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October 26, 2022
Work Appropriate
Big Office Feelings with Josh Gondelman

In This Episode

At work, we deal with people, and people inevitably bring up feelings. Host Anne Helen Petersen teams up with comedian and TV writer Josh Gondelman to answer questions that range from petty (what if I hate the company holiday gift?) to systemic (is it okay to give up on advocating for my voice to be heard?).

Thanks for listening to the first episode of Work Appropriate! Please rate and review us so other people can find the show. And if you’ve got a workplace quandary you want help figuring out, head to to tell us about it.




Anne Helen Petersen: Hi, everyone. My name is Anne Helen Petersen. And this is Work Appropriate. [music break] A new podcast where we answer your questions about the contemporary world of work. [music break] So this is an advice show. Maybe you have a question about how to reduce the number of meetings that are clogging your calendar. Or maybe you’re wondering whether or not it’s actually time to quit your job. Or maybe you’re just trying to decide if it’s okay to donate that hideous fleece vest you got as a work gift. Nothing is too weird, too personal, or too hard. Because even if I don’t have the answer, there’s a good chance my guests hosts will. Every week, I’ll be joined by a new co-host with real expertise to guide us through these questions. Because the world of work is super complicated, often bizarre, never unexciting. And we have so much to talk about. [music break] Now, I’m not someone who has ever been really interested in the history of work, like I’ve never taken a business class or even my econ class. I don’t have an MBA. I was a mathlete in high school. Just like a stone cold nerd. And I then became an academic in film studies, film and media studies. And then I became a journalist. But when you look at those fields, even if they have some of the shittiest work cultures out there, academia and journalism, just garbage work culture. So I think I learned really early that any time that I felt like I was working all the time, that that was fantastic. And anytime that I felt like I was resting, that that was horrible. And I just had this terrible, truly toxic relationship with work. Like, I remember working one day on Christmas and being like, this is really great. Like, I was writing, I was writing a dissertation or writing an article and being like, Christmas, great day to work. No one’s on the internet, can totally get things done. And I just I’m trying to understand now, like, how I internalized that work culture. Why did I think working on the weekends, even though no one, not my boss, no one told me that I should be doing that. Why did I think that was so great? And why did I allow, you know, every hobby, every activity, every friendship that was not directly related to work, to just die on the vine. So at some point around 2018, I realized that I was experiencing something like I just couldn’t work the way that I had before. And my coping strategy for that was to try and write an article about it. And that article turned into an article about burnout and about millennial burnout in particular. And it’s a burnout book, but really, it’s a book about work. And since then, I’ve continued to think about the history of work, how work got to this particular place in our lives and what we actually mean when we say things like work culture or any of the other words that get bandied about in terms of how we work, where we work, why we work. So even though I don’t have this background in business, I have spent a lot of time thinking and talking about work. And during that process, I have accumulated this long list of people, experts, who do have really interesting things to say, who do have things like LinkedIn optimization tips, but who, more importantly, are really equipped to give us advice on how to think about the nitty gritty components of our work days, but also these larger questions about where should work be in our lives. Why does work matter? Because the way we relate to our jobs. For many of us, it’s the way we relate to our entire lives. It really matters. For this first episode, I want to start with something really universal, and that’s big office feelings. I mean, ultimately at work, we all deal with people and people bring up feelings. So I wanted to bring on someone who I always go to for these types of big feeling questions.


Josh Gondelman: My name is Josh Gondelman. I am a television writer, often standup comedian. I am a Wait Wait Don’t Tell Me panelist. And I’m currently kind of like between full time gigs, I think. And my friend Dan Crohn has this great standup joke about like, I’m between girlfriends assuming I ever get another girlfriend. [laugh] And that’s how I feel about jobs. But I was the head writer at Desus & Mero. I was there for all the seasons at Showtime and was the head writer for the fourth season that concluded recently and abruptly. [laugh]


Anne Helen Petersen: Josh is truly one of the funniest people I know. He knows a lot about what it means to work in a writer’s room and to be a boss in a writer’s room. But he’s also incredibly thoughtful and kind, just generous and an empathetic thinker, which is why I wanted to have him on the pod today.


Josh Gondelman: So I’m trying to let myself off the hook a little bit now because I’m really trying to, like, give myself a little space to think. And I know that I will compulsively take on work. That’s like a characteristic, a longstanding characteristic of my personality—


Anne Helen Petersen: Same.


