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Why Saying Yes Is Making Things Worse | A Bit of Optimism: Feelings at Work | PART 1

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* 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.

Alex Simonguest
Jul 14, 202658mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 2:00

    Why We Need to Talk About Feelings at Work

    1. SP

      Today what I want to talk about is people pleasing.

    2. AS

      Mm-hmm.

    3. SP

      Um, 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.

    4. AS

      Are you people pleasing me?

    5. SP

      Yes.

    6. AS

      [laughs] It works.

    7. SP

      [laughs]

    8. AS

      I'm so pleased. [laughs]

    9. SP

      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? 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, then congratulations-

    10. AS

      [party blower]

    11. SP

      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 Lifeshop, where she teaches 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, theirs

  2. 2:00 – 4:20

    What People Pleasing Actually Looks Like

    1. SP

      and ours. We will cover three big themes in this episode. 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 overcommitment. 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. 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.

    2. AS

      Mm-hmm.

    3. SP

      And it is, um, the desire to sometimes avoid conflict, sometimes to ensure that somebody else is getting what they want, feels good, you know, going out of your way to make sure that everybody's okay. But the reason it can be dangerous and destructive, 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.

    4. AS

      Yeah.

    5. SP

      It amplifies all kinds of insecurities. It also sometimes makes them do things they don't wanna do, uh, break their own boundaries, all kinds of things. And very often it doesn't actually please the people they're trying to please, so it's sort of like-

    6. AS

      In the long term, yeah

    7. SP

      ... in the long term, so it's kinda like a zero zero.

    8. AS

      I think the, 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 wanna be generous and to, to say yes to things and to want to be liked, and I think that the, where it tips over into people pleasing is when it becomes almost like an existential need of like, "Oh, I feel like I'm gonna 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 am, like, over-apologizing even though I know it's not my fault, or yeah, like, taking on too much work. There are so many different ways that it exhibits itself,

  3. 4:20 – 7:00

    Why People Pleasing Hurts You and Your Team

    1. AS

      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-

    2. SP

      Or teach people how to...

    3. AS

      [laughs] How to stop people pleasing

    4. SP

      Let me, let me teach you how to be a better people pleaser.

    5. AS

      Well, that's actually-

    6. SP

      More yeses, more apologies

    7. AS

      You can teach that one. [laughs]

    8. SP

      I can teach that one, yeah.

    9. AS

      So yeah, when I, when I teach stopping to people please-

    10. SP

      [laughs]

    11. AS

      Uh, I'm shocked by how many examples... Most people, uh, many, many people have examples that have to do with work. Um, and it's 'cause it's a- an area of our life in which we're constantly being asked for things.

    12. SP

      Can you-

    13. AS

      We have to say yes and we have to say no all the time.

    14. SP

      Can you be a be- can you be a people pleaser at work but not in your life?

    15. AS

      Yes.

    16. SP

      Or do you think, like, it's, like, you're a people pleaser and it just exaggerates at work?

    17. AS

      I mean, I think that there's overlap, but I th- I know people who are really people pleasing at work but not in their personal lives.

    18. SP

      Huh.

    19. AS

      And I also know the, the reverse, where you're really people pleasing in life, but at work you're like, "Oh, no, no, no, I, I can maintain my boundaries and I can s- say yes, I can do this. No, I can't do that." It's, it's really interesting to me how it shows up in different areas of our, 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.

    20. SP

      Right.

    21. AS

      I think it's more... Like, to me, people pleasing is about how can I say yes when I mean yes, and how can I say no when I mean no? And so it's, it's a subtlety and it's a gray area, and it's happening all the time.

    22. SP

      Yeah. I think, I think it's, I think what we're talking about is the dial, which is important.

    23. AS

      Yeah.

    24. SP

      I think all of us are people pleasers at some point.

    25. AS

      Totally.

    26. SP

      Even s- when it's a lightly, slightly unhealthy.

    27. AS

      Yeah.

    28. SP

      Um, and for people who are people pleasers who are hearing this, even that word, they're like, "Ugh, that's me." And it always comes in that sort of way as, like, nobody's ever like, "I'm a people pleaser." People are like, "Ugh," you know? It's, it's, it's... What I think's so interesting about it is it, there's a lot of self-awareness for people who are, and it is... I don't know if it's sh- in the most extreme, I think it is shame, but, but I think people are kinda like either resigned to it or don't know how to get out of it, but it's always, "Ugh, I'm a p- that's me."

