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Nicole Lapin
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Jason Pfeiffer
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Nicole Lapin
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Jason Pfeiffer
This is Help Wanted, the show that makes your work work for you. I'm Jason Pfeiffer, Editor in Chief of.
Nicole Lapin
Entrepreneur Magazine, and I'm money expert Nicole Lapin. On Tuesdays, Jason and I answer the.
Assistant/Co-host
Helpline and help callers solve their work problems.
Jason Pfeiffer
And on Thursdays, I give you one way to improve your work and build a career or company you love.
Assistant/Co-host
And it starts now.
Morgan Lavoie
Jason Nicole hello Morgan.
Jason Pfeiffer
Great to have you here. You're going to tell us something that we don't know. We don't know what you're going to say.
Morgan Lavoie
Yes, you have no idea. And I'm going to say what we're talking about Today, which is nightmare bosses. We've all had them. But I will say, working as a assistant in entertainment, just to be clear.
Jason Pfeiffer
You were an assistant in the entertainment industry?
Morgan Lavoie
I was for two years. And I saw a lot of nightmare bosses in that position. And so I always wondered, why do people stay when they're being treated like garbage like that? Is the money worth it? Are they getting something so valuable that going through, you know, all of the things that they go through becomes worth it? So that's what we're going to be talking about today. I'm going to kick that back to you guys. But first, I need you both to tell me, think through all of the bosses you've had. What's the most ridiculous thing a boss has asked you to do?
Assistant/Co-host
In South Dakota, I was sawed in half as a job assignment.
Jason Pfeiffer
Oh, my God.
Assistant/Co-host
I covered, like, the local magician or Sioux Falls or something.
Jason Pfeiffer
Wait a second. Okay, wait. This is going to derail this for a second. But what happens when you're the lady getting sawed in half? What happens?
Assistant/Co-host
It's a mirror.
Jason Pfeiffer
It's a mirror. Like, do you have to contort yourself in some way? No, you just lay there. It all just happens.
Assistant/Co-host
You literally just sit there, and then you make faces.
Morgan Lavoie
What? Yeah, I do feel like that's a little bit of a hard act to follow.
Jason Pfeiffer
Yeah. Well, now that Nicole has ruined everyone's sense of magic and awe, childlike wonder out the window, I actually feel like the thing that I'm about to say will rival that for weirdness. When I was at Men's Health, I was so. I was an editor at Men's Health. I was in my 20s. It was my first national magazine job. It was fairly early in my tenure there.
QuickBooks/Northwest Registered Agent Sponsor Voice
And.
Jason Pfeiffer
It was the election of 2008, and we learned with fanfare that Barack Obama was going to be on the COVID And this happened very late in the cycle. Like, it was like a whole magazine that we were producing. We didn't know who was going to be on the COVID And then the editor in chief revealed he's been working on this negotiation. Candidate Barack Obama is going to be on the COVID And this means some changes in the issue of the magazine. And the change that I had to manage was that in the section that I edited, there was a page of sex advice. And for reasons that I never have known whether or not this was. This was a request from the. The office of Barack Obama, candidate for president, or if this was just something that the editor in chief came up with, I had to. And There was no time to scrap this page and just come up with something else because it was, like, days away from shipping to the printer. I had to try to rewrite this page of sex advice to remove any sexy language. So I remember, for example, the word nipple not allowed. I had to come up with some other term. I cannot remember what I did for that. The. The phrase phone sex not allowed. I replaced it with E Hyphen relations. This was. I was at the office late into the night. I would send my changes to somebody, I can't remember, who would relay them to the editor in chief, wherever the hell he was. Then I would get notice back 30 minutes later. Your euphemism for nipples is not euphemistic enough. I need another one. And this. I mean, I was at the office till, like, two in the morning rewriting a sex page to be less sexy for Barack Obama. That's the weirdest thing that a boss has ever asked me to do.
Assistant/Co-host
That's crazy. You know that they, like, get it on Rahu. Obama is all about that.
Jason Pfeiffer
Oh, yeah. I cannot imagine that this request came from. Came from Barack Obama. I don't know.