Josh Gondelman: Is that like, yeah, people will ask me to do things and I’ll be like, oh, that sounds really fun I’ll do it. Or I’ll see an opportunity and I’ll dive at it and not think about like how that affects the overall kind of mosaic of my schedule. And so I’m trying to really work on stuff that I think is fun and productive, but also say no to enough things that I like have space in my day to like not only, like read books and catch up with friends, which I haven’t had as much time to do until recently, but also to like think about my own work and career in the long term and try to be like a little more self-directed about where I want to go rather than just like knocking on every door until one opens. Because I think hopefully I’m at a point that I can chart my own course a little bit more than like the last time I was actively looking for a job and didn’t have one.


Anne Helen Petersen: Part of why I wanted you to come on the show today is because I think a lot of people sometimes our tendency is to really always go for all of our worst scenarios and our worst experiences and our worst case understandings of how things could go. And I think that you have this energy and this outlook on the world of like, what if it went really well? [laugh] Like, what if what if it went in a way that we would all look back with admiration and appreciation? What if that’s the way things go?


Josh Gondelman: I mean, I do feel I’ve like had some real good luck professionally. And I don’t ever want to come off like a guy that’s like, yeah, I’m like a straight, white, cisgender, [laugh] able bodied man, and I’ll work out for me. It’s like, what are you complaining about? But I do think that it is like when things go well, it is like a nice thing you can do is to be like an ambassador of gratitude and optimism in addition to like equity and equality and those kind of broader help and not pulling the ladder up behind you. But I do think like it is kind of a service to be like, hey, sometimes things are good and that’s like, okay.


Anne Helen Petersen: Yeah. And I mean, you have a regular feature on I don’t know if you’d call it a feature, a thing that you do on Twitter from time to time. It’s like I’m here for 10 minutes for a pep talk.


Josh Gondelman: Yeah, yes.


Anne Helen Petersen: Just to strangers, right?


Josh Gondelman: Yeah, and I think a lot of them are professional. It’s like I have this job interview and I’m really nervous.


Anne Helen Petersen: Yeah.


Josh Gondelman: That’s like a big one that I get when I do the pep talks, because sometimes people are very sometimes people are just like, hit me and I just have to, [laugh] like, come up with something encouraging to say. Generally, I’ll go to their profile or whatever, and then other times they’ll have something more specific. And it’s a lot of job interview nerves and I think like that is kind of like, look, go in knowing that they asked you to come in, you didn’t trick them. So unless you did, in which case maybe be a little nervous or you’re so good at lying, just like keep on keeping on, you know. [laughter] But if it I think generally like they asked you to come in, be you, and if that doesn’t work out, it’s because you’re not a good match with the people that are there or they’re not a good match for who you are, rather than the fact that, like, you aren’t enough. I think like it’s not really about you is such a helpful thing to think about sometimes, especially like I work primarily in like entertainment and there’s so many, you know, they could you can walk into an audition and they could just be like, nah, no beards, you know? [laughter] And you’re like, and I really thought I did a good job. And they’re like, no, we like a guy whose whole chin we can see. And it’s like, Okay, sure. And they might never tell you that. You just have to know that you had the wrong face.


Anne Helen Petersen: So this helps explain a little bit about why you agreed to go on and participate in this show, answering questions from people you’ve never met in jobs very different than your own.


Josh Gondelman: Yeah, I’m very arrogant. [laugh] That’s one part. But I do I do have a lot of like for someone who is like at the moment predominantly doing like a little freelance stuff, a lot of stand up. I do feel like I have a bunch of varied work experiences in like classrooms and offices and like nontraditional workplaces like comedy clubs. So I do feel like I do work. [laugh] I promise. I promise. I have jobs. I’m a professional at something.


Anne Helen Petersen: I promise I have worked at jobs in the past.


Josh Gondelman: I have worked.


Anne Helen Petersen: And have advice to give other people—


Josh Gondelman: Yes.


Anne Helen Petersen: Who also work at jobs and same—


Josh Gondelman: Yeah.


Anne Helen Petersen: This is how I feel. [music break] So we’ve pulled together a few questions—


Josh Gondelman: Great.


Anne Helen Petersen: About this theme of big office feelings. And the first is from someone named Stephanie.


Josh Gondelman: Mm hmm.


