A Bit of Optimism - The Hidden Cost of Always Saying Yes | A Bit of Optimism: Feelings at Work | PART 1

Episode Date: July 14, 2026

Welcome to Feelings at Work, a special series from A Bit of Optimism with Simon Sinek.  Work isn't just about deadlines, meetings, and getting things done. It's also where we experience frustration, ...excitement, trust, anxiety, belonging, conflict, and joy. If we want to build healthier teams and better workplaces, we have to get better at understanding the emotions that shape how we work together. That's what this series is about. In each episode, Simon Sinek sits down with Yale professor and Lifeshop founder Alex Simon to explore one emotional challenge that affects how we work, lead, and relate to one another. Together, they unpack the emotional skills most of us were never taught—but use every single day. This episode is about saying yes. Have you ever agreed to something... and immediately regretted it? Maybe you didn't want to disappoint someone. Maybe you thought, I'll figure it out somehow. Maybe your calendar is packed, your to-do list never gets shorter, and somehow you're still worried you're letting people down. Most of us don't think of ourselves as "people pleasers." We just want to be helpful. We want to be dependable. We want to be someone others can count on. But what if constantly saying yes is actually making things harder—for you and everyone around you? Together, Simon and Alex explore why so many thoughtful, capable people take on more than they can realistically handle. They unpack the hidden patterns that lead to overwhelm, resentment, and burnout—and why trying to keep everyone happy can quietly make us less reliable. The good news? This is a skill we can learn. In this conversation, you'll discover practical ways to communicate more honestly, set healthier boundaries, and build stronger relationships—without feeling selfish or letting people down. In this episode you'll learn:  ➡️ Why saying yes too often can actually make you less reliable ➡️ The hidden connection between overwhelm, burnout, and self-betrayal ➡️ The simple phrase that creates space before committing  ➡️ A better alternative to saying yes or no: how to "share the dilemma" ➡️ What leaders can do to create teams where people feel safe telling the truth ➡️ Why healthy boundaries strengthen relationships instead of hurting them Whether you call it people pleasing or simply trying to keep up with everyone else's expectations, this conversation is a reminder that taking care of yourself isn't selfish. It's one of the best ways to show up for the people who matter. This... is A Bit of Optimism. + + + Chapters Chapters 00:00:00 Why We Need to Talk About Feelings at Work 00:02:00 What People Pleasing Actually Looks Like 00:04:20 Why People Pleasing Hurts You and Your Team 00:07:00 Why We Say Yes When We Mean No 00:10:00 Different Types of People Pleasing 00:13:00 Why Approval Can Become Addictive 00:15:00 How People Pleasing Leads to Burnout 00:18:00 The Hidden Cost of Being "Hyper Competent" 00:21:00 Why People Pleasing Doesn't Actually Help People 00:27:30 Simon's Experience With Saying Yes to Too Much 00:31:00 How Leaders Can Help People Pleasers 00:38:20 The Power of "Let Me Get Back to You" 00:40:00 How to "Share the Dilemma" 00:44:00 The Difference Between Being Reliable and Being Available 00:47:00 Building Healthier Boundaries at Work + + + Website: http://simonsinek.com/ Leaderful: https://simonsinek.com/leaderful Podcast: http://apple.co/simonsinek Instagram: https://instagram.com/simonsinek/ Linkedin: https://linkedin.com/in/simonsinek/ Twitter: https://twitter.com/simonsinek Facebook: https://www.facebook.com/simonsinek + + + About Alex Simon Alex Simon is a Yale professor and the founder of Lifeshop, a school for adult emotional education. She teaches the emotional and communication skills we all should've learned in school—but didn't. She facilitates experiential workshops on how to have hard conversations, stop people pleasing, listen better, navigate major life transitions, and build healthier relationships. Her sessions are practical, deeply connective, and somehow shockingly fun. When she was 27, Alex created The Self & Other: In Theory and Practice, one of Yale's most sought-after courses. In 2025, she founded Lifeshop in New York to bring emotional education beyond the classroom and into everyday life. She also launched The School of Life in New York and leads workshops for organizations around the world. Before dedicating her career to emotional education, Alex worked as a management consultant at Bain and held strategy and operations roles across industries. She has also lived and trained at Plum Village and Esalen and completed dozens of programs in mindfulness, communication, and personal development.

Transcript
Discussion (0)
Starting point is 00:00:00 Today, what I want to talk about is people pleasing. Just before we get going, I just want you to know that I want this to be the best experience for you, and I will do anything I can so that you're happy. Are you people pleasing me? Yes. It works. I'm so pleased. Think about the last time someone asked you to do something at work, and you said yes. When you said yes, did you mean it?
Starting point is 00:00:25 Was it like a real full-bodied hell yes? or was it more like a, yeah, yeah, totally. Did you say yes with confidence? Or was there a tiny voice inside you screaming, what are you doing? You don't have time for this. Followed by total remorse or self-loathing, as you slowly recognize that the future you now has more work than you can handle. If any of this sounds even vaguely familiar,
Starting point is 00:00:47 then congratulations, you have people-pleasing tendencies. And even if you're not a full card-carrying people-pleaser, we've all done this to ourselves out of a desire, to be a good team player or out of fear of saying no. Here's the irony. Whoever was asking us would actually have been fine with a no. If only we knew how to give it. Instead of taking a summer hiatus, we're presenting a special five-episode series of a bit of optimism to go deep on human skills, the things that help us connect, collaborate, and succeed in any human relationship. That's why I invited Alex Simon to join me. She's an adjunct professor at Yale and founder of Life Shop, where she teaches a
Starting point is 00:01:27 emotional intelligence. And over these five episodes, we will tackle some of the messier human interactions, like having hard conversations, taking accountability, listening and giving feedback, and in this one, people pleasing. While so many people are focused on what skills to learn in the age of AI, the people that will succeed are the ones that are doubling down on their human skills, because even in a world of computers, we still work with people. And being a good colleague or friend means learning how to manage expectations properly. There's and ours. We will cover three big themes in this episode.
Starting point is 00:02:04 First, we debunk the myth that always saying yes is how you get ahead, that it's how you earn trust or get promoted and become indispensable. In fact, saying yes can actually hurt those things. We talk about what actually works. Then we'll explore a six-word phrase that can get you out of almost any over-commitment. You can use it today. No therapy, no personality overhaul required a guilt-free solution for people-pleasers everywhere. And finally, we offer ways to spot people-pleasing behavior before those good intentions turn to burnout. That high performer who can never say no, they're closer to the edge than most people realize.
Starting point is 00:02:44 And before you get too good at saying no, please listen to this episode. And if you enjoy this episode, also please remember to subscribe. This is a bit of optimism. So people pleasing affects a lot of people, more than I think people realize, and it is the desire to sometimes avoid conflict, sometimes to ensure that somebody else is getting what they want feels good, going out of your way to make sure that everybody's okay. But the reason it can be dangerous and destructive,
Starting point is 00:03:25 and the reason I wanted to talk about it today, because in theory, it sounds like a nice idea, but it can very often be very self-destructive to the people-pleaser. Yeah. It amplifies all kinds of insecurities. It also sometimes makes them do things they don't want to do, break their own boundaries, all kinds of things. And very often, it doesn't actually please the people they're trying to please.
