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Ryan Holiday
Foreign welcome to the weekend edition of the Daily Stoic Podcast. On Sundays, we take a deeper dive into these ancient topics with excerpts from the Stoic texts, audiobooks that we like, hear or recommend here at Daily Stoic, and other long form wisdom that you can chew on on this relaxing weekend. We hope this helps shape your understanding of this philosophy and most importantly, that you're able to apply it to your actual life. Thank you for listening.
Hey, it's Ryan Holiday. Welcome to another episode of the Daily Stoic Podcast. I hope you're summer is going well. Mine is going well. I am on a roof in Athens. My kids are having a little screen time before bed and my wife and I are detoxing after a delightful day. But a stressful day. Having kids is stressful. Other people are stressful. Tourists are stressful. I'm sure I am stressful for other people. I'm sure I was a difficult person in somebody's life. Today, that is the reality, right? Marx Willis opens his famous passage in meditations about how the people we're going to meet today are this and that and this and that, and it's mostly not good things. But he says, look, you can't let these people implicate you in ugliness and you're made to work with them. You are made to work together. So basically, dealing with difficult people is where meditation starts. It famously deals with difficult people in the obstacle is the way passage. Right? The impediment to action advances, action withstands. In the way becomes the way. What is the obstacle Marcus is speaking about in that quote? He is speaking about difficult people. He says, people who obstruct us. In today's episode, I wanted to do a little deep dive into how we communicate effectively with difficult people because we can't change them, but we can change some of our communication strategies. I had a great conversation with Jefferson Fisher. If you haven't seen his viral videos, you know you probably have. You just don't even know it. But he's a lawyer. He records these sort of viral videos in his car between court appearances and mediation and all that. We had a great episode on the podcast. If you haven't listened, I'll link to that. But he has this awesome book called the Next Conversation, which is all about that. Strategies he's learned over the course of his career about how to deal with difficult people and communicate effectively with them. We have the same imprint, Penguin Random House Audio, there who do my audiobooks. They did his audiobook and I reached out and asked if I could run this section in the book that I really like. So I wanted to do a deep dive into that. You can watch my episode with Jefferson on YouTube and hopefully this makes you a little bit better. Now look, difficult people are inevitable. It is not inevitable that we have to be difficult. It's something I'm working on. I hope you're working on. And anyways, that's today's message. You can grab a copy of the next conversation, Argue less and talk More at the Painted Porch. Follow him on Instagram and Twitter effersonfisher. You hear those church bells? That's because it's 10:30 here in Athens. And follow him jeffersonfisher on Instagram and Twitter and then on YouTube it's effersonfisher or TikTok. Just ask Jefferson. Enjoy.
Jefferson Fisher
Legal disputes between family members are the worst. Between friends is a close second. The people you let into your life know a lot about you, what makes you happy and what makes you upset. When close relationships go south, they can be the nastiest sort of conflict, the type that brings out the absolute worst in a person. Sometimes the most difficult people in your life are either related to you or have a history with you, making the tough talks even tougher. Maybe you can relate I once had a case involving two middle aged sisters and it was about as fun as it sounds. My client wanted to keep the business that the two had inherited operating and successful. The other sister wanted to sell the business and split the profits on account of her having, well, let's just say, different life goals. They needed a clean break from what had become a constant source of conflict between them. The plan was for my client to buy out her sister's shares. Despite multiple attempts to negotiate, my client's generosity and patience were continually met with stubbornness and at times outright hostility. The other sister insisted on painting my client as the antagonist of the story. When my client presented reasonable solutions, the other sister would find a way to twist her words and resort to hurtful comments and insults that went back as far as when they were kids, things she knew would hurt. How long do I have to keep playing nice? My client asked me during a phone call. Well, you always play nice, I said. That doesn't mean you play soft. You don't need to push back. You just can't be pushed over. Acknowledging that she tried everything to keep it peaceful and respect what her parents would want, my client had finally found her limit. Trying to work it out wasn't working. She needed a different strategy. Using the lessons you'll learn in this Chapter My client began standing up for herself in conversations with her sister. She started to find her voice. The two agreed to meet in person with attorneys to try one last time to resolve their issues. My client was nervous walking in, but I could tell she had a new sense of confidence when she spoke. The discussion started off fine, but it wasn't long before the sister began ramping up the drama. At one point, she threw out something that was more than a comment. It was a grenade. And I've never liked you. You're dead to me anyway. My client went silent. I knew from our many conversations that her sister's words had cut like a knife. After using a long pause, my client finally spoke. I need you to repeat that. Her sister looked uncertain. She wasn't expecting that response. She looked as though she was about to say it again, but she couldn't. I'm. I'm not repeating that, she said, almost shaken. Then I won't be repeating this, my client said firmly. I'm getting off this rollercoaster. If you want to get off with me, do it now. And I've always loved you. The sister teared up and asked for some time to speak to her attorney alone. A few minutes later, the case settled. You've heard the advice that in difficult moments like these, you need to be empathetic and try to reach common ground. I think that's right, and it's noble, but sometimes it's not practical. What do you do when you feel like your compassion has been exhausted? How do you communicate when you believe your empathy is being exploited or taken advantage of?