Anne Helen Petersen: And it brought up some memories for me, but we’re going to have her read it here.


Stephanie: I always find the end of the year or anniversary gift a bit of a slap in the face. I’d rather just get the money allocated per person for the said gift in my paycheck. I know it’s supposed to be a nice gesture, but usually it’s something that just collects dust or I throwaway immediately. Do others feel this way? Are these tokens of appreciation actually good for workplace culture? And I’m the anomaly?


Anne Helen Petersen: Josh, before you answer, I want to know what’s the weirdest or worst or maybe best gift that you’ve ever gotten from work.


Josh Gondelman: Oh, I got sweat pants one year from a job, a sweat, sweat pants sweatshirt and the sweat shirt, totally pleasant and wearable. I like it a lot. The sweat pants, they were like, what size are you? I said, large. I could have gotten medium. I’ve been going medium since then with sweat pants, but they are for the biggest person who’s ever lived like they’re for Shaquille O’Neal. They’re Shaq sized sweat pants. [laughter] And I’m just like, uhhh, well, I feel bad throwing them away like this. This write this letter writer advice asker. But I also have no use for them. I guess. Like if I went camping I could sleep under them. But it is like truly a useless garment. Nobody I know is big enough to wear these sweatpants. [laugh]


Anne Helen Petersen: And I love too, like the idea of you’re like, okay, if I donate this and then it somehow ends up at Goodwill or thrift shop or whatever—


Josh Gondelman: Yeah.


Anne Helen Petersen: Who wants these Shaq-sized, sweat pants embroidered with the name of my company?


Josh Gondelman: Yes, yes.


Anne Helen Petersen: I used to work at BuzzFeed News and BuzzFeed is interesting in that it starts were as like an upstart digital journalism site. That was also a startup, right? So it has like I think some of the good and bad bits of culture of both. And the lavish Christmas present was one of those things. So every year we would get like, I don’t know, 8 to 10 pieces of BuzzFeed swag.


Josh Gondelman: Wow.


Anne Helen Petersen: And we’re talking about hoodies, sweatpants, socks, multiple hats, you know, just like piles. And you would accumulate these piles of BuzzFeed clothing. But it was somewhat like what you were saying that like you kind of like the team sweatshirt.


Josh Gondelman: Yeah.


Anne Helen Petersen: And there was this idea of like, you’re on the team if you’re wearing this, when, you know, a lot of my younger colleagues, especially people in their first couple of years out of college, they were barely getting paid enough to to survive in New York. So, you know, one of the reasons that they wore their, BuzzFeed things every day was because it was a free sweatshirt.


Josh Gondelman: Yes.


Anne Helen Petersen: And also one of the reasons why they ate a lot of the the free food that we had in the office was because that made it slightly more affordable to live in New York City on $40,000 a year, which is like what some of the early employees made. The other thing that we received when there were rumblings of the beginnings of what would become the unionization drive, is everyone in the company received an Apple Watch, the first Apple Watch.


Josh Gondelman: Wow.


Anne Helen Petersen: Which, like, you know, that’s a big deal. Like, it’s hard to be like, screw this. I’m getting an Apple Watch. And some people definitely resold it as soon as they got it.


Josh Gondelman: Sure, yeah.


Anne Helen Petersen: But it also felt like bribery.


Josh Gondelman: Yeah, definitely.


Anne Helen Petersen: Like, instead of coming together to push for, like, fair pay and severance, if they laid us off—


Josh Gondelman: Yeah.


Anne Helen Petersen: It’s like, take this Apple Watch and and be happy with it.


Josh Gondelman: I feel like, though, when it’s a company like that, like this isn’t the mob, right? You can take the bribe and agitate for the other things. [laughter] And I think that’s not unethical right. If you’re like a politician and you take a bribe and you don’t do the thing, it’s like, oh, that’s not come on, that’s not the deal. [laugh] But with the company, it’s like, no, you got to bribe me better. Like, that’s, that is the deal. [laugh]


Anne Helen Petersen: Right. And in hindsight, I should have sold the Apple Watch and instead, because I was, like, angry about the Apple Watch. But then I also felt like it’s weird to resell it. I didn’t do anything with it. And now I have an unopened box for an Apple Watch, first generation Apple Watch. And it’s worth, I think, 70 cents.


