Building Confidence with Josh Gondelman | Crooked Media
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February 22, 2023
Work Appropriate
Building Confidence with Josh Gondelman

In This Episode

Workplaces are often very, very skilled at making us feel very, very bad about ourselves. Sometimes you need structural reform of the whole workplace, and sometimes you just need a good, old-fashioned pep talk. Whether the crisis in confidence comes from imposter syndrome, or from feeling like you’re the only one who thinks it’s weird to give a CEO a holiday gift– we’ve got some advice. Comedian and writer Josh Gondelman joins host Anne Helen Petersen to answer questions from listeners who are struggling to feel confident at work. 

If you’ve got a workplace quandary you need help figuring out, get in touch! Check out submission guidelines at, or send a voice memo with your question to







Anne Helen Petersen: Hi, everyone. I’m Anne Helen Petersen, and this is Work Appropriate. [music plays] Workplaces are often very, very skilled at making us feel very, very bad about ourselves, or at the very least like the least confident version of ourselves. You can go from feeling like you know exactly how to work the system, exactly who to talk to when you have a problem, exactly what you do and do not know at one job. And then you start a new job and you’re back at square one, you have to learn all the new written and unwritten curriculum for that job, the right person to email, the right emojis to use when it’s okay to actually log off or leave the office on a Friday. It takes time to rebuild your work confidence, and sometimes, depending on the workplace itself, that confidence never comes. You wake up after five or ten years and realize you still feel like you might be doing everything wrong or pissing everyone off. First off, I’ll say that if you’ve been at a workplace for more than a few months and you don’t have a clear idea of how you’re doing, that’s a management problem and we’ll dive more into that next week. But sometimes the problem is less structural. Sometimes what you need is a good work pep talk. And if you’ve been listening to this podcast from the beginning, you know exactly who I wanted to bring back to give it. 


Josh Gondelman: Hi, my name’s Josh Gondelman. I am. I’m back on the podcast, which is very exciting. I am lately mostly a touring standup comedian for the last few months, but I’m also a TV writer and producer and author. I have a pug who is famous in the neighborhood and my Twitter bio, if I were a very religious person, would also say like husband, brother, son. [laughter]


Anne Helen Petersen: Hustler—


Josh Gondelman: Hustler, yeah, grind mode, yeah exactly. I know this is a podcast about work, but I’m like, here’s a bunch of work stuff I do. That’s how I define myself. The end. [laughter] Feels, still feels weird.


Anne Helen Petersen: Wait but you are also officially the first repeat guest host. 


Josh Gondelman: I’m the first repeat guest, yeah thank you. 


Anne Helen Petersen: On, on Work Appropriate. And I know you’ve been touring, but you also started something new since we last talked. 


Josh Gondelman: Oh, yes, that’s true. I have a newsletter called That’s Marvelous, where I do pep talks for readers, but also like people in the news or just concepts I’ve been thinking [laughter] about, and it goes out every Monday. is where you go where you can find it. I like link to it on my social media all the time and it’s really fun. I’ve had a really good time. It’s free and I’ve had a really nice time doing it. 


Anne Helen Petersen: I will also say I am a subscriber. 


Josh Gondelman: Thank you. 


Anne Helen Petersen: That one of the great things is that people can write in if they need a pep talk. 


Josh Gondelman: Yeah. 


Anne Helen Petersen: And then you can give them a pep talk. 


Josh Gondelman: That’s really fun. There’s no like a specific mechanism other than just me asking on Twitter, but it is, I should say that it’s like wide open. And if you write to me, I will almost definitely answer, especially if I haven’t solicited and I’m like deluged with like two dozen or whatever, 50 if you’re if you just write off peak hours, you know [laughter] cheap train times, I will almost definitely respond within two weeks in the newsletter. 


Anne Helen Petersen: So what is your own experience building your own confidence? Like, do you think of yourself as a confident person? Most— 


Josh Gondelman: I would say—


Anne Helen Petersen: I feel like most stand up comedians don’t right? 


Josh Gondelman: Well it’s both right. Like it’s there’s definitely there are definitely times where I feel nervous or anxious. I feel like my lack of confidence is often situational. 


Anne Helen Petersen: Yeah. 


Josh Gondelman: And sometimes it’s undue and sometimes it’s due, right? But I feel like my baseline is like, I know what I’m good at. I know where I’m deficient, and then it’s a gradient from one pull to the other, like, okay, I’m going to do a good job at this. I might not do a good job. Like if I’m I’m pretty confident of like going to the places where I normally do standup, then I’m not like, oh, what if this audience hates me? 


Anne Helen Petersen: Right. 


Josh Gondelman: And then one step, you know, towards nervous is like, oh, this is a new place in a new city that I’ve never been. I hope I fit the vibe there. And then on the other end of the spectrum is like slam dunk contest where I’m like oh oh, this is not going to go well for me. [laughter] Do you know what I mean? Like, I feel like I have a pretty good handle on like, obviously there are things that probably I think I’m great at where I’m like, man, I make a killer omelet. And then I serve it to people and they’re like, this is adequate at best [laughter] or stuff that I’m like, this isn’t really my strong suit and I do it fine. But I definitely feel like a comfort with like the stuff I do, mostly professionally and, and personally. I feel like a pretty comfortable person, but I don’t know if that always translates to like outward confidence. And I think people have said that my standup at times is like self-deprecating. I prefer to think of it as, like, self-aware. 


Anne Helen Petersen: Yeah. 


Josh Gondelman: Like, I know what I’m like. 


Anne Helen Petersen: Right. 


Josh Gondelman: And I’m not like, I stink [laughter] but I am like, yeah, I know. I’ve got kind of like a I’ve got kind of an egg shaped smooth head with a little patchy beard underneath. [laughter] Like, that’s that’s something I’m aware of. I don’t think I’m Jason Momoa [laughter] but you don’t have to be Jason Momoa to be like, I’m doing all right. 


Anne Helen Petersen: Yeah, no, I, I think my I’m like, I’m confident in going on a podcast and that confidence only—


Josh Gondelman: Oh yeah. 


Anne Helen Petersen: —only derived out of doing a lot of podcasts, right? 


