Ep. 30: Are We Still Supposed to Act Professional at Work? (w. Cindy)

EPISODE DESCRIPTION

Welcome to It's Gonna Be Fine, the podcast where we highlight current topics and trends you may have missed, cut through the noise, and dig deeper to understand what's really going on.

This week, it's all about the workplace. From helicopter parents calling recruiters on behalf of their adult children to workplace hookups, office shorts, Crocs, Zoom pants, and increasingly honest out-of-office messages, the rules at work seem to be changing.

Matti and Cindy unpack what’s behind those changes — and whether some workplace norms are outdated, some are worth keeping, and some were maybe never that important to begin with. Along the way, they get into generational differences, authenticity, boundaries, privacy, and the strange ways we decide what is — and isn’t — appropriate at work.

And obviously, we do a quick check-in on where Cindy's at with The Pitt (a "workplace" in and of itself!).

Referenced in this Episode

• Good Morning America - "⁠Bosses say ‘helicopter parenting’ now extends into workplace⁠" (via YouTube)

• Inc. - "⁠Gen-Z Wants In-Office Sex to Be a Totally Acceptable Thing⁠"

• The New York Times - "⁠Accept Your Fate. Don't Wear Shorts to the Office⁠."

• Instagram - ⁠Unhinged Out of Office messages you really wish you could send⁠ (via @heyellenmeyer)

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TRANSCRIPT

Matti: Okay, Cindy, quick question: the Emmys. You and I used to watch the Emmys together all the time. They just happened, and for some reason, I told myself I had to watch. As I was watching, I thought, “Why did I tell myself I have to watch?” They’re very different from what I remember, probably because I didn’t watch as much TV back then. But did you get a chance to see them?

Cindy: We did. I just watched the opening because I was very interested in Mariska Hargitay being the host. I know she’s been nominated for a zillion Emmys, but hosting is very different from being nominated, so I was curious. Then I thought, okay, I can’t do this. I didn’t watch all the shows that were nominated, so I watched TV instead.

Matti: I was underwhelmed. I love her, but I was underwhelmed by the bits. They didn’t land for me. Speaking of you watching TV instead, one of the shows that did very well in terms of nominations and wins was our favorite, which we talk about all the time: The Pitt.

Cindy: Which I finished! Yes, I mean to tell you. I finished it! Whew. That’s a good show.

Matti: It’s a good show. Literally, it was like, “Have you been on The Pitt? You’re nominated for an Emmy!” The whole thing was this person and that person.

Cindy: I know! But they all should be. Everything about that show is Emmy-worthy, so good for them.

Matti: As I was getting ready to record this, I thought, “It’s been like four months. I wonder if Cindy’s made any progress on The Pitt.” It’s coming back in January, I want to say.

Cindy: I’m very excited. I found season two easier to handle emotionally. I don’t know if it’s because I knew the characters and could take myself out of it, thinking, “Okay, this is happening to them, not to me.” Maybe that helped, or maybe I just grew a thicker skin. Whatever it was, I could get through the episodes without needing a two-month break to emotionally recover.

I’m curious about your thoughts on the girl with the sunburn. It’s just this visual gag: there’s a sunburned woman in a bikini walking around in season two—spoiler alert—and they never really engage with her. She’s just there as this subtle comic relief that no one draws attention to. I thought it was genius. It was like, “Okay, we’re going to be okay. Sunburn Girl is here. We’re going to be fine.” I’m curious whether you had a similar perception or noticed her, or if I’m the only person who was locked in on her.

Matti: It’s funny because when you first mentioned Sunburn Girl, I thought you were talking about someone at the Emmys. I was like, “The sunburn girl at the Emmys? Who?” Then I realized you were talking about The Pitt. It took me a second, but yes, I absolutely remember her. And now that you mention it, she was just kind of around.

We’ll check the Pitt box. I think we’ll always do that. But believe it or not, even though you’re the perfect person to talk about TV, you’re also the perfect person to talk about what’s happening in the working world, as we’ve already done. For those who have forgotten, Cindy is a career coach who helps people get jobs and gives them career advice. Her company is called Hollywood Resumes. So whenever I have topics about work, you’re the go-to.