    29. AS

      Yeah.

    30. SP

      The reason I think it's important to talk about it, obviously 'cause I wanna help some of those people overcome, um, 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, if you, because if you work with somebody who's a people pleaser-

  4. 7:00 – 10:00

    Why We Say Yes When We Mean No

    1. SP

      to the deadline-

    2. AS

      Yeah

    3. SP

      ... and then didn't meet the deadline.

    4. AS

      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 are so many other things. It's like, oh, it's incompetence, it's lack of communication, it's this and that. Like, there's so many other things, but really she was just saying yes to something that was beyond her capacity.

    5. SP

      Because she didn't wanna disappoint.

    6. AS

      Yeah.

    7. SP

      And it's not because she was lying, hiding, and faking. Let's, let's make it... Because there's a lot of people who say yes to things because they're lying, hiding, and faking. They don't want-

    8. AS

      Yeah

    9. SP

      ... it's, it's, it's a bit of an imposter syndrome and they don't want... That's d- this is not what we're talking about.

    10. AS

      It's different, yeah.

    11. SP

      This is saying yes because you don't wanna go against the grain.

    12. AS

      Yeah.

    13. SP

      'Cause you, y- you find going with the flow, and everybody else has agreed to it, and I, I don't wanna, I don't wanna disrupt it even if I have information that everybody needs to know.

    14. AS

      Yeah.

    15. SP

      I don't wanna be the one to, to be the, I don't wanna be the, the, the, the negative Nelly here.

    16. AS

      Yeah. And I also think, I totally agree, and I think in the moment, uh, her experience was like, "Oh, I can, I can do that."

    17. SP

      Yeah.

    18. AS

      You know? Like, it do- it's not lying and betray- it's not, uh-

    19. SP

      Lying, hiding, faking

    20. AS

      ... it's not lying, hiding and faking because in the moment it feels like she can do it.

    21. SP

      She talks herself into it.

    22. AS

      Yeah. And then the-

    23. SP

      It's so interesting

    24. AS

      ... second afterward there's like the, "Shit." Like-

    25. SP

      Yeah

    26. AS

      ... and then there's resent- there's resentment everywhere, right? There's, then she resents herself, like, "Why did I do it again?" She resents the team or she resents the assignment, and-

    27. SP

      And now she's getting in trouble 'cause she missed the deadline.

    28. AS

      Yeah.

    29. SP

      And now she's letting the team down, and now all the-

    30. AS

      The sh- the shame spirals

  5. 10:00 – 13:00

    Different Types of People Pleasing

    1. SP

      passive aggressive.

    2. AS

      Mm-hmm. There's something in our system that believes, like, the world will end if [laughs] -

    3. SP

      [laughs] If I-

    4. AS

      ... if I say no.

    5. SP

      If I say no. Yeah.

    6. AS

      And-

    7. SP

      [laughs]

    8. AS

      ... and the, I think, like, the, the, like, calculus there, or if I'm trying to, like, unwind the inner logic that's going on in my head, it's, there's a part of me that's like, "Well, that'll just be future Alex who has to deal with that." [laughs] You know, like-

    9. SP

      Yeah

    10. AS

      ... present Alex wants the easy thing. But it's kinda like you're hungry and you wanna eat junk food.

    11. SP

      Yeah.

    12. AS

      You know, you just like wanna, you're like, "Okay, I wanna eat all the, I always wanna eat all the shitty food," but then you know you're gonna feel bad later. You know it's not gonna impact your health in the long term.

    13. SP

      One, one of my close friends, Kim, uh, sh- her, her mantra, and I, I tr- and I try and remember it, "If it's not an, if it's not an, a, a heck yes, it's a heck no."

    14. AS

      Mm-hmm.

    15. SP

      You know?

    16. AS

      Yeah.

    17. SP

      And like, the, 'cause... Or, 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-

    18. AS

      Future

    19. SP

      ... would love to do that."

    20. AS

      Duh.

    21. SP

      It's like an amazing thing to do. And the question is, "Would you do it tomorrow?" I'm like, "No." "Well, then if you don't wanna do it tomorrow, you don't wanna do it in six months."

    22. AS

      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 ambivalence. 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. I personally-

    23. SP

      It's not a heck yes, it's a... Yeah.

    24. AS

      Yeah.

    25. SP

      So what you're saying is-

    26. AS

      N-

    27. SP

      ... it's fine in theory, but things are grayer than that in reality.

