Where Should We Begin? with Esther Perel - I Took My Boss to Therapy

Episode Date: May 19, 2025

This is a classic session, from the second season of How's Work? From day one, they’ve described their relationship as “tumultuous," but there are highs as well as lows. One is new to the work force, the other is new to this particular work place. One manages the other. And while they like each other on a personal level, they clash over their fundamentally different approaches to getting the job done. Over the last few years, workplace culture has been transformed by remote work, inconsistent in-office presence, and an intergenerational workforce. Where Should We Begin? At Work is a new game designed to transform your work culture – one story and one relationship at a time. Brought to you by Esther Perel and Culture Amp, this isn’t your typical icebreaker. It’s a new data-backed game that will help you create community at work. Details at www.estherperl.com Learn more about your ad choices. Visit podcastchoices.com/adchoices

What you are about to hear is a classic session of Howe's Work with Esther Perel. Howe's Work is a one-time unscripted counseling session focused on work. For the purposes of maintaining confidentiality, names, employers, and other identifiable characteristics have been removed, but their voices and their stories are real. Some of the more interesting conversations that I have had around the workplace are intergenerational conversations. And I was reminded of an episode that I did a while back with a manager who was a Gen X and a new Gen Z employee who was entering into the workforce. And, you know, we have five generations at this moment that are currently working together in the workplace.

The traditionalists, the boomers, the X, the millennials, the Gen Z, and fast coming up, the Alpha generation. So it's a unique experiment for building relationship cultures and relationships in the workplace as a whole. Now we know that strong relationships are at the core of high performance. And we also know that there is a social atrophy going on and that people need as many skills and practices to really enhance their social skills. So I created a new version of the game, Where Should We Begin, that is specifically for at work.

And I really was hoping to design and transform work culture one story and one relationship at a time. You know how much I believe in the power of stories because they are bridges for connection. And what I also very much liked is the fact that it's a collaboration between me and Culture Amp, which is a company that provided me with tremendous data science on people. And we could test every card until it finally found its way into the deck. So I hope you enjoy Where Should We Begin at Work. Support for Where Should We Begin comes from Ferragamo. Fatherhood can express enduring love and ongoing support, marking the important milestones as well as creating

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five gigabyte plan required equivalent to $15 a month. New customer offer for first three months only, then full price plan options available, taxes and fees extra. See Mint Mobile for details. details. We generally remember the first day we met our manager, the impression they left on us or the first impression we left on them. I was really nervous about having a new manager, feeling really good about my position.

I think I had just been promoted and then this woman comes who's like a bull in a china shop. The day that she came in, she looked so pretty. She had her hair done and she was kind of like flipping it around and she started making jokes immediately with people and it just seemed like she got like very comfortable very quickly. I remember taking a breath like oh oh my gosh, she's a lot. But first impressions sometimes are hard to undo. Like in this case, the manager, she arrived in full speed and now she has to slow it down. And that's not coming so easy.

I'd like to think of myself as a servant leader. On the other hand, I have like very passionate intent and like, it probably can be tough if you just haven't completely invested in me and jumped on board when I can probably seem like a train that's just going really fast and doesn't look like I'm stopping anytime soon or I'm making space for anybody to jump off. It's been an up and down. I've likened it to like an abusive relationship in the cyclical way of it where it's like we are really good for a stress of time and

then something happens and everybody is upset. Like in some ways our relationship is very personal because like from the beginning we have discussed what's not working between us, which is like intimate. Their relationship is organized around one word tumultuous. And tumultuous doesn't just mean negative, but it means intense. Intense in every aspect. They appreciate the intensity, and at the same time, they would like to make it slightly less so.

I mean, I think what was tough is that I had felt like building strong relationships that work was a strength of mine and was feeling like it was a nut I couldn't crack. I've grown to really love her just as like a person, but it's just hard. It's very hard to work with her and it hasn't gotten easier. So I feel like definitely conflicted about all of this because she probably won't feel like blindsided by me asking her like, Hey, would you put it on this podcast with me?

But it's definitely like, I don't wish her any ill will or anything like that, you know. It's not that common that a manager will accept the invitation of their direct report to come and talk on a therapy podcast. So I keep that in mind and I see this as a very positive sign. But then I realized that they have become so organized around their problem narrative about what's the problems between them. And I just think it's important to meet people before I meet their problems. So give me a little bit of a sense of who you are, where you work, where you come from.