Cindy: Thank you! I love talking about it.

Helicopter Parenting Goes to Work

Matti: What I wanted to start with is a video segment from Good Morning America about helicopter parenting—not just helicopter parenting in general, but helicopter parenting when kids are looking for jobs. It was kind of funny, but also very cringey. We’ve got parents of people in their early twenties calling recruiters and talent acquisition leaders to ask, “Hey, why didn’t my kid get this job? He interviewed three times. Why didn’t you choose him?”

Can you imagine your parent calling and asking what happened? And then, on the flip side, if someone gets fired or let go, the parents call HR and ask, “Why did you fire my kid? He doesn’t deserve to be fired. He deserves another chance.” I found this super uncomfortable. I definitely want to get your take, and I’m curious whether you’ve come across this in your own work. Do you find that parents get a little too involved? To me, it raises the question: Where’s the separation? This is getting weird.

Cindy: I definitely think it’s weird. I have seen it, but I don’t know that it’s exclusive to Gen Z. Maybe it’s worse with Gen Z, but I remember when I was working with a lot of interns. You were also in that ecosystem at the time. I had this crazy internship, and I hired interns after starting out as one myself.

One of the people I hired as an intern showed up with her mom four hours before the interview to scope out the office and make sure everything was okay.

Matti: Were they checking that the snacks were there?

Cindy: They just came to the office and said, “Hello, there’s an interview at 1 p.m. We’ll be back.” Okay! This was in 2011, I want to say. We were in our early twenties, so Gen Z wasn’t really the generation we’re talking about. We were elder Millennials.

Matti: So it was a dry run.

Cindy: Exactly. We were the age Jesse is now, but we weren’t that generation. That was my first exposure to it, and I thought, “God, my parents don’t even know I’m here. I don’t know that they know my job title!”

Matti: My parents are very supportive, but from a distance. I can relate to that.

Cindy: It definitely happened back then, too. I’ve also had a lot of coaching clients over the years whose parents either come to me and buy my services, which is fine, or want to be involved in the process. When you’re 18 or 19, you might not have the income to hire a career coach, so I understand why parents want to vet the person they’re paying. I’m totally on board with that.

But I’ve also had parents insist on being on the phone calls with the person I’m career coaching.

Matti: The initial call or all of them?

Cindy: I don’t allow it for coaching because things sometimes come up where a parent is pressuring the person to do something, and I try to draw that line. For resume consultations, though, I’ve sometimes had to let parents join. When I’m learning about someone’s work history, a parent might be on the call. Most of the time, they don’t chime in, but sometimes they do.

A parent might interrupt and say, “Excuse me, I just want to tell you that Jane is really good at this, and she’s underselling herself.” And I’m thinking, wow. Sometimes dads will say, “I’ve been giving her the following advice. What do you think, expert?” So moms tend to champion the child, while dads tend to offer their own advice and ask for my opinion.

This has been happening for a while, too. I don’t like it when I send something to a client and their parent takes over responding. If you can’t talk about your work history or send an email yourself, that might be part of why you’re not getting a job. That’s not something I can fix through career coaching.

Matti: Here’s my question, though: Is it a reflection of the kid not being capable, or is it a reflection of the parents being overbearing?

Cindy: I think it’s a reflection of overbearing behavior. Another interesting thing is that I’ve seen it with husbands and wives, too. I’ve never had a husband call on behalf of his wife or demand to be on a call with her. But I’ve had men who need career help whose wives found me as their coach. That’s fine. Their wives might join the consultation call for ten minutes to make sure I’m a real person, but sometimes they stick around.

Again, I don’t let them into the coaching sessions, but they might have the notes shared with them or join resume calls. I’ve definitely had wives try to get me on their side by arguing that their husbands aren’t doing enough. I have so many questions about these dynamics, and I’m curious about your perspective.

Matti: I was thinking about the parent-child relationship, but the spouse dynamic is so interesting. With parents, it might be about wanting to take pride in their child and help them succeed. But at some point, as Ethan Weiss discussed on his episode, you have to let them go and figure things out. You can be there to support them and provide a shoulder to lean on, but they’ve got to stretch and learn for themselves.

