Difficult People: A Stoic Masterclass

0:00SPEAKER_00:All right, so let's crack into why we are joining today, why we want to discuss difficult people. Okay, so I don't know if you have experienced this, but most of the suffering that I've experienced in my life comes at the hands of difficult individuals. Um it's really, you know, obviously things like you know, a car that breaks down or some bad luck affects us, uh, but it's usually uh relationships that cause the most grief. Uh so this talk is going to be all about stoic tools to deal with difficult individuals.

0:39SPEAKER_00:And we're going to talk about how we can stay calm, how we can set boundaries, how we can manage triggering situations using the wisdom of the Stoics. All right, so the question, okay? Why would we want to deal with difficult people? And more importantly, the question that I want you to think about and hopefully have an answer to at the end of this talk is how do we remain ourselves around individuals that keep hooking us, keep forcing us to take the bait?

1:11SPEAKER_00:So the daily friction that other people make us experience in our relationships is one of the most sort of severe and consistent threats to our peace of mind, to our tranquility. And the Stoics knew this, and they wrote extensively about relationships and social situations, more so than any other practical subject. Marcus Aurelius opens his journal with it, and Seneca devotes three books to anger. Epictetus returns to it over and over again in his discourses.

1:47SPEAKER_00:The difficult person that we have to deal with is not a detour from a philosophical life. It's not like you have philosophy over here with your books and your quietude and your still lakes. No, as a practicing philosopher, you have to engage publicly, you have to engage with other people. And this is where stoic theory actually holds up really well. Okay. And you'll get to see with some of these tools if it works in your own life or if it doesn't work.

2:15SPEAKER_00:So that question I want you to think about. How do we remain ourselves even when people are hooking us? All right, so there's a Marcus Aurelius quote from his Meditations, okay, book two, chapter one, Gregory Hayes' translation. He says, When you wake up in the morning, tell yourself the people I deal with today will be meddling, ungrateful, arrogant, dishonest, jealous, and surly. But I have seen the beauty of good and the ugliness of evil, and I have recognized that the wrongdoer has a nature related to my own, not the same blood or birth, but of the same mind, and possessing a share of the divine.

2:54SPEAKER_00:We were born to work together like feet, hands, and eyes, like the two rows of teeth upper and lower. So what do you think is going on there? There are lots of different approaches and systems, and there's been a lot read into this quote. So on the surface, Marcus is preparing his mind, and we're going to look at some of these techniques before he begins the day, right? He's saying, When you wake up in the morning, the people I deal with today will be meddling, ungrateful, arrogant, dishonest, jealous, and surly.

3:28SPEAKER_00:It sort of takes away the sting. You know, he's expecting to meet these people, so it's not going to surprise him. You know, sometimes when we get frustrated, it's mostly because our expectations of reality didn't match reality. So Marcus is saying, hey, you probably are going to be frustrated today dealing with these types of people. But it doesn't end there, right? So Marcus continues after he reminds himself of this, he says, Hey, we're actually connected though.

3:55SPEAKER_00:They are like me and I'm like them. They may not have the training that I have. They don't know necessarily right from wrong. They don't understand virtue. But we all of us have something divine in us. We have the ability to reason. We have a part of God in us, even the people that annoy us. Um, so as you can see, he's reminding himself of the types of people that he's going to meet. He's already forgiving them beforehand, and he's also saying, I'm actually quite like them, and we both share divinity.

4:27SPEAKER_00:And then he ends with, you know, we are born to work together, like feet, hands, eyes, two rows of teeth, upper and lower. Okay, so there's a lot going on in that quote. And um if you unpack it, you can find a whole training manual in there. So let's be honest about stoicism. Okay, there are three main types of difficult or troubled relationships. We have green, which we could say are just standard difficult, amber, which would be harmful, and red would be dangerous.