So I'm 28 years old and I am the oldest child of my family. And my mom is white, my dad is black, and my dad is a black person who thinks he's white. I have been working in nonprofit for about five years now, and I've been working in the role that I'm in for about two and a half years. Tell me what is important in the way that you described your dad. There was a reason for that statement. He's been top of mind for me over the last couple days.

He voted for Trump. Probably I think he did so both times and I look more like him than I do like my mom. And I am more like him in some ways in terms of wanting to be right or can be like argumentative. And I guess I just like find places where I can just kind of make jabs at my dad because I don't really talk to him that much. So when I say like, you know,

my dad is this black man who thinks he's white is kind of my way of just being like, yeah, fuck you dad, without like actually saying that to him that much. So when I say like, you know, my dad is this black man who thinks he's white is kind of my way of just being like, yeah, fuck you dad, without like actually saying that to him. How about you? So I, my family's from Puerto Rico. I'm 47. My father was a Philadelphia native, so he's white.

My mother was someone who, she's only 19 years older than me, so she kind of got herself together when she had me. We got our college degrees at the same time, and my father's a self-made, he was a self-made businessman who was raised in an orphanage. So very scrappy parents

who made a really great life for themselves, that's where I come from. And you say that with admiration? Of course, yes. So much admiration and pride. Definitely one of those people that understand I stand on the shoulders of other folks. But in general, I've always worked for nonprofits, community-based organizations. So I came in as what they call a manager. You came in as her manager, okay. She had someone before me. Describe the relationship to me, either one.

And remember, a relationship is a story. So you're gonna tell a story of this relationship. And that sometimes involves how it started or the aspirations, the mistakes, the misunderstandings, the laughter. It came to mind was tumultuous. I think that probably the only manager I've had who's made me laugh as much as she does, we have had really, really good times and we've had really, really bad times. And I define good and bad. There's all encompassing words. And for you, there's a whole life in each of them.

Yeah. When I say good, I mean, like we work really well together. We don't have too many power struggles going on at the time. We produce really great content and work for our teachers. And when it's bad, we are either not communicating or not communicating well. And I'm feeling really impatient and stubborn and also probably not really understood or heard. I wondered why she brought in that particular information about her father, but I wasn't thinking about him

when I asked that question. I was really thinking about what she was telling me about her and her father that would give me information about her and the manager. And here she gave it to me. I'm stubborn and I'm impatient. Yeah, I think the word that came to mind for me was like a relationship of circumstance. So you know, when you come in, it's like you build your team, or you grow together into like new roles to come in to fill a role that someone else had that that person brought you on.

So that's why I think of circumstance. You know, besides the history you bring with me as like being a woman of color who's always had to prove herself for every leadership role or any role in general and always just takes, assumes I'm going to have to work harder. So I I try to, um, definitely felt a feeling of like, why do you have this job? Why are you my manager or boss? Why did you get this? It's a shame to you in your head. I felt that. I mean, there were things said that made me interpret them that way. And so I was doing a lot of work of understanding that sometimes people's words in the moment or

how they feel in the moment are during adjustment periods and trying not to internalize that a lot or to behave differently because of that and try to work to build trust in a relationship. I think when it's tough is when we are almost trying to prove the other person wrong more than trying to get back to where we work together. So I think there's definitely many more, it's more like that now, but I think a lot in the beginning was there was a lot of proving, a lot of proving different ways.

I think when it's good, it just feels like there's trust. And I think the strength is that like, we have been through a lot of uncomfortable moments and we have also like achieved incredible feats in a short amount of time during COVID at the same time. So yeah, I guess tumultuous is a good word as well. I guess for me, for much of that time, I was like, okay, this is part for the course. If you come into a new organization in a role that's taking over a different team lead,

you know, kind of ready for the pushback. I think I didn't think it would take as long or or I thought we would settle into a trusting relationship sooner. When you say as a woman of color, I have to prove myself more. Is it different if you oversee a black woman? Do you feel that did you have an assumption that things would be faster and more complicitous between the two of you? Well, in general, like folks of color are quickly bonded was just my experience. I think part of me expected the same thing. So one, I didn't feel that necessarily

on our staff in general. And I do think that there was like a little assumptions I made, of course, of how like we could connect more quickly. So that's where I took a few steps back of like, okay, those are not assumptions that I can just make. And I think that I can just make. That we were just going to be able, there were going to be certain, there are going to be certain understandings or connections or comfort level or rapport or whatever that is that I might not have otherwise with someone else that wasn't a person of color right off the bat.