Starting point is 00:03:44 So it's sort of like in the long term. So it's kind of like a zero-zero. I think the tricky thing about people-pleasing is that it's kind of like an extreme version of things that are good and adaptive. Like it's normal to want to be generous and to say yes to things. and to want to be liked. And I think that where it tips over into people pleasing is when it becomes almost like an existential need
Starting point is 00:04:03 of like, oh, I feel like I'm going to combust if I don't say yes to this thing or tell them I can meet this deadline even though I know I can't. Or I'm like over-apologizing even though I know it's not my fault. Or, yeah, like taking on too much work, there's so many different ways that it exhibits itself. And I think that we think of it as like a personal characteristic. And every single time I teach people pleasing, I'm shocked by how many...
Starting point is 00:04:27 Or teach people how to... Let me teach you how to be a better people pleaser. More yeses, more apologies. You can teach that one. So, yeah, when I teach stopping to people please, I'm shocked by how many examples. Most people are many, many people have examples that have to do with work.
Starting point is 00:04:45 And it's because it's an area of our life in which we're constantly being asked for things. You have to say yes and we have to say no all the time. Can you be a people pleaser at work but not in your life? Yes. Or do you think like it's like you're a people pleaser and it just exaggerates at work? I mean, I think that there's overlap. But I know people who are really people pleasing at work but not in their personal lives.
Starting point is 00:05:04 And I also know the reverse. You're really people pleasing in life. But at work, you're like, oh, no, no, I can maintain my boundaries and I can say yes, I can do this. No, I can't do that. It's really interesting to me how it shows up in different areas of our life. I also don't think it's like a binary. I don't think it's like, oh, I am or I'm not a people pleaser. I think it's more like to me, people pleasing is about how can I say yes, what I mean?
Starting point is 00:05:25 and how can I say no when I mean no? And so it's a subtlety and it's a gray area and it's happening all the time. Yeah. I think what we're talking about is the dial, which is important. I think all of us are people pleasers at some point, even when it's slightly unhealthy.
Starting point is 00:05:41 And for people who are people pleasers who are hearing this, even that word, they're like, oh, that's me. And it always comes in that sort of ways. Nobody's ever like, I'm a people pleaser. People like, oh, you know, it's what I think so interesting about it is there's a lot of self-reasing
Starting point is 00:05:55 awareness for people who are, and it is, I don't know if it's, in the most extreme, I think it is shame, but I think people are kind of like either resigned to it or don't know how to get out of it, but it's always, oh, I'm a, that's me. The reason I think it's important to talk about it, obviously because I want to help some of those people overcome the extreme people pleasing, but even for people who wouldn't classify themselves as people pleasers, I think it's really important to understand it if you, because if you work with somebody who's a people pleaser, you're sometimes accidentally pouring gasoline on their little fire and not making them feel good at work. And so it's an important thing to talk about even if you're not a people pleaser.
Starting point is 00:06:35 Because probably you work with one. You probably work with one. And it really impacts the whole team. Like I remember I used to work with someone who I was really close with personally. And she had a kind of chronic people-facing situation. And it took me a while to figure it out because we would all. agree, okay, we're going to do this, we're going to do it by Thursday, we're going to do this and that, and then she just wouldn't do it.
Starting point is 00:06:58 And she was in the room agreeing to the deadline. Yeah. And then didn't meet the deadline. And I'd be like, hey, where is it? You know, what's going on? And then nothing. And I wouldn't have thought of that as people pleasing because there's so many other things. It's like, oh, it's incompetence.
Starting point is 00:07:11 It's lack of communication. It's this and that. There's so many other things. But really, she was just saying yes to something that was beyond her capacity. Because she didn't want to disappoint. And it's not because she was lying, hiding and faking. Because there's a lot of people who say yes to things. because they're lying, hiding and faking.
Starting point is 00:07:24 They don't want, it's a bit of an imposter syndrome. They don't want, this is not what we're talking about. This is saying yes, because you don't want to go against the grain. Yeah. Because you find going with the flow, and everybody else has agreed to it. I don't want to, I don't want to disrupt it. Even if I have information that everybody needs to know, I don't want to be the one to be, I don't want to be the negative Nelly here. Yeah, and I also think, I totally agree.
Starting point is 00:07:48 And I think in the moment, her experience was like, oh, I can, I can do that. Yeah. You know, like, it's not lying in betray. It's not, lying hiding, faking. It's not lying hiding faking because in the moment it feels like she can't do it. She talks herself into it.
Starting point is 00:08:03 Yeah, and then the second afterwards, there's like the shit. And then there's resentment. There's a resentment everywhere, right? Then she resents herself. Like, why did I do it again? She resents the team or she resents the assignment. And now she's getting in trouble because she missed the deadline. Yeah.
Starting point is 00:08:18 And now she's letting the team down. And now all the shame. The shame. Now it shows up. Right. Totally. I've, of course I've done that. Of course I've done that.
Starting point is 00:08:27 And of course I've been intimidated by the room or the project. And like, and I can, I know when I'm people pleasing because my tone of voice is different. Right. So like, Simon, you game? I'm like, yeah. Yeah. As opposed to, yeah. And what do you think you're trying?
Starting point is 00:08:46 Like, what do you think is going on for you? In my brain is like, you're, you sure? Like, in my brain is like, is like the little, you know, the angel and the. devil on my shoulder and the devil's like, you know, do it. You know, and the angel's like, do you want to do this? You know, you sure? And I'm, I don't want to disappoint the other person that I'm not interested or that I'll offend them. You know, hey, Simon, can you do me a favor? And I want to be like, no, no. And so I'm like, okay, you know. And now I'm at the position where I've had to, it's exactly what's happened, where I have to unstick it.
Starting point is 00:09:18 where I'm like, hey, remember I said I was going to do that? Yeah. And the lesson that I have learned, and I'm better than I used to be, but the lesson than I've learned, and this I think is the first lesson to combat people-pleasing, I think, is people are actually very comfortable with the no up front. And it's, and... How do I clean that out?
Starting point is 00:09:42 I don't. Fuck that, right? What I've learned is, like, if you just tell somebody no up front, They're actually okay with it. I've learned more people are comfortable with a no. When they say, can you do this? They're actually asking, can you do this by this deadline? And it's not passive-aggressive.
Starting point is 00:10:01 There's something in our system that believes, like, the world will end. If I say no. If I say no. And I think the calculus there, or if I'm trying to like unwind the inner logic that's going on in my head, there's a part of me that's like, well, that'll just be few. Alex who has to deal with. You know, like, present Alex wants the easy thing. But it's kind of like you're hungry and you want to eat junk food.
Starting point is 00:10:24 Yeah. You know, you're like, okay, I want to eat all the, I always want to eat all the shitty food, but then you know you're going to feel bad later. You know it's not going to impact your health in a long term. One of my close friends, Kim, her mantra, and I try and remember it, if it's not a heck yes, it's a heck no. You know?
Starting point is 00:10:42 Yeah. And like, because, or the other one that I was like, you know, would you do this tomorrow? It's like, hey, in six months, can you do this? You're like, yeah. Future Simon would love to do that. It sounds like an amazing thing to do. And the question is, would you do it tomorrow?