Josh Gondelman: Wow. [laughter] Well, I think anything that you can flip is a better gift than something you can’t like. If they if you get, like, a really, really nice winter jacket, but it has, like, big company branding on it. That’s not as nice as just the winter jacket. Right?


Anne Helen Petersen: Right.


Josh Gondelman: Because at the very least, you can turn a profit on that. And your, it’s like they spent money on it. And it’s not just in the glorification of the company. It’s like actually a nice it’s like here, this is a thing conceivably you could want. And as long as it can’t be like super traced back to, you know, it’s not like a one of one. [laugh]


Anne Helen Petersen: Yeah. So like to answer a question, I think that it’s really okay to feel angry and resentful about these presents, particularly if they feel unuseful and it feels like the company’s way of deflecting from cost of living increases things that would actually make work life easier on an everyday basis. And it just feels it does feel like a bribe.


Josh Gondelman: Yeah. If it’s not something that would be a good gift from like a regular person. It’s not a good gift from the company. And in fact, even if it would be a good gift from a regular person, you’re not, like, obligated to feel gratitude for it—


Anne Helen Petersen: Yes.


Josh Gondelman: Because, just because it’s coming from your employer and they don’t have to do it, I think like absolutely. Going back to what you said it, you can feel any kind of way about it. You are not a bad person for being like, well, this costs like $150 or like this cost $50. You know, you don’t have to like feel like you’re looking a gift horse in the mouth. You can just be like, I don’t this is the this horse is a dickhead. I don’t care. [laugh]


Anne Helen Petersen: Right. And also use that as an opportunity to think about like, oh, well, maybe this is indicative of a much larger issues at our company. And that, I think, is the moments when it really pisses people off because it’s a symbol, right? It’s like when my step mom would give me Black Hills Gold for presents when I was growing up, like I hated jewelry and I especially hated Black Hills Gold. [laugh] It’s anyone from, like, the Mountain West would know what Black Hills Gold is. And to me, like, it wasn’t about the actual jewelry. Like, I people like Black Hills Gold for various reasons. It’s it was that it was indicative of the fact that she didn’t know me or know what I wanted. Right?


Josh Gondelman: Yeah, yup, totally. [music break]


Anne Helen Petersen: Our next question is about the whole big feelings process of changing the workplaces culture. So here is the question from Lisa.


Lisa: I started a new job recently. I love this job. I love the work. I love my coworkers. I just love everything about it. My boss and I manage our organization staff, which is maybe 50 people. My boss hired me. She and I get along great. She’s also relatively new to the organization. Before he arrived, my boss started to establish a detail oriented and high performance oriented culture, which was a bit of a change. I want more help thinking about how to make sure the team feels like we have their backs. I want the team to feel like they can tell us what’s going on. I want them to come to us with problems. And then I also want to maintain this detail oriented and performance oriented culture. These are not mutually exclusive, and I know that. But sometimes they can feel like they’re going in opposite directions. For example, we can get a lot of haranguing when we give input on something or ask for rework. So I want the team to tell us if we’re like completely missing something, but also start to adjust their expectations that this is customary. I also have truly felt at some points like this organization can be a bit resistant to change. Like lots of people can. But as a result, I want to be open. And then also I think at some stage we might just have to deliver tough messages. Mostly, I think this is just going to take time and attention and communication. And I’m curious if you have any reactions or advice on how to navigate this balance. I want the team to trust us. I want to feel like we’re all in this together. And I also really want to do great work.


Anne Helen Petersen: All right. This is a this is a hard one, I think. But also, I think that Josh, like, I wonder if you have some experience or thoughts about how you have pushed a team like your team to deliver excellent work when maybe they haven’t been pushed like that in quite the same way before.


Josh Gondelman: I think that one thing that is always helpful when you’re talking about this because this is something that did not come up in the question and I wonder if it’s because it’s taken as a given, is that I think you have to give hard notes to people or hard messages. Being equally effusive about the stuff that they’re doing well and specifically the stuff that comes from their specific experience and taste and ability at being like equally encouraging and nurturing of that I think is like is where I would start. And not that it’s like a bad question to have left that out. But I do think like focusing on that, right, giving the like encouragement and like enthusiasm for people’s good work in addition to like the kind of growth opportunities, as you’d say in a performance review is like really important because like and it can feel like it’s going by the wayside because you’re like, Oh, I don’t have to worry about that. And it’s like, well, the person who’s doing it and is receiving criticism is worried about that. [laugh] So that’s like my first thing for sure.


