Optionality’s office hours this week are open to all. We’re doing an AI Show & Tell…showing specific ways we’ve used AI tools to expand and enhance our wisdom, agency, capacity…and I’ll show a couple of epic fails too! Join us here on Wednesday the 13th at 12PM PT.

Each generation annoys the ones that came before…but should it?

I’ve been around long enough to remember when GenX was considered the “slacker” generation, Millennials were considered “entitled” and now GenZ is considered too sensitive on top of being entitled. (And let’s not forget the Boomers were the original “Me Generation,” i.e. selfish and yuppified.)

Not only that, but no matter how vociferously we may complain about the indignities of the jobs or disrespect by the managers we had in our 20s, by the time we get even a decade down the road, our roses glasses are decidedly on…and we end up subjecting people in their 20s to the same rigmarole. Only now we call it “paying your dues” instead of “bullshit.”

It’s like we get initiated into a secret society that we worked so hard to get into, we’d never consider giving our membership up.

It’s not just my memory, I can confirm. I asked AI to do a scan of business media dating back to the 60s to pull out common narratives in the business press about the youngest generation in the workforce. It found no shortage of examples:

Every Generation Has Trashed the Next One at Work:
A quick scan, courtesy of Claude

1950s — The "Grey Flannel" Problem: Fortune magazine lamented the young Silent Generation entering the workforce for their "grey flannel mentality" and penchant for "taking no chances." (Note: Perhaps the last time, and maybe only time, a youth generation was criticized for being too staid!)

1960s — Hippies Won't Work: Business publications of the era fretted about young workers being more interested in social revolution than career ladders.

1970s — Tom Wolfe's "Me Decade": Tom Wolfe coined the label that stuck to Boomers as they prioritized self-actualization over institutional loyalty. Business press coverage reflected employer alarm at young workers who questioned hierarchy and wanted meaning from their jobs — a radical notion at the time.

1990s — Generation X: The Slackers: Business press really got savage. TIME magazine published a 1990 piece on the twentysomething generation that leveraged the dominant caricature of "slackers" with short attention spans and no work ethic. A Washington Post piece of the era was headlined, "The Boring Twenties: Grow Up, Crybabies, You're America's Luckiest Generation.”

2000s–2010s — Millennials: Entitled: In an May 2013 TIME magazine cover story, writer Joel Stein opened by acknowledging he was about to "do what old people have done throughout history: call those younger than me lazy, entitled, selfish and shallow." The headline: "Millennials: The Me Me Me Generation. Lazy, entitled narcissists who still live with their parents."

2020s — Gen Z Gets the Treatment: According to a 2024 survey of nearly 1,000 U.S. business leaders, six in 10 employers said they had already fired Gen Z workers, with their primary gripe being lack of motivation or initiative. A 2023 survey from ResumeBuilder found 49% of business leaders identified Gen Z as difficult to work with most or all the time, and a majority agreed Gen Z lacked effective communication skills, motivation, and effort. A Wall Street Journal report noted that Gen Z workers need additional guidance on "workplace norms."

Claude prompt: Can you source articles in top tier business magazines (or the Wall Street Journal as another example) in each decade, starting with the 60s, that disparages the youth generation coming into the workforce?

So, it’s a case of “Plus ça change, plus c’est la meme chose.” (The more things change, the more they stay the same.)

But things do change, often thanks to “‘da yutes”

Every generation brings their baggage to the workplace (packed with having seen how work was for their parents and grandparents even). But every generation has also brought pushed those “workplace norms”…and I would say pushed them forward.

You can go back to that silent generation to find the glory days for unions and the protections and workplace reforms that became new norms. The laws to facilitate unions may have started being passed in the 30s, but it was several decades before the heyday for unions.

Boomers actually saw the idea of employee ownership take root. Again, the legal infrastructure began before the actual usage exploded…and that Slacker GenX generation saw the concept of equity and ownership as motivator explode into reality.

You can thank later generations for the concepts of work-life balance, and de-normalizing harassment and hazing. But it’s still a patchwork, with some industries making steps toward more humane treatment of their employees on the lowest rung of the career ladder, and others still led by people who consider the hazing they received early in their careers as the price for admission to the higher rungs.

My contention is that if you have a junior employee asking for a level of humane treatment that you would consider table stakes for staying at a job at your level, it’s time to re-consider why what they’re experiencing is acceptable 🤷🏻‍♀️

Why this topic this week?

While watching my Buffy episodes this week there’s a moment when Buffy, at 16 years old, is the one who is more qualified, more capable, more appropriate to tackle a problem. More than her mom. More than her Principal. She takes command, and they defer. Good call, grown-ups.

Afterwards, Buffy’s mom…who has often been passive aggressive and “not mad, just disappointed” thus far in the series…recognizes all the leadership she displayed in that moment (see quote below) and shares her pride in Buffy’s growth. But the Principal remains suspicious, resistant, resentful, and unwilling to let go of the idea that simply by virtue of his seniority, he will always know best. I don’t think he actually says “whippersnapper” in the episode, but he might as well have.