4:59SPEAKER_00:For green relationships or difficult relationships, these would be annoying, draining, recurring, but not dangerous. Right? These would be people like uh, do you know anyone who just talks too much? Someone who constantly complains, uh, like a critical friend or a critical parent, the passive aggressive colleague, the person who's competitive with you and you don't know why, the person who gives you the cold shoulder. These would be difficult types of individuals.

5:28SPEAKER_00:And here, stoicism is amazing, works extremely well, and we have tools for these. When we have amber relationships, which would be harmful relationships, this would include some form of manipulation, narcissistic patterns, contempt, elements of bullying, controlling behavior, someone who likes to push boundaries. We would say that stoicism is absolutely helpful, but we would start leaning towards less contact with that individual and potentially documenting your interactions and maybe getting some expert guidance.

6:05SPEAKER_00:Okay, so stoicism is generally useful as the background, and then you may need some extra interventions. When you come to red relationships, this would be dangerous. This would include things like threats, coercive control, surveillance, stalking, financial control, fear of retaliation, sustained gaslighting as part of coercive control. Here, I would say that stoicism is good for your own mental health always, but you need specialist help here, you know, when you're in a dangerous relationship, because you may not be able to just deal with it uh in a way that's safe for you and the people around you without having some kind of um well-thought-out safety plan um and expert guidance.

6:49SPEAKER_00:So let's just be honest, right? Like if you came here and your life is in danger, this is not really the place to be. I still recommend you listen to the ideas, but ultimately you want to use these ideas plus find other support, ASAP. Uh whereas for the harmful and difficult relationships, stoicism can absolutely be a great use. Um, 100%. Um and sometimes for the dangerous relationship, sometimes you're afraid, and maybe the virtue of courage that is given to us from the Stoics might be useful for you to seek help.

7:26SPEAKER_00:All right, so let's look at the practice that we're gonna be going through. There's gonna be five moves, okay, and we're gonna run these through in a loop. It's gonna be a before, during, and after, okay? So just like Marcus Aurelia, step one is expect them before. So when you're dealing with someone who's difficult, this takes the surprise off the table. The Stoics call this pre-meditatio malorum or pre-meditation of future ills or future evils.

7:55SPEAKER_00:So when we we know we're gonna deal with someone who's difficult, we imagine dealing with them beforehand. This is the first step of the practice. Second, when we're actually in the midst of working with someone who is difficult, we find the hook, right? We notice where the trigger is in our body, we pay attention to it. In Buddhism, we may say this is mindfulness. In uh Stoicism, we would say this is prosoke. This is the mindful attentiveness to your thoughts.

8:27SPEAKER_00:And we notice where we are getting triggered, where the hook is, right? And we start to investigate it. Step three is we're gonna drop the rope. This is happening during, right? So we refuse the contest. We're not gonna get involved in the game they want us to play. We're gonna stay ourselves. We may leave, we may stay, but we stay ourselves. The the fourth step is that we look at the boundary as behavior, during. Okay. So a boundary is not something you request from other people.

8:59SPEAKER_00:A boundary is not something like, hey, can you please do this or can you please do that? A boundary is something only you need to do. Your behavior itself is the boundary. A boundary is simply put something that you will accept or you won't accept, and that's it. If you don't accept it, you've got to behave accordingly. And then step five is we're gonna turn the mirror. So the same patterns that we experience in the difficult person also live in us, and we're gonna find our shade humanity there.

9:29SPEAKER_00:We don't do this to like the person, we don't do this to forgive the person, we don't do this to say that the person acted right. We just we take away this uh idea of holding on to ill will. If we walk around with hatred and a sense of contempt and vengeance, we slowly over time corrupt our character and become subtly like the person that we are affected by. Okay. So we want to be able to deal with these difficult individuals without losing our own peace of mind and corrupting our character in the process.