Anne Helen Petersen: Yeah, I think one thing that we sometimes forget is that a lot of people are really scared at all times about losing their jobs.


Josh Gondelman: Mm hmm.


Anne Helen Petersen: Right. And they feel like they’re doing an adequate job. And so the more that you can emphasize, like you were doing a great job as described, we’re trying to figure out how to do more with this.


Josh Gondelman: Yeah. When you’re trying to foster especially, like, diversity and diverse experiences and opinions of a staff, I think like valuing what they bring to the table and not just like using people as data and then kind of puppeting them to make things come out the way you want them to come out—


Anne Helen Petersen: Right, right.


Josh Gondelman: Is like a really valuable thing to do. Letting people do things in an excellent way that is not the way you would do them is I think like really like high tier management. That is really hard because it’s hard to trust. Like, well, I wouldn’t do it this way, but it’s but this is like a really cool, thrilling way that this turned out.


Anne Helen Petersen: Yeah. Well, and sometimes it makes me think of, like, how we have this expectation that everyone figures out a math problem the same way.


Josh Gondelman: Mm hmm.


Anne Helen Petersen: Remember how you used to have to, like, show your work.


Josh Gondelman: Yeah, yeah yeah.


Anne Helen Petersen: And if you didn’t do it the way that you were instructed, then there would be points out for, for not following the order of operations.


Josh Gondelman: Yeah.


Anne Helen Petersen: A lot of people’s minds work really differently.


Josh Gondelman: Yeah.


Anne Helen Petersen: Then the one way that we teach and if you empower someone to say if you can figure out how you get to this answer or if you can figure out how you get to excellent work, like whatever these reports are, like what the workflow is or what the way that you double or triple check things are like. If you figure out your own system and if you empower someone to figure that out for themselves and praise them and give them the security to figure that out, then they are going to feel much more like it’s their project, it’s their excellence.


Josh Gondelman: Right, and they’re not doing a karaoke version of what you would do. Because I think that is really demoralizing to feel like, oh, I was brought in because I have these skills and what I’m I’m a cover band now.


Anne Helen Petersen: Uh huh.


Josh Gondelman: For for someone else’s point of view. I will also say building in expectations at the beginning, right, of like this is what we’re trying to get to and building in if there’s going to be rework people knowing that ahead of time.


Anne Helen Petersen: Yes.


Josh Gondelman: I think it is such a bummer when you’re like, I’ve knocked this out of the park and then someone else is like, oh, actually we need to like totally redo this part with these other expectations in mind. And I think like knowing that that’s possible coming into it and like what might result in that other than like unsatisfactory work is really helpful. So like going, oh, it might take the first draft to know what we want in the final draft and that’s part of it. And like thank you for your effort getting us to this point because this is really spectacular and really clarifying or going, look, this is what we’re shooting for. We didn’t quite hit it, so let’s try it again. And I think like it is knowing that multiple revisions are part of it and knowing that like what you’re shooting for as close to what the final product is from the beginning is really helpful because I think some of the most like, uh, I’ve been at jobs is when I did something and then you hear like after the fact, like, this is great. You worked so hard on it. Actually, we’re going in a totally different direction and now you have to do that. And it’s like you couldn’t have decided that three days ago before I started. And I think those kind of conversations are really difficult and being really mindful of your staff’s investment and time is really important.


Anne Helen Petersen: Yeah, that that to me speaks to disrespect of someone’s time.


Josh Gondelman: Yeah, right. Because you need the job done. Offices are made of people. So it’s not you’re not dealing with a bunch of sims or like robots that you can like reprogram and nor should you be. And I think to think of it as like it’s their whole day, [laugh] you know what I mean?


Anne Helen Petersen: Yeah.


Josh Gondelman: It’s like it’s a bummer to, like, go into work and knowing that like, oh, I could have just not come in Monday through Wednesday and then you could have just given me this assignment on Thursday.


Anne Helen Petersen: Right, if you would have just given me, equipped me to do it right. The first time—


Josh Gondelman: Yes.


Anne Helen Petersen: I would have done it that way.


Josh Gondelman: Yeah.


Anne Helen Petersen: Yeah. And I think that that creates like a resentment cycle that’s really hard to pull out of.


