Apr 7, 2015 · 6 minutes

In the annals of technology writing, few are quoted as often as early Facebook employee Jeff Hammerbacher, who in 2011 gave such a convincing and devastating verdict on the new advertising economy that writers have leaned on it over and over again as a pithy prologue to their unworthy thinkpieces.

I swear I tried to resist that urge, here. But like the words of Shakespeare and Humphrey Bogart, sometimes a line becomes cliched simply because it's just that good. And considering I already kicked off the article with one cliche ("annals"?) I might as well go full hack:

"The best minds of my generation are thinking about how to make people click ads." - Jeff Hammerbacher, April 2011.

The quote addresses how the world's smartest and most creative scientists and engineers aren't working on ambitious technologies like carbon remediation or quantum computing. Rather, they're being recruited by companies like Facebook and Google to collect and parse user data which is offered at top-dollar to brands -- brands who serve up hyper-targeted advertisements, increase sales, and then start the whole cycle over again with ever-increasing concentric circles of cash. (See also: "We wanted flying cars, but instead we got 140 characters.")

But Silicon Valley in the 21st century isn't the only time and place to which this pessimistic prognosis applies. Upon climbing into bed last night to watch the newest episode of the greatest show on television -- eyes glued to my laptop as it balanced precariously on my mid-section to avoid microwaving my genitals -- Hammerbacher's iconic line kept entering my head. As it happens, the quote would have held equal relevance five decades earlier in the liquor-stained corner offices of Madison Avenue skyscrapers: The setting of television's Mad Men.

Through this lens, clear lines can be drawn between Mad Men's depiction of New York ad agencies in the 1960s and today's tech firms of Silicon Valley -- two ecosystems where men (and, to a lesser degree, women) go to trade their dreams of changing the world in return for big greasy handfuls of cash. And because New York in the 60s and Silicon Valley today are the uncontested centers of industry for their respective eras, these dynamics signify broader cultural and economic tailwinds in America -- tailwinds that, if Mad Men's tireless and unflinching examination of human suffering is any indication, inevitably push us toward loss, loneliness, and disillusion.

Hammerbacher knew this too -- though often people forget to include the second part of his legendary quote:

"That sucks."

Even as early as 2007, when Mad Men debuted in earnest as a deceptively straightforward yet painstakingly stylized time capsule, the socioeconomic parallels between these two booming hearts of commerce began to show. The historical faithfulness that bobbed above the surface belied an anachronistic ocean of modern social commentary beneath that spoke directly to 21st century audiences. By Season 2, a disruptive new medium emerged -- in Mad Men's case, television -- but it might as well have been Facebook considering the ways in which it gave rise to powerful new delivery systems for branded experiences. It made lots of men very rich, while the women who contributed to the success of these firms not only witnessed their male colleagues receive most of the credit, but they did so while continuing to suffer appalling patterns of sexual harassment. From Ellen Pao to Whitney Wolfe, the fact that the tech world's gender politics most closely resemble those of Mad Men is unconscionable.

But the allegory didn't fully take shape -- at least not in my mind -- until last Sunday's premiere of the show's final seven episodes. And the vessel for this allegory was the one-eyed, eyepatch-wearing, tap-dancing accounts executive Ken Cosgrove. Secretaries, copy writers, and even partners came and went, but Cosgrove was one of only a handful of characters to feature prominently in all seven seasons. But although he's a survivor and a loyal servant to Sterling Cooper, Cosgrove finds no joy in advertising. He's a fiction writer and a decent one at that; one of his stories was even published in The Atlantic Monthly. And with plenty of money saved up, a wealthy father-in-law, and a wife who is supportive of his literary ambitions, there's nothing holding him back from quitting the agency and finally writing that novel of his -- a novel he describes as being for people “who don’t have the guts to live their dream.”

But just as he's about to quit, he gets fired instead -- collateral damage resulting from a recent acquisition. And whether out of fear of change or fear of poverty or fear of walking away from a corporate world that, good or evil, at least matters to a great deal of people (unlike most novels), by the end of the episode Cosgrove himself proves that he lacks the guts to live his dream. Following a woefully practical conversation with the woefully practical Pete Campbell -- who advises him to write adventure stories because, after all, he has an eyepatch and just think of the book jacket! -- he takes a white-collar job someplace even worse than an ad agency: a chemical company.

The rest of the episode is full of subplots charting dashed ambitions and broken dreams, though most of them are related to love, children, death, and other personal issues. But it's Cosgrove's story that shines most brightly as a reflection of the modern American economy. The safe jobs are in advertising -- though today these jobs are less about writing copy and more about writing algorithms and scraping data sets for those giant for-profit surveillance machines we call "social networks."

And contrary to what the old Valley counterculture warrior James Currier told me, the problem isn't just that Silicon Valley has become a place that attracts wealth-hungry individuals as opposed to the creative hippie souls who flocked there in decades past. It's that once they're embedded in Valley culture, the creative souls have few avenues to do what they do best, and are instead tasked with making brands happy, as opposed to making beautiful or life-changing artifacts for themselves and other human beings.

It's maybe even worse in journalism. Each year, students spend tens of thousands of dollars to go to journalism school, only to graduate and find that, at best, they can become a bargain bin blogger -- aggregating other people's stories for clicks, likes, and other metrics that make advertisers happy -- or worse, they can become content marketers and write directly for the brands, without any illusion of ethics or pride.

I always loved Mad Men for the ways it spoke to the human condition. The one thing I didn't always understand, however -- at least not instinctively -- was how the audience was supposed to emotionally connect with the characters' professional ups and downs. I mean, it's just advertising. It's a skill that requires talent, but these characters aren't writing the great American novel here. They aren't building electric cars or putting on plays or creating anything that isn't completely subjugated to the brand that's paying for it.

But as we saw in last night's episode, most of the characters hate advertising as much as the audience does. It's only fear that keeps them in the ad game. And whether the setting is Silicon Valley, Madison Avenue, or the booming economy of 14th century Florence documented by Dante Alighieri, when business is good, fortune shines on the cog, not the creative.

[illustration by Brad Jonas]