10:02SPEAKER_00:Now, there's a stoic image called the inner citadel. So if you think of like a castle with strong walls, like a fortress, the Mark Aurelius would say that we have one of those within ourselves. We can go into this inner citadel and find peace there whenever we like. So one way to look at it is we could say that inside the inner citadel is our mind, our thoughts, attention, and all of these things, what we control. And that's where we should stake our peace of mind.

10:35SPEAKER_00:Outside of the citadel, outside of the fortress, there's so much going on, so much chaos, so many things outside of our control. We shouldn't really get caught up in this. All right, and we should look at what can the external world reach and what can the external world not reach. And someone who's practicing stoicism, they have stronger walls around their citadel. They don't allow externals to just come in and they have clearer lines between what is theirs and what is not theirs.

11:05SPEAKER_00:So let's start by looking at what is not yours, what is not your responsibility, what is not yours to control. Other people's tone of voice. You just don't control it. You never will. If you're gonna lose sleep and get frustrated over how other people speak in their tone of voice, sure you can make a request, sure you can decide who you want to spend time with, but you cannot manage another person's tone. It's exhausting to even try to do that. Another person's opinion of you, whether they apologize or don't apologize, whether they ever change, how they remember the conversation that happened, what they say or do ultimately is not within your control.

11:44SPEAKER_00:It's not within your realm of responsibility. It's not inside the citadel's walls, it's outside. So then the follow-up question is well, what is inside the walls? What is yours to control? Okay. Well, your judgment of what is happening or what has happened that is inside the walls. Whether you say something or remain silent, yours to control. What you say, the content of your speech, whether you stay or whether you leave, the story that you tell yourself about the incident, the kind of person that you want to be.

12:17SPEAKER_00:Okay. So some of you may know this as the dichotomy of control. Uh in 2025, a book came out that was all about the what's called the let them theory. And the idea is that we want to let them, when it comes to other people, just be themselves, do what they need to do. And we want to let me, let ourselves, uh, take responsibility of the things that are up to us. This is the dichotomy of control. It's a stoic idea that is dressed up in modern self-improvement language.

12:48SPEAKER_00:There's a term called the hegemonicon, and this is another way of thinking about the inner citadel. So the first exercise we're going to do, because I want this to be interactive, and the more that you can take action during this workshop, the more you're going to benefit from it. So the first exercise is I want you to map your inner citadel. So bring right now a difficult person to mind. You've got to have someone, right? It could be someone right now, it could be someone that you will have to deal with, it could be someone from your past.

13:15SPEAKER_00:I wouldn't say bring like the worst person in your entire life to mind. If you want to, I won't stop you. But ideally someone who just shows a difficult pattern on a fairly regular basis, like a parent, a colleague, an ex, neighbor, you know, uh a name or an energy that keeps surfaces when you're trying to fall asleep. Hold them in your mind. Okay? This is the person that you're going to be using in the next exercise. Right, so this is what I want you to do.

13:46SPEAKER_00:I want you to bring to mind this person. Think about the recurring behavior that they use to trigger you, to hook you the most. And I want you to quite simply ask yourself what elements of this situation are in your inner citadel, are yours to control, and genuinely yours to defend, and what's not outside of your control, what are outside the walls of the fortress, never yours to take responsibility of. Right? So have a moment to think about this.

14:19SPEAKER_00:Even just a few seconds of trying to sort this out is good practice. It's good practice for you. So think of this person, think of this situation. Now look at their behavior, look at your behavior, look at the context of the situation. What is truly yours here? What is inside your citadel? Is up to you, is your responsibility, is on your side of the line, and what is not yours to defend. I'm gonna go through a few lists now just to remind you. So inside the walls is your judgment, what you say, whether you say anything, whether you stay or leave, and the story you tell yourself, the person you choose to be.

14:58SPEAKER_00:Outside of the walls is basically them, their tone, their opinion, whether they apologize or change, right, what they think, what they say, how they criticize. So spend a moment now thinking about that. So bring to mind a difficult individual, a strained relationship of some kind. And then I want you to sort out the situation, their behavior, your behavior, the context, into the things that are up to you, the things that are inside the inner citadel, and the things that are not up to you, things that are outside of this fortress.

