You have a chance to ask me some questions. As the
folks did in today's episode. Back in February, which seems like an eternity ago, I was in Salt Lake
City, went to a nice rare bookstore, although I got terribly lost because it moved, forgetting
the name. It was annoying, but Jeff Goins told me about it. Then I gave a talk to the Salt Lake
City chapter of YPO. We had a nice little chat. That's where these questions are from. I'll just get right
into it. If you want to ask me a question, as I said, come see me in Austin on, what is it,
the 17th, and then come see me in San Diego this coming February. More dates will be on the website
DailyStyoicLife.com. Thanks to YPO for having me out. Heidi Fry is the one asking me these
questions. She's the CEO of Ace IP Solutions. Thought it was really cool. Let's talk soon.
How do you know when to validate an obstacle is hard and when to change your perception and push against it?
Do you ever acknowledge that something is hard or is changing perception and taking action the first thought?
I mean, I didn't think you minimize an obstacle when you're in the middle of it.
I like to go into things going, hey, this is going to be tough.
This is going to challenge me.
But that's what I'm looking forward to.
Like when I start a book, I don't go, this is going to.
be fun. It's going to go great. Never going to, like, I actually do the opposite. The Stoics talk
about actually meditating. They have this exercise called premeditacio Malorum, which is a sort of
premeditation on the difficulty. So they want to think about how it's going to be hard, how it's
going to challenge us, where it could go wrong, not because they're going to shy away from it,
but because they want to have their eyes open and that being naive or being delusional is a good
way to get yourself in over your head or to be, you know, shocked by something. I'd rather be
pleasantly surprised that it is less hard than I thought than unpleasantly surprised that it's
harder than I thought. So I kind of try to be real honest. Like, I think people think, oh, that's
pessimistic. No, I'm still intending to do it. To me, the optimism is like, it's hard and I'm doing
it anyway, not, oh, it's going to go exactly the way that I wanted to go. Like, even when I did sit
down when my wife and I were opening this bookstore. We thought we didn't imagine exactly a global
pandemic and a supply chain logistics that we didn't imagine any of that. But like, you know,
you plan to have more runway than you need. You understand you're going into something you've
never done before. You do want to think about how it's going to be hard. How do we balance a life
of trying to improve ourselves, be disciplined and practicing virtues with giving ourselves
grace and acceptance and loving ourselves without constant self-criticism?
I don't know if I necessarily see the contradiction there. Stoicism to me is a philosophy about pushing yourself and challenging yourself, sure, but it's not whipping yourself. You know, it's not beating the crap out of yourself. There's a quote from Seneca. Seneca, most of his writing comes to us in his letters. He's writing these letters to his friend Lucilius. And he's saying to Lucilius, you know, you ask me, how do I know that I'm making progress in my
my pursuit of the philosophy, and he says, I know it because I've become a better friend to
myself. And I think what he means is like a friend supports you and believes in you, but they also
call you out and they hold you accountable. Friendship isn't just cheerleading. It's more than that,
good friendship anyway. And there's an honesty to it and a connection to it and a belief in it. That's
what he's talking about. And so if that's what the philosophy is doing for you, it's supporting
you, but also challenging you, I think you're doing it right. If it's just making you feel
inadequate or not enough, then you're doing something other than what the Stoics want you to do.
So this is about focusing on what's in your control. It's about, you know, holding yourself to
these standards and then also understanding that they are ideals and that we are inevitably going
to fall short of them. And what matters is what do we do after we fall short of them? Do we make
excuses or do we sort of pick ourselves up and try to learn from it and then get better and grow and learn
from each thing? Yeah. And I think part of what I have gained from your teachings is just
acceptance, right? Acceptance of what is and not beating ourselves up, but saying, hey, this is hard
and it's okay. It's okay that it's hard. Yeah, look, acceptance is really hard for entrepreneurs and
leaders and people who have built things because you're like, I didn't get where I am by accepting
things. I get that, right? Like if we were inherently passive, we would have stopped a long time ago
or we never would have gotten started. And so there is something sort of forceful and kind of
fundamentally irrational about anyone that changes things, right? Because it would have been
easier and made more sense to just not. I read your book obstacles the way about four years ago
during a very, you know, challenging time of my life.
And it definitely has changed the way that I look at the world,
how I show up, and how I embrace kind of some of those difficult things in my past.
So thank you.
Well, yeah, I'm honored to hear that.
And that's a reflection not of me.
That's a reflection of that these ideas have been tested by an emperor on one end of the spectrum
and a slave on the other end of the spectrum.
And in between there, you have power brokers and soldiers and merchants and, you know,
mothers and daughters and husbands and wives and people who are sent into exile, people who
are, you know, thrown in jail on false charges, people who started businesses, people who, you
know, built institutions and organizations. And then we're all, they're all dealing with this world
that, you know, isn't the way that we want it to be. And instead of sort of shying away from that
or becoming cynical about that, they decide to try to do what they can inside it.
and to make the most of it, and that's what inspires me about stoicism and what I try to communicate
in the books. So I'm glad you're, I'm glad it stood up for whatever you're going through.
Thank you. And thank you so much for joining us.
Of course.
All right. Let's get one.
Thank you.
Hey, it's Ryan. Thank you for listening to the Daily Stoic podcast.
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