    28. AS

      Yeah. I think-

    29. SP

      Including our own, our own-

    30. AS

      Yeah. There are many different parts of me and those parts want different things. And I think that the heck yes, heck no dichotomy doesn't often map onto my experience.

  6. 13:00 – 15:00

    Why Approval Can Become Addictive

    1. AS

      what's going on at work is, like, I wanna know what I have to do, I wanna do it, and then I wanna be patted on the head and told that I did a really good job. 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, in doing it, I'm contributing to something that's beyond myself and I just, like, get the satisfaction, the very simple satisfaction of being useful-

    2. SP

      Mm

    3. AS

      ... and then I can be recognized-

    4. SP

      Mm

    5. AS

      ... and someone can give me praise for what I've done, like, that, those three things scratch a lot of our, like, core human needs.

    6. SP

      There's a very important nuance here which is you said addicted to the approval, right?

    7. AS

      Yeah.

    8. SP

      I think everybody wants to know they did a good job-

    9. AS

      Totally

    10. SP

      ... and everybody wants their, their bosses to say, to, to, to recognize them.

    11. AS

      Yeah.

    12. SP

      Um, and it's, it's healthy to want it.

    13. AS

      Yeah.

    14. SP

      Uh, it, it drives a lot of us to, to do good, you know, for those we serve and, you know, wanna make them proud. Especially if it's a good boss, we really wanna make a, we wanna make, make our leader proud, you know?

    15. AS

      Yeah.

    16. SP

      They've invested in us and we wanna show them the investment was worth it.

    17. AS

      Totally.

    18. SP

      But you didn't... That's not what we're talking about here. We're talking about the addiction to it, the need, which is it's not... And it stops being about the work-

    19. AS

      Yeah

    20. SP

      ... and it starts being about the approval.

    21. AS

      I-

    22. SP

      And that's an important nuance.

    23. AS

      I totally agree, and I think it's about what is the, 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. That's, like, a healthy, beautiful system.

    24. SP

      That's healthy, yeah.

    25. AS

      Whereas e- when it slips into more kind of extreme behaviors where I'm sacrificing, where I'm betraying myself in order to get that approval-

    26. SP

      Can you, can you... So give us an, give me an example of that.

    27. AS

      Uh, 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. Um, you're sacrificing, like, your own life and your own wellbeing. Not just on, like, I'm, I'm working one late night or I'm working one, two crazy weeks. It's, like, on a longer term basis and you're consistently not doing-

    28. SP

      So regularly not coming home in order to

  7. 15:00 – 18:00

    How People Pleasing Leads to Burnout

    1. SP

      make, do good, do right by your bo- not even do right by your boss. Do whatever needs to do to get your boss's approval. You're, you're sacrificing weekends, nights, family.

    2. AS

      Yeah.

    3. SP

      Again, as you said, not occasionally, but habitually.

    4. AS

      Yeah. And over time, uh, 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 wanna do, and then staying up late and, uh, 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. And so that's, I think, where the people pleasing really 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.

    5. SP

      I think we've talked about this before, but we had somebody on our team who burnt out and her workload was not enough to burn somebody out.

    6. AS

      Yeah.

    7. SP

      And we couldn't understand it. And, and I think we talked about it in a different capacity where she was an em- an empat- an empathetic ear to a lot of people who were coming to her with all their problems, not just work problems.

    8. AS

      Yeah.

    9. SP

      And her desire to please them and always be available to them, she, it, to, it got to the point where she... I mean, the whole thing collapsed.

    10. AS

      Yeah.

    11. SP

      You know, she was, she was exhausted. Done. I mean, she quit. She quit her job. Um, completely burnt out.

    12. AS

      Yeah. To me that, like, that screams, like, invisible self-betrayals.

    13. SP

      Yeah.

    14. AS

      Like, where you know in your system that you're betraying yourself over and over and over again.

    15. SP

      Because you don't wanna let them down.

    16. AS

      Yeah.

    17. SP

      Oh, they're in pain, they're angry, they're sad.

    18. AS

      Yeah.

    19. SP

      You know, they need somebody to talk to.

    20. AS

      Yeah, the-

    21. SP

      I don't wanna upset them

    22. AS

      ... the image that I always think about is, you know the game Jenga?

    23. SP

      Yeah.

    24. AS

      Where you stack the bricks. Yeah. Like, the... It's like if your, if your sense of self is this Jenga, and each time you betray yourself you're, like, taking out one brick.