15:31SPEAKER_00:So what are you willing to defend, and what are you willing to let go? Is it changing any of your assumptions? I'm gonna ask some questions now, and you can just meditate on them, think about them, or you can journal about them. What's something you'd been carrying as inside the walls of this inner citadel that turned out to really be something that was on the outside? What's something that you've been carrying as inside the walls that turned out to be outside?

17:35SPEAKER_00:Did anyone notice here that they were spending energy defending something that was never really under attack in the first place? This is a common one. We spend so much of our life fighting against things that are not up to us, that are not our responsibilities, that are not in our control. It gets us nowhere. And what feels different about this difficult person now that you've drawn this line? I want to move on to a concept. Imagine a hook in your mind like a fisher fisherman's hook, a fisherperson's hook.

18:29SPEAKER_00:Imagine a glistening hook. And then also imagine a rope. We're gonna be walking with the metaphors of the hook and the rope. And these are the two moves that are at the heart of every difficult interaction. The hook is the physical sensation of the trigger. It could be where you have tightness in your chest, clenching in the jaw, drop in your stomach. Your body knows when it's been hooked. It's a place in your body where the hook lands. And when your body reacts before your mind is away, you become flooded.

19:18SPEAKER_00:And one of the things we have to do is separate the hook in our body from the response in our mind. And the way that we can do this is simply through the breath. And the best breath work practice for this is the physiological sigh. You take two breaths in, a breath in through your nose, then a tiny sip again at the top of the in-breath, and then a sigh breath out. So breathe in. Breathe in, a tiny sip at the top, and then breathe back out. This opens the gap.

19:55SPEAKER_00:This loosens the hook. This stops your mind diving in head first, following the body. And then the second part is the rope. We need to get better at refusing the games, refusing the contest. We don't need to defend, counterattack, counterattack, comply, withdraw. Any of these are still part of the game. A high conflict difficult person wants the fight. Because that's where they feel comfortable. If they were skilled at compassionate, healthy communication, they'd be doing it.

20:32SPEAKER_00:They're not. So they feel powerful and in control in the dominating role. And when you defend, they can tell you that your defense is pathetic. When you counterattack, they'll counterattack ten times harder than you. When you comply, they'll make you feel like a slave. And if you withdraw, they'll make you feel scared. All of these options are still part of their game. When you drop the rope, you're saying, I'm gonna just choose to be free. You can stay in the room or remove yourself from the room, but the rope, either way, is dropped.

21:10SPEAKER_00:There's a lot of talk at the moment, unfortunately, about stoicism being like um like a form of being like an alpha male. There's like the manosphere movement, right? And it's like stoicism is about not having emotions and being tough. And that is actually not what stoicism is about at all. And if you read Marcus Aurelius, he's constantly reminding himself to be compassionate and gentle and um loving and tolerant. I mean, the quote we started this talk with, you know, comparing himself to other people as team members and all saying we share a piece of the divine.

21:50SPEAKER_00:Well, he said that when someone does you wrong and is not nice to you, the best revenge is to not be like that. Those are his actual words translated by Gregory Hayes. The best revenge is to not be like that. And so many of us, and then by the way, this is Marcus dropping the rope, right? And so many of us, we say things like, I'll give them a taste of their own medicine. Right? Or I'm going to um I'm just reading the comments here. Uh yeah, it's a I'm gonna give them a taste of their medicine, or I'm gonna treat like with like or do tit for tat or whatever it is, and you're playing that individual's game.

22:35SPEAKER_00:Marcus is saying, hang on a second. If you're acting in any way like them, you've already lost. Ask yourself the question how can I respond in a way that is nothing like this person? Then I've truly won. That's the that's really the ultimate revenge. And I do. Think there is a sense of satisfaction that a high conflict individual tends to get when they can make other people lose their cool and make other people like them and high conflict. Like, ah, I got them.