Starting point is 00:10:57 I'm like, no. Well, then if you don't want to do it tomorrow, you don't want to do it in six months. I think that's a really useful thing. I think I personally struggle with the going back to the heck yes, heck no. I kind of struggle with it because more often than not, I feel really intense ambivalent.
Starting point is 00:11:11 Some part of me wants to do it, some part of me doesn't. Or all of me wants to do it, but another part of me knows that I can't. And I think when things are more obviously a black and white yes or no, I find it easy. It's not, heck yes, it's like, yeah. So what you're saying is it's fine in theory, but things are grayer than that in reality.
Starting point is 00:11:28 Yeah. Including our own. Yeah, there are many different parts. I mean those parts want different things. And I think that the heck yes, heck no dichotomy doesn't often map onto my experience. Like, yeah, it just doesn't. I find that my,
Starting point is 00:11:45 the context is much richer and more dynamic and more complex than I often think it's going to be. So when you teach, people come to your stop people-pleasing class. And I'm very curious, obviously you go around the room and you ask people to describe their experiences. I'm very curious what patterns you've noticed. Is there one kind of people-pleasing, four kinds of people-pleasing, you know, infinite numbers of people-pleasing? Like, what do you hear in the classroom? There's so many. it's a really good question.
Starting point is 00:12:15 There's so many different types. I think one big one is like a conflict avoidant people pleasing, which is like any tension, any rocking of the boat feels like it's, the world is ending. And so I'm going to just do anything to avoid a hard conversation. Another one is like a kind of addiction to approval. I think that's a big one. Interesting.
Starting point is 00:12:36 And I think this is a really interesting one that plays out at work because sometimes if we, like there's this like a parental boss dynamic where like, Our boss can almost become like our parental figures and our worth feels conditional on them saying like you did a good job. And you'll do anything to get that. You'll do anything to get that. And there's a part of me that really believes that a lot of what's going on at work is like I want to know what I have to do. I want to do it. And then I want to be patted on the head and told that I did a really good job.
Starting point is 00:13:07 And like if I can do those things, like if I had enough clarity on what needs to be done, if I can feel useful in doing it, I'm contributing to something that's beyond my and I just get the satisfaction, the very simple satisfaction of being useful. And then I can be recognized and someone can give me praise for what I've done. Like, those three things scratch a lot of our, like, core human needs. There's a very important nuance here, which is, you said, addicted to the approval. I think everybody wants to know they did a good job. And everybody wants their bosses to say, to recognize them. Yeah.
Starting point is 00:13:41 And it's healthy to want it. It drives a lot of us to do good for those we serve and want to make them proud, especially if it's a good boss. We really want to make our leader proud. They've invested in us. We want to show them the investment was worth it. But that's not what we're talking about here. We're talking about the addiction to it, the need,
Starting point is 00:14:02 which is it's not, and it stops being about the work. And it starts being about the approval. And that's an important nuance. I totally agree. And I think it's about what is the price that I'm willing to pay to get that. And so for me, the way that I think about it is if I'm willing to kind of like do my work and do the things that need to be done and I'm setting clear boundaries and I'm, you know, kind of like doing my thing and then I'm getting approval, great.
Starting point is 00:14:26 That's like a healthy, beautiful system. Whereas when it slips into more kind of extreme behaviors where I'm sacrificing, where I'm betraying myself in order to get that approval. Can you, can you, so give us an example of that? I have so many different things. Like you're saying yes to things that are. beyond your capacity without even checking in with yourself if you can do it. You're sacrificing your own life and your own well-being,
Starting point is 00:14:50 not just on like I'm working one late night or I'm working one in two crazy weeks. It's like on a longer-term basis and you're consistently not doing it. So regularly not coming home in order to make, do good, do right by your boss, not even do right by your boss, do whatever needs to do to get your boss's approval, your sacrificing weekends, nights, family. Yeah. Again, as you said, not occasionally, but habitually.
Starting point is 00:15:12 Yeah. And over time, my experience has been that that's led for me, to me, feeling a lot of resentment. And then the accumulation of that, that's how you end up in burnout. It's like saying yes hundreds of times to things that you don't actually want to do. And then staying up late and taking on other people's work and managing other people's emotions. And I think a lot of people think of burnout as like, oh, I'm just like exhausted over time. When actually I think the difference between giving a lot of energy to your work, versus burnout is burnout involves self-betrayal.
Starting point is 00:15:47 And so that's, I think, where the people pleasing. You're like comes in is you're betraying yourself over and over and over again. And that is what actually compounds and leads to burnout. It's not just exhaustion. I think we've talked about this before, but we had somebody in our team who burnt out and her workload was not enough to burn somebody out. Yeah. And we couldn't understand it.
Starting point is 00:16:04 And I think we talked about it in a different capacity where she was an empathetic ear to a lot of people who were coming to her with all their problems, not just work problems. And her desire to please them and always be available to them, it got to the point where she, I mean, the whole thing collapsed. Yeah. You know, she was exhausted, done. I mean, she quit. She quit her job. Completely burnt out.
Starting point is 00:16:29 Yeah, to me that, like, that screams like invisible self-betrayals, like where you know in your system that you're betraying yourself over and over and over. Because you don't want to let them down. Yeah. Oh, they're in pain. They're angry. They're sad. Yeah. You know, they need somebody to talk to. I don't want to upset them.
Starting point is 00:16:45 The image that I always think about is, you know, the game Jenga, where you stack the bricks. Yeah. Like, it's like if your sense of self is this Jenga, and each time you betray yourself, you're like taking out one brick. Oh, great analogy. You're taking out another brick. Each time you say yes to something. Each time you over-apologize, each time you rescue someone else because they can't do the thing that they need to do. It's like, brick, brick, brick, brick, and then all of a sudden your whole life is unstable.
Starting point is 00:17:09 I think it's such a great analogy because we all do things that are slight betrayals, but it's okay, it's healthy. Doing it occasionally, the Jenga stack is stable, even if you remove some bricks. What we're talking about, you know, the chronic people pleaser, that that brick removal continues and continues and continues. And, you know, it's healthy to take one piece out of the time, but eventually if it's habitual, you know, it has consequences and it's going to collapse. What about you? How do you feel like you've seen people pleasing to show up at work? So I think, I know of one example where, uh, Somebody is a high performer, and they're highly competent, very good at what they do.
Starting point is 00:17:49 And they've, I don't know where it comes from, but they have to communicate hyper-competence at all times to everyone. And so what they end up doing for fear of saying, I don't know, or fear of saying, I'm stretched too thin, or fear of saying, I don't even know where to begin, they end up saying, they end up saying, yes to everyone because they're maintaining it's not just maintaining their view of themselves of hypercompetence, but it's maintaining the image they've projected to everyone else of hypercompetence
Starting point is 00:18:25 and that's the pleasing part, which is don't worry, I can take care of it, that's why you rely on me because I'm hypercompetent. And the problem is as they are. The problem is as they actually are, like, is the incompetent ones that are people pleases are easy. Those are easy to spot and we can
Starting point is 00:18:41 rush in and help them and coach them. But I think the hypercompetent ones, and I know as for somebody who's had a hypercompetent people please are on my team, what ends up happening from the leadership standpoint is we make it worse by accident because they start to gain the reputation of being hypercompetent. So we start relying on them more. And I know. And I'm pretty good about sort of like people in balance. And I ask questions expecting it on us answer. So I'll be like, hey, I got another thing for you.