Josh Gondelman: Yes. 


Anne Helen Petersen: And not even just like hosting them, but going on a lot of them. And then I’m so unconfident if someone asked me to like, be part of a volleyball game. 


Josh Gondelman: Mm hmm, totally. 


Anne Helen Petersen: And I like manifest that by being like, fuck, volleyball. Like volleyball is the worst. 


Josh Gondelman: Yeah totally. 


Anne Helen Petersen: You know, like, just classic. 


Josh Gondelman: Right. I, I think I haven’t played like, pickup basketball. I haven’t been, like, as active as I would like to be over the past few years. And so I have some friends that play pretty regularly and like my being like, oh, I’m not quite like in game shape. Like, not even just like in terms of like my physical body, but just like, oh, I’m rusty. Like I’m not ready to go yet. And that manifests in me continuing to not get the reps in that—


Anne Helen Petersen: Yep. 


Josh Gondelman: —would help of build skills and build confidence. 


Anne Helen Petersen: Yep. 


Josh Gondelman: But I think one thing that you said is so important and something I think about all the time, we’re like, I think a lot of people in in creative fields and maybe other fields, but I mostly, you know, have a lot of friends that are in creative fields write off the stuff that they do naturally and that they feel confident as— 


Anne Helen Petersen: Yeah. 


Josh Gondelman: —as like not important or not worthwhile. 


Anne Helen Petersen: Yeah, like it doesn’t count. Yeah.


Josh Gondelman: Or like it doesn’t count. Yes, exactly. Or you’re like, oh yeah, of course I’m confident at that. That’s like the thing I do all the time, is that’s what confidence is. [laughter] It doesn’t mean you think you’d make a good astronaut. 


Anne Helen Petersen: Right. 


Josh Gondelman: It means like you have a reasonable level of like, you know, your own proficiency and you feel comfortable and not like undue anxiety over stuff that is in your wheelhouse, in my opinion. 


Anne Helen Petersen: Yeah, yeah. And I think, like, sometimes we only recognize confidence in things that have like flashing red lights around them as, like, brave. So like someone who can get up on a stage. Right? That is something that we think of as confidence. But like, you know, there’s all sorts of like incredible proficiencies, Like someone can be really confident in knowing how to clean a bathroom really well. 


Josh Gondelman: Yeah. Absolutely.


Anne Helen Petersen: And that’s not celebrated as confidence. 


Josh Gondelman: Right. 


Anne Helen Petersen: So you give pep talks to other people. Do you ever give yourself a pep talk? 


Josh Gondelman: Yeah, I’ll psych myself up. 


Anne Helen Petersen: Yeah. What does that sound like? 


Josh Gondelman: I think it’s like you’re prepared for this. There’s nothing to be afraid of. 


Anne Helen Petersen: Yeah. 


Josh Gondelman: Is, like, really helpful. This is within the realm of things you can do. Is always helpful for me to tell myself. 


Anne Helen Petersen: Mm hmm. 


Josh Gondelman: Or like, nobody is here to get mad at you. [laughs] That really helps too. Like whether it’s a show or a meeting or whatever kind of thing, just be like, people didn’t come here lying in wait to ambush me, right? Even if it’s like, oh, the stakes of this are high. There might be people that are hard to impress or have tough questions or, you know, if it’s a job interview or something, but it’s like I’m there because someone wanted me to be there and I know what I’m doing enough that like, probably it’s not going to be adversarial. 


Anne Helen Petersen: Yeah, yeah. And this, you know, this connects with, I think, a larger conversation than that a lot of people have in the workplace about imposter syndrome, right? 


Josh Gondelman: Mm hmm. 


Anne Helen Petersen: Like people being feeling like over and over again, I don’t belong here. And I think the most common strain of advice is like, you wouldn’t be here if you didn’t belong here, right? 


Josh Gondelman: Yeah. 


Anne Helen Petersen: Like you were hired for a reason. And I know that there’s an inner voice inside of you that’s saying, like, somehow you deceived every single person who did this hiring. But—


Josh Gondelman: Yes. And not only that, but the people who recommended you for this job—


Anne Helen Petersen: Every single person—


Josh Gondelman: —yeah totally.


Anne Helen Petersen: —you are a master at deception. 


Josh Gondelman: You’re the talented Mr. Ripley. Yeah. [laughter]


Anne Helen Petersen: Yes. That’s how you got this job. And so for today, our questions, we get a lot of questions that I think could be put under this larger umbrella of confidence at work. But the first ones kind of deal with that, that voice in your head that say, I’m scared, I’m fucking everything up, then I’m a fraud, that everyone hates me, all that sort of thing. And then the second category we’re going to get to this a little bit later is about building confidence to deal with awkward situations with your coworkers. So our first question is about moving on from a bad time in your professional past. Here’s Erika. 


Erika: I was terminated from my first professional job. While I owned my mistakes. I was young and naive and didn’t understand what was happening when my supervisor kept writing me up. Although this was over ten years ago now, I still carry a lot of shame about it. I work in health care where disclosure of work history is routine. How do I talk about this In interviews and on forms? I feel that this history and my feelings about it are holding me back from confidently putting myself forward. 


Anne Helen Petersen: Josh, what do you think? How can Erika give herself a pep talk here? 


Josh Gondelman: Erika I understand this feeling of shame, right? It feels so bad when something at work goes badly. You feel so embarrassed, especially when you’re like, oh, there were warnings and I didn’t see them—


Anne Helen Petersen: Right. 


Josh Gondelman: —because I was too naive for that. Like, that feels so bad. And you, I’m sure you like, think about that period in your life. And like, your face gets hot and you sweat and it’s like, that’s none of anyone’s business. 


Anne Helen Petersen: Yeah. 


Josh Gondelman: Frankly. It was ten years ago, and I truly understand the feeling of shame, but like, this is like going into a job interview and being like, I cheated on a spelling test. [laugh] Like, it doesn’t matter and it matters to you and I don’t want to discount that. But it is none of truly none of the business of the people, you don’t have to disclose every bad thing that you’ve ever done or that’s ever happened to you. And just because something feels like a visceral shame to you doesn’t make it extra important to disclose like it doesn’t. It’s not you didn’t kill a guy. 