    25. SP

      Oh, great analogy.

    26. AS

      You're taking out another brick each time you say yes to something, each time you over-apologize-

    27. SP

      Yeah

    28. AS

      ... each time you rescue someone else 'cause they can't do the thing that they need to do. It's like brick, brick, brick, brick, brick, and then all of a sudden your whole life is unstable.

    29. SP

      And I, I think it's such a great analogy because we all do things that are slight betrayals, but it's okay. It's healthy.

    30. AS

      Yeah.

  8. 18:00 – 21:00

    The Hidden Cost of Being "Hyper Competent"

    1. SP

      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, "This is, I don't even know h- where to begin," they end up saying yes to everyone- Um, because they're maintaining... It's not just maintaining their view of themself of hyper competence, but it's maintaining the image they've projected to everyone else of hyper competence-

    2. AS

      Mm-hmm

    3. SP

      ... and that's the pleasing part.

    4. AS

      Mm-hmm.

    5. SP

      Which is, "Don't worry, I can take care of it. That's why you rely on me, 'cause I'm hyper competent." And the problem is is they are.

    6. AS

      Yeah.

    7. SP

      They're... The problem is is they actually are. They're, like, 'cause the incompetent ones that are people pleasers are easy. [laughs]

    8. AS

      [laughs]

    9. SP

      Like, those are easy to spot and we can rush in and help them and coach them.

    10. AS

      [laughs]

    11. SP

      But I think the hyper competent ones... And I know as, as a, for somebody who's had a, a hyper competent people pleaser on my team, what ends up happening from a leadership standpoint is we make it worse by accident because they start to gain the reputation of being hyper competent, so we start relying on them more. And I know, and I'm, I'm pretty good about sort of like people and balance and I ask questions expecting an honest answer. So I'll be like, "Hey, I got another thing for you. Do you have space on your plate?" "I do." "Are you sure? I just wanna make sure." "Yeah, yeah, yeah, no, it's, it's good." Like, "And can you do this? I don't know if we've ever tried this before, but do you..." "Oh, no, no, no, I, I got this." So I am checking in, and they're lying to me.

    12. AS

      Yeah.

    13. SP

      Lying, I mean, lying.

    14. AS

      Lying, lying is a strong word, but yeah.

    15. SP

      Lying is, lying is a strong word. They're, they're deceiving me and/or themselves.

    16. AS

      Yeah.

    17. SP

      The point is is, like, even a well-intentioned leader who really wants to check in with somebody and make sure they have the bandwidth or the capacity, I, I, I can't help.

    18. AS

      Yeah.

    19. SP

      And so one of the things I wanna 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 s- the signals so that even if well-intentioned in asking questions, that we, we can actually find out what's going on so that we can intervene even if they say yes.

    20. AS

      Mm-hmm.

    21. SP

      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?

    22. AS

      Mm-hmm. It's so hard because, because the nature of it is very confusing to the people around you because it feels authentically 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." [laughs]

    23. SP

      [laughs]

    24. AS

      And so that's why you're checking, right? Like, you're checking.

    25. SP

      But that's hard too, right?

    26. AS

      It's hard.

    27. SP

      Because what if you just doubt somebody who is competent?

    28. AS

      Yeah.

    29. SP

      And so it's... I mean, this, we, 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-

    30. AS

      Work is messy

  9. 21:00 – 27:30

    Why People Pleasing Doesn't Actually Help People

    1. SP

      who are, who are the people pleasers-

    2. AS

      Yeah

    3. SP

      ... but also how do we offer practical things to people who work with people pleasers?

    4. AS

      Mm-hmm. I think it's such a good point and I think often w- to your point, we th- we're thinking about it in terms of the people pleaser, of like what's going on in my system when I'm saying yes to 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 whole team or on the whole-

    5. SP

      Mm

    6. AS

      ... 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 internalizes.

    7. SP

      Mm.

    8. AS

      For me, one of the greatest myths about people pleasing is that somehow it'll work. You know, like [laughs] you really think it's gonna work.

    9. SP

      Yeah.

    10. AS

      And that's because in the short term you get this like hit of a good feeling. You know?

    11. SP

      Yeah.

    12. AS

      Like you say yes to someone and someone's like, "Th- thank you. Thank you so much." Right?

    13. SP

      Oh, thank God you're on the team.

