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Welcome to the Sunday Scaries: Work Edition, a podcast for hot takes and real talk on all your workplace quandaries, hosted by two burned-out girl bosses who've seen it all.

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I'm Bijal Mehta. I started my career building warehouses and super fast delivery for the Internet's magical two-day shipping. I've worked in Africa, Asia, Europe and North America with both big tech and startups. Over 15 years, I became a vice president leading drone delivery operations. I've managed more than 500 people across the world. And these days I raise my playful daughter and chat with my good friend, Emily.

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And I'm Emily Tao. I got my start making coffee as a production assistant at CBS News. Eventually, I became the first director of communications at the largest entertainment union in the U.S. and Canada. My 15-year career, and counting, has taken me from red carpets to political fights to Ivy League admissions offices.

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We're here for your weekly dose of workplace reality. Let's jump in!

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So I was just telling you, I'm at the point of my pregnancy where I'm huge and when people look at me, they say, “Wow, you're huge” and I can't fault them for it because I am huge. And I keep saying, I can't understand how people work through pregnancy, not even before getting huge. I’m just so tired, I’m so sensitive.

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Like, my husband would be like, “You look nice,” and I'll just break down into tears for no reason. I mean, there's a reason, right? But, and I just can't imagine that in a workplace and trying to, like, “function,” air quotes, “normally.” Yeah. And so I wonder if you have- You do have experience with that and I'm curious. I guess I have a little bit of experience with that, but I don't know. I just don't know how pregnant people do it.

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I mean, I did it, and I still don't know how pregnant people do it. Oh my God. I did it for- I had a weird pregnancy experience because I was working a very intense job, like, three or four months before... I got pregnant in May. And I think the prior March or Feb., my colleague left really unexpectedly, and I inherited his work on top of the work I already had. So I was managing an entire business portfolio, whereas before I managed half of it. Ugh.

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Yeah, and it was, like, stuff that was very new for me. Like, I basically took over not just operations, but also sales and business revenue and growth. And then I'm first-trimester pregnant. Oh my God. 

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I slept like 12 to 16 hours a day when I was first-trimester pregnant. Yeah, I slept a lot. One thing that worked well for me was I wasn't in the office, and so much of my work was international, so I basically would get up early and work a lot. But by my 4 p.m. or so, like, I was, I no longer had meetings. I remember doing a lot of my work horizontal.

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I had really bad nausea, and not the kind of nausea that's, like, you're actively throwing up all the time. It was, like, the kind where you're just, like, seasick and queasy-feeling. Yeah, I had that too. And then I had zero motivation.

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Okay, so this might be how pregnant people get through it. I found that one of the great things about pregnancy is you don't give a fuck. Like, you, it's,there's some kind of, like, almost ruthless prioritizing that happened to me in my... I cannot believe I just used that term, “ruthless prioritizing.” It's such a business term. That’s exactly what I think of you, ruthless prioritization. Yes, yeah, it's so business-speaky. Anyway, but there is some kind of, like, focusing thing that I found in pregnancy where it's just, like, you know what matters, and then nothing else does, almost like that...

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It's weird because you're right. You are also hormonal and crying a lot, but there's that other side of it of, like, you know that phrase they have, like, don't sweat the small stuff or having thick skin. It's, like, all of a sudden I grew a super thick skin where I'm like, “I get that this is a problem, but is it really?” And I found that really helpful for the things that other people would call fires. Yeah. Yeah, they didn't feel like fires to me.

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Wow. Uh-huh. Was there any instance in which that was actually wrong or did it all end up working out okay? No, it was – well, hmm, that's a good question. I don't think my judgment on any of that was wrong. I, in general, do feel like it's a self-aggrandizement here. I think I have really good judgment around, like, what's important, what's not important, especially in a business setting and, like, around firefighting because I just think ops is all firefighting. So you develop that decision-making muscle, that intuition really, really well, and what this did was it just helped me, like, not emotionally be burdened by the fact that other people weren't there yet. They didn't agree it wasn't a fire or they thought I should be jumping through hoops.