Anne Helen Petersen: Yeah. 


Josh Gondelman: So the pep talk is you’ve had ten years and this hasn’t happened again. This isn’t who you are. It’s like a thing that you did once, a decade ago. Like think about your haircuts a decade ago and like, the pants you wore. [laughter] Everything is so different. Your body has replaced all its cells. Is something that might be true. I don’t know. The thing you did was not so severe, nor was it so recent that you have to disclose it unless people like really, really, really are prying for the specifics. 


Anne Helen Petersen: Right. Right. And it’s at least from the question, I do not get the sense that there was an ethical violation. 


Josh Gondelman: No. 


Anne Helen Petersen: Or that like you said, that like someone died, anything so severe because those are things that like sometimes that means legal prosecution. 


Josh Gondelman: Sure. 


Anne Helen Petersen: Or not being able to practice in the field, all those sorts of things. It just seems like she didn’t know how to do her job well at that moment. And also, like she said, she was naive and young man, I messed up on jobs all the time when I was in my twenties, like— 


Josh Gondelman: Absolutely. 


Anne Helen Petersen: —in part because I hadn’t worked at jobs for that long. Like I started working. Besides babysitting, like my first job was when I was 16. This not that long to have worked at jobs. And I think—


Josh Gondelman: Yeah. 


Anne Helen Petersen: —that sometimes we’re hard on ourselves about things that we didn’t know to know. 


Josh Gondelman: Agreed. Yes. And I think like when something feels really shameful, it feels really like important and definitional, but it’s not to other people. 


Anne Helen Petersen: Yeah, yeah. 


Josh Gondelman: And I think like, that is really important to like, allow yourself to feel it’s okay to have been bad, it probably wasn’t like that okay at that job. [laughs]


Anne Helen Petersen: Yeah. 


Josh Gondelman: But it’s okay now. Again, if it is something where you’re like, oh, I was so negligent that all these horrible things happened and you’re going to read about them If you Google me because it was a national news story, then like, yeah, maybe get out ahead of that. But if it was just like, oh yeah, I did kind of sloppy work and I didn’t realize that I wasn’t pulling my weight. And it’s like you’ve had ten years to turn it around and it seems like you have and you don’t have to like, anticipate that everybody is like x-ray visioning through you to see your darkest secrets and shames. 


Anne Helen Petersen: Yeah. I think one thing that would be useful and this might sound like very woo woo, but is to actually forgive herself for— 


Josh Gondelman: Totally. 


Anne Helen Petersen: —whatever happened. You know, I have this recurring dream where I used to be a nanny and sometimes I would have real anxiety that, like the parents would come home and the diapers would be too full. Like any time that they pooped. Obviously I changed their diapers, but sometimes they pee a couple of times and you just kind of do it every couple of hours. You change the diapers. 


Josh Gondelman: Sure. 


Anne Helen Petersen: And in my nightmare [laughs] they come home, the parents come home, and the diapers are, like, just overflowing. Like the weird absorbent material is somehow like, coming out the top. 


Josh Gondelman: Yep. 


Anne Helen Petersen: There’s a reason why I have this stress dream, and it’s that I was always scared that, like, I was somehow doing a bad job and failing these kids in some way. Right. And what I need to say to myself is, like, you were a really good nanny. You did not mess up. I can be forgiven for sometimes taking, you know, changing diapers every 2 hours in 15 minutes instead of 2 hours. But I need to say that to myself in order to stop having this dream. And what she’s essentially having in her work application cycle here is that dream coming up again and again. That moment of shame. 


Josh Gondelman: Yeah. And even if you did screw up, it’s okay to forgive yourself. Like, even if you were really bad at that job. 


Anne Helen Petersen: Yep. 


Josh Gondelman: It’s okay to be like, yeah, I’m forgiven for being [indistinct] I’m forgiven for doing sloppy work that other people had to cover for or for ignoring protocols in a way that like was inconvenient and people didn’t get necessarily like the best results for what they were asking for it. Like most of the time. Again, if what you’re embarrassed about or feel this lingering shame over is like the way you were naive rather than specific outcomes that were genuinely hugely destructive. 


Anne Helen Petersen: Right. 


Josh Gondelman: Then it’s okay to let go of that. And it’s again, if it was as bad as I’m insinuating it might have been, as Anne said, there probably would’ve been [laughs] some kind of legal consequences. Because if you’re if it’s just like, oh, I feel bad that I did a bad job, it’s like it’s okay to have done a bad job. 


Anne Helen Petersen: Yeah. 


Josh Gondelman: Bad at the time. You’re not like the bad job queen. 


Anne Helen Petersen: Yeah. 


Josh Gondelman: That’s like toting this bag of trash everywhere you go. 


Anne Helen Petersen: Yep. 


Josh Gondelman: You’re a person who, like, learned from having made mistakes. 


Anne Helen Petersen: Yeah, And I think, too, there’s nothing that says that you have to say exactly why you left any job unless, of course—


Josh Gondelman: No. 


Anne Helen Petersen: —there was like legal ramifications. So on your resume or on your application, you had a job for that period of time, and then you had another job and another job and all of those other jobs where especially where your references are coming from, those are speak so much more strongly about Erika’s qualifications than anything that happened in this job ten years ago. But also, I know that sometimes jobs have that little box where it says, have you ever been fired from a job? And then that will probably come up in an interview. So if that happens, how does she answer that? Like, what is her script? 


Josh Gondelman: I feel like because it was so long ago, it’s easy to lead with. Like, yeah, the first job I ever had, I like, wasn’t a good fit. It like wasn’t I think wasn’t a good fit is like such a good euphemism. [laughter] And you’re just like, yeah, I was a young person and I just like, didn’t quite have the skills for this demanding job yet. And I was in a little over my head and it was like a great learning experience that I really buckled down and redoubled my effort in future workplaces and it hasn’t happened since. I think like the distance from it is so important. The ten years is like makes it such an easy, smooth thing to like excuse, and then it gives you that job interview permission to like pivot to talking about your strengths actually. 


Anne Helen Petersen: Josh, you’re hired. I love your—


Josh Gondelman: Thank you. 