    14. AS

      Yeah, yeah.

    15. SP

      Yeah.

    16. AS

      Like, "Oh, you are so competent."

    17. SP

      At least s- at least somebody is. Yeah. [laughs]

    18. AS

      Yeah. And like, "Oh, that so and so, like she's really like this," you know? And, and so that... Or in, let's say you're-

    19. SP

      And that's the addiction part, right?

    20. AS

      That's the addiction, yeah. It... Let's say you're fearing the conflict. That's, that's the type that you are. Like in the moment you do get to avoid the tense situation.

    21. SP

      Right.

    22. AS

      It's like, "Oh, thank God it worked," 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.

    23. SP

      Oh, by the way, like any addict. Like-

    24. AS

      Yeah

    25. SP

      ... like-

    26. AS

      Yeah

    27. SP

      ... you know? So it's, it's, it's very consistent.

    28. AS

      And what's so interesting is that you, you face those consequences every single time.

    29. SP

      Yeah.

    30. AS

      You know? My sister always asks this question, what's the mistake that you keep on making? Which I think is such an amazing question, 'cause 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.

  10. 27:30 – 31:00

    Simon's Experience With Saying Yes to Too Much

    1. SP

      is not the ability to execute everything. Rebla- reliability is accurately managing expectations.

    2. AS

      Mm-hmm.

    3. SP

      And I became more reliable when people are like, "We need this," and I'd be like, "I, I, I can't."

    4. AS

      Yeah.

    5. SP

      Or if you, "If I can, if I can take something else off my list."

    6. AS

      Mm-hmm. Yeah, it's like also zooming out and being able to see the big picture.

    7. SP

      You know? And, 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.

    8. AS

      Yeah.

    9. SP

      Or if somebody else can do it, or it'll, it can maybe happen at another time.

    10. AS

      Mm-hmm.

    11. SP

      And that's, I, I had to reconfigure what reliable means in my own head.

    12. AS

      Mm-hmm.

    13. SP

      And to be reliable it means accurately managing expectations.

    14. AS

      Yeah.

    15. SP

      And by the way, saying no to everything is also unreliable.

    16. AS

      Yeah.

    17. SP

      Because that's also-

    18. AS

      You're not relying on them-

    19. SP

      Um-

    20. AS

      ... to do anything

    21. SP

      ... but to do that, but that's, that's also n- not managing expectations because I have to do something.

    22. AS

      Yeah.

    23. SP

      Um, 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-

    24. AS

      What I'm capable of

    25. SP

      ... of what I'm capable and, and 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.

    26. AS

      Mm-hmm.

    27. SP

      And I never said, "Let me check," which by the way is a, a, a viable answer. "Can you do this?" "Let me check. Let me get back to you."

    28. AS

      Yeah.

    29. SP

      And it was always a desire to, to be a great team player.

    30. AS

      Yeah.

  11. 31:00 – 38:20

    How Leaders Can Help People Pleasers

    1. SP

      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, I screwed that up." I went, "Oh, okay. Well, what's the ri- right answer then?" She went, "I think it's this." I'm like, "Okay, great." And for her to see, like nothing happened.

    2. AS

      Yeah.

    3. SP

      And, uh, and very high performer. Ve- It's one of the reasons she was a high performer.

    4. AS

      I think that's beautiful. There's an idea that I'm obsessed with, which is this idea of a positive corrective experience of when you have something that you think is gonna go one way, "Oh, if I make a mistake, Simon will hate me forever," uh, and then instead of the worst fear being confirmed, you have an opposite experience. It, it corrects your assumptions about what's gonna happen in a positive way.

    5. SP

      Yeah.

    6. AS

      And it like rewires something in your system that's like, "Oh, I can make a mistake."

    7. SP

      Well, that's what happened.

    8. AS

      Yeah.

    9. SP

      Over... It didn't happen immediately, but it didn't happen over the course of time. She had to, she had to dip her water, her toe in the water and to discover. And, and, and so like when we think about if you work with a people pleaser-

    10. AS

      Exactly, yeah

    11. SP

      ... right? Which is... And, and I remember I, because I couldn't just tell her. It... Like telling her-

    12. AS

      Isn't enough

    13. SP

      ... isn't enough, and she ma- she wouldn't believe me.

    14. AS

      Mm-hmm.

    15. SP

      You know? I'm like, "I-"

    16. AS

      Or maybe she would believe you on a rational level, but her, something in her system-

    17. SP

      Mm-hmm

    18. AS

      ... would still fear it.