23:04SPEAKER_00:I got this calm person to lose it. Satisfying. They're not so perfect after all. Let's talk about boundary as behavior, right? So a boundary is not a request, it's something that you do. So this is how simple now, right? You from this point on, you're always going to know how to do boundaries. This formula. If the behavior is X, I will do Y. That is it. If the behavior is something, I will do your action. So let's imagine some examples now. Family.

23:41SPEAKER_00:If you criticize my parenting in front of the kids, I'm going to leave the room. We can talk about it later when it's just us. Boundary. Not if you criticize my parenting in front of the kids, I'm going to bring up all the stuff that you used to do when you were younger or whatever it is. That's not a boundary. Yeah, that's a form of punishment, retaliation, just trying to control the other person. You don't need anything from the other person, set a boundary.

24:08SPEAKER_00:In the realm of work, if the criticism turns personal rather than about work, I'm ending the call. We can reschedule. Relationships. If I want to keep talking, then I'll only do that if we stay on the actual issue. Okay? So if someone's trying to detract you into all these different things about the future and about the past and these side tangents, you can just say, look, hey, I want to keep talking, but I will only do that if we stay on the issue.

24:40SPEAKER_00:Your behavior is the boundary. Behavior is boundary. Just say that to yourself a few times. So bring to mind that difficult person that you thought about already in this talk from the first exercise. Now, what I want you to do is I'd like you to create a behavior as boundary for them. Alright, so write this out. If insert specific behavior, I will insert specific action. So think about what they're doing. If this person does this specific behavior, I will insert my specific action.

25:32SPEAKER_00:Okay, take a moment to do that. Sadly, you you can't expect other people to change. You need to change. You know, as much as I'd love to say you can just remain the same, but cure like five different secret techniques you can use to win an argument with a high conflict person. Sorry to say that's not how it works. It's very difficult to change people, it's very difficult to change individuals. Um, you know, think how difficult it is to change yourself.

26:01SPEAKER_00:Um and so the best bet we always have is changing how we respond and how we relate. And one of the absolute best ways of doing that is start starting to see all boundaries as forms of behavior. Okay, so if you want to share any of your boundaries, I would love to check them out. And a couple of questions from you, right? Did you have any guilt when you were doing this? Any guilt come up? And if so, where do you think that guilt came from? Another follow-up is if we use premeditation here, when we first set a boundary with this person, they're probably gonna pull a bit harder on the hook.

26:49SPEAKER_00:And what's something simple you can say or do if that happens? We want to be prepared. Now I want to talk about some practices, simple practices that you can do each day. Um, there's gonna be a morning practice, a midday practice, and an evening review. What is opposite of someone who chooses to ignore you when I'm a small group? Will answer a simple inquiry I ask, not never look at me, responds to others. I didn't want to become like her, but it hurts, so I keep trying to keep my end clean.

27:35SPEAKER_00:What's the opposite behavior I could practice? So you're saying that when you're in a group, there is someone who just ignores you a lot, doesn't look at you, responds to others, sort of like blanks you, doesn't take you, doesn't act like you exist. Is that right? Um you know it's it's interesting, right? My um my stepdaughter, she there are different forms of like shyness. Um some kids like blush, right? So she's like she's nine. Some kids blush, some kids get visibly nervous and a bit shaky.

28:22SPEAKER_00:When she meets someone new and they talk to her, she will like look at them but not actually say the words. Um like as if her words are stuck, and they interpret that as being as being rude. Uh but she's in her mind, it's like there's a stuckness, she can't actually speak up until she gets to know someone a bit better. Um, so it's it's a tricky thing because on the one hand, we could say that like the silent treatment absolutely is a form of bullying.