If this is happening with husbands and wives, I wonder whether there’s an element of the wife feeling burdened by her husband not having a job. Is it simply that she wants him to work, or does it say something about their relationship? Maybe she doesn’t want to be the person in her community whose husband is out of work, so she feels the need to get involved.

Cindy: I’ve been thinking about this, too. When I listen to these helicopter parents or spouses, the impression I get is that they see a problem and want to solve it. They have extremely strong problem-solving skills, and they really like being in control. They see a solution for someone they love and want to make it happen.

There are often stakes involved. If you’re supporting your 24-year-old child or your 50-year-old husband, you might think, “I know how to do X, Y, and Z, so why aren’t you doing it? You must need help. Let me get you that help. I can take control of this.”

I’ve never met a problem I can’t solve! I definitely have some of that instinct myself. I like solving problems and taking control, but you have to know where the boundary is. Where is your involvement actually helping? Is your child or spouse a project? Are you giving them the ability to stretch and figure things out for themselves, as Ethan talked about? Are you listening?

When I think back to that intern who showed up with her mom, she didn’t live it down. For months, we talked about how she’d brought her mom to the interview. She did get hired, but people thought she was weird because of that first impression.

As an adult now, I’m thinking we probably should have been nicer. I don’t know that she did bad work, so if you’re listening, I apologize for whatever role I played in that.

Matti: So she got hired?

Cindy: She did! You also have the phenomenon of people getting their kids hired when they’re the boss. They’ll say, “Take my kid as an intern,” and everyone has to bow down to the intern. I’m curious whether you’ve seen this in your workplace or elsewhere. Have you ever had to run interference with a parent or loved one who calls and says, “Who are you? Why are you talking to me?”

Matti: I haven’t, actually. I was trying to think of whether I’ve ever dealt with a situation like that, and I don’t recall external forces showing up in my work. Even thinking over the last eight years, when we’ve been non-23-year-old adults, I can’t think of a time when I’ve encountered it. Maybe if I’d been more involved in this when I was younger, I might have seen it more.

But there are so many places where it can happen. It can happen during the recruiting process, after someone is hired, or when someone is already an employee. It’s not just, “Help my kid get this job.” It can also be, “Why did you let my kid go?” or “Why did my kid get a less-than-satisfactory performance review?” Where does it end?

You brought up a really interesting point about problem-solving, because people take on roles in relationships. Maybe this is giving us a view into how that relationship works. The behavior is showing up in this particular situation, but it might also tell us something about how decisions get made in that relationship more generally.

And I guess you want to understand whether the person being helicoptered—the helicopteree, if that’s a word—ever learned the tools to solve problems themselves.

Cindy: Let’s just call them the propeller.

Matti: Well, if people want a little guide on how to approach this, there’s a video I’ll link to that interviewed a recruiting leader. I thought they put it in a really balanced way: You can coach from the sideline, but don’t step onto the field.

If someone’s interviewing for a job or working in a role, you can give them advice and consult with them behind the scenes. But don’t insert yourself into the process. There’s a line there. Stay on the sidelines; don’t go onto the field. I thought that was very sound advice.

Cindy: I love that. I absolutely love it. People shouldn’t be left floundering, wondering what to do, and you should be able to rely on your family when you’re struggling with something work-related. That’s a positive way to frame it.

Gen Z Wants to Hook Up at the Office?

Matti: Well, great. We’ve got helicopter parents helping us get jobs. You’d think that once you’re in the job, you can be successful and build your career. Maybe! But according to Fast Company and Inc. magazine, Gen Z apparently wants private spaces at work to hook up.

So they’re having their parents help them get the job, and then they’re saying, “Thanks, Mom and Dad! Now I’ve got more opportunities to hook up with coworkers.”

Cindy: You sent me this article, and I was like, what? I know there have always been people who want to have sex wherever they can, but my first instinct was to wonder whether this was about the prevalence of porn and people thinking you can just do that. Is that a thing?

Matti: Can you imagine a conference room door with a sign saying, “This room is reserved for OnlyFans. Book it in Outlook”?

Cindy: I don’t know. I’ve heard weird things, but this feels crazy to me. So I read the article, and then I wondered who conducted the survey. I’ve been doing some research, and I have a pretty high bar for this kind of thing. I’m also doing research for the narrative-change organization I work with, so I have a lot of questions about how surveys are conducted.