Starting point is 00:19:14 Do you have space on your plate? I do. Are you sure? I just want to make sure. Yeah, yeah, yeah. No, it's good. And can you do this? I don't know if we've ever tried this before, but do you?
Starting point is 00:19:23 Oh, no, no, no. I got this. So I am checking in and they're lying to me. Lying. Lying is a strong word. Lying is a strong word. They're deceiving me and or themselves. The point is, like, even a well-intentioned leader
Starting point is 00:19:36 who really wants to check in with somebody make sure they have the bandwidth or the capacity, I can't help. Yeah. And so one of the things I want to explore in our conversation is not only how does the people pleaser advocate in a way that doesn't disappoint or let anybody down, but helps them protect themselves, and how does a leader or a colleague who works with a people pleaser, how are we able to recognize the signals so that even if well-intentioned and asking questions that we
Starting point is 00:20:10 we can actually find out what's going on so that we can intervene even if they say yes. So if they say yes, I can do it and I go, you know what? Don't worry about it. I got this, you know? It's so hard because the nature of it is very confusing to the people around you because it feels authentically
Starting point is 00:20:27 like, oh, they can take it on. Even though a small part of your intuition is like, wait, I really don't think you can. And so that's why you're checking, right? That's hard too, right? It's hard. What if you just doubt somebody who is competent? Yeah.
Starting point is 00:20:37 And so it's, I mean, you and I have, this has been our mantra since we started this, which is people are messy, this stuff is messy, work is messy, this little messy. You know, none of this is crystal and clear. It's hard. Yeah. I think to your question of, what was your first question?
Starting point is 00:20:53 I just want to, number one was, I want to, how do we offer practical things to the people who are the people pleases, but also how do we offer practical things to people who work with people pleasers? I think it's such a good point and I think often, to your point, we're thinking about it in terms of the people who of like what's going on in my system when I'm saying yes, it's something that I'm not a yes to. And I think the way trying to understand what are the different impacts that it has on the
Starting point is 00:21:19 whole team or on the whole or on our relationships is a totally other side of it that I find to be really important because it goes against a lot of the things that the people pleaser internalized. For me, one of the greatest myths about people pleasing is that somehow it'll work. You know, like you really think it's going to work. And that's because in the short term, you get this like hit of, a good feeling. You know, like you say yes to someone and someone's like, thank you. Thank you. Thank you. Thank God. You're on the team. Yeah. Yeah. Like, oh, you are so confident. At least somebody is.
Starting point is 00:21:48 Yeah. And like, oh, that's so and so, like she's really like this, you know. And so that or in, let's say you're, and that's the addiction part, right? That's the addiction. Yeah. Let's say you're fearing the conflict. That's the type that you are. Like in the moment, you do get to avoid the tense situation. It's like, oh, thank God it works, you know. And then you're not thinking about the long term impact. Like, you're not thinking about the way that it's confusing other people. By the way, like any addict. Yeah. Like, you know, so it's, it's very consistent. And what's so interesting is that you've faced those consequences every single time.
Starting point is 00:22:18 You know, my sister always asks this question, what's the mistake that you keep on making? Which I think it's such an amazing question. Because like, we all have the mistakes that we keep on making, even though we have to face the music after 10 minutes, after 10 days, after whatever it is, like, we still sometimes, like, have to make the same mistakes over and over and over again. And so I think something that I have found a lot of solace in is reminding myself that I'm going, like future Alex is going to have to deal with this. And, and that it's also not just me. And that kind of makes me think about the other element, the other myth of people pleasing, which is that you're somehow doing it for other people. Like, oh, if I'm saying yes to
Starting point is 00:22:52 something that you're asking me for, then I'm a good person. I'm a good, generous, selfless person who's, like, sacrificing and there's like a kind of moral righteousness to that. And we also associate, like, if I'm saying, no, that makes me bad. Like, I'm not doing something that you want me to do. That's bad. and that's selfish and ungenerous. And I think the internalized idea that when I'm saying yes to other people, it's about making their lives better, I actually want to kind of turn on its head.
Starting point is 00:23:19 The way that I think about it is that it's actually paying a price of the truth so that you can soften your own discomfort. I mean, let's be very blunt and let's be harsh. And I say this with love. Okay. What are you going to say? Not to you. Okay.
Starting point is 00:23:34 But people pleasing, not making people pleased and not saying yes, but we talked about it as Jenga, but the uncontrollable urge to keep pulling bricks out of the Jenga pile, right? We're distinguishing between healthy pleasing and unhealthy. It's, and I think you're saying this, I'm just going to be blunt about it. It's a selfish act, which is you're not doing it actually to serve the other person. You're doing it to either avoid the conflict or you're doing it to feel the little dopamine hit of, well done. And, you know, it's actually not even dopamine. It's serotonin.
Starting point is 00:24:06 But probably both, actually. But it's the desire for the approval that you become addicted to. And it is, like any addiction, it is actually quite selfish. And this is what you're saying, I think, which is to turn it on its head and recognize that by saying yes constantly, though you're pleasing yourself in those moments, yes, you hurt yourself over the course of time, but you're actually hurting and disappointing the other person as well
Starting point is 00:24:30 that you're trying to please. Because now you have to unstick. something or, you know, try and you, you, the example you gave is, is from your own experience with somebody who said yes to something, missed the deadline, and then shut down and couldn't even respond to emails when people like, hey, what, how, and by the way, those are like, hey, I can help you. Like, you know, if you haven't made the deadline, that's okay. We've got a whole team here. Like, what's going on?
Starting point is 00:24:52 But their ability to be like, I shouldn't have said yes or I've screwed up the shut. Now there were ripples. There's now discontent. There's now the ripples of like, when you miss your deadline, it affects other people's lines. Like we're waiting on your work to do this work, you know? And I, and it's, it's all because of, and again, I'm being, I'm exaggerating the point to make the point, but all because of the selfishness of the desire to get that, that approval and make somebody else happy in that moment, it actually becomes not the selfless act you think it is. I think I resonate
Starting point is 00:25:24 with what you're trying to say. I think for me, labeling it as selfish, to me activates like the shame part of my mind, which, for me, shuts down my capacity to, like, engage with it in a self-competitive. Yes. To me, it's,
Starting point is 00:25:40 I'm trying to do something. Well-intentioned. Well-intentioned. And to the impact of it isn't what I think it is. And it's not, I'm not trying to act out of self-interest. It's probably some protective thing
Starting point is 00:25:53 from my childhood. Probably some time in my childhood, I had to internalize that I couldn't both be myself and be safe and accepted by someone else. And so I picked being safe and accepted by someone else over staying true to what I know my needs are. That's a much better way of putting it.
Starting point is 00:26:10 Thank you. You're right. And I think maybe if my instinct is, oh, I think I'm doing this for the other person, I find it helpful to turn that on its head and say, okay, if I think I'm doing this for the other person or for my team or for my boss or for whatever it is for my company, actually trying to show myself that it's not saying yes that will be the best, saying yes when I can't do something, it's not that that will be what's best for my team or for my boss or whoever it is,
Starting point is 00:26:40 but actually saying the harder but truthful thing in this moment is in the long term, that's how I'm integrity to my team and to my boss in doing all these things. You know, maybe I am a people pleaser. I realize, you know, I've had to learn to say no because I ended up hurting myself and others because I just, I became, I became unreliable. Yeah. You know, don't give that to Simon. He's unreliable.