And what did you do with her assumptions? They're well-meaning. They're meant to bring you closer sooner. They're meant to assume a certain level of understanding, of shared reality, of shared struggles, et cetera. So I'm curious how you took them. Yeah. I mean, honestly, the whole, like, people of color terminology in general kind of assumes that like we are all, you know, familial and I, I haven't even really felt like that familial within the black community.

So looking for it just in the general people of color community has never really been like, like a thing. And I've very recently just started to get in touch with my identity as a black woman and the people in my life that are also black women, I'm really starting to build relationships with them. And it's been kind of ongoing since towards the end of college, but I had, first of all, never been managed by a person of color. My managers from previous jobs were all white men or white women and I didn't know how to accept just a relationship based on our race when we weren't of the same identities, especially from someone who was like in power in regards to my

position. So at the time like I had not known that that's what was happening until she named it and I was like I think probably like at that time my first interview was like why would you do that and now I'm like obviously you would do that like we're we're by a minority in general at our organization. It's starting to flip, but it definitely makes sense to me now, but at the time it definitely did not. You're saying yes with your head, you're nodding? Listening and affirming, yes, yes.

It's a small team. So I think that like two of the new hires, one was me, one was a black man. I think it's a team that's not always in the same office together at the same time. But in general, like right at that time, I was the only Latinx person on the team. And then just aren't, it was just outnumbered.

We were not that diverse of a team. Can I ask you something? Do you have a different relationship in the reverse when your manager is white? There's white woman and you've had white woman and white men. I would say that I have noticed I act differently with white women, with white men. I mean, my partner is a white man and he's probably like the only one that I actually

like respect. With white men, I generally just, I don't, unless they have proven themselves to be aware of like, you know, their privilege and things like that, I generally don't. They're just not really part of my sphere. But my mom is like a white woman and I have noticed my own ways of being around white women is definitely different than it is with other people. And in the workplace, how does that manifest? Uh, it can depend, but for the most part, I don't. I'm very sensitive to their fragility and, and almost, um, I can be, I don't,

I don't think protective is the right word. I'm just kind of fumbling around that, but that's the word that's popping up in my head. So I feel like protective of white women. And I hate that, I hate that. I don't want that, I don't want that feeling. And so when I'm outside of work, it's like, no, fuck that. But when it's like somebody that I'm working with, all the white women that I've worked with

have really endeared themselves to me in one way or another. And it's made it very hard to just to feel like I can be very blunt or straightforward or even like angry or like aggressive in any way. I'm sure that there's something to it because of my mom. And I'm also sure that there's like, I don't want to be a black woman stereotype of any kind. So there's definitely like some of that there too. Had we continued the conversation, I would have wanted to explore further with her the legacy of the white mother with whom she can't identify because of color and of the black father with whom she can't identify because of values and identity. And maybe it would have shed more light to understand her relationship to the white managers,

men and women, and to the current manager, another woman of color. But it's not only the legacy of her parents, it's also the cultural and racial legacy and the bind that she finds herself in as a black woman who does not want to be seen as the stereotype of the black woman. We have to take a brief break. Stay with us. Life, break. Stay with us. Support for this show comes from Shopify. When you're starting your own business, finding the right tool that simplifies everything

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are coming in as new leadership and making it seem like nothing we did was that great before. And then we were kind of coming in like, what's all the resistance? Like, we're just here trying to be part of the team and get work done. So that was like the overall from my perspective, like the overall vibe for a while. It was very much like. Like, it wasn't there wasn't a lot of like of a learning period, I think. Both of them came in and just had to hit the ground running. And that was tough because I did, like I had a nice like two month period where I was learning.