Anne Helen Petersen: —description of a job ten years ago. [laughs] All right. So our next question is something that I know a lot of people are going to identify with. Let’s hear from E! 


E: I’ve always felt very uncomfortable claiming my expertise, experience, skills, etc. in any context, but especially at work. I always kind of assumed that this discomfort would start to pass as I got older and more established in my career. But I turned 32 this last December, and I’ve been in the workforce post-college for nearly a decade and I feel as uncomfortable as ever. A trusted colleague was shocked to hear that I have a perpetual crisis of confidence because I’ve gotten really good at faking it. Being a young, formally woman, presenting person in the workplace meant I had no other choice. My strategy for faking it is to try to think what a mediocre 25 year old Ivy League white dude would say and use that as a guide. My question, though, is how do I deal with this? How does one become confident in their own competence and expertise when it’s been constantly challenged based on demographics? 


Anne Helen Petersen: So I feel like E understands exactly how to project confidence, but has not given themselves that inner pep talk. So how would you advise them? 


Josh Gondelman: Okay, this is maybe controversial. But I think the kind of directive almost, you know, seven year old Sarah Hagi tweet of Lord grant me the confidence of a mediocre white man. Like, I think that is in some ways like a really helpful signpost on the way to, like, feeling confident. Right? I wish I could be as confident as these chumps that, like, stumble through the world and when they fall down, it’s like into a big pile of money. And. And everybody’s like, hey, you fell into the money pile. You get to keep it or whatever. And I think that that’s like aspirational in the way of, like the quantity of confidence. But I think in this case, right, you’re going like, what would this incompetent or mediocre dickhead say or do? And I think it’s okay to not use that as a rubric. And like, you don’t need to hear this from me. I would say slightly above mediocre white man, but like the the idea of like, what if you were really good at your job, what would you do? Do you know? Not just going like, oh, if I were like a different kind of fraud, I would be confident like this. But being, like, if I were really proficient, how would I act? And I think, like, other people see you as confident, right? 


Anne Helen Petersen: Yeah. 


Josh Gondelman: And. And other people see you as capable. Nobody’s like you seem confident but not capable. It sounds like people think you are confident and think you’re getting the job done. And so take everyone else’s word for it. Take everyone else’s word for it that like you’re doing okay and like, internalize that instead of going like, hmm, what would this this person I have contempt for do in this situation, I’ll act like them because then you’re just going like, oh, I’m acting like this. This kind of person that I don’t think has a lot of value. 


Anne Helen Petersen: Right, Right. So basically the the posture that they’re emulating is a posture for which they have no respect. 


Josh Gondelman: Yeah. 


Anne Helen Petersen: And it’s hollow, right? 


Josh Gondelman: Yes. 


Anne Helen Petersen: So if you emulate that posture, of course, you yourself are going to feel hollow because you think that those mediocre white men don’t have anything to back up their confidence either. Right. 


Josh Gondelman: Totally. 


Anne Helen Petersen: It’s ultimately, an empty performance. And you’re going to feel that emptiness the more that you do it. So like you said, I think the solution here is to be like [laughs] listen, my referent isn’t these assholes. 


Josh Gondelman: Yeah. 


Anne Helen Petersen: My referent is well, myself. But then also I think maybe find other people that aren’t mediocre people just generally. 


Josh Gondelman: Totally. 


Anne Helen Petersen: Who you really respect and be like. The confidence that I am emulating is their confidence. 


Josh Gondelman: Yes, I think picking role models because I think again, the quantity of confidence of like, God it would be so nice to have the blind confidence of a rich idiot like that. That would feel amazing. But if you don’t have that, then being like, what would a rich idiot do? You’re aiming too low. You are someone who is competent and who is capable of creating this facsimile of confidence. It’s like, right, fill it in with something that’s worthwhile to you. Role models as Anne said that are like worthy of emulation and going, I want to be like this person. So I will attempt to be like this person, you know, whoever I don’t want to patronize by being like this, you know, be Beyoncé or whatever. [laughter] But like, you know, if you were some, if, if you were thinking about someone you admire, whether it’s a Beyoncé or Michelle Yeoh or, you know, Andre the Giant, like [laughs] Tig Notaro like who, it doesn’t matter who it is, as long as you’re like, I would like to be like this person in quality and in confidence. 


Anne Helen Petersen: To say, I navigate the world with the confidence of Tig Notaro. You know, that is aspirational. 


Josh Gondelman: Yeah. 


Anne Helen Petersen: Like to say like that is that that is the the way that I want to enter the world. I’m glad that we managed in this question to both give advice and also deconstruct an incredibly popular meme. 


Josh Gondelman: Because I think the meme is a great meme. 


Anne Helen Petersen: Yes. 


Josh Gondelman: What Sarah was saying isn’t like I’m going to act like a rich idiot. 


Anne Helen Petersen: Right. 


Josh Gondelman: She’s like, I wish I had. I wish I was full of as much self-assurance as this kind of person routinely is not I’m going to try to be like them. 


Anne Helen Petersen: Yeah. 


Josh Gondelman: And I think that is like a subtle difference, but like a worthwhile one. If you’re trying to not just project confidence, which you’re really capable of doing, but to try to like, actually cultivate it within yourself. [music plays]


Anne Helen Petersen: Our next question is about that special kind of confidence crisis that comes when you’re bored. Here’s Meghan. 


Meghan: I’m in my mid-twenties and two years into a corporate job. I have an adequate job. It’s good pay, good job security, but I’m worried I have stagnated and have just become an imposter worker. Specifically, I’m worried that I’ve become a deadweight in the team, squandered my tertiary education and resigned to becoming more boring and unimaginative in my work life. My role can provide ample opportunity for growth. But for a while I haven’t been motivated to go out of my way and put my hand up and ask for more. I feel like because my brain does menial tasks all day, I’ve become used to it and my brain switches off when it has to face anything challenging. What advice do you have for getting out of that rut? 


Anne Helen Petersen: Josh. 


Josh Gondelman: Yeah. 


Anne Helen Petersen: What advice do you have for Meghan? 


Josh Gondelman: Get out. 