Morgan Lavoie
Okay, so I ask because there's this Instagram account called Assistants vs. Agents, which is, like, the best online destination for trauma bonding if you're an assistant in the entertainment industry. And they submitted on Instagram one of those, like, ask me anything type things. And they asked people to share their craziest, most traumatic, ridiculous requests from their bosses. Here's a smattering.
Assistant/Co-host
I can't wait.
Morgan Lavoie
I had to find flying squirrels for my boss's kids and get them to California where transportation of them are illegal.
Masterclass Sponsor Voice
What?
Morgan Lavoie
That's one. Delivering my boss's stool sample to their doctor in the middle of my lunch break.
Jason Pfeiffer
Oh, no. I was like, should I say this? And the answer is yes. So recently, I had to mail a stool sample, and I really didn't have the time. Like, I needed to get it in the mail the day that you, like, do the sample. But I didn't have time. I was literally. Actually, I had to run to the airport because I was going on a trip, but I had to get to the FedEx office to send this thing out. And, you know, it's in, like, a whole biohazard bag. And so I thought, I don't have the time to do this. It would be really helpful if I could ask. We have a nanny who picks the kids up from school at the end of the day and then watches them. It would be really helpful if I Could really helpful if I could ask her to just bring this to the post office. And I. And then I said, I am not the person who hands a stool sample to somebody and says, touch this. Mail it anywhere. But I did. I did briefly engage with the question of whether or not I could ask her to bring this to FedEx and not tell her what's in it. Because it doesn't say stool sample on the front. So the point of this is. The crazy thing is the boss said that it was a stool sample. That was unnecessary. That was unnecessary. It could have just been. Can you take this to FedEx? Why does the assistant know that it's a stool sample? That's the problem here.
Morgan Lavoie
Because they wanted the assistant to feel like shit. Okay, a few more. What's the most ridiculous thing your boss has ever asked you to do? Tell his kids that their cat died.
Assistant/Co-host
It's terrible. Why would you ask your assistant to do that?
Morgan Lavoie
Canceling an entire trip to Australia because he got on the plane and didn't like his seat. Had to fly to Paris to locate a lost bag that was found before I even landed. So there are many stories like this on assistant versus agents and elsewhere. We all have them. And so I think something that would be very helpful to hear both of you guys talk about is, when is it worth it to deal with with a nightmare boss? And when is it not? Is it worth it to say something to them? Will they change? And how do you know if they will change?
Jason Pfeiffer
I feel like the second question is more straightforward to answer than the first. The second question is, they're not going to change. I often wonder. And we should. We should definitely get to the question of do you stay? That is, Morgan, you raise an immense, valuable question. But before we get there, can we just ponder for a second the thing that I always wonder when I hear these stories, which is, how did someone become that boss? How did that happen? Like, I understand being busy. I understand that, like, I'm busy. I understand that there are busier people in the world than me. I understand asking people to do dumb tasks like, can you get me a coffee? Because I just don't have the time to get it myself. But at some point, you cross into a territory where you don't seem to recognize what is inappropriate anymore in just basic human interaction. And I don't understand why and how people become that. What is the answer to that question? I mean, I have only one guess. And that guess is, it's an oral tradition. Like, you came up with that person as your Boss. And that's how you learned to be a boss. And it just got passed down and you just have a skewed sense of what's appropriate because that's just how you learned how to be a boss. That's the only answer that I have.
Assistant/Co-host
Yeah. Like you think you're going to break the cycle, you're going to be different, but surprise, you're asking your Assistant, fast forward 20 years to take your stool sample.
Jason Pfeiffer
That's right.
Morgan Lavoie
I think there's a lot of truth to that. I think that there is. Just from what I saw, there was definitely a cycle of I paid my dues and it's almost like hazing in a fraternity. Like, this was my initiation and I earned the right to treat other people this way.
Jason Pfeiffer
Yeah.
QuickBooks/Northwest Registered Agent Sponsor Voice
And I guess you throw money into.