I went to a conference within like my first two weeks to learn more about my role. So I would say that there was not as much, it didn't feel like from our perspective, me and other people who had been on the team, that there was a lot of curiosity when they were coming in. It was more like, okay, well, we're told that this is what we need to do, so we're going to get started with our ways of thinking and being. And it was tough. The one thing that stood out in what you just described was a way of seeing not just what was happening to you and to the rest of the team, but also what basically was the mandate

of these new people who were coming in. When I hear anybody who is able to look above them and feel for the people above them and understand the predicaments that they are in and the fact that everyone is involved in certain power structures, basically everybody is accountable to somebody And the person above you is a person below somebody else That in itself stands out immediately that you that you saw it. It's easy to see what's being done to me It's not so clear sometimes that what's being done to me is the consequence of other things that are being done to you Or told to you or demanded from you or expected from you same

You you arrive and um, and you basically indeed have to start to prove yourself immediately. So you look for shortcuts. And one of the shortcuts is to assume familiarity. Another shortcut is to basically not spend enough time learning how things are being done and why they're done the way they're done because we need to instantly change something. Another shortcut is to not take enough time to build the relationship necessarily because we've got shit to get done. We've got a mandate. We need to fulfill the requirements here.

You seem to have done that, actually. You've actually done a terrific job. And so now you kind of go back and you say, okay, we've done the work Now let's go see what happened to the people Because if the people don't get along they can't fully celebrate the work they've done either and What you're also saying is that it goes from high to low That sometimes you really feel like you know, we connected we got it with we're in this together we laugh together all of it and

and that it actually is a very personal relationship and and that it then goes equally to the other side, but with intensity and equally to the other side but with intensity. And when people experience that kind of intensity in the workplace in a very short amount of time is because each one actually evokes something for the other. So then you start to ask, you know, what is it about this behavior that triggers you, that make that engenders a reaction in you, you know, and when else have you felt this? Because it's so immediate, you know, so soon that you don't like it, that the not liking it was learned somewhere else.

It doesn't just come from these two people. So that's a question I have, it's like, what was it that each of them kind of kind of felt that that the other one was pressing somewhere? And didn't necessarily know that they were pressing nor what they were pressing, but they knew they were pressing. That make sense? Yes. us. When I try to understand the tension between these two people who work together, I continuously

straddle three levels. What is organizational? What is interpersonal or relational and what is personal or individual. What does each woman bring with her from her own history of relationships? What is being triggered between the two of them? And what is actually the consequence of something that is organizational and systemic, present in the room, although invisible? present in the room, although invisible. Now tell me how. It just resonates a lot with the first day that I remember just like thinking, oh my gosh, she's a lot. And then she would like refer to herself as like a bull in a china shop.

And that is something that like i've come to appreciate but i'm now very curious about why that affected me so because it really did influence the just the ways that i showed up in spaces and conversations with her afterwards and you know other bulls in china shops You know other bulls in China shops? My sister my sister Yeah Describe the bull or the China shop

My my sister who I'm referring to is two years younger than me but she is very like Look at me and she's beautiful. And we are like, when we're all together, we are all very loud and very boisterous and fun. But she can definitely get like she has like a temper and she can be very stubborn. And she has to have her way. She's not very great at listening sometimes. When she's insecure about something, it's very, she displays it in a way that is like, it's almost like angry, angry about it. Like she hasn't, she didn't go to college. I was the only one of my siblings who went to college and I was the like quiet one where I was, I had my head in a book at all times. My dad used to compare all of my siblings to me and be like, why aren't you reading?

Why don't you just sit down and be quiet? Up until probably when I got to college, when I started to come out of my shell a little bit more, I was definitely more withdrawn. What are you learning as you listen to this? What are you learning as you listen to this? Some I've, she shared some of it with me a little bit. I did not know about her being the most bookish and a little bit of what I'm picking up on possibly is

getting lost in the shuffle a little bit too with all of these other bigger voices that she had around her and how they expressed what they needed and how they needed. Yes. I'm trying to let that sit with me for a second and see if it resonates, you know. Definitely, I definitely could see, I think, as I moved away from home and learned about just different things,

like I've definitely found more of a voice and a willingness to speak up about things at home. But most of the time I'm happy to just kind of be in the midst of my family being like loud and buzzing around, and that's usually fine. How does that training come to work with you? I don't have a lot of, it's not in my nature, I guess,

to climb the ladder towards like promotions and things like that. I'm happy to be in a room learning and not as much leading or facilitating. I love being on a team and there's this duality where I'm starting to have opinions and give voice to them more than I have ever really done in my life, but also I'm really happy

to just sit back and and listen. Do you experience her as more shy withdrawn and pleased to be on the team happy to learn but not necessarily to claim? And how do you manage that? Do you have a view of her as capable of so much more and if she only takes that seat at the table? That's pretty much right on the money. How I feel. I see a lot and expect a lot and want her to expect a lot for herself too, because I've seen what she can do. I feel like I want to leave as much space for her to see that in herself and want to grow,

but also feel like I don't want to back off just because I get pushed away. Sometimes I also feel like I'm really aware that I've never felt like I could just sit back and just take in what's going on and not have to one, either perform or participate. So I also see just a difference in that and also appreciate, like I've said to her before,

