NYT Article: Millennial Bosses Afraid of Gen Z Employees

• 26:07Tim notes that 37-year-old millennial bosses are afraid of 23-year-old Gen Z employees.
• 26:31Gen Z has a productive nihilism rooted in watching institutions lose credibility and fail during their lifetime.
• 27:06These young people are self-starters who don't wait for institutions to give them a shot, unlike previous generations.
• 27:30Tim acknowledges Gen Z independence as positive but critiques the fetishization of mental health and sexual politics in the generation.
• 28:14At 36 heading toward 37, Tim recognizes his own irrelevance and that his beliefs no longer matter culturally.
• 28:51When people hit their career stride in their 30s and 40s, they're too busy to steer culture like younger people do.
• 29:33The New York Times article portrays millennials as soft, emotionally manipulative, institutionalist, and desperate for approval.
• 30:06Millennials were raised with a fear-driven culture that threatened them about college, framing it as essential to survival.
• 30:54Gen Z appears more nihilistic and less approval-seeking than millennials, though all humans crave validation to some degree.
• 31:34Gen Z workers ask their bosses if they can leave once their tasks are done, rejecting millennial office performativity.
• 32:29Gen Z has no respect for their bosses and recognizes many of them only succeeded by playing corporate games and failing upwards.
• 33:22A young employee asked their manager to do a task, shocking the boss who isn't accustomed to being asked to work.
• 33:44Gen Z is much more political and expects companies to take political stances, while older generations want politics left out of business.
• 34:27Tim avoids office work because offices hit diminishing returns and he's spent too much time in them already.
• 34:58Young people recognize they could build their own business on OnlyFans, Patreon, YouTube, TikTok, or Twitch instead of sitting in an office.
• 35:25Tim tells a story about Doreen, a sweet office mom who became a loan officer, then was fired for stealing deals.
• 36:14The article itself is hard to care about either way, despite the generational culture clash it describes.
• 36:53Older business founders say they sell tomato sauce, not politics, while younger workers insist everything is political.
• 37:20Maybe one good thing about millennials is that they know when to shut up, unlike Gen Z.
• 37:44At a company retreat, a meditation instructor ran an exercise called the Suffie Awards where staff shared personal suffering around a campfire.
• 38:15Millennials turned suffering into a game where recognition is earned by admitting the most painful personal stories.
• 38:35Gen Z employees got vulnerable at the Suffie Awards, discussing cheating partners and quarantine loneliness with their bosses.
• 39:02Tim warns that admitting vulnerability to coworkers at corporate exercises gives them ammunition to use against you later.
• 39:14Even in sales, Tim avoided corporate retreats and campfire bonding exercises because he refuses to participate in forced intimacy.
• 39:33Corporate friendship-building exercises are not for Tim and represent where he draws the line on workplace culture.

millennialsGen ZBill BurrThe Big LebowskiEmily FletcherOolaDoreen