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And, you know, honestly, I think a lot of men do this naturally, and I, in particular, tend to care a lot about what other people think. And so for me, it was nice to be like, oh, this is a taste of what it's like when you are just, like, kind of bold and bossy about what you want and, like, actually don't care. Like, you don't afterwards go and cry in the bathroom because that was so emotionally vulnerable, you know, or, like, go, like, emotionally hangover yourself over, like, takeout food and, like, shitty TV because that's how you have to cope at the end of all that emotional work, right? It didn't feel that way. Instead, while pregnant, I continued to lay on the floor and watch bad TV, but not because I was trying to emotionally cope. It's just because there was, like, nothing else I could muster the energy to do while totally nauseous. Yeah.

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I think I didn't go into pregnancy knowing honestly how biologically transformative it is in like, a very scary way, actually. I didn’t either, even though I suppose we did learn in Texas sex ed, which is its own topic. No, in Texas, sex ed- It was very bad, that’s the joke, it was horrible.

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It just feels like, oh, if you are a woman, you, I assume I would know. And I'm like, oh, I actually knew nothing. And I think being in it, I’m like, all American policies are set up to really punish you for being pregnant. Oh, yeah. To punish pregnant people. I did get one of the most furious I've ever been in my whole life during postpartum, recognizing how my medical leave, which was like five months, is one of the most generous in the country. And so many people end up having to go back to work within four to six weeks or less. It’s wild. Right?

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It's wild because FMLA doesn't even apply, I believe, if you're like a small enough organization or depending on your employment status, you know. Yeah. And so, you know, some people go back within weeks. And I think that's just insane. And, you know, there's- I'm hearing as I'm talking out loud the voice of like, my mom and other women who are just like, “Yeah, but we did it. We toughed it out.” And it's like, yeah, you did do it. But there's so much about our ecosystem that's so different from then till now. But also like, Mom, like you did it, but you didn't get to be a very present parent. Yeah, also, don't you wish you didn't have to do it? Exactly. Don’t you wish it was better?

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Exactly. Like, like, there are, there are costs to that. It's like we can all do it. There's just a tradeoff felt somewhere. And almost always that tradeoff is going to be felt in your personal life, on your relationships. That's my opinion. And on your physical health down the road. Yeah. Yeah.

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All right, should we get to our question today? Yes, please. Okay, this is, I think, a very interesting one. Okay. Okay.

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“Dear Sunday Scaries: I just started working for a nonprofit, and my boss wants us to get money from a philanthropy, and he's asked me to be the point person. But my very, very, very good friend, the kind I talk to about my workplace drama, is the main decision maker at this philanthropy. Eek! My boss knows this, and I think it's part of why he put me in charge. What are the things I should keep in mind when asking my friend for money? Signed, Eek!”

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Oh, my God. I did think that, I was like, oh, y'all know each other? Yeah, put that person on the project. I would do that. Oh, yeah. I think if I was the boss in this, I would totally do that and not give a second thought to how it might make someone feel. Oh yeah, be like, they're friends? Great. That's absolutely a plus. Your feelings? Doesn't matter.

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So I have worked at a nonprofit before, and I have done some, I think they call it development work. And so I've done some grant writing, but it was much less personal. Grant writing is just putting the paper together and submitting it for thought, you know, or for consideration. So I was quite early in that process when I was learning how to do it. I think it sounds like this person knows exactly who's going to be reading it, their best friend at this other philanthropy. Yeah.


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And for me, I'm like, I'm trying to imagine this. I'm like, what if it was you? And I'm like, I think I would have to have a conversation with you, like this friend, right, outside of work, and be like, “Hey, man, I feel really weird. We know each other so well. This is going to happen.” And I would do some sort of transparency up front, and maybe some boundary-setting, or at least share some of my feelings, because I'm just a very direct person and I just- I was going to say, you do this anyway. I run headlong into that. Yeah.

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Like, just for background, guys, Emily has done this in context of us doing this podcast together, because we are friends now in pursuing a more professional goal together, project together. Oh, yeah. And she was the one to be like, OK, let's have a conversation about our friendship versus our working relationship. And like, you know, when there's been conflict, she's often the more proactive one to be like, let's just be transparent. Let's just have clear communication.