Ryan Holiday
Thanks to Toyota Trucks for sponsoring this episode. When I bought my ranch in 2015 out here in Bastow County, I drove my car about halfway down the dirt road that we live on. Thought, this isn't going to work. Stopped, parked it walked the rest of the way home, borrowed my wife's car, drove into Austin, and bought a tr. What I bought was a Toyota Tacoma. And this truck wasn't just transportation getting me to and from my house. It unlocked a whole different style of living for us. Not just on the ranch, but in our little Texas towns. There were places I could go now that I couldn't go before, especially out here in the piney forests, through the fields, and on the unpaved roads like the one that I lived in. We got to go deep into the Hill Country's wild beauty. We've driven all the way out to East Texas. We've driven it across the country. And by we, I mean not just my wife, but both my kids, who I drove home from the hospital in that truck. Toyota trucks are built for those who understand that the best adventures happen when you're willing to veer off course, because you never know when you'll end up on a Toyota Adventure Detour. And of course, this is stoicism, too, because every detour, every obstacle is an opportunity. But it's helpful if you can handle the difficulty inherent in that. If you've got the resilience and the right companion to make it wherever the road takes you, discover your uncharted territory. Learn more@toyota.com Trucks Adventure detours.
Jefferson Fisher
When Push Comes the Shove Kindness alone doesn't always work. No amount of patience or gentle explanation makes a difference. The person is committed to misunderstanding you. When it happens, you'll be tempted to do one of two things. You'll walk on eggshells, constantly adjusting your words and actions to avoid the conflict altogether, at the expense of your own authenticity and peace of mind. Or you'll double down, matching their negative energy, tit for tat and round for round. I want you to do neither. There's a third option. It involves using your new assertive voice to create responses that leave no room for misinterpretation, responses that have all the boldness of aggression with none of the disrespect. There comes a point when it's time to stand up for yourself. When push comes to shove and you need to voice your disapproval. Yes, you're still going to show integrity. Yes, you're still going to show respect. But your response should be about showing that you respect yourself enough to speak up and say what is unacceptable to you. The first thing to know about standing up for yourself is when to do it, because not everyone is worth getting out of your chair for. It's a know you're worth mentality. Not everyone is worth your peace of mind. You have to know and consciously decide if the person standing in front of you is one who means something to you. To assertively disagree and stand up for yourself is both an art and a skill. Here are the advanced tools you'll need the next time someone goes too far. How to Deflect Insults, Rudeness, and Belittling when you hear someone say something rude or insulting, understand that they're wanting something from you. That something is dopamine, the feel good hormone that motivates and rewards you. Their search for dopamine has little to do with you personally. It's often a reflection of their own insecurities. Belittling others can make the powerless feel powerful the ignored feel seen, and the jealous feel like they've gained something. They get dopamine from the attention of the spotlight or from their sense of control over your negative reaction. It also distracts them from their own vulnerabilities by allowing them to focus on perceived or projected weaknesses in you. In the same way you may catch yourself judging someone, the other person feels less insecure, even if momentarily, knowing that they can give you insecurities too. They'll feel less upset knowing that you're upset. It's a cycle in which their temporary high comes at the cost of your confidence. The key is to see these types of comments for what they truly are. An attempt to elicit a response Remember, it's not about you, it's about their need for your response. So when they say something for their hit of dopamine, the worst thing you can do is give it to them. That's why you're not going to when they insult or offend you, you're an idiot. You're a loser. You're ugly. Whether it's name calling or personal attacks on your character, looks, ability, or identity, these comments are meant to hurt. They might be aimed at your age, race, gender, or background. They're meant to cut deep. And they often hurt more because they're direct. I know that when you get an insult, it feels better to throw it right back. Oh, I'm an idiot. Well, you're. But that only ratchets up the problem. Maybe you can convince yourself that you're okay with that, but now you're the one wanting dopamine. The blows will continue to get thrown until one of you bows out and receives the momentary win. It's not worth it. Your value is too high for such low behavior. When someone insults you or offends you, I want you to try these. 1. Give it a long pause. The long pause gives their words a chance to echo back to them. The pause also allows their words to fall before they get to you. As I'll discuss in chapter 11, which keeps you from getting defensive, a long pause makes them rethink their words and question whether they will stand by them or take them back. Remember, the awkward pause will make them squirm, and that's okay. And most of all, the silence takes away their dopamine. 