I appreciate what a good listener she is and how good she is at like listening, taking it all in and then having an assessment or an opinion. Where did you get the training of I can't sit still, I have to act, I have to make things happen, I can't just be a passive witness? Yeah, I think, you know, to have a mom who didn't have a high school degree and had me as a teenager and then a dad who dropped out of an orphanage at 18 to like work and then build their own business, I almost feel like there's something in that, like, if you're not proactive in working in that way, like you are left to a less fortunate situation. You know, I think it's called, I think it's survival and progress.

I think for a long time, I understood survival and progress to mean that you can't ever sit back and that if you don't take control of something like you're going to be at the mercy of someone else's decisions. And how does that enter into the dynamic between the two of you? That I'm urgent to wait. Go ahead. Please share. No, I just suddenly saw it's like you, you know, in your world, you don't wait, you don't sit, because it's the difference between moving ahead, creating a life, having protection versus being at the back. And in your world, part of what gave you

your strength is that you may have been quiet, but you listen and you think things through. You don't jump. You are deliberate. It's like both of you in front of a certain precariousness have a different response. One of you says, things are not sure. Let me watch and sit and study this. And the other one says, things are not sure. I me watch and sit and study this." And the other one says,

things are not sure. I can't just sit here. I got to act and fast. That's what suddenly came to me. Does any of this resonate? Yeah. Yeah. 100%. I just felt this suddenly. I just thought, I saw you in your younger versions I just thought, you know, I saw you in your younger versions, and then I see how it enters into the workplace direct. And then you feel that she's pushy when you don't like it in the lows, and she thinks you're too slow and passive and not what. What's the word for you?

Sometimes I think interested. And not what? What's the word for you? Sometimes I think interested. I know that like, yeah, sometimes I think not interested. But that's enough. That's like if she was really interested, she would already have done this. She hasn't done this means that she may not be interested enough. Or see it in a certain way. Often what we might think what we differ on, differ on what focus we think we should be taking. So I think that's what impacts it as well.

It's like, I feel like I'm like, we gotta make it happen. And I think then she's like, let's see what happens and then we're gonna do this, right? So I feel like that's how I would translate that into my own words. How would you put it? I mean, that it all sounds right. I definitely am resisting the mold.

I don't want that to be the idea of me, but I think it's, I can't deny it. It's definitely a thing that I named about myself. Like I am, I do want to see how things play out. I try to be thoughtful before making decisions and moving forward with things. And I cling to like just feeling safe about things, I think. So this is an interesting lens. It's not a definition of you.

It describes an aspect of you. There's so many others. Let's not reduce ourselves to one thing. But it probably is one of the things that stands in the way of your tensions. That's why I picked on this one, because you can feel it. It's energetic. I hear you talk about how you got to take things in hand. You got to make things move, and then I suddenly felt when you have that energy, I can imagine that the tension comes because on the other side is someone that says, wait a minute, those two stances create an interesting dance.

It's stance, stance, dance, says my colleague Terry Reel. And this is it. You have a stance, you have a stance, and together this becomes a dance. So now let's describe the dance. And I'm gonna listen to you talk to each other actually. I listen to the core beliefs that both of the women are highlighting, each specifying her own survival strategy. I must act, I must not react.

One says, I must act, I can't sit idle, and the other says, I have to be careful not to react. One finds clarity in thinking with some categories and structure, and the other finds resistance in being labeled, in feeling confined by words that are more general and don't capture the uniqueness of her individuality. Both of them though have really nuanced understandings of each other and of themselves, but they're caught in this dance at this moment that I hear very, very often.

The expectations from the manager to not just be a manager that looks at the work being done and the deliverables, but looks at my growth, my sensibility, my emotional health, etc. And the manager who is asking, how do we set up expectations and parameters without having to be a therapist at all time. We'll be back with a session right after this. And while we love our sponsors, if you want to listen to this session ad-free, click the Try Free button to subscribe to Astair's office hours on Apple Podcasts. to subscribe to Astaire's office hours on Apple Podcasts.