Matti: The article said 38%.

Cindy: Exactly. Thirty-eight percent is a high number. I wanted to know who conducted the survey and how it was done. So I found the survey and read through the whole thing. The questions were really leading.

The article was about return-to-office policies and how Gen Z supposedly wouldn’t want to go back to the office because they could have sex during the workday at home. If you make them go into the office, the argument seemed to be, you have to preserve that perk. Okay, but what questions did you actually ask?

The survey offered people choices, and I could imagine 38% of respondents saying they were fine with having sex during the workday if it were an option. I could see how someone might be open to that. But the survey also referred to both partnered sex and self-pleasure. It wasn’t necessarily asking whether someone had a willing partner in the office.

Matti: Okay…

Cindy: I wanted to know what company conducted the survey. It turned out to be an essay-writing company where you can pay eight dollars a page to have someone do your homework. So I had even more questions. Who did they survey? People whose homework they do? Were those people Gen Z? Were they actually working? I don’t know how valid the results are.

Maybe the findings are true, maybe they’re not, or maybe 38% of the particular respondents they surveyed felt that way. But why is Inc. spreading this story? It’s so clickbaity.

I’ve personally never walked in on anyone having sex in the workplace. I’ve mostly worked at small companies without a lot of private space, so maybe that’s why. At the larger companies I’ve worked for, the conference rooms had glass walls. I guess the bathroom would be the only option!

Matti: When I was an intern, about 20 years ago, I worked at a small office. One day, I was working a little late, probably until 5:30 or 6 p.m. There were three of us left: two regular employees and me. I decided it was time to go, so I left and crossed the street to Subway to get a sandwich.

I was sitting there, looking across the street at our office, when I saw the two of them in the window, making out intensely. Nothing crazy, but they were clearly happy I’d left so they could have some time alone.

The best part of the story is that they eventually got together formally. They’ve now been married for more than 20 years and have a couple of kids. I’ll never forget that image of me looking up from my sandwich and thinking, “Whoa! Am I seeing what I think I’m seeing?” It was really funny.

Cindy: First of all, good for them that it worked out. Office romances don’t always work out. As you were telling the story, all I could think of was the “My Eyes! My Eyes!” scene from Friends.

Matti: Right!

Cindy: They didn’t even look for somewhere private. They waited until after hours. I think people have always been having sex in the workplace. It’s a fantasy for a reason.

Matti: It happens on TV, too.

Cindy: But to make it a workplace requirement? I’ve never had a coaching client say they want a place to have sex at work. When I ask people what they want from their workplace, they talk about health benefits, flexibility, and other things. I’ve never had someone, Gen Z or otherwise, say that they want a hookup space.

I’ve also never had anyone say the reason they want to work remotely is so they can have sex. People want to do laundry, pick up their kids, or have the flexibility to go to doctor’s appointments and therapy. Those are the things I’ve heard.

I would love to see job postings start listing benefits like a 401(k) match, health benefits, office friends with benefits, and a designated hookup location on the third floor that requires booking 24 hours in advance. Or imagine it being listed in the benefits overview you get when you start a job. Soft benefits, no pun intended!

Matti: Friends with benefits!

Cindy: My number one takeaway is that you should wash your hands after using the bathroom or any conference room. Just wash your hands when you leave.

Matti: Other than that, it’s sex, and that’s delicious. What do you think the survey or Inc. was getting at with the whole return-to-office versus remote-work debate? Where do you stand on it?

Cindy: I think it’s more of a statement about today’s generation. Maybe it’s less about what someone needs in an office and more about how normalized sex has become publicly and online. We’ve got things like OnlyFans, and I’m planning an episode about dating where I want to talk about privacy, too.

I’ve seen this on Instagram: people take photos of attractive people on the beach and post them online, saying, “Look how hot this person is.” These are human beings! Maybe some of them consented, but I get the sense that many didn’t. Some accounts even say, “Don’t report me; just ask me to take it down if you don’t want it posted.” What? That’s what I think is happening here. Things that weren’t as normalized 20 years ago have become commonplace.