Anne Helen Petersen: [laughter] I know yeah—


Josh Gondelman: Get out physically, like remove yourself from this. I mean, obviously it’s not as easy as that, but like in a perfect world, it, like, the way you’re talking about your job is like the way people talk about their partner right before they’re like, oh, we should get a divorce. 


Anne Helen Petersen: Yeah. Like, I really love my partner so much. Like, but. 


Josh Gondelman: They’re so adequate. That’s what I love about them [laughter] is that they’re adequate and they provide opportunity for growth and like, gosh, isn’t that what we all want? And it sounds like there’s opportunity for growth, not in the direction you’re interested in growing in. You know, like you buy really big pants, like, sure, you could maybe you’re going to grow to fill the pants or maybe you’re like, done growing that way. Maybe you’re like, oh, I need a different kind of growth opportunity. You know. 


Anne Helen Petersen: Right. 


Josh Gondelman: You can’t you don’t want your JNCOs anymore. [laughter]


Anne Helen Petersen: Big, big shoes. 


Josh Gondelman: Big shoes. 


Anne Helen Petersen: Pants, pants that are like really tall–


Josh Gondelman: That’s what I mean just like too big. And you’re like, right, I could grow to fill to fill this garment or like, maybe you’re done with that kind of growing. Maybe you’re not going to get taller or maybe like, yeah, it’s and you don’t want them dragging with the cuffs, getting all frayed in the back because you keep walking over them with your Doc Martens. I don’t know if anyone else went to high school in the late nineties early two thousands— 


Anne Helen Petersen: You know what she, yeah no, she’s, because she’s in her mid twenties. This is going to be unfamiliar to her. 


Josh Gondelman: Oh, sorry. Yeah, right—


Anne Helen Petersen: But, but but us, we know and many listeners of this show, especially anyone who bought an expensive pair of like Seven’s jeans and then you’re supposed to wear it with heels and you don’t wear with heels. And then they get all frayed at the bottom like you’re talking about. 


Josh Gondelman: Yeah. 


Anne Helen Petersen: And then they have just like, mud. And then you’re like, what do I do about this? This is my expensive jeans. But again, it’s she, she bought a pair of jeans that she doesn’t really want to wear that way. Right. 


Josh Gondelman: Yep. Yeah.


Anne Helen Petersen: And it, I will also say just being in your mid twenties two years into your first corporate job, it’s a real place, you know, like it is. That is a feeling where you’re like, okay, I made it. I, things are kind of okay, but also like, what now? What you know, who am I going to be? I thought I was supposed to figure these things out. Like, my life is supposed to be wild and dynamic. But also, why does it feel this way? Why does it feel flat like all of these things are so normal? And really, I think broadly felt especially two years out of college, right? When you’re in college, you’re growing all the time. You’re always getting all of this new knowledge just like thrown at you. And then suddenly you’re in this job where you’re not learning anything any day. That muscle has kind of atrophied. That’s not your fault.


Josh Gondelman: Right. I mean, not to come on the like work podcast and be like, the American dream is a myth. [laughter] Jobs are hollow and are not worth your— 


Anne Helen Petersen: This is the theme of every episode Josh don’t worry. [laughs]


Josh Gondelman: But it is. But it does like it sounds like you are specifically up against a form of labor that does not suit your needs. 


Anne Helen Petersen: Right. 


Josh Gondelman: And like just because it’s good on paper doesn’t mean it’s good for you. In this moment. It might even maybe five years from now you go, oh, I would like a job like this because I want the stable hours so I can get home at a stable time or oh, it’s nice to do something that I feel really competent at already. But this I don’t think the problem is like I was a curious and excited person my whole life and I pursued this higher education and then higherer education. And then I got to this job and now I’m stupid and lazy. It’s like, no, it sounds like you have a job that’s like doesn’t cultivate your curiosity or play to your strengths and like it is not you, it’s job. 


Anne Helen Petersen: I think she has two options here, right? Either she can decide. It’s really important to me that my job does cultivate that curiosity and that impulse for growth and use the stability of this current job to look for other job. Right? 


Josh Gondelman: Yeah. 


Anne Helen Petersen: Or she can decide. I want the ability to be ambitious and to be encouraged to grow in different parts of my life. 


Josh Gondelman: Absolutely. 


Anne Helen Petersen: That aren’t my job, which intersects with a lot of things that Rainesford Stauffer and I talked about a few episodes ago about ambition. Like there’s so many other places where she can feel really alive. 


Josh Gondelman: Yeah. 


Anne Helen Petersen: That aren’t her job, so she can kind of figure out which one of those paths is the right one for her. 


Josh Gondelman: And not to mention, on top of that all, you don’t owe your job being bright eyed and bushy tailed. 


Anne Helen Petersen: Right. [laughs]


Josh Gondelman: You know, like you don’t owe, like giving 110% because at most they pay you for 100%. [laughter] And so even if you feel like I’m kind of mailing it in, all you really owe is like the work you agreed to do for the money they agreed to pay you and then like being a reasonable person to the other people you deal with— 


Anne Helen Petersen: Yeah. Yeah. Well–


Josh Gondelman: If you’re showing up everyday like throwing a hot coffee in someone’s face because you’re so miserable. Then maybe you can seek the exits, but like, you’re not bad for being like, it’s bored and I don’t try that hard. [laughter] 


Anne Helen Petersen: Right. And I just. I hope that this generation of older Gen Z-ers younger millennials who have seen this discourse of quiet quitting, thrown at them as if like that was somehow quiet quitting is like a bad thing. 


Josh Gondelman: Sure. 


Anne Helen Petersen: Don’t internalize that. Like you not giving 110% at your job doesn’t mean that you’re bad at your job just the same way that, like boomers telling millennials that we were lazy and entitled when really we were out of work and it was the Great Recession, [laughs] like, don’t internalize those messages that don’t know anything about you or your life. And so I hope that this person can really look at where they are and say, I am in a place of of actual stability in this job. Where do I want to go from here? You have a lot of choices, like if you like to have an income right now, right. A steady income and health insurance, that’s a platform from which you get to decide how you want the rest of things in your life to go. 