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That's O-P-E-N-P-H-O-N-E dot com slash begin. And if you have existing numbers with another service, OpenPhone will port them over at no extra charge. OpenPhone, no missed calls, no missed customers. If I see you discuss something, it doesn't have to be the most difficult thing. I will see the moves of the dance, basically. And not just I will see, we will see. I mean, one that came to mind was hiring, like where there would be hiring fairs, and at the last minute there would be one-off interviews,

or we would schedule hiring fairs that weren't originally last minute there would be one-off interviews or we would like schedule hiring fairs that weren't originally a part of the plan and that just would feel really chaotic for me. So that's just a like that's a situation that came to mind that I wonder if it would apply here. Well I think I would say that if I'm thinking about how we're going to do it again this year, I want to know what is going to make you more comfortable with those types of moves, because we have to make them. I'm open to being like, what would you like to try to still meet that need,

but it not make you your high you feel like the hiring fair is chaotic. It's not going to not feel chaotic. So my, my thought of this was almost like I don't want to lead it. I don't want to like, be the one in charge of it if it's going to be something that's like, that I feel like I can't control or just like have some feeling of like, this is, this has an order to it. And I don't think that that means it shouldn't happen that way because ultimately what you did worked. It's just that I, I'm happy to just like not be the lead on it, not be the person scheduling things

and holding people accountable to RZPing and things like that if I just know that that's not something we're gonna do and I'll just help with tech support. I mean, I think I'd wanna push and be like, two things I would say is one, like the hiring fair should run, there's a lot of ways that should run

exactly how you run it. What I'm interested in are some tweaks that also meet the needs of the people that we're serving. So it's like, I don't know how I can frame it for you so that like, it doesn't feel like a tweak is ruining your entire system. And maybe the other option or another option too is like telling you what it is that we're thinking about we need and being like, okay, so given these things,

how would you tweak the way this is the way the hiring process goes now to still serve this other need versus telling you how I want you to serve it? Like I would want us to play at least like two of those out before we just decide like you're not going to be on it or you're only going to do tech support. Because one, I don't think that's sustainable for our team to like get everything we need to get done and then two, I just think like you are more than just tech support. I think you are more than just tech support. Do you know that what she would like to hear from you is not what you cannot do, but what you would like to learn to do better?

No, but I mean that's... The place here goes to, then she starts to think you're not interested, which I don't think is what you mean. But you're talking about what no to this, no to that, can't here, can't there. And what she wants is to sense an energy. It's the energy of getting it done that we were just talking about before. She wants a little bit more of that energy. Yeah, I mean, I think, give me something I can work with, is

how I'm thinking about it. I feel like you don't want it to be different or you don't want it to change because I'm doing it. If I'm going to be really like, that's where it starts to get like a tug because I'm like, I want opportunities to think of it in a different way, but it kind of feels like a little bit of what I walked into also on a bigger sense of like, if we can't keep doing it this way, then I don't want to do it at all. And then you have to do it?

And then I have to do it. That's honestly what's happening in my head is that then I'm going to have to find other ways to do it or, you know, because ultimately it still has to get, it still has to happen. It has to get, it still has to happen, it has to get done. And then I honestly never want you cut out of anything that we would do as a team. Like one, you're an asset, two, that's not a good look for you. I don't want anything that's not a good look for you.

Tell me, have you had experience within helping her and infusing some confidence? I mean, I don't know what that, exactly what you mean by that, but I feel like, yeah, I feel like, I don't know if I can infuse confidence in her. I feel like I try to express the observations and times where I feel confident in her.

Same, yes. the observations and times where I feel confident in her. Same. Yes. Yeah, without, because like, I never want to patronize you. I always want to have high expectations because I'm always clear of like, how awful it feels when there's not high expectations feels terrible too. So I'm always trying to have that dance. How are you receiving that? Uh, I am struggling.

I'm struggling. I'm thinking about the times where I think I feel like I was energetic or like about it. energetic or like about it and it was misinterpreted as not believing or not buying in when I was like asking questions or I'm trying to offer like my feedback or just thinking like this just to me doesn't make sense so I don't like I would rather retry something else. So I'm just struggling with the feelings that I've that I've had in the past, having brought me to this point of just tell me what to do and I'm going to do it. Because whenever I pushed back or whenever I tried to become energetic or offer something, it was met with what felt like, no, no, no, like this is, that's not

what we want. And it was always just like a fight. So I'm just like, well, fuck it then. I'm just not going to do that anymore. I'm not going to push back. I'm not going to pressure test things if it's just going to feel like I'm starting a fight or causing an argument or something like that.