Jason Pfeiffer
The mix, which is to say there's these people have endless resources so they don't have to. You get, you get less and less tethered to reality. The more and more money you have and the more and more money you're making and the more and more money you are working with in your budgets and you start to just live in a land of, of excess. Right. Because that, like this, this stuff seems to happen most in industries where there's a lot of money being made. Right. Like, I don't hear about this stuff happening as much in nonprofits. It happens in entertainment where there's just like piles of cash swimming around. And, and also, and also, you know, this used to happen more in magazines. Like these stories used to exist in magazines and now they don't because magazines have less money. Which means that the, like the, the leaders of the magazines have, have less of a less free reign. They can't just do whatever the hell they want. And so they have, they, they can't act like obnoxious gods. Stick around. Help wanted. We'll be right back.
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Nicole Lapin
Helpwanted Lets talk about something every business owner needs. It's a well managed cash flow. Because when your cash flow is off, everything feels off. But when it's in sync, everything flows smoothly.
QuickBooks/Northwest Registered Agent Sponsor Voice
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Nicole Lapin
It's like having a financial dashboard that updates with every payment and bill automatically. That means no manual matching, clearer insights, improved decision making, and more time to grow your business to transform your cash flow and your business.
QuickBooks/Northwest Registered Agent Sponsor Voice
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Jason Pfeiffer
Welcome back to Help Wanted. Let's get to it.
Assistant/Co-host
Some of it sounds outrageous, but I'm thinking about the Australia trip. If somebody had an assistant to book travel and things and then needed to cancel it. I guess the point of having an assistant is to buy back some of your time for doing some of the things that can be outsourced. Like some of the other stuff can't necessarily be outsourced. So it's, it's not ideal. But also it's not like you're not getting paid for your work. So I'm not sure. I think there is a threshold and assistance isn't a good example because Morgan, what is the average salary of an assistant? I don't know. Like in entertainment, does it show on the account?
Morgan Lavoie
There's a mix. There are some assistants that get minimum wage, but in my case I made more as an assistant than I did as a producer. I got paid very well. I made 70k and I was also overtime eligible. So I made over $100,000.
Jason Pfeiffer
That's a lot more than I would expect an assistant to make feel like.
Assistant/Co-host
$100,000 is like a good amount to be, like, this is a lot of money and I am going to do some weird shit. Like, in theory, you could ask, you could pay somebody $1 million a year to take your stool samples to the fucking FedEx or the doctor or whatever. And like, that is a job. And if somebody want, they will do the thing. You know, like, we always hear those hypotheticals, like, would you, you know, dance around naked for $3 billion? Like, I don't know, we always come up with these things and people do some crazy stuff when you offer them an outrageous amount of money. And I'm not saying, like, this is necessarily an outrageous salary, but I think when you're working, it's work like you're hired to do a thing. It's not ideal. People that, you know, work in meat processing factories. Also not like an ideal situation, I'd assume. I take issue with this idea that, like, you have to get enjoyment from the place you get money. You can get enjoyment out of a lot of different places in your life. The place you get money is the place you get money. Like, and if you signed up for a weird thing, it's. It's great Instagram fodder, but I think it's sometimes.
Jason Pfeiffer
Okay, this drives to the question at hand, actually. I think, I think, like, Nicole, you set it up really well because the question that Morgan asked at the very beginning of this is, how do you decide when it's worth it? And Nicole, what you just said is you challenge the assumption, the belief, the statement that you have to get enjoyment from the work that you do. And I think that that's true. But here's what I do think people need, and that's. They need to know the outcome of the work that they do. They need to know what they're working for and towards. And if you are working a crappy job, define crappy however you want. But you either know why you're doing it right, which is to say maybe, like, this is, this is the choice that I have made because, you know, based on XY criteria, like, and I need to pay the bills, I'm going to. This is what I'm going to do. Like, and, and I, I have an idea of the pathway forward, then you are going to be more satisfied than if you are in a job that you hate and you don't see a pathway forward and you don't really know why you're showing up every day. McKinsey did a study a couple years ago trying to understand, like, quiet Quitting when that was a thing. And they found that the number one reason why people would quit their jobs was lack of clear advancement opportunities. People want to know what they're working for and towards. And I think the question that I have for the assistants and for anybody who's dealing with a crappy boss is, do you know exactly where this leads? And is that worth it to you? Because you're making a trade off, and the trade off is that you are moving towards something and you're taking this crap along the way. Now, that is not to excuse all the crap. Crap is terrible. I think that these bosses should all be better. They're all obnoxious, and I don't like any of them. Thumbs down to all of you. Carry your own stool samples. But this is the reality of the situation. So do you know where you're going now? I think the big challenge is that the answer is generally no. Right? Like, I mean, Morgan, you were working these jobs and you had these peers, so you can tell us. I assume that people were working these crappy assistant jobs because they believed it was the entry point to better work in the entertainment industry, and that's what they really wanted. But was that guaranteed? How many of them actually got those better jobs? And how many of them just, like, worked in these jobs for a year or two and got totally burned out and then did something completely different with their lives? Like, do you know what the actual exchange here is and what the path forward was?