Starting point is 00:27:04 And that didn't feel good. Like, I got a feedback. Like, you're unlaw, you know, we can't rely on you. And I was like, what? And it's because, it wasn't because I'm irresponsible. It's because I said yes to too many things and couldn't do it all. And I've had to learn that saying no made me, made me reliable. Yeah.
Starting point is 00:27:24 And I confused getting everything done as, reliable and rather reliability is not the ability to execute everything. Reliability is accurately managing expectations. And I became more reliable when people like, we need this and I'd be like, I can't. Or if I can, if I can take something else off my list. Yeah, it's like also zooming out and being able to see the big picture. And now they get to decide with me if they really need me to do it, then we have to take something off the list. Or if somebody else can do it. Or it can maybe happen at another time. And that's, I had to reconfigure what reliable means in my own head. And to be reliable, it means accurately managing expectations. Yeah. By the way, saying no to everything is also
Starting point is 00:28:06 unreliable. Yeah. Because that's also, you're not relying on it. I'm afraid to do anything. But that's, that's also not managing expectations because I have to do something. Yeah. So very interesting. Yeah. And it was never selfish when I said yes. It was always well-intentioned. And sometimes an exaggerated sense of, I mean, this is an exaggerated sense of, I mean, this is an exaggerated sense of, what I'm capable of, what I'm capable of time. And it was not a conscious desire or ignorant. It was never ignorant. It was really well-intentioned and sometimes forgetful of what else I've got going on.
Starting point is 00:28:38 And I never said, let me check, which, by the way, is a viable answer. Can you do this? Let me check. Let me get back to you. And it was always a desire to be a great team player. Yeah. So I guess I've never described myself as a people pleaser, but I've definitely had elements of that. I've worked very hard to work out because I got negative feedback.
Starting point is 00:29:00 Yeah. And I think tracking the long-term impact of saying yes when you don't mean yes is a good way to check in with yourself. It sounds like that's the journey that you were on is you were saying yes to all these things and then you weren't able to follow through. Then you felt disappointed. Or I was putting myself in horrible positions where I'm just working too hard for fear of, you know, being unreliable.
Starting point is 00:29:21 Yeah. And I think people who have people pleasing tendency can really recognize that of like the intensity of the experience of being asked for something that you know you can't do, saying yes to it, then feeling self-loathing, then feeling, then not being able to do it, then feeling shame that you're not able to do it, then feeling accountable, but also then even more intense self-loathing, and then you're kind of just like in this spiral, and then you're fixating on all of these emotions that you're having instead of actually just doing the thing, you know, it's a whole, it's really a rabbit hole and it really,
Starting point is 00:29:52 I have a lot of compassion for it, and I've done it a lot of times. The thing that I think is so interesting about people pleasers, there's some deep-seated childhood, like, overbearing dad stuff. You know, like, if she let down her dad, you know, she was the worst person in the world. And so I became that figure, that parent figure. And so I remember, like, when we would work together and she would show me stuff, and I could, I would ask a question because, like, it didn't add up. Like, it didn't make sense. Like, literally the math didn't make sense, you know? and I'd ask a question, and she would lie to me.
Starting point is 00:30:27 I mean, she'd just flat out lie about what happened. Because for her, telling the lie and being right was actually the better option than just saying I screwed up and fearing that she was letting me down. I would rather that. And I'm like, because once I sniff the lie, I'm going to keep asking questions because it won't make sense. And that's when it's going to feel stressful for you,
Starting point is 00:30:53 because I'm going to keep pummeling you with questions because it doesn't make sense. It's because you're lying. And I remember once, like, I even remember where we were. We're on a plane on a business trip together. And like something didn't make sense. Something wasn't aligning. And I said, what happened here? And she, like, sort of like, oh, I screwed that up.
Starting point is 00:31:10 I went, okay, well, what's the right answer then? She went, I think it's this. I'm like, okay, great. And for her to see, like, nothing happened. And very high performer. It's one of the reasons she was a high performer. I think that's beautiful. There's an idea that I'm obsessed with,
Starting point is 00:31:26 which is this idea of a positive corrective experience of when you have something that you think is going to go one way. Oh, if I make a mistake, Simon will hit me forever. And then instead of the worst fear being confirmed, you have an opposite experience. It corrects your assumptions about what's going to happen in a positive way.
Starting point is 00:31:43 And it like rewires something in your system that's like, oh, I can make a mistake. Well, that's what happened. Yeah. It didn't happen immediately, but it didn't happen over the course of time. She had to dip her toe in the water to discover.
Starting point is 00:31:54 And so, like, when we think about if you work with a people, please, right? Which is, and I remember, because I couldn't just tell her, like, telling her isn't enough. Isn't enough. And she wouldn't believe me. You know, I'm like. Or maybe she would believe you on a rational level, but something in her system would still fear it. Right. And so, like, even when we had the conversation more than once, I'm like, you've got to just tell me,
Starting point is 00:32:17 and I'm cool with it. Don't, you know. But at some point, I think I said, you have to trust me. Just try it out. next time, like just tell me what happened or tell me something went wrong or you made a mistake or you screwed up or you didn't know, you needed help, like any of those things. And I want you to see how I will respond because I guarantee you it's different than what you're experiencing now because you feel unbelievable pressure now because the work is wrong and you're defending it and that's why there's a tension between us. You need to try it out. And she did.
Starting point is 00:32:48 And the first time it went okay and the second time it went okay and the third time it went okay. and over a course of trials, eventually she became very relaxing. Ah, man, I screwed that up. It's such a beautiful thing. And to me, you executed it with so much love and grace. And that's also, when I, you asked a question earlier of what do you do as a leader or as a teammate when you're working with someone who has this tendency? And this is one of the things that I do is I try to create a positive corrective experience.
Starting point is 00:33:18 I want to say that again because it's such a great phrase, a positive corrective experience. I like this idea of a positive corrective experience because corrective by itself sounds punitive. Like, you know, when you have anything corrected, it's just like, oh, please, you know, but a positive corrective experiences, which is I am correcting something here. I'm correcting a behavior, but it's going to be such a positive environment for you that you will find yourself craving it or at least being okay with it. I really love it and the way that I try to do it. So, for example, my chief of staff who I adore and trust completely, I love her so much. she also has this tendency.
Starting point is 00:33:53 And so whenever she's not communicating with me about something, I know that something has happened. And I'm trying to create the sense of safety so she knows that she can come to me. And instead of withholding information out of fear, she can be honest. And so the way that I tried to craft this positive corrective experience is, first I try to do what you did of tell her.
Starting point is 00:34:13 So on a conscious level, she knows, hey, it's going to be okay. I just really want to know. I trust you. And it's going to be okay. But that, like you said, is kind of not enough. And so then I tried to give her some experience that allows her to feel in her system. Oh, I have this fear that I'm going to be abandoned or I'm going to be rejected or I'm going to let someone down.
Starting point is 00:34:32 I'm going to disappoint them. I'm going to have this fear. And then instead of confirming the old fear, the old belief, then I give her this other experience. And so that's a lived thing. And then what I try to do is the thing that I would maybe add on is I try to name it. So I try to be like, I bet you thought that this was going to happen. And now can you feel in your system that this other thing happened? And then I try to offer this kind of over the long term.