Josh Gondelman: That’s a great way to look at it I think. [music plays]




Anne Helen Petersen: So for the second half of the episode, we are going to do a couple of questions about having confidence to tell coworkers no. Do you remember, Josh in our last episode, we talked about like really bad gifts that people got? 


Josh Gondelman: Mm hmm, yeah, for sure. 


Anne Helen Petersen: So I also posted that question on Instagram. And like so many people told me about gifts that are like, absolutely boggle the mind. Like, someone told me that their boss got them mugs with photos from his vacation on them. 


Josh Gondelman: Wow. That’s um, [laughter] that’s like in terms of like inciting a class war. That’s like the assassination of Archduke Franz Ferdinand. That’s like the shot, that’s like what, in history books, people are going to be like this boss gave his employees mugs, then had pictures of his vacation on it. [laughter] Anyway, there’s no more capitalism because every office building has been burned to the ground. 


Anne Helen Petersen: So this question is like the sequel to that question. It’s about gifts for your boss. It’s from Alex and our colleague Brian is going to read it for us. 


Alex: How do you feel about getting a gift for your boss? I work at a small nonprofit with a staff of like 15 people, and I’ve worked here for about a year and twice when we’ve had employees leave for new jobs. Our CEO’s assistant asked us how to chip in $10 to get them, like a going away present. And my coworkers have already told me that they all pitched in to buy our CEO a Christmas gift last year. And I guess I’m just wondering, is it okay not to participate? And if so, how do I go about doing that without being a jerk? I like my boss, but I’ve always kind of hated the idea of buying your boss a gift as if hiring you is some act of kindness rather than a business necessity. Appreciate your help. 


Anne Helen Petersen: So when Melody, our producer, told me about this question, the way that I responded her was that these people have been nonprofit pilled, like this idea—


Josh Gondelman: Yes. Yeah.


Anne Helen Petersen: —that somehow you, [laughs] that you should be buying your CEO a gift. I just. I can’t. What is your thoughts here? 


Josh Gondelman: Yeah. So, first of all, this stinks. [laughs] I will say employee leaving like a like a coworker leaving, and everybody chips in $10. That seems like, if not standard, like, not unreasonable. A nice thing to do for someone $10 is like, it’s not nothing. And it’s two times ever. 


Anne Helen Petersen: Right. 


Josh Gondelman: So $20 total. That seems like an okay expense for like being a part of the social fabric of an office. That doesn’t seem unreasonable. And if you can’t swing it, that seems okay too like just say, you know. So not saying that everyone should have unlimited $10s but $20 over the period of a job seems like, yeah, for coworkers. The expectation to buy a gift for your boss is ridiculous, especially when that boss is the CEO. [laughs] And this is yes, nonprofit pilled is exactly the way to put it. They’re like they bought into the we’re a family culture and and it’s not your family. Even your family, you don’t have to buy a gift. However, you might look like a jerk. And that’s okay. [laughter]


Anne Helen Petersen: Right. Do you think that this person should lead the revolution of saying, this is bullshit we shouldn’t be buying a CEO a gift? Or should they just politely declined to participate? 


Josh Gondelman: I think. Look, I think it’s whatever you want to do. If you’re like, we shouldn’t do this. And this [laughs] sends the wrong message to the CEO. Fine. I it seems like the culture in the office will be such that people go, but we want to. 


Anne Helen Petersen: Yeah. 


Josh Gondelman: And they’ll do it anyway. 


Anne Helen Petersen: [laughs] And then they’ll just be like, you’re the weirdo. 


Josh Gondelman: Yeah. 


Anne Helen Petersen: You’re not. You’re not a nice person. 


Josh Gondelman: Yeah. And again, if it’s $10, my advice would just be like, eat it and then talk shit about it to other friends and colleagues. 


Anne Helen Petersen: Yes. Write into a podcast to talk about it how ridiculous— 


Josh Gondelman: Absolutely. 


Anne Helen Petersen: —and then be totally affirmed that the hosts really agree with you. 


Josh Gondelman: Yes. I think this is going to I think this might come up again later in the podcast. But there is like there is an element of like, this is a thing that stinks, but I’m going to agree to do it. Go along to get along. That is like, this isn’t abuse, but it is so annoying. [laughter]


Anne Helen Petersen: Yes. 


Josh Gondelman: There’s no way. Unless you’re willing to say, which is I can imagine this feeling very uncomfortable. Like this is an onerous financial commitment. That is the non jerk way to do it. Everything else, I think they will see you as a jerk, even though what you’re saying is like because at the minimum, what you’re saying is like this thing you’re doing is stupid and I don’t want to be a part of it. 


Anne Helen Petersen: Right. 


Josh Gondelman: And even if you’re right, that is a hard thing for people to hear and go like, yeah, they’re right. We are stupid. [laughter]


Anne Helen Petersen: Yes. And I think, you know, this person clearly from the shape of their question, they see that buying your boss a gift is treating being hired as an act of kindness instead of a business relationship. They see this clearly. So it’s not like we have to emphasize to them like, no, you know, this is the reason why this isn’t okay. They get it. So if you feel like do I, would I rather just not have this be a problem in my life and, like, go along with it and then maybe try to reform some of our more egregious nonprofit pilled practices, right like whether that’s trying to unionize the workforce. Right. 


Josh Gondelman: Sure. 


Anne Helen Petersen: Or like, there are things that I think can actually substantially change that model. That are not just resisting paying for the CEOs present. Does that make sense? 


Josh Gondelman: Totally. Like if this feels so egregious but is also substantively such a small thing that it’s like this is the straw that broke the nonprofit worker’s back. 


Anne Helen Petersen: Yes. 100%. [laughter] 


Josh Gondelman: Where it’s like, it’s especially if the scale is $10, $20 once a year, you’re like, I can just like or gritting your teeth like, I can’t believe I have to do this, but it’s like, that’s not what’s making your life hard or harder than it has to be, let’s say, the rest of the year. 


Anne Helen Petersen: Right. 


Josh Gondelman: And so I do. I think focusing on the the bigger picture stuff is like a a way to soothe your legitimate frustrations without dying on every hill and picking every battle. [laughter]


Anne Helen Petersen: And just to be clear, Josh and I very firmly agree with the idea that this is bullshit. So.