Morgan Lavoie
There was definitely no clear path forward. I don't know, you know, what the average is for the industry, but I would just say, anecdotally of the cohort of assistants that were at this company that I was at, I would say that a third of them advanced, and then a third of them are still assistants five years later, and another third of them got burned out and left. And. And I think that in. In my experience, though, the person that I was working for, who was my boss, so I was his assistant, he helped me move up. And it felt. And from. From I. I felt lucky because this was, you know, I would say, yeah, this was the case for maybe 30% of the people that I worked with. But he, from the beginning was like, I want two years of your time, and then I will help you.
Jason Pfeiffer
That's great.
Assistant/Co-host
I mean, I have friends that are actually hiring assistants right now. And it's really interesting because, Jason, you assume that there needs to be an outcome. And I know one of my good friends is about to hire an assistant who is just like, I Want to be an assistant. That is my life's goal and ambition. I don't want your job. I will do the things I need. A nice salary, I need to feed my family, Period. The end.
QuickBooks/Northwest Registered Agent Sponsor Voice
Totally.
Jason Pfeiffer
Well, let me clarify then. I totally agree with you. And at whatever level of work anybody wants to do, if that's an intentional choice, and that's wonderful. I was not meaning to dismiss that. I'm engaging with the question of should you tolerate the crappy boss? And I think that inherent in that question is a decision about whether this is the right way for you to spend your time and whether it's the worthy trade off for something. So if you recognize that it's a crappy boss and there are things about your job that you are unhappy with, then you are making a trade off. You are saying, I am willing to tolerate this unhappiness because of blank. And I think the more than which you know the answer to that question, the more in which you can decide whether or not that trade off is worth it. If you just want to be an assistant and you work for someone that you enjoy working for, and that's what you would be happy doing for decades, then fantastic, like, excellent, you found something that's great. You're not making a trade off at that point. There's no trade off that you're, you're like calculating. But if you're saying, this boss is crappy and I hate this job and I'm not sure if I should stay in it, then you're making a trade off. You better know what you're trading off. Because the more in which you know the answer to that, the more in which you can start to pace yourself or focus on where you can get these things that you need. Maybe you guys have heard me say this before, but like a psychological theory that I'm obsessed with is self determination theory. Self determination theory says that you, me, all of us, every human being needs three things in order to be happy. And those three things are autonomy, relatedness, and competency. So autonomy, you need to feel in control of what you do. Relatedness, you need to feel connected to others around you. And competency, you need to feel like you're good at something. And when you're in a bad work situation, particularly with a crappy boss that starts to strip you of those things, you don't feel autonomous, you don't feel connected to others. Or maybe you do, but the only way you connect to others is by. Is like by wallowing in your mutual sadness. And you don't feel good at what you do because you're like constantly being destabilized by this boss who's just like telling you that you're crappy. That sucks. And I think that the only way in which you can really get through that is to have an understanding of when and where you get those things back. And if I am going to go through a situation and say, you know what, for six months I'm going to feel like I'm pretty bad at what I'm doing and it's going to be a crappy situation. But I know that after six months I get X or like I'm working towards this and I know this is the only way through it. Then it becomes a lot more manageable and I can make a more conscious trade off between immediate misery and future gain. And I think the problem is when you don't know what you're working towards.