Josh Gondelman: People like to feel appreciated for specifically their hard work and what they do well rather than just like gold star, you’re a good cog, you know? [laughter]


Anne Helen Petersen: Right, right. And to feel seen in the work that they’ve put in to see that, appreciated.


Josh Gondelman: And there are some times where I’ve been like, hey, I think these two sections are like equivalently good, but maybe a little duplicative. And if you have one that you prefer, I trust your judgment. You know what I mean?


Anne Helen Petersen: Yup, yup yup.


Josh Gondelman: Like giving it giving people agency. And again, not just feeling like you’re shoving your hand up their butt, and or like I guess a less gross way is like ratatouilling them to the result that you want, right? Like I really think that the more you can give people the structure to succeed, to set their expectations for what you want as clearly as you can, and then trust their expertise, the better an experience it is for them. And then conversely, right, if you give them all these expectations and it’s too much, if you’re just like, do it this way, and then it’s just like, screw you, you do it. [laugh] You know what I mean? If you’re going to, like, stand over my shoulders making pottery, like, a ghost and like, no, this isn’t a collaborative experience. This is you being too controlling. So I think it’s like that balance is really helpful. I think the kind of to sum up, give people clear expectations of what you want from them, right? So that they know what the objective is and why there might need to be edits done right or changes made once you see how it turns out and empower them to do things that showcase their perspective, their expertise and what they’re bringing to the table. And that way it’s less like you’re operating your staff like a machine and more like you’re empowering them to do their best work rather than a photocopy of your best work.


Anne Helen Petersen: Perfect. [music break] Our last question is from Emily, who seems to feel a responsibility to speak up about her work, but she is also just really freakin tired. So let’s hear from her.


Emily: I work in advertising right now, and one of the things that I stood up against in my career is figuring out when I should have a voice at the table and how to create room and space for that. As a woman, I thought I would feel more empowered once I got promoted to a director level position. But recently I’ve realized that a title alone or confidence or more doesn’t really create that. So my question is how do you find the mental and emotional energy to continually advocate for your voice and perspective to be heard? Is it even worth it to try? Or does the fact that you have to push for that space indicates something more broken and toxic about the workplace dynamic?


Anne Helen Petersen: Oh. Well, I think the fact that you do have to push and try is indicative of the fact that there’s something wrong with the workplace dynamic. But I think that that’s also incredibly common, particularly in any industry that is historically masculinized in some way. And it’s also probably in most of these similar workplaces, it’s also usually really, really white. So even in industries like nonprofits that are dominated by women, there’s a similar feeling about like only white women feeling like they’re able to have that space to speak up and that sort of thing, no matter how high they rise in the organization. So I think part of it is just real structural resistance and it takes a lot of effort to resist or to rework structures when you are the individual. And I think that that’s why so many people who are marginalized in whatever way in their particular industry end up burnt out. Because in addition to doing their everyday work, right, whatever their job description is, they are also doing this resisting and rewriting and rethinking work all of the time. They have to strategize consistently. How do I make people trust me? Grant me the authority that they would automatically give to someone who is a white male in the room or a white person in the room? And then also how do I make them not think just because of like the tone of my voice, the way that my face looked on Zoom, the way I responded to an email or a slack that like that I’m a bitch and that I have too much power? It’s just an incredible balancing act that I think is really difficult, and I want to just acknowledge that like that is a ton of work. Josh have you ever worked with anyone that like has spoke up in this way and that you admire how they’ve handled it?


Josh Gondelman: Yeah, totally. I don’t have the first seen first hand experience, but I have seen four seasons of Mad Men and then I didn’t have cable for a while, so I missed out on the last couple, but that’s fine. So I’m an ally. [laugh] No, one thing that I’ve seen that is really helpful is like someone who feels this way coming to people that they trust and that they they feel are good collaborators and saying like, Hey, these are the kinds of things that would be really helpful to me, especially if you’re a person who is wants to encourage that kind of like speaking up from all the voices at the table, but there are louder voices than you. Learning how to support those things is really helpful, and I think it’s not right that you necessarily have to coach people to be your cheerleaders, but I think that that can be really helpful is like talking honestly with the people that you trust and feel like you have good relationships with and can go like, you know, I don’t feel like there’s space for my ideas here. If you could help create that space for me by asking me for my input or seconding something that I say it so it doesn’t get scuttled and shouting me out by name instead of just like I think this and then getting taking the credit for it. It’s one way, one avenue that I think there are probably people that are really open to doing it. And I will say if there is no one that is open to doing that because you don’t have those relationships with anyone, or if they’re like, no, it’s too risky for me, that does sound like an incredibly toxic place. Like an over the line, toxic place rather than like you were describing in a baseline toxic place. [laughter]