Josh Gondelman: Yes. Oh it’s such bullshit. And we don’t know if the rest of the year feels this way, right? Like if this this is the kind of non profit pilled stuff that’s happening all the time. 


Anne Helen Petersen: Also, Josh what would you say? Like if there are any CEOs of nonprofits listening right now or assistants to CEOs of nonprofits who are facilitating these sorts of gifts, what would you say to them specifically? 


Josh Gondelman: Tell them to knock it off. [laughter] Don’t don’t expect a gift, tell people not to give you gifts, not that you don’t, look, you work hard. It’s nice to be appreciated. Just a card. A card is plenty. Have everybody sign a card. 


Anne Helen Petersen: I don’t even like. You don’t even need a card. Like, what is the card, you’re like, thanks—


Josh Gondelman: Happy holidays. 


Anne Helen Petersen: Thanks for being our boss. 


Josh Gondelman: Right. Just tell them to stop. If they’re getting you gifts be like, no, this is you’re making it weird [laughter] stop it. You don’t, no, I want to bop you with a newspaper. 


Anne Helen Petersen: No, this is like one of those things where if you want that culture to stop, you have to model it as like someone who’s at a top level in organization. So I think of this with like PTO, you know, like if if you say we want to have a healthy boundary around PTO, like don’t respond to email when you’re on break and then you, the manager or the CEO are constantly on your email, you are modeling the sort of behavior that you want. So.


Josh Gondelman: Yeah absolutely. 


Anne Helen Petersen: Even if you graciously accept this gift that you’re underpaid, 15 employees have given you, you’re like, oh, it’s so nice, bla bla bla. 


Josh Gondelman: Yeah. 


Anne Helen Petersen: It’s not so nice. It’s compulsory and bad. 


Josh Gondelman: And if you want them to give you a gift. Gross. [laughter] Stop being a weirdo. Find love in your life. Make a friend. 


Anne Helen Petersen: You know what I would do is I would look at the salary proportionality, and I’d be like. 


Josh Gondelman: Yeah. 


Anne Helen Petersen: All right, so we will reverse engineer this. So maybe the CEO will get a $5 gift card to Starbucks. 


Josh Gondelman: Mm hmm. 


Anne Helen Petersen: Which is usually about the thanks that, you know, a nonprofit employee gets—


Josh Gondelman: Yeah. 


Anne Helen Petersen: —in terms of like a Christmas bonus. 


Josh Gondelman: Or you can give your boss a mug with a picture of [laughter] all of you on vacation just to show your commitment to work life balance and to have a healthy office. You don’t have to go on vacation together it can be a bunch of different pictures. [laughter]


Anne Helen Petersen: For our final question. Fellow introverts are on pins and needles and need an answer to this. This is from Brooke. 


Brooke: How do I get out of optional social activities like after work activities, happy hours, etc. with coworkers? I have limited social energy and just don’t have a lot in common and don’t have a good time with my teammates socially. It’s not awful, but it’s pretty uncomfortable. Though I know others on my team enjoy it. I don’t want to hurt my chances of career growth, but these activities like escape rooms are not my jam. 


Anne Helen Petersen: Oofta. So this is a hard one because I appreciate that Brooke brings up that it’s not as simple as being like, I don’t like to socialize, I don’t like this is just not my jam. I’m not going to hang out. She understands that the relationships that people build during this extracurricular socialization time also lead to career advancement. 


Josh Gondelman: Mm hmm. 


Anne Helen Petersen: And this is something that you usually actually see come up in reference to like golf. [laughter]


Josh Gondelman: Yes, golf is exactly where you go, which I think because it’s not that— 


Anne Helen Petersen: Yeah, people think it’s okay. People think it’s okay. They’re like it’s just an escape room. 


Josh Gondelman: Yeah. Yep. Because I think golf is like people get deals done on the golf course and so much of it is just the socializing. I think that the idea of an escape room is like, you’re missing out on the bonding and you and that might be something you want to think of ways to replace. But it’s also they’re not in an escape room coming up with project ideas for, like their own spinoff company. You know what I mean? Like, you’re not that no ink is drying in the escape room unless there’s, like, a puzzle with invisible ink. [laughter] So I think that that is it is not. What you’re missing out on is the bonding and not the like. This is actually where the real work is being done in my, is my guess. 


Anne Helen Petersen: Yeah. I think if this person is concerned about career opportunities and really dislikes this sort of thing, which I totally get. What I would do is funnel some of your energy into more formalized mentorship type conversations, like make yourself a presence in people’s lives. 


Josh Gondelman: Yeah. 


Anne Helen Petersen: But it doesn’t have to be, first of all, on your own time, right. It doesn’t have to be like, okay, from 6 to 8 p.m. on a Thursday, I’m going to go do this— 


Josh Gondelman: We’re going to do axe throwing at a craft brewery.


Anne Helen Petersen: 1000%, and then you still can feel like I have these connections to people in a way that matters. And that is it is really focused on work itself. And I also, I just want to say that, like if you are at a workplace that does this, it can be so exclusionary to so many people and not just introverts. I’m talking about people who don’t drink, people who have caregiving responsibilities. Like you were essentially self-selecting a group of people who have the time and wherewithal, and emotional— 


Josh Gondelman: A disability [?] I think for some events. 


Anne Helen Petersen: Yeah totally 100%. So you are whether even though you think you’re just having a fun time and like morale building, you’re actually reproducing a lot of the power hierarchies that are already in place for people who don’t have those caregiving responsibilities, who are able bodied. You know, all of these things. 


Josh Gondelman: Especially after work hours. 


Anne Helen Petersen: Yes. 


Josh Gondelman: If if everybody if they go look from 2 to 4 today, we’re going to have a social hour instead of doing stuff at the office. Then it’s like, you know, okay, they’re paying you to be there, be there. And. 


Anne Helen Petersen: Yeah. 