Assistant/Co-host
Yeah, there's some calculus that has to happen about the value proposition that you're getting, which is a combination of different things for different people. Money, upward mobility, if that's important to you, Stability, proximity, perks, health insurance, I don't know, like whatever this package of value is, you need to decide whether or not that's worth it for you. And if you look at like Maslow's hierarchy of needs, right. The bottom is physiological needs. So it's like sleep, shelter, clothing, water, air, basic things. Like those are the most basic things. And I think that that's what you optimize for when you work. You need to take care of your physiological needs. Then there's safety needs on top of that. So you know, security, protection, whatever. And then social needs, esteem needs, self actualization needs. Like these are all higher on the pyramid. And so it's cool if you want like self actualization at work. I think we just get confused that that's on the bottom and it's not. It's at the top of the pyramid.
Jason Pfeiffer
Most people don't know this at the very top of the pyramid is actually the better seat on the flight to Australia. As at the, as at the very top.
Assistant/Co-host
In Maslow, get it together, but also like part of it, you know. So I draw a super hard line against rudeness, belittling any, any sort of like anger or aggression toward people. Hard, hard pass. But then I also look at the story, like I don't know the full story, but getting a ticket to go to France when you're 20 and like you land and like surprise, like you don't need to do the thing and find the luggage that you. We're supposed to find. Like, okay, you just got. First of all, you got a great story.
Jason Pfeiffer
Yeah, that's a story of excess, but it's not a story of abuse.
Assistant/Co-host
You got a ticket to France. Like, I don't feel super, super bad for you. These are all really funny stories. But, you know, did you die? I mean, I was sent to get shot in half. God damn it. So, like, also, the other story I was gonna tell was when I got shot at when I was sitting at my desk at cnn. True story. There was a shooting at the Omni Hotel, which was right next door. It's probably somewhere online. And there was, like, a domestic violence dispute. And I was in the one area of the CNN building in Atlanta where, like, there was no double pane glass. And so I was sitting next to this glass door that I could see the elevator of the Omni at the CNN center. And the bullet, like, ricocheted into that glass.
Jason Pfeiffer
Oh, my God.
Assistant/Co-host
I did not get hit, but, like, I smelled gunpowder. Holy shit. It was a fucking wild story. And then I had to go on CNN and talk about it as, like, the eyewitness. There was, like, a shooting at the CNN Center. It was so wild and, like, breaking news. And, like, you could see, if you ever go there, there's like, an atrium area where there's a huge screen. And then you see, like, breaking news at the CNN Center. There's a shooting. And, like, I'm there, and then I go up and I'm panicking and sweating. And then my boss is like, you look too nervous on the air. And I was like, I just fudgeing got shot at. He's like, well, Christian Amanpour gets shot at all the time. And I'm like, fudgeing. Christian Amanpour is wearing a flak jacket and, like, not sitting at her desk in Atlanta with a bedazzled stapler, just minding her own fucking business. Anyway, so, like, did you die on your flight to Paris? Like, no, you did not die. You're 20 years old.
Nicole Lapin
You're make.
Assistant/Co-host
If you're making $100,000 to you, that's like, I wish I didn't make $100,000 at CNN and I got shot at.
Jason Pfeiffer
So boo hoo.
Assistant/Co-host
So I'm starting my own Instagram account, Damn it.
Jason Pfeiffer
Called Assistants versus Nicole. So, all right, what have we learned here, Morgan? If you were still an assistant in entertainment at the very beginning of your career, and you're being asked to do absurd things, and you were feeling Devalued and you heard this conversation. What's your takeaway?
Morgan Lavoie
I like the takeaway of what is all of this for? Because I do think to. To both of your points, if you're a career assistant, you still get to. You still get to answer that question, like, do you want to be treated that way? Is the paycheck worth it to you? I think another takeaway that is very helpful in tandem with that is just the settling on the fact that you can't change your boss, likely. So the change in your outlook around your job is really going to have to come through you. And so if you can stomach that, whatever you're doing this for is worth it. And you can find healthy outlets to deal with whatever stress, be it assistants versus agents and like, trauma bonding with other assistants or just other things that you can do to take care of yourself. Remind yourself that this is just your job, not your life. If you can find those ways to make sure that you are getting what you determine the value of the job to be, I think that's helpful because it just feels a little less senseless when one of the most ridiculous things that I did was I chartered a helicopter for my boss's dog. And remembering that one day I would get to produce podcasts was really helpful in those moments where I was like, damn, I have a neuroscience degree. But remembering that this is for something, I think that would have been advice that resonated with me at the time.