Starting point is 00:34:53 Two thoughts come to mind. One is if we go back to the real experience you had of the person who was people pleasing and then just started ignoring the emails. The problem is if you're the leader or the colleague and you get no response or not the response you need, the emails become terseer and angrier. And now we're reinforcing the negative corrective experience. That's a negative corrective experience. Okay, I screwed up, but look how it's going.
Starting point is 00:35:17 So I'm certainly not going to admit anything could go out. ever wrong again. What that does is just amplifies the shame. And being stuck in the shame spiral is not going to help you get out of the behavior. And the other thing that I thought of when you're in the rational part where you're explaining something, and I talk about this a lot because I love it, which is the human brain cannot comprehend the negative, right? I'll prove it to you.
Starting point is 00:35:35 You ready? Ready? Yeah. Don't think of an elephant. Right? You can't tell the human brain not to do something. Yeah. This is why they tell parents.
Starting point is 00:35:46 Never tell your kids, don't eat on the couch. you say to your kids, eat at the table. You tell them the behavior you want, not the behavior you don't want, because all it does is reinforce the thing you don't want. Right? And so when we say things like, no, you have to tell me the truth. You won't get in trouble. All we're saying is you're going to get in trouble. And so what we have to learn to say is, no, you have to tell me the truth.
Starting point is 00:36:07 I promise you it will be a nice experience in a safe environment if you tell me. Yeah. Right? We have to tell them what they're going to get, not what they're going to avoid. So that's another thing that's really important to use affirmative language. when having the rational conversation about consequences of the continued people pleasing. I love that. I've never heard that before. It's a good one. It's a good. Okay, now we've talked about the person leading the people pleaser a little bit. Let's talk about the people pleaser themselves.
Starting point is 00:36:35 Can you please share some of the tricks and techniques that you teach to actually help the people pleasers? Okay. There's so many that I love. One that I really loved, you kind of mentioned earlier, which is let me get back to you. And so I think for people who are really trying to work on this behavior, having a rule for themselves, a challenge, that whenever anyone asks them for anything, they have to say, let me get back to you. Even if they think that they're going to do it. No matter what. No matter what. Because it's a practice. It's a practice. And it's building the muscle of... And you learn when to deploy it later, but right now do it in extreme. Yes. Because the knee-jerk answer is always yes. And in the moment, it feels like an authentic yes. And so
Starting point is 00:37:12 creating a little bit of that distance of just for 24 hours or for two hours or whatever it is, I'm going to actually check in with myself and I'm just going to see I'm going to check in with my to do list I'm going to look at my schedule I'm going to check in with someone else and see what I need to actually get the information that I need can I say yes to this?
Starting point is 00:37:29 Another one that I'm obsessed with I call it sharing the dilemma maybe you have a different term for it. Sharing the dilemma going to be. Yeah because often when someone asks me for something I feel mixed right? Part of me wants to do it. Part of me knows I can't.
Starting point is 00:37:40 Part of me thinks maybe I can if I do this thing and we often put ourselves in a position of needing to say a yes or a no when sometimes we can share something other than a yes or no, and that can be true to our experience. So there are many different ways to share the dilemma. One way is to share the context of, okay, I want to do this thing. I'm also thinking about this.
Starting point is 00:38:01 These are the other competing priorities I have, and so you can just share the context. That's one. Another thing that you can do is you can share when you don't know. Because oftentimes when people are asking us for something, and we don't actually know the answer. I don't know if I can go to this event. I don't know if I can take on this piece of work because of this thing.
Starting point is 00:38:15 Then we like don't answer. And we like fear, we fear, we either say yes or we don't answer. Instead of saying, very simply, like, I don't know. These are the things that I'm waiting for. Let me get back to you. And then the other thing that I like to do is I like to share the full, like my full internal dilemma. And it sounds kind of crazy, but it really works because it creates a sense of like, oh, we're on the same team trying to figure this thing out together.
Starting point is 00:38:39 Let me understand what you mean. So I'll give you a real life example. So go to a colleague and be like, I need you to do this. Okay. So if I was trying to share the dilemma. I would say, okay, great, I really want to do this thing. And is my dilemma. So these are the other things that I'm thinking about.
Starting point is 00:38:57 These are the other things that are on my plate. And this is why those other things are important. And so I try to show why they're important to remind my teammate of, oh, our shared mission. We're both trying to work on this big thing. You have this one piece of it. I have another piece of it. So I try to share that I feel a yes to it.
Starting point is 00:39:14 I try to share kind of like the big picture, the bird's eye view of the competing priorities. And then I also try to acknowledge the other person's position or their need. So I'll be like, I know this is important to you because you need this and this and this, which also helps them feel like, oh, we're all on one team. We're all in this dilemma together. It's not like a kind of you versus me. I'm going to either say yes and you're going to be happy with me or I'm going to say no and you're going to reject me and I'm not going to be worthy or useful.
Starting point is 00:39:37 And so I try to share kind of like the big picture view. And it creates the sense of togetherness. and also instead of being the end of a conversation, like you ask me for something, I say yes or I say no, that's the end of the conversation. When you share the dilemma, it's the beginning of a dialogue of, oh, it's not that it ends here, yes, I'm doing it, no, I'm not. It's, okay, interesting.
Starting point is 00:39:58 Well, maybe if I take on this piece of work, then you can do this. Oh, cool, well, I can do, what about these three things? If so-and-so can do this other thing. And so we're kind of sitting in the problem together, trying to figure it out together. And that is the beauty of sharing the dilemma. It starts a conversation, it starts a dialogue to find something that works for everyone. There's a nuance here that has to be underscored and it goes back to that affirmative language.
Starting point is 00:40:22 So when somebody is sharing the dilemma, as I'm listening to you, that affirmative language really matters. So you don't want to say, you want to avoid saying, I don't want to say no, right? Because now what the person who asks you just heard is like, okay, you're about to, you're just telling me no. Yeah. Right? I don't want to say no, but. You know, I got this thing and this thing and this thing. That's actually not sharing the dilemma.
Starting point is 00:40:45 That's not making the other person feel affirmed in asking for help. Sharing the dilemma, as I'm learning from you, I'm sort of gaming it out in my own head. I need you do this. Ah, yes, that needs to get done. I'm working on this and I've got this. I'm trying to figure out how I can make time to prioritize that. So sharing the dilemma is literally that. It's the thinking out loud of trying to solve the problem
Starting point is 00:41:13 that they're asking you to solve by moving the pieces of the puzzle around. You're doing it out loud. That is sharing the dilemma. It is not. I want to say yes, I want to make sure this happens, but I don't want to say no. And it's not dumping your stuff on the other person's plate.
Starting point is 00:41:33 It's literally them watching you process what you have to move, around in your schedule or your day or your week to ensure that that thing that you think you agree is very important needs to get done. And simply sharing the dilemma, somebody else can say, oh, I didn't realize you were working on those things as well. Yeah, take that off your list and do this instead. Or, you know what?
Starting point is 00:41:56 Continue what you're doing. I think it's easier if I do this myself. Yeah. And you never actually said yes or no. And this is what I think is so valuable about the sharing the dilemma. It's not I want to say yes or I don't want to say no. It's not saying yes or no. That's your very point.