Matti: It’s become something you can talk about or think about, as though sex is simply part of life and therefore fits into the concept of work-life balance.

Cindy: I’m not saying we need to go back to a society where women have to hide behind whatever. No. But there’s an acceptance of judging people’s bodies because everyone thinks it’s their business now. People think they can post someone half-naked without consent because that’s just what we do.

So maybe someone can have an expectation of hooking up in the office because it’s become normalized. I’m exaggerating a bit, but that’s where my mind went.

I initially thought the article was going to argue that going into the office increases your chances of meeting someone. That makes sense. But the more I read, the more I realized it was literally talking about having locations where people could have sex.

And it wasn’t just about partnered sex. It was also about having a private space for self-pleasure. I wonder how much of this is Grey’s Anatomy’s fault. I say that with deep love for Grey’s Anatomy, but those doctors aren’t working in The Pitt.

Matti: They’re not running from one emergency to the next.

Cindy: Exactly! One of the things I loved about season one of The Pitt is that Dr. Robby can’t even find a second to go to the bathroom. He’s thinking, “I really have to pee,” and then an hour goes by and he’s like, “Forget it. I’m not going to.”

But on Grey’s Anatomy, there are 10 minutes between surgeries, so let’s find an on-call room and have inappropriate sex with a superior. That show’s been on for more than 20 years. At some point, you start thinking, “Maybe doctors do this in real life!”

Matti: Maybe people have taken what happens on TV and assumed it can happen in the real world, too.

Cindy: Right. And all of life is content now, isn’t it? You see an attractive body and think, “That’s a cool body. I want to take a picture of it.” All of life becomes content, and maybe the lines are blurred.

Matti: It’s like the shift from social media to content creation. What’s next?

Cindy: Plug for the previous episode ;)

Matti: Exactly. I love it.

Shorts in the Office

Matti: Okay, so sex in the office probably means you’re not wearing a lot of clothes. You can be wearing clothes, of course, but whatever. The New York Times recently published an opinion piece titled “Accept Your Fate: Don’t Wear Shorts to the Office.”

First of all, amen. You and I have talked about this on the podcast. I’m so anti-shorts in the office. I feel like we still need some standards. Maybe it’s the elder Millennial in me, but my personal office dress code is that I’ll never wear a T-shirt. I’ll always have a collar or at least a sweater, and I’ll always wear pants, no matter how hot it is.

There’s something about seeing someone walking through the office halls like they’re at summer camp, showing off their legs. Maybe they’re trying to attract a conference-room hookup. I don’t know! But I thought, “Amen. Can we stop with the shorts in the office?”

I don’t know when it happened or when things changed, but I’ve noticed shorts more and more recently.

Cindy: Does it differ by gender? Women wear knee-length dresses. If a woman wears a knee-length dress or a dress just above the knee one day, and Bermuda shorts the next, is that different? Is it about showing your legs, or are men’s legs just not for the office?

Matti: No, it’s less about the legs. That’s a great question. I don’t mind seeing legs, of course. It’s the shorts themselves. I actually saw a woman in my office recently wearing the shortest shorts. I didn’t say anything because she’s on a different team, but I was thinking, “What are you doing? This is borderline inappropriate.”

Cindy: This is where a parent or spouse could step in before someone leaves the house and say, “Hey, I don’t know if that’s the right look for the office.” That’s where the helicoptering can come in.

Matti: Assuming you have someone to tell you that! It looked like she’d rolled out of bed in whatever she wore to sleep. Look, I’m Mr. Comfortable. I’d much rather be comfortable than uncomfortable. I hate tucking in my shirt, and I love wearing polos. I’m casual at work, but I draw the line at shorts. I just think, “What are we doing? Let’s put in some effort.”

Cindy: For me, it’s shorts and sweatpants. It’s about casualness. You dress for the destination. I’d also find it unsettling if someone came to work in a three-piece tuxedo. I’d be thinking, “What are we doing?”

Matti: Are you interviewing for a job?

Cindy: Exactly! Or are you a cater waiter? What’s the goal? Or imagine someone in a prom dress. Certain things are appropriate for different locations. You want to fit within the norms of your workplace, but you also want to show respect for the fact that you’re in a workplace, around other people, and doing a particular job.