2. Slowly repeat what they said. Often, the silence is all you need to say, but if it requires more, repeat what they said back to them very slowly. Here, you're the echo. You're ensuring that they heard every word of what they said. And three Keep breathing out. When you repeat their words back, it will either clear up the confusion or add fuel to the fire. Go to your breath. In that moment, you need to rely on breath control to make sure that you don't tighten your body or muddle your thinking. If you enter into a state of shallow breathing, there's a higher risk that you'll have a delayed display of emotion or anger and lose that high ground. If needed, assert a boundary. As you'll later learn in the next chapter, when they belittle, patronize, or condescend, let me put this in terms that you'll understand. Oh wow, you finally lost some weight. Good for you. It's cute how you thought you did that right? These kinds of comments are meant to diminish your efforts intelligence or status. It's the idea that they're talking down to you and explaining what you already know. Unlike more aggravated insults, these remarks are often indirect. There is typically a sense of feigned or pretend praise or friendliness that's underscored with a put down to reduce your significance. When someone belittles, patronizes, or condescends to you, try these steps. 1. Make them say it again. Ask them to repeat it. That's it. When you ask the other person to repeat what they just said, you take all the fun, AKA dopamine, out of it. It's like throwing a wet, soggy blanket on over their words. They're also not expecting that reply. When someone makes a belittling remark, they expect the spotlight to turn to you. But when you ask them to repeat what they just said, the spotlight jerks right back to them. They'll become uncomfortable. The result is often a quick reply of nevermind or I meant. As they try to readjust their response. It can be as simple as saying, I need you to repeat that. I need you to say that again. I didn't get all of that. Can you repeat it? 2. Ask a question of outcome Regardless of whether they have the guts to repeat the comment, you're going to respond using a question out of outcome. This type of question seeks to highlight and project the reaction that they try to elicit. Again, you're verbalizing the echo they need to hear. It sounds like did you want that to hurt? Did you want that to embarrass me? Was that supposed to make me feel small? Did that feel good to say out loud? Number three Reply with silence. No matter their answer, let your silence be your reply. It's better not to respond. Most likely they'll have a terrible excuse or say they're just joking or start fumbling over their words or backtracking. Let their poor behavior linger as your silence shows you to be the one with control and and composure.
Ryan Holiday
Thanks so much for listening.
If you could rate this podcast and leave a review on itunes, that would mean so much to us and would.
Really help the show. We appreciate it and I'll see you next episode.
Jefferson Fisher
When too much work bogs you down, Asana helps you handle it. AI makes it easy to hand off routine tasks and stay focused on important work. That's how work gets handled.
Ryan Holiday
Visit us@asana.com look, ads are annoying. They are to be avoided if at all possible. I understand as a content creator why they need to exist. That's why I don't begrudge them when they appear on the shows that I listen to. But again, as a person who has to pay a podcast producer and has to pay for equipment and for the studio and the building that the studio is in, it's a lot to keep something like the Daily Stoic going. So if you want to support a show but not listen to ads, well, we have partnered with Supercast to bring you a ad free version of Daily Stoic. We're calling it Daily Stoic Premium. And with Premium you can listen to every episode of the Daily Stoic podcast completely ad free. No interruptions, just the ideas, just the messages, just the conversations you came here for. And you can also get early access to episodes before they're available to the public. And we're going to have a bunch of exclusive bonus content and extended interviews in there just for Daily Stoic Premium members as well. If you want to remove distractions, go deeper into Stoicism and support the work we do here. Well, it takes less than a minute to sign up for Daily Stoic Premium and we are offering a limited time discount of 20% off your first year. Just go to daily stoic.com premium to sign up right now or click the link in the show descriptions to make those ads go away.
Host: Ryan Holiday
Guest Excerpt: Jefferson Fisher
Date: July 6, 2025
In this episode, Ryan Holiday explores the Stoic approach to handling difficult conversations and people. Drawing inspiration from a recent conversation with lawyer and viral communicator Jefferson Fisher, Ryan features an excerpt from Fisher's book The Next Conversation, which lays out concrete communication strategies for when kindness and empathy aren’t enough. The episode provides listeners with practical, step-by-step tools—grounded in Stoic philosophy and real-world legal experience—to manage conflict without abandoning respect for themselves or others.
The episode blends Stoic wisdom with legal and psychological tactics for handling conflict without sacrificing one’s values or self-respect. Jefferson Fisher’s 3-step formula—Pause, Echo, Breathe—is a practical guide for listeners hoping to maintain composure and assertiveness in the most trying conversations.
Useful for:
Anyone facing regular conflict at work, in families, or in relationships, and for those seeking to apply Stoic principles to modern life’s interpersonal challenges.
For further reading:
The Next Conversation by Jefferson Fisher.
Watch Ryan’s full interview with Jefferson Fisher on YouTube.