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I guess, you know, the part that I can't resonate too much with this letter writer is I don't feel uncomfortable about this potential conflict. You don't feel the “eek.” Yeah, I don't. And I'm like, I can see it. I can understand it. And I can see why someone would feel that way. I just wouldn't feel that way. And like the Terminator, or like Thanos, I will be inevitable, and I will directly address it immediately. And then it'll be great! Did you just say like the Terminator? Yes! I’m like, sometimes this is a hard conversation that you want to avoid. And I'm like with me, you cannot avoid it. I will be there. So depending on your generation, take your, take your scary conversation avatar of choice.

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But, yeah, I'm curious on your thoughts. My thoughts are... I think, well, my initial reaction is I have a bit more sympathy for the “eek” feeling. I have had instances where I work with people that were friends professionally. One of my dearest childhood friends is somebody that I helped get a job with at my last company. And we were actually just talking about how, even so, our work didn't actually overlap very much. And in some ways we really like that because- How come?

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I think because it created a natural separation of, between church and state, you know? And I do think that that's really important for working relationships. It's some sense of, you know, when you're here to work, you show up in work mode. When you're here to have fun, you show up in fun mode. Right. You are definitely in our relationship, I think, the one to keep us kind of like on track and vigilant in which category we're at. Yeah. Which I really, really appreciate. I think that's not a natural skill of mine. I'm very like, oh my God, I have a story to tell. And I know this was meant to be a work meeting, but I just want to tell you this story right now. 	But that's what brings the fun. And there's the balance, right? Yeah!

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But we, I think you and I have a good balance in chemistry that way. And so we don't know this, what the balance or chemistry between these two individuals is. So, like, what if you had two just like fun, goofy off, goofing off people or two kind of more avoidant people? Oh, yeah. Right? You don’t know what their chemistry is. But also I wonder, is this like a very big grant that you're depending on for your organization, right? Right! If you don't get the money, will this affect your performance?

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And then there's extra embarrassment, that not only did you not get the grant, you couldn't manage to get it from somebody you're already buddies with? Yeah, and is there guilt, you know, on the decider's end to be like, “I could really affect my very good friend's career?” I don’t, I've never decided, you know, who gets money in that way. I've never been in that position either. Right. Have you ever worked with, besides our relationship right now, have you ever had to bridge the personal and professional?

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I actually have not. I think out of all my friends, most of them became finance, lawyers, doctors, tech. And I am the odd one that went off to do nonprofit entertainment and, like, political organizing work. Okay. And so I made friends at the job after the fact and we still have good friendships or professional networks, right? But, yeah, never the other way around. And I think about, yeah, I think you and I maybe, ours is like the biggest one, right? Yeah. We've been friends for a long time. But I, again, felt- I felt some discomfort, but it wasn't anything that precluded me from talking to you about it basically immediately. Right. 

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Yeah. I do think if you had a difficult topic to bring up with me and you did like a very, “Hey, we need to talk” and then we'll talk in two days. I would not feel good. I'd be very sweaty. Right. I'd be very uncomfortable. And then once you actually talk to me about it, it probably wasn't as bad as I was making it out to be. Yeah, yeah, yeah. But that goes back to, I would have the conversation immediately. Right. Yeah.

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But there's actually something great about what you just said. It's almost like there will be moments of sweatiness. Yes. Yeah. You know, because there's a little bit more on the line in this kind of imaginative space when you work with a friend. When you work with someone and it's purely a professional relationship, the worst case scenario is only so bad. Yes. When it's a friendship as well, the worst case scenario can be like, just a lot more sad, frankly. Yeah. And so I think it might be normal to have a little bit of sweatiness or a little bit of that “eek” feeling.

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And, but maybe to your point, just lean heavily on communication skills as your way out. Don't overindulge that feeling either. Yeah. And just try to be less avoidant. Which is much easier said than done, of course. Yeah. Yeah. You know what’s interesting is- this conversation we’re having is making me think about how, when friends go into projects together, or even if they’re not friends but you end up being like, cofounders or something, it’s not uncommon to do a version of couple’s therapy. Yes, I've heard of this! Yeah. Yeah, where co-founders have an actual therapist and they work on the relationship with the therapist, which I kind of love?