Matti: Right. Are we going to start seeing tank tops and people coming to work dressed as though they’re going to the beach? Are we going to see people with no shirts on? Let’s draw the line somewhere, please.

Cindy: I’m on board with that. It comes down to decorum and professionalism. I don’t think we all have to wear business suits. I’m all for sneakers in the workplace, but flip-flops? Not a fan of sparkly flip-flops, either. Adidas shower shoes? No. That’s not for the office.

Matti: Right, things you’d wear to the beach. Now I have an image of the socks-and-Crocs look. For some reason, I notice it particularly among men, probably because I tend to notice men more than women in general. What’s the deal with people in their early to mid-twenties walking into the grocery store wearing socks and Crocs? It looks really disheveled to me.

Cindy: Socks and Crocs for the grocery store? You do you!

Matti: I guess. But I notice it everywhere, sometimes at work or in restaurants. Maybe even when I’m at an appointment somewhere, where I’m not working but I’m there for the appointment. I’ll see people standing in line wearing that, or someone shuffling down the street, and I’ll do a double take. It’s just a weird look.

Cindy: For a brief period, I lived in heaven, aka Long Beach, California, right by the beach. I felt like I finally had permission to go to the grocery store in sweatshorts or walk to get coffee in whatever garbage home outfit I was wearing. It felt so freeing. I thought, “It’s because I’m near the beach. I could be coming from the beach, and it’s okay. No one’s looking at me.”

At one point, I wondered if I even needed clothes anymore. Could I just wear loungewear all the time? But now that I’m in New York, I feel like I need to put on jeans just to go to the grocery store. The people and the situation call for something different.

When everyone’s a little beachy, be beachy! I miss that freedom of being able to think, “I need some milk. I don’t need to change out of my pajamas because we’re all in these beach vibes together.”

Matti: I think some of this probably started during the pandemic. We were all on camera from home, wearing whatever the hell we wanted, and we got comfortable with it. Now we’re supposedly back to the office, but we’re carrying some of those habits with us. So whether it’s casual dress, no dress at all, or sex during the workday, maybe it’s all connected.

Cindy: What do you think about people who are still showing up on Zoom calls without pants? I’m not talking about the situation in 2020 when someone wasn’t wearing pants, the doorbell rang, and they stood up in their boxers. That was understandable. But it’s 2026, and I’ve seen people get up in the middle of a Zoom call for an unplanned reason, and they’re essentially bottomless. I’m seeing their underwear!

It’s 2026. You know the doorbell might ring, or your dog might need something. You don’t have to wear formal trousers, but put on some sweatpants or turn your camera off for a second if you’re not wearing pants.

Matti: I’ve heard stories about this, too. I’ll get texts from friends or siblings about something that happened on a work meeting. Apparently, someone once came on camera literally shaving, thinking they were off camera. A coworker also told me she was interviewing someone who appeared completely shirtless on the call.

Cindy: Probably wants to have sex in the office!

Matti: That’s what I’m saying! Let’s see what happens over the next couple of years and whether things get even more extreme. We’re going to track it, monitor it, and come back with updates.

Out-of-Office Messages That Say the Quiet Part Out Loud

Matti: Okay, can I share some very funny, charming, and sassy out-of-office messages? According to Instagram, these are messages people have left when they’ve been away from work.

Cindy: I feel great about this. I’m so excited!

Matti: I’m going to share them with you. I think we need one that says, “Thanks for your email. I’m currently searching for an office hookup and need about 45 minutes before I’m back. Wish me luck. I’ll get back to you in the next three hours.”

Cindy: Bones on vibrate!

Matti: My God. Okay. We’re going to need some fun music for this, too. Here we go.

The first one says: “Thanks for your email. I’m out of office. I know it’s urgent. It’s always urgent. And when I drop everything and reply in four minutes, it sits unread in your inbox for six business days. So calm your tits, Steve. You’ll be all right.”

Cindy: I don’t think that’s real, but I like it.

Matti: It’s from an Instagram account called Hey Ellen Meyer. And why does it say, “You’ll be all right”? It should say, “Calm your tits, Steve. It’s gonna be fine!”

Cindy: Yes! Come on, go with the branding!