Anne Helen Petersen: Yeah, yeah, yeah, yeah. Like just modern modern work culture. Yeah. I think that in an ideal world, that person might be Emily’s manager or Emily’s mentor at the organization. But most people don’t have that ideal situation. And sometimes, if anything, their manager, especially I’ve seen this with a lot of women, like there’s a scarcity mindset, right? That like only one woman can be the like powerful woman in this situation. And so I’m going to undercut that other woman.


Josh Gondelman: Sure.


Anne Helen Petersen: Which is incredibly toxic and and regressive in so many different ways. But sometimes you can’t trust the other woman in the who’s in the room to do that for you. And so I think developing that sort of trust and asking for low key collaboration in that way to say, like, to have someone else in the room that is looking out for moments when say you’re continuously interrupted.


Josh Gondelman: Yes.


Anne Helen Petersen: And to have the one who calls bullshit on that person like, who keeps doing the interrupting to have that be another dude that is incredibly powerful, right?


Josh Gondelman: Yeah. And it coming from a man is sadly helpful. And then when it’s on behalf of someone else, I think, like redirecting of, like, oh, I think Emily was, I had a really good idea about that rather than just like, like the what you want to say, right? Which is like, shut the fuck up. I’m talking.


Anne Helen Petersen: Right.


Josh Gondelman: And so, like, I think that there’s a real value in having someone who, in the optics of the room like, doesn’t have the same skin in the game is like really helpful, especially when they have like a kind of professional or social standing that, that you feel like isn’t being granted to you fairly.


Anne Helen Petersen: Yeah, I do think that it would be important, like let’s say it’s you and me in this situation and I felt this way that like I really didn’t know or I was exhausted with advocating for myself. But I hadn’t told you about this.


Josh Gondelman: Yeah.


Anne Helen Petersen: And you had noticed it. And like, you started coming to my rescue. Not in the more subtle way that you were describing, but more in the way that I was talking about, about like calling people out and be like, you should respect Anne. And that sort of thing. It borders on ickiness because it can feel like—


Josh Gondelman: Totally.


Anne Helen Petersen: The guy is like trying to protect the women—


Josh Gondelman: Right right.


Anne Helen Petersen: And so if you if you were noticing that the way that I think a great way to handle it would be you to approach me and say like I’ve kind of noticed this dynamic. Is this something you’re thinking about? Is there a way that I could be helpful?


Josh Gondelman: Yeah, right. What I don’t want. Right. The goal is for that. Your ideas in perspective have space. Not that like I’m a hero [laugh] or that like, you know, like I’m such a fucking cool guy, but that it is, you know, to create that space in the way that is most comfortable for you. And that opens up a lane in a way that you feel like you can do your best work rather than creating like possibly like a self-aggrandizing, self centering conflict in the room to be like, oh, okay, man, listen up. An ally is talking. [laughter] And I think that that’s, you know, so coming from if there are listeners that like have that I think you’re so right to like center the experience of the person who you’re trying to like throw that alley oop to rather than center your own experience—


Anne Helen Petersen: Yeah.


Josh Gondelman: Of like yourself in that meeting.


Anne Helen Petersen: And I think this extends, you know, we’re talking about kind of a doofy male doing that, but it would definitely extend to, I think, any white person—


Josh Gondelman: Mm hmm.


Anne Helen Petersen: Who’s trying to be kind of like attract attention to themselves as an ally.


Josh Gondelman: Yeah.


Anne Helen Petersen: Have that conversation with the person that you’re trying to make more space for and try to figure out how they would like it to be handled.


Josh Gondelman: Yeah.


Anne Helen Petersen: The other thing that I would say is that like, yeah, it’s really exhausting. And the one thing like, you know, our our question asks, how do you find the mental and emotional energy to continually advocate for this? Like, is it worth it even to try? And I do think it’s worth it because I think that we are still doing that really hard work of resetting expectations and re figuring what power looks and sounds like, all of those different things. So it is worth it. But also we don’t have to martyr ourselves on it and it does not have to be like if I quit this job or if I stop trying to do this at 100% of the time all together, I am failing my gender or my race or whatever.