So that's those are these are things that are kind of just like going in my head right now because I do want to feel like I am. I want to feel like I'm an asset to the team. Most days I just feel tired. I hear, I'm hearing it, I'm processing it. And I think that, and we can look at like what you're saying is pushback or coming, being excited about something and like what I perceive it as like if there's misses in that as well.

What did you hear her say? That the words that I heard were like that when she has other thoughts or has other ideas or expresses another way or why she wants why she's invested in the way that it is being done if I'm asking for something different, that she doesn't feel like that's embraced, that that is kind of pushed aside. Or that it becomes the source of a battle. Definitely becomes the source of a battle. And you see that? Yes. You see it as well?

I see it, I know it. Okay. So you agree on On that on the on the on what happens because that's a very different answer that i'm not just Not engaged i've chosen to not be engaged when My experience has been that if I do bring that energy My questioning my discussing is experienced

or is responded to as if we're in an argument. I think there are times. I think that if I'm not feeling like the questions have to do with how to do this better, and if I'm feeling like the questions have to do with like resisting change You're right. I I am taking that i'm responding to that differently than I might to like new ideas or problem solving So go a step further Sometimes you can experience her questions as curiosity and engagement and sometimes you experience her

statements as resistance and rigidity. Like she closes off and you can't, you know. But the more she goes that way for you, that's when you start to chisel away. I have no choice. That's how it feels. I know that I need to develop in my own skills, but in that moment it feels. I know that I need to develop in my own skills, but in that moment,

it feels like I have no choice because I can't let this stop us. And that's kind of the narrative that happens in my head that creates what Esther talked about, that I feel like I need to chisel away, which can't possibly be a pleasant experience for... No, I would not say that it was pleasant. But that's a fact. And do you see how the chisel machine gets activated? Yes. Because I think that part of what

you're doing so beautifully here is to get a sense as to how each of you in some way elicits some reaction in the other person by virtue of your own behavior. Both of you agree, you know, there's a shared sense of reality here. It's not like one that you have completely separate stories and you kind of wonder if this is happening to the same people. So there are times when you actually do succeed very well in bringing her in, where she engages from the place of how can we do this rather than I can't do it. I won't do it.

Let's study those. What have you done then, each of you, by the way, that made you be able to bypass the impasse? Well, the first thing that came to mind was that when I've had a good night's sleep, things generally go better. I like, when I am taking better care of myself, I feel better overall. And that's one thing that I have not been doing a lot of for a long time. And I do feel like a sense of ownership

for when things did not go so great. And I think that when things did go well, it was coming from both of us more. And why has it been challenging for you to take care of yourself? I have self-diagnosed depression. I have consistently just, you know, gained weight over the last five years since I moved from my home to where I am now. And I am very comfortable with being comfortable.

I don't overextend myself in my personal life to many regards. If I don't want to do something, I don't do it. If I want something, I get it. And that's just kind of like, I feel so disgusting, like saying that out loud. But that's just like what my life has been like, especially during quarantine, but really leading up to that as I started to have like my own financial

like independence and stability and just freedom really from like my mom, my family. Say more. Is there more there? I am not the same person that I was when I lived at home. When I go home, I have to pretend like I am still that person, that I can't show too much of like who I am. So COVID has definitely allowed me to just,

just be, just be, be at home and just not, I wouldn't say that relax is even a word because I haven't been relaxed. I've been working, I've been not taking care of myself. When I've had opportunities to take care of myself, I play video games instead or something like that. And I think that when I, when I had discipline, when I had any semblance of discipline for myself or self-control, I was probably, probably in, I would say the latest was college,

but the last time I really remember was high school when I had to get to school on time or else I would have been kicked out again. I had to get up and get my mom awake, so and give her and make her coffee. And those were the times where I remember like having to be disciplined. And then once I started to get out of the house and not have to do those things, it just discipline flew out the window.