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Right, because maybe to your point, like if the chemistry isn't quite naturally balancing the way you engage in and work through conflict, you might just need a mediator to facilitate that, which is also no big deal. It doesn't sound like this dynamic or the premise of like, this working relationship is going to require that. Right. Because it sounds like it's kind of a discrete project they're going to work on. Yeah. But for more elongated or sustained relationships, like eventually, potentially, no matter how good you are at conflict management, there might be some crud that needs to get swept through that you need some help with. Yeah. Which is not a bad thing to admit. I actually think it is something that strengthens a person overall, not just in a professional way, but in how you handle all your relationships, which is so important.

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Okay, Emily. So, what do you think is the actual worst-case scenario out of a working relationship like the example that Eek just gave us? Yeah, I'm giggling because I'm like, my mind always goes to worst-case if you give me long enough to dwell on it. Which is to say- Or short enough! Yeah, yeah. 30 seconds? Here we go.

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Okay. I'm like, okay, if this is a really important grant and I am the one, you know, I'm the letter writer. I'm like, what if I don't get it? What if my boss sees me as an incompetent worker? Because I'm supposed to have this good working relationship, this strong friendship. And I still can't get it done. And then, of course, just pile on the self-flagellation on that. You can go down that route. There's also, what if my friend has never actually seen my work? Maybe this is something you talk about, but it's different when you actually see the final product. Let's say it's a final report and you're like, “Oh my God, is my writing good enough? Are the reasons good enough? Are they going to judge me based on this product? And will this affect our-” Right? Maybe that's the final, “Will this affect our friendship?” Like, what if, what if your friend actually is like, “I don’t think you’re as good as you think you are?” Yeah, yeah! That would wound me deeply!

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That would be tough. And even if I got the money for the job, I'm like, they think I'm a piece of shit! I actually think you're pointing out one of the reasons I hesitate a little bit to do a merger of the personal and the professional. I think something that a lot of my friends don't always know about me is, I'm a really tough critic and I have a really high standard. And I tend to keep that version of myself just in the work environment.

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Oh! Are you hard on yourself or on other people around you? Everybody, I have very high- It’s- I don't take it out personally, I don't think I do. Most people who work for me don't tend to receive it that way. But I have very, very high standards. Okay. And I also, I think- This sounds, I'm aware of how this sounds in my head. Let me just say it out loud.

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I am a lot smarter in the workplace than I am in my just personal everyday life. Uh-huh. And so I feel like somebody might go into working with me with one set of expectations around how the experience is going to be. But the reality is, I'm going to be like, “I love you. I've always loved you. I want to be friends forever. But I actually don't think you're as smart as you think you are on this.” And- I don't know in what professional context you could ever give that feedback to someone!

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Oh, my gosh. I definitely had to have. I mean, so much of my job in operations is making sure people have the same definition of performance. Because a lot of my job has been to basically establish metrics that tell us what we're achieving. And then as soon as we hit our targets, to up the metrics. And it has been really fun and interesting to do. I love doing this because I see it more of a communication job than anything. Right. It's to get everyone on the same page, rallied around the same goal. Yeah.

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But, you know, when you work with people from different cultures, I've had a lot of resistance to this too, right? That makes sense. I mean, I work literally in ultra-fast delivery. And when I say, oh, I have high standards, I mean we need to be on time at the level of granularity down to minutes and seconds. So if you say you're going to deliver by 1:13 p.m., it is 1:13 p.m. and not 30 seconds more or a second more, even. Right. 

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And the debate that I've had with my teams who are just angry at like, a deep, almost like, personal level of being like, how dare you think that we aren't doing good enough because we were a second late? Because it's also, I see that argument! Right.That's kind of absurd, right? Yeah. That's like, I got a ticket for going five miles over. What the fuck, right? Exactly. It's so infuriating, right? Yeah. I also just need to tell everyone, I'm a deeply not on-time person.

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See, this is why I don't like to merge. I'm like, I'm never on time in my personal life, right? But then at work, I’m going to have these standards. But I don't care about data, so- And it's just because I think it's right to have a different standard in the professional than in your personal. I think your goals are just fundamentally different, right? And so, yeah. I think I might be the friend to say, like, “I don't think that's good enough yet.”