Matti: The next one says: “I’m out of office through Friday. For questions related to my role, I’ll respond when I’m back. For anything related to the two other roles I’ve quietly absorbed with no title and no raise, whatever.”

Cindy: I really, really hope that’s real. That’s such a specific fantasy: having a full-time job, deciding you’ve had enough, and quitting because you just can’t take it anymore. It’s not my life, but I’d love to have the gumption to leave a job I hate and make my out-of-office message say something like, “Cindy Kaplan is no longer working for this toxic company. For inquiries related to this, contact someone else.”

Then you could list all the things you were doing that you were never paid for! It would be like an exit interview with your clients. My God, I would never do it, and I don’t recommend that you actually do it if you don’t want to burn a bridge. This is not career-coach advice. But it’s a great fantasy: burn the whole thing down on your way out. I love it.

Matti: Speaking of burning bridges, I’ll never forget something that happened at work about ten years ago. I was dealing with a normal situation I didn’t want to deal with, and instead of saying, “We’ll cross that bridge when we get there,” I said, “We’ll burn that bridge when we get there.”

Cindy: Freddy!

Matti: The person was like, “What? Why do you want to do that?”

Okay, here’s another one: “I’m out of the office until the 22nd. You’ve asked to ‘hop on a quick call.’ There has never been a quick call. So consider this a pre-decline of the 47-minute call to rehash the thing we’ve rehearsed and rehashed 12 times prior.”

Cindy: I don’t think that one’s real, either. It’s a little wordy, and there are too many numbers in it to be effective. I like the previous one better, although I do appreciate the sentiment about wasted meetings and rehashing things.

Matti: This next one really resonates with me because I’ve been in the position of wanting to write something like this. There are two more left. Here’s the second-to-last one: “I’m away until next week. If your question can be answered by the document I’ve already sent three times, linked in my signature, and named clearly in the shared drive, I suggest starting there.”

Cindy: I love a good “per my previous email.” Or “As we discussed.” Anything that basically says, “You weren’t fucking listening to me.”

Matti: Right! But there’s one more, and I really like it.

Cindy: Let’s do it! I also have a question for you about out-of-office emails, so if you have time to discuss that afterward…

Matti: For you, anything. Here’s the last one: “Thank you for your email. I’m out of office and fully unplugged. For updates on that project, please contact the colleague who routinely presents my work as his own. I’m sure he’d be thrilled to step in.”

Cindy: That’s another fantasy of quitting a job and finally getting to say, “Judd can take a turn doing my job!”

Matti: Exactly. Remember when Judd gave that update in the meeting and everyone clapped, even though I did all the work? He can get the credit and do the work now.

I know these ultra-honest messages aren’t real, but I’ve noticed a trend in recent years toward people being more honest in their out-of-office emails. I was always taught to say something like, “Cindy Kaplan is out of the office for a period of time. Please contact so-and-so in my absence.” If you were really nice, you’d give the dates. That’s it.

But then I started noticing people writing where they were or why they were out. “I’m out of the office for my wedding.” “I’m out of the office for vacation.” “I’m recovering from surgery.” People were being much more open about it.

At first, I thought it was weird. I didn’t need to know! But then I had a moment when I thought, you know what? I want to own some of this myself. I specifically thought about the Jewish holidays. I used to write that I was offline from sundown on Monday to sundown on Tuesday or Wednesday, and I’d be so apologetic about it. I wouldn’t explain why.

Then I saw other people being honest about their lives, and I thought, “Would the world end if I said I’m out of the office for Rosh Hashanah? In my absence, please contact so-and-so.”

Or now that I’ve run my own business, if my partner and I are both out at the same time, we’ll put up a message saying we’ll respond as soon as we’re able.

I felt this especially strongly around maternity leave and dealing with medical conditions. When I was going through IVF, I think I put “medical leave” in my out-of-office message. I wanted people to understand, at least a little, that I’m a person.

Matti: Right.

Cindy: There was a big part of my life when I thought that if people found out I observe Rosh Hashanah or Passover, they’d never want to talk to me again. I don’t know where I learned that or internalized it, but eventually I thought, “If so-and-so can say they’re in Madrid, I can say I’m off for this holiday.”