And with that any sense of like urgency to get back to it. What do you learn from that? with that any sense of like urgency to get back to it? Why do you learn from that? And thank you for telling. Yeah, thank you for sharing that. I mean, I've learned that if you, one, it's that how hard it is to not feel like you can be who you are when you're home with your family. And then also how it would just feel so uncomfortable to feel like somebody else in

this other setting is imposing or in some way wanting you to do anything outside of what you're comfortable with. It's almost like you're a little spent. Yeah. I was also thinking, you know, what is the responsibility of a manager towards the health and mental health of your direct report? How much is it important to know? How much do you need to take that into consideration? How much does that go to work? What is the relationship here between the personal and the professional? And probably, without knowing, you

know the days when she has slept well and the days when she has spent her night on video games. You don't necessarily know why, but you know the difference. Yes, and I do think like other times that it's been more pleasant and less battle, I think are when like that part of me kicks into where I'm like, take the time you need or do the thing you need to do, because I do value so much like your well-being and your health and mental health. So if you talk about when is it right, Esther,

I feel like we definitely have that compassion for each other. That is really there. I've had to have two surgeries during COVID. I've had several deaths in my family and she's just compassionate and understanding and picks up whatever she needs to pick up because of that. And I try and hope that she's felt, I think she's felt the same from me. So I think if you just ask what works. If what works, that's definitely, we are both very in tune with our humanity and like the humanity of others.

The manager is a caring and empathic person and she wants to know about the mental health of her employee. At the same time, she wonders what is her responsibility? To what extent does she need to adapt her expectations when her worker tells her that they spent a weekend playing video games? This is one of the foundational questions in the moment about management as an empathic guide versus management who make sure that their deliverables are up to date. Let me ask you something else. You work with teachers who work in school with dire needs. Do you ever discuss that aspect of your work, the real bigger reasons of what's compelling

about this here? You graduate at the same time as your mother from college. You are the only one in your family who went to college. This is an important subject in your lives for both of you. Do you ever have those conversations that actually remind you why you're there? We don't, you know, I'm so glad that you were able to like align where our experiences could be similar because I think a lot of times those conversations go into where like where it appears that we have completely different experiences or think about the work in such different ways. In many ways, we do have experiences that don't differ. In some ways, you know, so much. And it would, I would love to talk about like how we feel and think about the work that we do and how we're still here. I want to highlight, as she says,

the places where they align, and especially education. Their shared passion for the opportunities that education has provided them and could provide to the many students that they work with. And so I think that the best way to end this conversation is one of my favorite questions. What's one of the best teachers you had? I would say probably when I was in high school, I was in this AP psychology class and he noticed everything that happened in the classroom

and he could tell immediately when I became disengaged, when I would just start, like I would usually sit in the back of the classroom and he could tell when I would start to like drift off into my brain and he would just call me back uh and just clearly really cared about like the students actually being a part of what was going on in the learning. So a good teacher starts with the teacher you remember. You remember the best and the worst of the teachers that we've had, right? But that, to me, if you had more of those conversations,

social justice, training of new teachers, what makes a good teacher, how do you become a teacher that's remembered? What does it mean for these teachers to come out of college right now and to suddenly go and teach virtually? I mean, it's like the weirdest thing they've ever... nobody thought about that. Your passion for education, what education has meant for you. To me, if you include those things in your work and in your conversations, it will change your relationship. You just heard a classic session of How's Work with Esther Perel.

We are part of the Vox Media Podcast Network in partnership with New York Magazine and The Cut. To apply with your partner for a session on the podcast, for the transcripts or show notes on each episode, or to sign up for Astaire's monthly newsletter, go to astaireparell.com. Astaire Perel is the author of Mating in Captivity and the State of Affairs. She also created a game of stories called Where Should We Begin? For details, go to her website, estherparell.com. Tribeca Festival returns to NYC, June 4th through 15th. Every summer, the festival takes over New York City's famed movie theaters and concert

venues and this year is no exception. With groundbreaking films and television, musical performances and talks, live podcasts and immersive art, there's something for everyone all across the city. Featuring the world premiere of Billy Joel and So It Goes at the Beacon Theatre, Becky G at the United Palace, a live recording of This American Life at Spring Studios Indeed Theatre, and so much more. Tickets are on sale now at trybeckafilm.com. Tribeca Festival returns to NYC June 4- through 15th. Every summer the festival takes over New York City's famed movie theaters and concert venues, and this year is no exception.

With groundbreaking films and television, musical performances and talks, live podcasts, and immersive art, there's something for everyone all across the city. Featuring the world premiere of Billy Joel and So It Goes at the Beacon Theater, Becky G at the United Palace, a live recording of This American Life at Spring Studios Indeed Theater, and so much more. Tickets are on sale now at trybeckafilm.com.