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Which could be beneficial professionally, right? If you were the one receiving, you were the decider and I turn in something. I mean, this could maybe be a best case scenario. You do me a favor and you're like, “Hey, I think this needs some work. I need some more data here. I need some more information here. Your argument could be stronger here.” Yeah. Right? Which, that could be some boundary violation within the professional context of how this all works. But we don't know. So, yeah.

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Okay, I think you're very much on to something there. The best and worst case scenario probably isn't that there was conflict. The difference between best and worst case scenario- And not just that there wasn't conflict, the best and worst case scenario might, the difference isn't even going to be whether you agree. Like, in this case, the successful outcome is probably, you know, this individual is asking for money. And then the friend agrees that they are the best organization to receive this money. Right. That is like best-best scenario, right? Yeah.

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But that's also a scenario where there's not a lot of conflict. And it's not something you can control for. Yeah. There's also the version where, you know, the individual asks for money and the friend decides that's not the right project or organization to invest the money in. Right, which could be absolutely the right choice. Yes. So rejection, basically, is a very possible outcome. But I think what you're getting at here is rejection isn't necessarily the worst case scenario. The worst case scenario, probably more accurately, is either rejection or not being on the same page. Or even like the friend agrees to give the money but is only doing it out of friendship and doesn't really think that they're deserving but does it anyway.

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Right. Like, all those are versions where there's like an underlying lack of transparency or there's like, an immaturity in how you handle it. Like, as someone who might have to be on the receiving end of rejection- so this person, Eek, might have to be on the receiving end of rejection. Right. How they handle it or how they're able or how the friend delivers the news has more to do with what's going to happen to their personal relationship than the fact that there is a rejection. Yes.

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I can imagine a situation, especially- Eek says that this is the kind of friend that they talk about their work stuff with, they talk about everything with, right? And I'm like, oh, if I was the letter writer and my, my request for funds got rejected and then we never talked about it, professionally or personally, I would remember that forever whenever I saw this friend. I would carry that with me. I would want to talk about it with them at like, in any, any respect. But it feels like it has to be acknowledged somehow, right? Right. It's like you need to talk about it so it doesn't become the elephant in the room. Yes. Otherwise it'll just keep growing and growing and growing. Yeah, and fester, yeah. Yes, yes. Yeah. I think that's very true.

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OK. What's your net takeaway here? What's your actual advice for Eek and anything you've learned for yourself also? I think for myself, I am learning perhaps it is not common for people to run into a potentially high-conflict conversation like I do. I'm just like, everyone should do this. I don’t think it’s hard. Yeah, I don’t think most people have your degree of comfort. This isn't it normal? Isn't it normal? Because I do it.

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And so for, for this, for letter writer, I think for Eek, take a second or some minutes, right, and really try and figure out why you're feeling uncomfortable. Is it because of fear of a worst case situation? Is it because of how your friendship might change? Because, you know, friendships feel very fraught, right? Like losing a friend is, or even having that friendship being damaged in any way, it feels really different than a romantic relationship, a family relationship or a working relationship. Friendship is special, right? And so I think giving that like the time and the actual understanding it deserves is very valuable.

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And then for me, I'm like, I would set boundaries, right? So I would suggest that with you. Of course, I would suggest having a conversation with this friend. And for you, you're like, what feels uncomfortable to me to talk about? What feels comfortable to me as we establish this new kind of more professional aspect of our relationship in working on this project? And it could be just a one-time thing, right? Yeah. It could just be this one thing. It could be something that goes on forever. But as a one-time thing, it is a new thing to explore. And I think with a really strong friendship, you do have some give to bend and stretch, right? And to deal and weather with conflict. So I think having trust in that, in your friendship, is also really important. I love that. Yeah.

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Yeah. We didn't talk so explicitly about the best case scenario. But that's part of the best case scenario, right? Yeah. Is that you can have, you're starting off the working dynamic with a good amount of trust. And a good amount of goodwill. And that's, that’s beautiful. Yeah. Right, you don't have to start with, “My name is Bijal and this is why we should work together!” “How many siblings do you have? How long have you worked here?” “This is why I’m a credible person to be speaking with.”

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And that trust goes far. In fact, a lot of people I know who start businesses, they start businesses specifically so they can work with people they really trust with. There can be a smoothness and a flow to the conversation in the relationship and that's quite nice, almost like when, you know, they say you complete each other's sentences. Yeah. I think you and I actually have a lot of this and I think that's part of our chemistry that really works. Yeah!