    19. SP

      Right.

    20. AS

      Yeah.

    21. SP

      And so, like even when we had the conversation more than once, I'm like, "You gotta just tell me, 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."

    22. AS

      Yeah.

    23. SP

      "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, 'cause I guarantee you it's different than what you're experiencing now."

    24. AS

      Mm-hmm.

    25. SP

      "'Cause 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."

    26. AS

      Mm-hmm.

    27. SP

      And she did. 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 relaxed, saying, "Ah, man, I screwed that up."

    28. AS

      It's such a beautiful thing. And to me, you, you executed it with so much g- love and grace, and that's also, like I, when I... You're, 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.

    29. SP

      I wanna say that again, 'cause it's such a great phrase, a positive corrective experience.

    30. AS

      Mm-hmm.

  12. 38:20 – 40:00

    The Power of "Let Me Get Back to You"

    1. AS

      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 'cause it creates a sense of like, "Oh, we're on the same team trying to figure this thing out together."

    2. SP

      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."

    3. AS

      Okay. So if I was trying to share the dilemma, I would say, "Okay, great. I really wanna do this thing, and this is my dilemma. Um, so these are the other things that I'm thinking about. These are the other things that are on my plate, and these are, this is why those other things are important." And so I try to show why they're important to remind that 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 sh- share that I feel a yes to it. I try to share kind of like the big picture, the bird's-eye view of, of the competing priorities, and then I also try to acknowledge the other person's position or their needs. 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 gonna either say yes and you're gonna be happy with me, or I'm gonna say no and you're gonna reject me and I'm not gonna be worthy or useful. 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, um, oh, it's not that it ends here. Yes, I'm doing it. No, I'm not. It's, "Okay, interesting. Well, maybe if I take on

  13. 40:00 – 44:00

    How to "Share the Dilemma"

    1. AS

      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's, it starts a, a, it starts a conversation. It starts a dialogue to find something that works for everyone.

    2. SP

      There's a nuance here that has to be underscored-

    3. AS

      Okay

    4. SP

      ... and it goes back to that affirmative language. So when somebody's sharing the dilemma, um, as I'm listening to you, that affirmative language really matters. So-

    5. AS

      Yeah

    6. SP

      ... you don't wanna say, um, you want to avoid saying, "I don't wanna say no."

    7. AS

      [laughs]

    8. SP

      Right? 'Cause now what the person who asked you just heard is like, "Okay, you're about to, you're just telling me no."

    9. AS

      Yeah.

    10. SP

      Right? "I don't wanna say no, but-"

    11. AS

      Yeah

    12. SP

      ... you know, "I got this thing and this thing and this thing." That's actually not sharing the dilemma.

    13. AS

      Yeah.

    14. SP

      Um, that's not making the other pe- the other person feel affirmed in, in asking for help.

    15. AS

      Mm-hmm.

    16. SP

      It, it would, sharing the dilemma, it would, as I'm learning from you, I- I'm sort of gaming it out in my own head, um, "I need you to do this." "Ah, yes, that needs to get done. Um, I'm working on this, and I've got this. Um, h- I'm trying to figure out how I can make time to prioritize that."

    17. AS

      Mm-hmm.

    18. SP

      So sharing the dilemma is literally that. It's the thinking out loud-

    19. AS

      Yeah

    20. SP

      ... of trying to solve the problem they're asking you to solve by moving-

    21. AS

      Together. Yeah

    22. SP

      ... to moving the pieces of the puzzle around. You're doing it out loud. That is sharing the dilemma. It's, it is not, "I want to say yes. You know, I, I, I, I, I, I d- I, I wanna make sure this happens, but, you know," it's like, "I, I, I don't wanna say no," you know, and it's not dumping your stuff on the other person's plate. 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 or 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? Continue what you're doing. I think it's easier if I do this myself."

    23. AS

      Yeah.

    24. SP

      And you never actually said yes or no.

    25. AS

      Yeah.

    26. SP

      And this is what I think's so valuable about the, 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.

    27. AS

      Mm-hmm.

    28. SP

      It is removing the binary nature of a question, "Can you do this?"

    29. AS

      Mm-hmm.

    30. SP

      And it is literally going through the steps of trying to get to yes.