Jason Pfeiffer
Morgan, I just have one final question. Did the dog get there okay?
Morgan Lavoie
Of course. Course. I was an amazing assistant.
Jason Pfeiffer
Help Wanted is a production of Money News Network. Help Wanted is hosted by me, Jason.
Nicole Lapin
Pfeiffer, and me, Nicole Lapin.
Masterclass Sponsor Voice
Our executive producer is Morgan Lavoie.
Nicole Lapin
If you want some help, email our helpline@helpwantedoneynewsnetwork.com for the chance to have some of your questions answered on the show.
Assistant/Co-host
And follow us on Instagramoneynews and TikTokoneyNewsNetwork.
Nicole Lapin
Work for exclusive content and to see our beautiful faces.
Assistant/Co-host
Maybe a little dance.
Jason Pfeiffer
Oh, I didn't sign up for that.
Assistant/Co-host
All right, well, talk to you soon.
Podcast: Help Wanted
Hosts: Jason Feifer (Entrepreneur Editor-in-Chief), Nicole Lapin (Money expert)
Guest: Morgan Lavoie (Former entertainment industry assistant, producer)
Date: December 16, 2025
In this episode, Jason, Nicole, and guest Morgan Lavoie dive into the thorny subject of "nightmare bosses": why people stay despite bad treatment, the most ridiculous requests bosses make, and—most importantly—when (and whether) it's worth putting up with a terrible boss. Drawing from personal experiences and listener anecdotes, they break down the emotional and practical calculus of deciding if a bad boss is ever worth enduring, and what the “tradeoff” should look like for your own sanity and future.
“Why do people stay when they're being treated like garbage like that? Is the money worth it?” (05:18)
“I was sawed in half as a job assignment.” (05:59)
“Your euphemism for nipples is not euphemistic enough. I need another one… I was at the office till, like, two in the morning rewriting a sex page to be less sexy for Barack Obama.” (07:27)
“I take issue with this idea that, like, you have to get enjoyment from the place you get money. You can get enjoyment out of a lot of different places in your life.” (19:33)
"People want to know what they're working for and towards. ... If you're making a tradeoff, you better know what you're trading off.” (21:08, 24:21)
“When you're in a bad work situation...that starts to strip you of those things...the only way in which you can really get through that is to have an understanding of when and where you get those things back.” (25:00)
“There was definitely no clear path forward… It felt like luck if you had a boss who actually helped you.” (22:52)
“It's cool if you want like self-actualization at work. I think we just get confused that that's on the bottom and it's not.” (28:09)
“Most people don't know this at the very top of the [Maslow] pyramid is actually the better seat on the flight to Australia.” (28:09)
“So I draw a super hard line against rudeness, belittling, any sort of anger or aggression toward people. Hard, hard pass.” (28:18)
“If you can stomach that whatever you're doing this for is worth it… Remind yourself that this is just your job, not your life… I chartered a helicopter for my boss’s dog, but remembering that one day I'd get to produce podcasts was really helpful.” (31:11)
“If you recognize that it's a crappy boss and there are things about your job that you are unhappy with, then you are making a tradeoff… The more in which you know the answer to that, the more you can start to pace yourself or focus on where you can get these things that you need.” (24:21)
The episode’s central message: Surviving a nightmare boss is about understanding your own value proposition and what you’re truly working toward. If you’re miserable but on a stepping-stone to something worthwhile (and you’re not being abused), it may be worth the pain, but only if you’re clear-eyed about your tradeoff. If there’s no clear outcome, or if the abuse is severe and unyielding, your sanity is likely worth more than whatever you’re being paid. And, above all, as Morgan puts it, “Remind yourself that this is just your job, not your life.” (31:11)