


In this episode of The Daily Stoic, host Ryan Holiday discusses effective communication strategies in the context of difficult conversations, featuring insights from communication expert Jefferson Fisher. The episode reflects on the challenges posed by difficult people and how to navigate conflict, especially when kindness and empathy seem insufficient.
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0:04Welcome 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 here 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.
0:42Hey, it's Ryan Holiday. Welcome to another episode of the Daily Stoic Podcast. I hope your 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? Mark Sourilis 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.
1:28But 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. What stands 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. So 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.
2:11I 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.
2:40They're 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 at Jefferson Fisher.
3:11You hear those church bells. That's because it's 1030 here in Athens. And Follow him, Jefferson underscore Fisher on Instagram and Twitter. And then on YouTube, it's at Jefferson Fisher or TikTok, just ask Jefferson. Enjoy.
3:27Legal 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.
4:21The 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.
5:16Things 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.
6:03The 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.
6:57Her 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 not repeating that, she said, almost shaken. Then I won't be repeating this, my client said firmly. I'm getting off this roller coaster. 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.
7:49But 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?
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9:01When push comes to 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.
9:55Responses 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-your-worth mentality. Not everyone is worth your peace of mind.
10:45You 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.
11:43Belittling 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.
12:29The 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.
13:25I 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. mean. 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 steps. 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.
14:27A 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. Two, 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.
15:28In 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.
16:16It'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 over their words. They're also not expecting that reply.
17:10When 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, never mind, or, uh, 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 of outcome. This type of question seeks to highlight and project the reaction that they tried to elicit.
18:06Again, 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 composure.
18:55Thanks so much for listening. If you could rate this podcast and leave a review on iTunes. That would mean so much to us and it would really help the show. We appreciate it. I'll see you next episode.
19:54We'll be right back.
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Looking for practical strategies to deal with difficult people? In today’s episode, communication expert Jefferson Fisher shares a 3-step process for navigating conflict, especially when kindness and empathy no longer work.
Jefferson Fisher is one of the most respected voices on communication and arguments in the world. He is a Texas board certified personal injury attorney and law firm owner of Fisher Firm. Millions of people and some of the world's leading brands come to Jefferson for advice and practical strategies to communicate more effectively.
Follow Jefferson on Instagram and X @Jefferson_Fisher, on YouTube @JeffersonFisher and on TikTok @JustAskJefferson
📚 Grab a signed copy of Jefferson’s book, The Next Conversation: Argue Less, Talk More, at The Painted Porch!
🎥 Watch Jefferson Fisher and Ryan's full conversation here: https://www.youtube.com/watch?v=cs6rPU1lH3Q
🎙️ Listen to Jefferson and Ryan's full conversation on Apple Podcasts or Spotify
Audio excerpted courtesy of Penguin Random House Audio from THE NEXT CONVERSATION by Jefferson Fisher, read by Jefferson Fisher. © 2025 Jefferson Fisher, ℗ 2025 Penguin Random House, LLC. All rights reserved.
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