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But we also had like, a very big conversation before we started working on any of this. Yeah. To ensure we were on the same page- We did do that. Same values, same boundaries. And when we had a point of conflict in our working relationship because I was not hitting deliverables on time, and not being very communicative about it, and like, that was, I could tell, bothering you. And we had a conversation around it. And it was- There was a part of me that wanted to make that bigger than it was and take it personally. And then there's another part of me that realized, I was like, no, she's literally just talking about working behavior that will make the working relationship better.

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It’s like, you can take that conflict conversation as a “What's wrong with me? Oh my God, we got here in the first place.” Right. Or you could take it as, this is additive. This is like the sprinkles on top. How do we go from already a glorious sundae, rich, yummy, sugary, wonderfully delicious relationship and make it just even better? Yeah. And I think that's the cool part or the best case scenario of getting to work with people that you already have a really nice relationship with. Yeah. And I use the sundae analogy, but I'm just realizing the way simpler way to explain it would have been “glass half empty, glass half full” but... I love dessert, I love that analogy. Yeah, we always have to come back to yummy food. And it's just not water.

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Okay, my takeaway for myself and for Eek. My takeaway for myself, or my learning for myself, is I think that reflection that I actually show up differently in a professional setting versus a personal setting and I have different things, my line is different, my standards are different, where I'm going to push and engage and care more is like a different threshold: I kind of like that actually about myself. Yeah. And I think what I'm recognizing in this conversation is that's a really good thing to bring up in the proactive conversation you're suggesting friends have when they talk about the norms and what to expect when you work together. I should bring this part up. It's like, oh, I tend to have higher standards. I tend to be a little less just, yes person or easygoing. And I always do it with the purpose of trying to make the product, the business product better. Right. The working product better. And I love this about myself, but I just want you to be prepared and to tell me if it's being too much. Yeah. So that's something I learned about myself, which is kind of cool, actually. It is really neat. Yeah. Yeah.

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And then my advice for Eek would be: prepare for rejection. Think about rejection. And try not to frame it as the worst case scenario, but just as a possibility. And it can actually be a great scenario because you can learn from it. But you might get rejected from your friend in terms of them not giving you any money or not all of the money or not on the terms that you want, because it does sound like what you're pursuing fundamentally is a negotiation, right? And just imagine that and imagine it in a way that it's less about being personal.

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And then the other thing I think going with that is it's okay to take space. Yes. And I don't think that's a sign of a bad thing either. Friendships naturally, all relationships naturally have a rhythm of sort of intimacy and space and intimacy and space. And if one of the outcomes of this working relationship is going to be space in response to the work project, maybe they are not the person you talk to about work and dish all the gossip with during the time period that y'all are having this project, right? Yeah, that's such a good point. And that's okay! I don't think that's a bad thing at all. Yeah. Right? I think it goes back to what you said. It's just have trust and faith that y'all's relationship is deeper and more complex. And just let the relationship have breath to it and natural movement to it. You're introducing a new variable to the relationship, but like, the underlying relationship probably is, I'm going to assume, a healthy one. Yeah. And healthy relationships are like organisms: they breathe, they move, you don't need a control for it. Right. Yeah. So that would be my advice to Eek. That’s really lovely.

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Good luck, Eek. Good luck. I think you got this. You got this. And I really hope that, you know, you get to add more richness, another layer to your relationship. It's clear that you and your friend work in a similar enough industry, too. Yeah! So it could be the start of something really beautiful. Yeah, I hope it flourishes. This is the beginning of something that could be good.

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That's it for this week's Sunday Scaries: Work Edition. If this episode resonated with you, subscribe wherever you listen to podcasts and leave us a review!

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Got a workplace horror story or a burning question? Send it our way at sunday.scaries.work.edition@gmail.com. We might tackle it in a future episode. Or just have a good private laugh.

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Sunday Scaries: Work Edition is produced by Emily Tao and Bijal Mehta. Our theme music is by Bitter Old Men and artwork is by Erin Leeder. Until next week: may your inbox stay manageable and your work-life balance tip towards life. Bye!