Josh Gondelman: Right. Like chalk one up for the patriarchy. [laughter]


Anne Helen Petersen: Yeah, I got too tired.


Josh Gondelman: I’m deficient, yeah they they broke me. Right. And I do think there is that walking that line and figuring out the answer to the question, like, is this place uniquely ill suited to offering me the kind of input and autonomy and agency that I want? Or is this a place that, like, there can be strides made because you don’t want to bang your head against the wall? Right.


Anne Helen Petersen: Yeah.


Josh Gondelman: You want or you want to find a softer wall that you kind of Kool-Aid, man or woman through it. Why hasn’t there been a Kool-Aid woman? Now am I just fully [laughter] spiraling.


Anne Helen Petersen: This is a joke that is like so particular to like a certain—


Josh Gondelman: Yeah, yeah, yeah.


Anne Helen Petersen: Age group. That’s why we are just like elder millennials—


Josh Gondelman: It’s true.


Anne Helen Petersen: Ourselves all over the place.


Josh Gondelman: Yeah the Kool-Aid man was a very central figure for elder millennials, I don’t know if he’s still doing kind of amateur demolition the way he was back in the day. [laughter] But that did it right. Like, I feel like if there was a Kool-Aid woman who was like, oh, yeah. And it’s like I’m leaning in and they be like, oh, this lady, she stinks, but she’s just breaking the rules. [laughter]


Anne Helen Petersen: Whereas she would have to, like, become, like, evil Kool-Aid woman. Right. Like, it would be like Ursula in the Little Mermaid.


Josh Gondelman: Yes. That’s exactly where I went too. Which is also the very same generation of, like, cultural reference and touchstone. [laugh]


Anne Helen Petersen: All right. So in summary, this is a normal feeling because this is how workplace culture is often structured. You don’t have to martyr yourself in order to fix it. It is not your personal responsibility to fix all of these problems, and it might just be organizational. And the only solution is to quit and find another organization that is trying to change some of these norms or another industry sadly. But then also that there are ways that you can find people who are willing to play on the same team as you. Right. Like there are people who also want the culture to be different. And so how can you seek out and trust those people to try to figure out strategies to do that moving forward? Do you have anything to add there or was I perfect?


Josh Gondelman: I as a man, I agree. [laugh] I feel like this is not my place to be like. Yeah, and another thing, but I was, I was, I think that was a great answer and I, it’s so tricky. It’s so hard because you’re up against culture, right? You’re not just up against, like, one guy or a roomful of guys or like one company stodginess. You’re up against, like, the expectations of society.


Anne Helen Petersen: Yeah. You’re up against, like, norms that have taken centuries to ossify around how we think about women in authority.


Josh Gondelman: Yeah. Yes. Yes. And I think what you said about, like, whatever works for you is the right thing. You’re not like an ambassador for everyone.


Anne Helen Petersen: Yeah. Josh, I am so grateful that you took the time to come on this show today. Not just because you made me laugh like at least 17 different times, [laugh] but also because you are a person who takes feelings seriously. And I really love that.


Josh Gondelman: Thank you. That’s very kind. Again, I really appreciate that compliment. It means a lot to me.


Anne Helen Petersen: It was a total pleasure to have you today. And I will I would love to have you back on any time to talk about the problems of people who you’ve never met in situations you’ve never been in.


Josh Gondelman: Terrific. I feel it’s I love doing it. Love working with you. We’ll come back anytime. I have a lot of unstructured time these days. [laughter]


Anne Helen Petersen: Thanks so much for listening to the first episode of Work Appropriate. I’m so excited this is happening and if you have a workplace quandary you want help figuring out. Get in touch. You can find submission guidelines at or send a voice memo with your question to  Some of the episodes we’re working on involve managing your time and energy as a freelancer or the weird stuff that happens when you’re starting a new job or what to do when the work you love is grinding you into a pulp. 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 by Ari Schwartz and special thanks to Katie Long and Sarah Geismer. You can follow me on Twitter at @AnneHelen or on Instagram @AnneHelenPetersen. You can sign up for my newsletter at And meet me back here next week as we try to get to the root of why modern workplace culture is so hostile to parents.