It might make someone stop and think about what that experience is like. Maybe it helps someone be kinder to a Jewish person or more sensitive to what they’re going through. With medical conditions, it might help people understand that someone is dealing with something and respond with a little more compassion when they return.

Are they refreshed from a vacation? Are they genuinely unreachable? Are they struggling with something? Is it nice to ask how they’re doing? It reminds people that there’s a human being in the workplace.

And now I feel free about it. Not free enough to write, “Fuck you all! I’m so glad not to be here for four days!” I’m sorry for the profanity.

Matti: This episode is definitely getting that explicit mark, especially after our earlier conversation. Anyway, let it rip!

Cindy: Great! I’m not going to write that in an out-of-office email, but I will be more honest and less like a professional wall robot. I’m curious whether you’ve experienced a similar shift or whether you do something similar when you’re out of the office.

Matti: I love everything you said. At one point, I was smiling because you were essentially laying out our It’s Gonna Be Fine moment: be authentic and be okay with what you’re doing. If you’re celebrating a religious holiday—Jewish, Muslim, Christian, Catholic, whatever—be proud of it. It’s okay for people to know who you actually are. Thank you for that.

As for my own out-of-office messages, I’m more general. I usually give the dates. I remember one Veterans Day when our office was closed, and I was feeling extra inspired when I wrote my out-of-office message. I said we were closed for Veterans Day and included a link to official U.S. government information about the day.

Cindy: I love that!

Matti: I remember writing it and thinking, “This needs something more. What are we doing? Let’s add something!”

Cindy: Why do you even need an out-of-office message for Veterans Day? Why isn’t the whole world closed? Or at least America?

At that internship where I wore the fancy halter top we talked about earlier…

Matti: Yeah, that got a lot of comments.

Cindy: I hope they were asking for pictures!

Matti: I did get requests, but they weren’t willing to pay what I was charging.

Cindy: People liked the story. They thought it was endearing: this young person making a mistake.

Matti: I’m glad my mistakes were endearing!

Cindy: At that same workplace, one of my co-interns used to walk around listening to music on her iPod. I’m dating all of us here. One of my bosses complained to me about her and asked me to tell her that listening to music was making a bad impression.

Now, as an adult, I’m questioning why a boss had one intern tell another intern to stop listening to her iPod. That feels like it should have been the boss’s responsibility. She wasn’t in a department or anything, but she was my friend, so I did tell her that people were getting a certain impression of her.

Today, I think that would be totally fine. If someone has earbuds in while organizing books and bookshelves at a publishing company, that’s a task where listening to music makes sense. No one would bat an eye. But the halter top would still be inappropriate.

So I guess some professional norms shift, while others shift less. Maybe in 20 years we’ll start seeing…

Matti: Maybe we’ll all be dead by 2030 because of AI! That’s a whole other topic. As you can imagine, I’ve got a lot of thoughts about it.

Cindy: My God, I’m always happy to talk about AI with you. I could collect AI experiences and ask, “What are Matti’s thoughts on this?”

Matti: Amazing. I think we’ve got the next topic you’ll be back for.

Cindy: I’m so excited!

Is It Gonna Be Fine?

Matti: Any more It’s Gonna Be Fine thoughts? I know we’ve touched on this, but I want to give you an opportunity to weigh in. Is it gonna be fine?

Cindy: I think it will be fine. Everything we talked about today actually makes me think that work is just gonna be fine, because a lot of the things we have issues with at work are both new and old at the same time. To me, that’s how you know something’s going to be fine. It feels crazy, but it’s also not that crazy, and we’re surviving it. It’s gonna be fine.

Matti: And we’ll deal with it. Hopefully, someone somewhere in some workplace will decide that we can still have boundaries when we need them.

Cindy: Some boundaries would be great.

Matti: Imagine getting an out-of-office email that’s just a link to someone’s OnlyFans account. They’re like, “This is what I’m doing in my off hours. Please subscribe!” At that point, it might not be fine. But we haven’t reached that stage yet, so I feel like it’s gonna be fine.

Thank you so much, Cindy. I love seeing you, of course, and everyone else, we’ll see you next time!

This transcript has been edited for readability.