  14. 44:00 – 47:00

    The Difference Between Being Reliable and Being Available

    1. AS

      But maybe tell the people listening-

    2. SP

      Is, is this, is this on fleek? Wait, that's old. [laughs]

    3. AS

      [laughs] I wouldn't go that far. Um, okay, so a, a villain era is like a m- it's a modern term.

    4. SP

      Yeah.

    5. AS

      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 gonna say yes to things that I'm not a yes to.

    6. SP

      So basically, you're, you're handing in your wings and your halo, and you're trying out the horns for size.

    7. AS

      Exactly. [laughs]

    8. SP

      [laughs]

    9. AS

      You, so you get it. And-

    10. SP

      I, I mean, like, I like the wings and the halo, but let me just see what this little pitchfork and horns are like. So it's, it's trying out the other is what you-

    11. AS

      Yes

    12. SP

      ... okay.

    13. AS

      But the reason it's called the villain era is because to everyone else in your life who's used to you being overly accommodating and kind of a pushover and being able-

    14. SP

      Ah, now all of a sudden the-

    15. AS

      ... all of a sudden that those things have changed. Like, we change our behaviors, but our relationships need to catch up with us.

    16. SP

      Right.

    17. AS

      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 or people at work, they're used to interacting with you in a certain way.

    18. SP

      Right.

    19. AS

      And so when we decide internally that we wanna change that, it takes other people time to catch up, and that reaction can feel quite intense, and that change can be quite surprising to people. And so I think the mistake-

    20. SP

      So are you advocating for villain eras, or are you not advocating for villain eras?

    21. AS

      I'm advocating for two things. First of all, when you make a big change that's gonna impact your dynamics with other people, I like to name it. Be like, "Hey, I'm really working on-"

    22. SP

      Do you have to tell people?

    23. AS

      I like to tell people. That way they know what's going on.

    24. SP

      Okay.

    25. AS

      And also maybe they'll even be on my team of, like-

    26. SP

      'Cause, 'cause otherwise you're gonna start acting differently, and people are gonna be like, "What the hell?"

    27. AS

      "What's going..." Yeah.

    28. SP

      And now they label you the villain.

    29. AS

      Exactly.

    30. SP

      'Cause, yeah.

  15. 47:00 – 58:04

    Building Healthier Boundaries at Work

    1. SP

      which is, uh, asking for help and letting others be a part of it, because I think one of the, 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-

    2. AS

      Yeah

    3. SP

      ... in order to overcome their people pleasing. And part, part of it is actually that's not true and that's not possible.

    4. AS

      Mm-hmm.

    5. SP

      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 gonna be practicing. One, I'm gonna start saying, 'Let me get back to you' when you ask me to do things. 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 gonna 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 'cause I forgot. Can you say, "Do you wanna think about this before you get back to me?"

    6. AS

      Yeah.

    7. SP

      Or if I, if I say, "Let me get back to you," and I come back with a yes, it's like, "Do you wanna share the dilemma with me?" You know? So I think getting the, your colleague, your boss, whoever to be a part of it is very reinforcing of the positive corrective environment.

    8. AS

      Mm-hmm.

    9. SP

      But also it b- it builds trust and collegiality be- In between the two of you-

    10. AS

      Yeah

    11. SP

      ... which is only a good thing, and, and, uh, I, and I really like that.

    12. AS

      And-

    13. SP

      And it makes, it makes the other person complicit in your success.

    14. AS

      Yeah. I like, I love the way you put it of it, it's building trust because I think often the people pleasers experience is this intense loss of trust, loss of trust with themselves.

    15. SP

      Yeah.

    16. AS

      And also the, like be- 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.

    17. SP

      People pleasing isn't just my problem.

    18. AS

      Yeah.

    19. SP

      We all have our issues, you know? Um, how do we all help each other with our issues? Which I love.

    20. AS

      Mm-hmm. Me too.

    21. SP

      'Cause you know my definition of a healthy corporate culture-

    22. AS

      No, tell me

    23. SP

      ... 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, uh, other technique that has really helped me, and it's a, it's, it's, um, I'm gonna try and make up a term like your, uh, positive corrective environment, which is affirmative deadline adjustment.

    24. AS

      Affirmative deadline adjustment? [laughs]

    25. SP

      Yeah, or, or, or ADA.

    26. AS

      [laughs]

    27. SP

      [laughs]

    28. AS

      Nothing like a good TOA.

    29. SP

      Yeah, yeah, yeah.

    30. AS

      Three letter acronym.

Episode duration: 58:05

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