Starting point is 00:42:10 It is removing the binary nature of a question, can you do this? And it is literally going through the steps of trying to get to yes. We don't want to say, oh, I really want to help you, but this and this. I really want to help you and these are the other things that I'm thinking of. So you're not. It's not negating. Yeah, you're not like fake saying, I want to help you. It's like, yeah, I want to help you and these are the other things that I'm thinking for.
Starting point is 00:42:33 You're not saying, however, but, except. I have to think that's a nice trick because I do this as well, which is I say to my team, I'm thinking out loud here. It's a different reason. It comes from, you know, people who think out loud. We can go. The addiction of thinking out loud. No, no, it is. But people, especially in a position of authority, people take it as a task when it's just a thought. So I've had to learn to say, I'm thinking out loud here as everybody puts their pens down, right? Everything's a muscle. Everything's a muscle. So work the muscle by overdoing it in the short term. When sharing the dilemma, I think it's a great, device to simply say, let me share the dilemma.
Starting point is 00:43:10 Or even like, yeah, I'm in a little pickle. These are the things that I think about. Pickle dilemma is like, I think the device of saying, yes, here's my dilemma. Yes, I'm in a bit of a pickle, is a nice way to get somebody to say it the right way and get it out. I love that. Yeah. What else? This is so good.
Starting point is 00:43:29 Another one that I love. Okay. Have you heard the term villain era? villain era or era or err or era villain era yeah like the era it's kind of like a modern term no i don't know the term villain era it's like when you're isn't that a isn't that an album by taylor swift maybe that's too modern for me um uh one of her eras so have you heard of the term villain era i have not is this modern slang is this about to make me feel old it's probably going to make you feel okay but maybe to other people Is this unfleak?
Starting point is 00:44:02 Wait, that's all. I wouldn't go there. Okay, so a villain era is like a modern term. And it's basically when you move from being your overly accommodating, like nice to everyone, people pleasing, you know, prioritizing everyone else's needs over your own to like, I'm prioritizing myself. And I'm not going to say yes to things that I'm not a yes to. So basically you're handing in your wings and your halo and you're trying out the horns for size. Exactly. You get it. I mean, like, I like the wings and the halo, but let me just see what this little pitchfork and horns are like.
Starting point is 00:44:38 So it's trying out the other. Yes. But the reason it's called a billionaire is because to everyone else in your life who's used to you being overly accommodating and kind of a pushover and being able. All of a sudden that those things have changed. Like we change our behaviors, but our relationships need to catch up with us. And so this is another thing that I think about is like when, especially if you have like a chronic people pleasing situation, whether it's people in your life, for people at work, they're used to interacting with you in a certain way. And so when we decide internally that we want to change that, it takes other people time to
Starting point is 00:45:09 catch up. And that reaction can feel quite intense. And that change can be quite surprising to people. And so I think the mistake... So are you advocating for villain errors or are you not advocating for villain eras? I'm advocating for two things. First of all, when you make a big change that's going to impact your dynamics of other people, I like to name it. Be like, hey, I'm really working on. Do you have to tell people? I like to tell people. That way they know what's going on. And also maybe they'll even be on my team of like. Because otherwise you're going to start acting differently and people are going to be like, what the hell? Yeah. And now they label you the villain. Exactly. So I try to name it and in a way that like hopefully inspires people to want to be on my team
Starting point is 00:45:46 with me. For me, let's say it's my boss or let's say it's a friend of mine or my partner. Probably they know they're feeling the long term impact of my people pleasing. And so I can maybe tell them like, hey, just want to let you know that I'm working on this. I'm trying not to say yes to things that I don't actually have capacity for, or I'm trying to be more authentic. Like, will you support me in this? And maybe will you check with me when I say yes to something? Will you check and say, are you sure? You know, are you sure you actually want to go to that thing?
Starting point is 00:46:11 So I try to name that I'm changing the behavior. And I try to do it in a way that is with warmth rather than harshness. I think when people first start setting boundaries or standing up for themselves, they're so worried that they won't be able to do it, that they're overly firm. and they're overly cold. And that is really freaky to people, and that also creates negative corrective experiences. And so I think especially when you're starting out,
Starting point is 00:46:38 or when I'm starting out, I'm setting a new boundary for the first time, something that I like to do is set it with warmth. The thing, okay, here's what I'm taking from this, that I really like. So we've got three things. We've got, let me get back to you. We've got, I want to share the dilemma,
Starting point is 00:46:54 share the dilemma. And what I'm hearing this one, which I really, really like, this plays to all my biases, which is asking for help and letting others be a part of it. Because I think one of the things that we're setting up people pleasers to fail is that they have to master all of these techniques that we're talking about all by themselves in order to overcome their people pleasing. And part of it is actually that's not true and that's not possible.
Starting point is 00:47:19 And I think saying to a colleague or a boss or whoever to just be open and say, I know something about myself that I'm not proud of, but it is what it is, which is I'm a people pleaser. And I know that in the short term, it feels good for you and for me. And I know over the long term, it hurts me and it probably hurts my work product. And so I'm really working to get over it. Here are the techniques that I'm going to be practicing. One, I'm going to start saying, let me get back to you when you ask me to do things.
Starting point is 00:47:46 Sometimes it'll only take 10 minutes or an hour, you know, but it's one of the techniques I'm practicing. The other one is I'm going to share the dilemma when you ask me to do things. And if I forget, can you please remind me? So, for example, if you come to me and say, I need you to do this and I very quickly go, yes, it's because I forgot. Can you say, do you want to think about this before you get back to me? Or if I say, let me get back to you and I come back with the yes, it's like, do you want to share the dilemma with me? So I think getting your colleague, your boss, whoever, to be a part of it is very reinforcing of the positive corrective environment. but also it builds trust and collegiality
Starting point is 00:48:28 between the two of you, which is only a good thing. And I really like that. And it makes the other person complicit in your success. Yeah. I love the way you put it of it's building trust because I think often the people pleasers experience is this intense loss of trust, loss of trust with themselves.
Starting point is 00:48:48 And also the feeling backed into a corner where they know that they're hurting the trust that someone else has given them. but they kind of don't know what to do about it. People pleasing isn't just my problem. Yeah. We all have our issues, you know. How do we all help each other with our issues?
Starting point is 00:49:03 Which I love. Me too. Because you know my definition of a healthy corporate culture is when everybody agrees to grow together. And so a healthy corporate culture is when we agree to grow together. Before we end, I just thought of one other technique that has really helped me. And it's a, it's, I'm going to try and make up a term like you're, positive corrective environment, which is affirmative deadline adjustment.
Starting point is 00:49:29 Affirmative deadline adjustment? Yeah, or ADA. Nothing like a good TLA, three-letter acronym. Yeah, so affirmative deadline adjustment. So I'll give you real-life scenario. Hey, Simon, can you do this? Yes. I need it by Friday, no problem.
Starting point is 00:49:45 Okay? And then I'm going nuts trying to get it done by Friday. And then I'm either successful at great personal cost. or I'm about to fail and I call and be like, I can't do this by Friday and it's probably Friday morning. I can't do this today and they're like,
Starting point is 00:50:06 let's fine, anytime next week we'll do. And you realize when you say, when do you need it by, people just make shit up. Everything in working is made up. It's like, when do you need this by? Friday? Okay, you know? And so what I've learned is
Starting point is 00:50:19 if they don't give me a deadline, I know my own schedule, let me get back to you, and say, Can I get this to you next Friday? Yeah, that's no problem. Oh, can you do next Thursday? Yes, yes, I can do.