29:00SPEAKER_00:On the other hand, is there anything that we could think about in the behavior that we could give compassion to? Are they struggling with something? Is there a deeper reason for this? Do we really know for sure with evidence that it's because they hate us? You know, or is there some other unknown variable at play? And, you know, the best unfortunately, um, the best thing I think we could do, um, the person who engages fully with others, others feels very passive-aggressive.

29:35SPEAKER_00:Um, yeah, I think the best thing you can do is you encourage them to keep doing that in your mind. You know, I think the suffering that you're experiencing comes from you don't want them to do this. You want them to be different, you want them to engage with you and validate you and talk to you, and they don't. So, as difficult as it is, I think you want to actually go, you know what? I actually would prefer her to be doing this. I don't want her to talk to me and engage with me.

30:05SPEAKER_00:I love it the way it is. Yeah, I'd actually start feeling a bit awkward if she started talking to me. I want her to keep doing what she needs to do. And I I don't just accept it, I want I encourage it. Keep doing it. It's good. Um and you know, because but what else is what else are you gonna do? You don't control her. You don't control her at all. You can't make her talk to you. What what can anyone name something better to do in this situation?

30:38SPEAKER_00:It is what it is, you know. Am or fati, love your fate. This is the relationship, this is who she is, this is the way she's responding. Are you just gonna suffer for the next three months about it? Or can you actually love it? And want fate to be no other way. Beyond that, you can have a conversation, you can talk to her directly. Um, but yeah, you really have two paths. Yeah, let them and now let me. It's really two, it's really two paths. If it's bothering you, you could like Marcus Aurelia says, either um teach them or endure them.

31:21SPEAKER_00:You could either go and have a conversation and be direct and be like, hey, I'm gonna be assertive now and I'm gonna tell you how I feel. In not an aggressive way, but in a really clear way and vulnerable way, or it's a case of full acceptance of the situation. You don't want to be stuck in between those two places. You just kind of secretly want them to be different. That's a recipe for suffering. So it depends which which path you want to take.

31:54SPEAKER_00:Um so yeah, I think the for me at least, uh that quote either endure them or teach them. And that means either teach them as in today I will show this person exactly what's going on in me, or today I will fully endorse their behavior and fully allow it. Anything other than those two things, you're now in this kind of gray zone and it's not gonna feel good. So let's talk about these morning practices, okay? So in the morning, pre-meditation of adversity.

32:24SPEAKER_00:Before you do anything else, name the individual or the couple of individuals that are gonna push your buttons, and then the specific move that you expect on their part. Pre-meditation of adversity. Takes a couple of seconds. The midday hook. When you notice that your body's reacting, you do the physiological sigh. Two short breaths, one long out. Then ask, am I letting this individual inside the walls of my inner citadel? Seneca said the greatest remedy for anger is delayed.

32:57SPEAKER_00:Seneca, the stoic master, the person who wrote one of the best texts ever written on anger, says the greatest remedy for anger is delay. Why would he say that if he didn't think there was a lot of validity to it? And then third, the evening review. Three questions. What have I cured today? What fault have I resisted, and in what respect am I better? What have I cured today? What fault have I resisted, and in what way am I better? That is your morning, midday, and evening review.

33:29SPEAKER_00:So the challenge that I want to take with you into this week is I want you to run this practice once a day, specifically for the difficult individual. 90 seconds in the morning, the hook, during the day in the review at night. Seven days. What's the Seneca writing on anger? He has a book called On Anger or D Era. Does anyone have any questions? Anything specific you want guidance from myself or other individuals in this talk? What were the three questions, please?

34:10SPEAKER_00:You mean in the evening review? So the three questions were what ill have I cured today? What fault have I resisted, and in what respect am I better? Okay, guys, well, thank you so much for uh for joining me today. Um I hope that was useful, and I hope you have a great rest of the day and sending you love and support and some stoic strength. Um, great contributions today, guys. Thanks for tuning in. Talk to you soon. Bye guys.