Josh Gondelman: That’s part of, that’s an annoying part of your day. But like, when it’s outside. Yeah, I think, I think you’re dead on with like if these are people that you have professional affinity for, if not like shared hobbies, find a way to cultivate that in the work day ideally. Or if you go, hey, would you want to have breakfast and just talk? You know, just just catch up, check in that way, or like lunch during the workday or a coffee or some kind of beverage of choice. You know, whatever your comfort level is after work and make clear it’s a professional cultivation thing, I think like it’s okay to cultivate those one on one relationships. But part of this also feels like you don’t have a lot to say to your coworkers. 


Anne Helen Petersen: Uh huh. 


Josh Gondelman: And so, like, maybe it’s just like, these are not the people that are going to have that long tail professional relationship for you. And that’s okay too. But it is like figure out the ways to to engage with the people that you want to engage with outside of whatever it is, like adult obstacle course or some nonsense. [laughter] And that and I think that that is that’s allowed and it’s and, and then it both gives you these opportunities to build professional relationships and find out whether you actually have things in common or mutual interest professionally, just stuff to talk about and cultivate these professional relationships with people that you’re like, well, we have nothing in common in an escape room like maybe you do in other situations, or at the very least, it takes some of the sting out of you saying like, I’m not going to do that. I don’t want to do that. Because then the people that you have these relationships with know that you’re like interested in them as a colleague, even if you’re not interested in like a trampoline room for an hour with them. [laughter]


Anne Helen Petersen: And you know, this this question asker doesn’t say how old her colleagues are or exactly what industry they’re in, but I think there is oftentimes an impulse in companies that have younger employees and especially anything that is related to like digital startup culture in any capacity. But there’s this feeling of like recreating college essentially, which is a place, like the understanding the place where you work is also the place where you find all of your friendships, all of your romantic partnerships, and have all of your fun. And I will also add that like places like Google and Facebook, like they purposely try to make that happen because they want people’s entire social circle to be really just their workplace, right? Because then you just work more because it’s all tethered to the workplace. 


Anne Helen Petersen: Yep. 


Josh Gondelman: This is not healthy. I know that it happens. It happened to me in various different scenarios [laughs] and it’s okay to be very conscious about like this is not the avenue that I want for myself. My strongest friendships are outside of the workplace. 


Josh Gondelman: Yeah. 


Anne Helen Petersen: You have an obligation to be friendly to your coworkers. You do not have an obligation to be friends, like best friends with them. And that’s okay. 


Josh Gondelman: Totally. And it’s if you feel like what you’re losing by not doing it is more than what you’re gaining. 


Anne Helen Petersen: Yeah. 


Josh Gondelman: Like it’s okay to do or to find a surrogate for as long as you’re being nice about like these escape rooms stress me out, but like, let’s find a different way to hang out as a substitute. I think you’ll feel like once you get out of the feeling of obligation, like once you’ve excused yourself and recused yourself a couple of times, there might be a little FOMO, but it won’t you won’t feel the same level of discomfort disentangling yourself from this? 


Anne Helen Petersen: Yes. So our clearest advice would be you can say escape rooms aren’t my thing. I would love to have lunch. Right.


Josh Gondelman: Yeah. 


Anne Helen Petersen: Great. Fantastic.


Josh Gondelman: I, that’s so, that’s such an. And then you get this one on one instead of, like, group fun. You get to, like, really connect with someone. If there’s someone you’re interested in connecting with a lot of work level. And then if you find out they’re not, then it’s like, what are you missing out on? Other than a bad time with people that you don’t have anything in common with. [laughter]


Anne Helen Petersen: This has been wonderful advice. I feel more confident already. Do you feel more confident? Do you feel like you could go into a workplace right now and be like, don’t want to go to the escape room but also, here’s a present? I don’t know. Like I’m just combining all of our different things. 


Josh Gondelman: This is how confident I am. I’m going to buy the escape room, I’m going to shut it down. [laughter] I’m going, I’m like Ben Gazzara in Roadhouse. I’m just gonna like, really throw my weight around in a small town. I guess it’s Kansas City, but I’m yeah, I feel I’m on top of the world. Or on the bottom of the world just punching it upwards. [laughter]


Anne Helen Petersen: Josh, thank you so much—


Josh Gondelman: Thank you for having me. This is such a pleasure. Always so nice to see you. 


Anne Helen Petersen: And I will also say to listeners that Josh is a recurring co-host on the show, and if you have other feelings, questions broadly conceived, please send them our way. And Josh, where can people find you on the Internet? 


Josh Gondelman: Oh, my gosh. Is my weekly newsletter. It’s free. I give most information about what I’m doing there. I also at my website, if you’re like, I just want to find out about live shows. I update pretty regularly. I’m kind of on the road off and on. I am frequently on Wait, Wait, Don’t Tell Me I’ve got a stand up special called People Pleaser. You can watch for free I think on Tubi at this point—


Anne Helen Petersen: Yes. 


Josh Gondelman: Definitely free for prime members and for rent all these other places and I have a book called Nice Try. So if you would like to become incredibly sick of me, hear me kind of repeat myself. Do all those things, but pick and choose if you want. [laughter] I think the stand up special, the newsletter, come see me on tour. Thank you so much for having me. 


Anne Helen Petersen: It’s like a Josh smorgasbord. They can find you so many places. 


Josh Gondelman: Kind of a human buffet. And in a way that’s not gross. [music plays]


Anne Helen Petersen: Thanks so much for listening to Work Appropriate. If you’ve got a workplace quandary and you need help figuring it out, let us know. One angle we’re exploring is the specific problems that arise when the higher ups say your workplace is like a family. Sound familiar? You can find submission guidelines at, or send a voice memo with your question to Work Appropriate at Work Appropriate is a Crooked Media production. I’m Anne Helen Petersen, your host. Our executive producers are Kendra James and Sandy Girard. Melody Rowell is our producer and editor. Alison Falzetta is our development producer. Music is composed by Chanell Crichlow. Additional production support from Ari Schwartz and a special thanks to Katie Long and Sarah Geismer. You can follow me on Twitter @AnneHelen or on Instagram @AnneHelenPetersen. And you can sign up for my newsletter culture study Next week. If you manage one person or 101 people, this episode is for you. We’re talking about how to be a better boss. Be sure to subscribe wherever you get your podcasts, so you don’t miss it.