It is beholden on us to be more like Buffy’s Mom than her Principal.

Curious: Do you have a “yute” in your life who you’re learning from on the regular?

I have a daughter who can take care of herself. Who's brave and resourceful and thinks of others in a crisis. No matter who you hang out with or what dumb teenage stuff you think you need to do, I'm gonna sleep better knowing all that.

-Joyce Summers

So, what Buffy episodes did I watch this week?

I watched Season 2, episodes 3 (School Hard live recap) and 4 (Inca Mummy Girl live recap)…which aired on September 29 and October 6, 1997, respectively. In a classic approach for similar shows of the time (back when they had two dozen episodes to work with over a season) one of these episodes leans heavy on the show’s mythology, the other is more of a classic monster-as-metaphor episode.

The core #BuffyLifeLesson in S2E3 is that leadership is about more than following the rules and rituals that came before you. In the episode, we see this play out on the side of the angels (with Buffy) and demons (with Spike). In real life, I’m not talking about the relatively palatable rejection of “But we’ve always done it that way” thinking. That kind of thinking has been an easy target for a long time. (Although, easy to target doesn’t mean easy to eradicate.) I’m talking about the reality that careers and advancement have been shifting to be much less linear and much less hierarchical for several decades now. The ageism is real (and pretty irrational in the face of actual data), but so is the ongoing hazing-as-paying-dues mentality. Right now the job market is brutal in your 20s and in your 50s+. It’s not sustainable. And unfortunately I don’t think we have a Buffy (or a Spike) coming to save us.

The core #BuffyLifeLesson in Episode S2E4 is that the young have always been considered easy sacrifices to perpetuate the status quo. Whether the literal sacrificing of young women or the sending of young men (and now women) to war, history has no shortage of the young sacrificed on the altar of the older generation’s mistakes, ambitions, or comfort. Is it any wonder each successive generation is disappointed in both those who came before and those coming after them? Maybe it’s time to break the cycle? Maybe it’s become obvious enough to all that we haven’t built a transitional pathway from one generation to the next, so perhaps we need to transform the blueprint we’ve been working with?

Both episodes feature a young woman attempting to assert agency in her own life, expressly against the wishes of older authority figures. In one episode it works out pretty well for her; in the other it does not. But in each case, the hierarchy is exposed and shaken and may never be the same. And it doesn’t seem like a bad thing.

Signposting and sharing

  1. Next week’s recapping will tackle Buffy Season 2, episodes 5 and 6. Episode 6 in particular is widely considered one of the best episodes of the season.

  2. Tool of the week: My fellow blogging OGs may be interested in this tool someone I follow has created.. Matthew Facciani, who’s an expert on identifying and combatting misinformation, has created an interactive tool to decide whether or not a disagreeable comment is worth engaging with. The tool checks out the commenter and their comment and tries to distinguish between someone with whom you can have a good faith debate (if that’s you’r thing) and someone who’s simply a troll. I haven’t put in through its paces yet, but it’s a fascinating concept. And maybe one I could have used more back in my era where I wasn’t quite so liberal with the Block button.

  3. Book recommendation this week: Pinprick Eyes by Danielle Hart. This pseudonymous memoir tells the story of a relationship that looked perfect from the outside (which I can attest to as someone who was on the outside) but was anything but. Mental illness, addiction, narcissism, coercive control, emotional abuse, gaslighting. These are not pleasant subjects by any stretch, but they are important ones. Especially for women who have always been the strong ones, the ones who can make things work, the ones who consider themselves “empaths” who convince themselves to see the “other side” by identifying with their abuser’s pain. And the writing…weird to say writing about such a tough topic can be beautiful, but if anyone can pull that off, it’s Danielle Hart.

  4. Over on Optionality: Jory and I discussed the May theme: Transformation vs. Transition in a Conversationality video podcast. Back in the day, I used to really detest the overuse of the word “pivot.” Maybe because as a theatre person a “pivot step” is a literal about face, and most business pivoting seems like reasonable evolution and adaptation. Anyway, even I say “pivot” sometimes now, but the new word I detest is “transformation.” It’s everywhere, and it’s always over-selling. So here’s a truly mini-clip of a way I came up on the fly to think about the difference: [Click the link above for full 30-minute conversation.]

So, tell me, would you say you’re in a life/work transitional phase, full-on transformation, or staying steady on?

Buffy tarot readings! Some of you may know me as an entrepreneurial and business coach, and I indeed do that. But I’ve also spiced things up a bit with tarot readings with my Buffy the Vampire Slayer deck, with or without coaching 🙂

Check out the options here: https://calendly.com/elisacp

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From now on we're going to have a little less ritual and a little more fun around here.

-Spike (aka William the Bloody)

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