Help Wanted – "My Boss Is Terrible. Should I Quit? Help!"

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

Episode Overview

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.

Key Discussion Points and Insights

Ridiculous Boss Requests: War Stories

• Morgan's Kick-Off: The episode starts with Morgan, a former assistant in the entertainment industry, posing the core question:

  “Why do people stay when they're being treated like garbage like that? Is the money worth it?” (05:18)

• Hosts Share:
  • Nicole (Assistant/Co-host): Once assigned to be sawed in half by a local magician for a story.

    “I was sawed in half as a job assignment.” (05:59)

    • Magic ruined: “Now that Nicole has ruined everyone's sense of magic and awe, childlike wonder out the window...” – Jason (06:32)
  • Jason: Had to rewrite a sex advice page at Men's Health to remove all “sexy” language because Barack Obama was to be on the cover.

    “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)

• Listener/Internet Submissions (from the Instagram account “Assistants vs. Agents”):
  • Finding and illegally transporting flying squirrels for a boss’s kids (09:27)
  • Delivering a stool sample for a boss
  • Telling a boss's children their cat died (11:04)
  • Canceling an Australia trip mid-flight because of not liking the seat (11:16)
  • Flying to Paris to retrieve a lost bag that was already found (11:19)

Why Are Bad Bosses So Common?

• Nature or Nurture?
  Jason: “How did someone become that boss?... 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 it just got passed down... That’s the only answer that I have.” (12:16)
• Morgan: Agrees – likens it to fraternity hazing and “I paid my dues.” (13:39)
• Money & Power:
  Jason: "The more and more money you have...you get less and less tethered to reality... You can't act like obnoxious gods [anymore].” (14:00)

Is It Worth Putting Up With It?

• Nicole: Pushes back on the concept that work must be enjoyable if it pays well.

  “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)

  • Context: Some assistants make high salaries (e.g., Morgan made $100k+ with overtime) but still have to deal with indignities.
• Jason:

  "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)

  • References a McKinsey study: People quit because of lack of advancement opportunities, not just job misery.
• Self-Determination Theory: Jason references the psychological idea that fulfillment in work comes from:
  1. Autonomy (control over what you do)
  2. Relatedness (connection with others)
  3. Competency (feeling good at something)

  “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)

• Morgan's Reality Check: Only about a third of assistants moved up; another third were stuck for years; the remaining third burned out and left.

  “There was definitely no clear path forward… It felt like luck if you had a boss who actually helped you.” (22:52)

Calculating Your Own Tradeoff

• Nicole: It’s OK to optimize for money, comfort, or stability rather than “self-actualization.” References Maslow’s hierarchy of needs:

  “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)

• Jason (with a joke):

  “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)

• Assholes vs. Abusers: Being sent to Paris for a lost bag? Eccentric excess. Being belittled or bullied? Unacceptable.

  “So I draw a super hard line against rudeness, belittling, any sort of anger or aggression toward people. Hard, hard pass.” (28:18)

Takeaways & Advice for Those Stuck With Nightmare Bosses

• Morgan, summarizing the lesson:

  “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)

• Jason:

  “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)

Notable Quotes & Memorable Moments

• Nicole (On weird requests): “I was sawed in half as a job assignment.” (05:59)
• Jason (On magazine editing): “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)
• Jason (On boss behaviors): "You get less and less tethered to reality. ...you can't act like obnoxious gods." (14:00)
• Morgan (On outcomes): “In my experience... I felt lucky [my boss was supportive]... this was the case for maybe 30%... A third advanced, a third are still assistants, and a third left burned out.” (22:52)
• Nicole (On work satisfaction): “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.” (19:33)
• Jason (On self-determination theory): “All of us need autonomy, relatedness, and competency to be happy. Your boss can take these away, but if you know you'll get them back, you can endure.” (25:00)
• Morgan (On survival): “I chartered a helicopter for my boss's dog... remembering that one day I would get to produce podcasts was really helpful in those moments.” (31:11)

Important Timestamps

• 05:00: Morgan introduces the nightmare boss theme and poses the “Why stay?” question
• 05:59 – 08:49: Ridiculous boss stories (being sawed in half, sanitizing sex advice, illegal squirrel trafficking)
• 11:54: Jason: “Crappy bosses don’t change.” Why do bad bosses exist?
• 14:00: Discussion on money, power, and reality distortion in high-paying industries
• 18:20: Assistant job realities—how much pay justifies how much indignity?
• 21:08: The key question: Are you making a conscious tradeoff?
• 22:52: Morgan breaks down assistant career outcomes
• 25:00: Jason on Self-Determination Theory: autonomy, relatedness, competency
• 28:09: Nicole reframes expectations using Maslow’s hierarchy
• 31:11: Morgan’s closing advice—focus on why you’re enduring the job and if it’s worth it

Conclusion: Advice in a Nutshell

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)