Starting point is 00:50:32 Or when they say, when do you need it by, Friday, is next Tuesday okay? Yeah, next Tuesday is fine. And I found out that very few deadlines that I was given are actually deadlines of which there were repercussions if that deadline is missed. And most of them just needed to be done by a certain period of time. And simply asking, is it okay if I do then? almost always it went my way. And so that's another little trick, which is affirmative deadline adjustment.
Starting point is 00:51:01 Yeah. It's so good. And it's also the opposite of what's normally happening, which is like, oh, I'm like, the whole world is caving in on me. Well, you just assume that whatever you're being told is like the thing. And there's also a terrible technique, which a lot of leaders have learned, and I wish they would do away with it, which is giving people fake deadlines. Well, if I give them a fake deadline, that way it'll get done on time. And if they miss it, well, it's okay.
Starting point is 00:51:22 were taken care of because the minute you figure out all the deadlines are fake, then I miss all the deadlines because they're all fake anyway. My publisher learned this the hard way. They used to always give me fake deadlines and I just started ignoring all their deadlines because they were all fake anyway. And I would tell them, tell me the absolute God's honest truth deadline because then I know there were serious consequences if I miss it and I'm going to hit the deadline because there's serious consequences.
Starting point is 00:51:45 So anyway, different conversation. Are there any other tips for people, please? either for the people who users themselves or for people working with people. I think this is a good list. I think what we have is a good list. I'm going to just review. Let me get back to you, done in the extreme to start, and then you'll habituate it. Two is, let me share the dilemma, or share the dilemma, which I think is wonderful.
Starting point is 00:52:08 The third one was... Like asking someone for support. Oh, asking, the third one was asking for support and getting help in what you're working on. And the fourth one is confirm the deadlines. Yeah. Confirm the deadline. Don't just take it for granted that whatever the deadline is is actually the deadline. Yeah. Or the workload or whatever it is.
Starting point is 00:52:27 You know, confirm the thing that needs to be done. One that I would add, I kind of started it, but I didn't, just to go back to it, is when we start setting boundaries and saying no, when we start, we're often, we often do it with this really intense firmness and harshness and coldness. Like, we like steal ourselves up because we think that if we're firm, the other person won't push back. And we think if they push back a little bit, I'm in a crumble because I know that I'm new to this. And so we're like overly firm and aggressive sometimes or or overly mean because we just think that that's what we need to do. We think that that's what boundaries are. And I would say you can still be firm while also being warm and while also staying in connection.
Starting point is 00:53:04 This is a very, very, very important point, especially younger generations who are learning about boundaries and boundary setting. They falsely believe that having a boundary is simply saying no to everything. Yeah. And there's no quicker way to disintegrate yourself on a team. than saying, these are my boundaries and I'm not, that's not a team player. And every technique that we are going through today is boundary setting. Because you are now taking some agency into your own workload, the expectations others have of you,
Starting point is 00:53:37 the expectations you have of yourself, and you're learning to adjust them in a way that helps you work to your natural best, and it manages the expectations of the people with whom you work. That is what healthy boundary setting is. everything we're talking about today is healthy boundary setting in a way that is constructive to the team. Simply saying, I have boundaries. The answers, no, that's you operating like an island, forgetting the fact that there are other people here.
Starting point is 00:54:02 And just as it is not a good idea to miss deadlines because there are implications, it's also not a good idea to simply start arbitrarily saying no to things because there are things happening that you don't know about. So this is a very, very, very important point that we're making here. These are boundary setting things that we're talking about and they're being done. in an extremely affirmative and team-oriented way. Okay, are there any other strategies or things? I learned this from the Air Force.
Starting point is 00:54:27 In private sector, it's very, this is how, this is a normal scenario. Like somebody works really, really hard on their PowerPoint presentation. They work two weeks on it, and they have the big meeting, and they do their presentation, and at the end they go, huh? Huh? Pretty good, right? Like, that's fairly normal in private sector. In the Air Force, it's totally different. somebody will work really, really hard on their PowerPoint presentation.
Starting point is 00:54:50 They'll come in to the meeting. They'll give their presentation. And at the end, they go, spears? Spears? At the end of their work, they ask for the room to throw spears at the work to make the work better. Whoa. I love that. It is fantastic. And so now in our office, it's very normal.
Starting point is 00:55:10 It's completely acculturated at our office where somebody will present their work and at the end they'll say spears. or somebody will just share an idea and be like, here's an idea, spear. Or somebody will say, I got a spear for you. And we now have this very relaxed feedback loop where we don't sort of give excessive amounts of praise unnecessarily just to make somebody feel good. Everybody actually wants the spears.
Starting point is 00:55:40 And the reason is we recognize we're all working in this together. Everybody wants everybody's work to be the best it can be, and we're all in this together. It's always done with love, right? The Spears. And they're always warmly received. What I've learned from one of the people pleasers on my team is that this culture of Spears has allowed them to experience
Starting point is 00:56:02 getting negative feedback and not feel bad. Yeah. And the stakes are low, right? It's like exposure therapy. It's exposure therapy. And especially because we're all really good about, instead of just saying, that's dumb, we go,
Starting point is 00:56:15 I got a spear for you. They're like, okay, bring it on. So it sets the, and everybody sees the meetings. Like, everybody's like, yeah, good spear, good spear, you know? And so all this negative feedback that's being thrown at the work, people are seeing, we're not attacking you. Yeah, it's like oriented towards growth. We're helping the work.
Starting point is 00:56:33 Yeah. It's always at the work. It's never at you because I think people pleasers very often confuse that the criticism of the work is criticism of me. Yeah. It's not. It's of the work. And Spears clarifies that.
Starting point is 00:56:45 I love that. Yeah, it's great. Yes. There's five techniques. Okay. One, first one is, let me get back to you. Let me get back to you. Work the muscle.
Starting point is 00:56:53 Work it a lot at the beginning. Number two, share the dilemma. Number three, ask for help. Yeah. Tell someone that your behaviors are going to change and to support you and even sometimes prompt you with scene number one and two. Yes. Number four.
Starting point is 00:57:11 Affirmative deadline adjustment. A really well-named. Terrible. is it. Behavior. It's terrible. Let's just call it like check the deadline. Number four, check the deadline. And number five, ask for spears. Proactively ask for Spears. Or if you're in a position of influence or authority, introduce Spears into the company because you not only will help with feedback, but you're helping all your people pleases on the team too. Oh, I love it. But more importantly than us feeling pleased, I really hope that everybody's listening is feeling
Starting point is 00:57:38 pleased. Until next time. Until next. Right. Thank you, Sam. Thank you, Alex. is a production of the optimism company. Lovingly produced by our team Lindsay Garbenius, Phoebe Bradford, and Devin Johnson. Subscribe wherever you enjoy listening to podcasts, and if you want even more cool stuff, visit simonc.com.
Starting point is 00:58:00 Thanks for listening. Take care of yourself. Take care of each other.

There aren't comments yet for this episode. Click on any sentence in the transcript to leave a comment.