The Uncanny Culture of the Workplace

There is never a blue sky in Beijing. Except for today, which is why I’ve spent most of the morning staring, with headphones on, outside of one of the city’s iconic office complexes.

Only when I notice the CEO is making a speech do I pull my earbuds out.

“It is time to storm the fortress. You and your colleagues are the advanced guard and the battle is about to begin.”

Around the room the staff are attentive, enraptured. I’m lost, but not because of the language barrier. The CEO is going on and on in bellicose language which feels like part of a larger tradition but is lost on me. Until he gets to the point.

“And so, I’m announcing our new goal for this year. Our marketplace’s gross market volume will reach $100 million by the end of the year!”

Those in the know were aghast. And not merely because of the tendency to use GMV as a vanity metric for a company with no revenue. Or that we were calculating it based on items available, not items sold. But because in the six months the company had been active we’d accumulated at a total of a mere $5 million in total market volume.

And with that, the rest of the team stood up in a round of applause.

Drinking the Kool-Aid

Two recent works have taken a skeptical view of the startup life, and both used the term “drinking the kool-aid.” The first is Dan Lyon’s hilarious memoir of his time within HubSpot, Disrupted. And the second is Anna Wiener’s more subtle creative nonfiction send up of her front-line startup experience in N+1 called “Uncanny Valley.”

“Drinking the Kool-Aid” is a reference to the Jonestown mass murder/suicide of 909 Americans in the jungles of Guyana. Watching the excellent PBS oral history documentary is unsettling. Not only for the violence, but for the fact that kind and rational people go along with it. They are seemingly normal people, but they are acting incomprehensibly.

This unsettling feeling is called the uncanny.

The Uncanny


Wiener’s title is a great pun on Silicon Valley and the phenomenon of the uncanny valley. A phenomenon affecting things like robots, or creepy baby dolls, the uncanny valley is an unsettling disjunction that happens when everything appears almost real, but something is not quite right.


The Uncanny is a site where there is a gap between something intimately familiar becomes something foreign and frightening. In Wiener’s piece it has two aspects.

The first is the employees themselves, who suffer from the “existential dread” of working as startup hacks, while they “gaslight” themselves into “reading from someone else’s script.” The impression Wiener gives is of a slow realization that she didn’t go to school to become a Customer Success Guru or write hyperbolic marketing copy.

These are the automatons, who talk like real people but can’t bring their full selves to work. And like Jim Jones’ followers, they are constantly being tested as to whether they are “down for the cause.”

The second instance of the uncanny is the culture of the team. Where there is an attempt to construct something that should be organic and fuelled from below out of stock parts.

The Perils of Culture from Above

There is something about the culture of a team while it remains small. Anytime you got together with a bunch of friends to make something, no one ever really has to think about culture. Or leadership for that matter. It is just assumed that everyone has unique skills that will slot together like tabs in an Ikea desk.

And so it is with our friends. Or with group projects in school. Until we get to the workplace.

An uncanny culture is one we recognize, but something is not quite right. Wiener’s pun reveals a real truth. There is something suspicious going on behind a forced culture. These speeches and culture decks are trying to make something, to force something into existence which is really a bottom up, not top down, process.

Thus morale is “just another problem to be solved,” like any other engineering challenge. The tools are incomprehensible motivational speeches (“‘We are making products,’ he begins, ‘that can push the fold of mankind.'”) and team-building exercises (“They schedule it on a weeknight evening, and we pretend not to mind.”)

For Lyons such uncanny cultures are fuelled by hype. Hype itself is a form of doublethink, where a smarter version of email spam is:

“is leading a revolution. A movement. HubSpot is changing the world. This software doesn’t just help companies sell products. This product changes people’s lives. We are changing people’s lives.”

A doublethink where “unlimited vacations” means “no vacation pay on termination.” Where “being fired” means “graduating” to a new job. Where “having fun” and the perks of beer fridges, foosball, and scattered musical instruments mean and “you can work all day and night, if necessary, for no pay.”

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HubSpot’s Culture Code is itself creepily uncanny. In its attempts to describe a healthy culture it is frighteningly prescriptive on how to construct one.

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Where the team is greater than the individual.

Note how it is just as easy to reverse this formula: we place the individual at the centre of the company, which makes for high performing teams, which means better customer service.

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And where we might might know everything about a company, but that doesn’t mean we have a say in where it is going.

What should be a kind of consensus, creating a thriving culture, is really “[CTO Dharmesh] creating a company that he loves and hoping to persuade his employees to love it along with him.”

Lessons Learned

There is ambiguity around the definition of a startup. For Paul Graham “Startup = Growth,” but that seems to also cover any new competitor to Coca-Cola looking to grow.

My own motivations when moving towards startups was the idea that “startups do things differently.” They weren’t bogged down by bureaucracy, or gatekeepers, or hierarchy. (Wiener: “now we are bureaucrats, punching at our computers, making other people — some kids — unfathomably rich.”)

The uncanny feeling people like Wiener, Lyons, and myself feel comes from the disjunction between the rhetoric and the reality. Are we really changing the world making software that puts a happy face on spam? Or working in a market with more than a dozen competitors with hundreds of millions in funding, all making zero dollars solving what is a minor annoyance?

For all that’s said about Industrial Era organizations, at least we weren’t expected to drink the Kool-Aid. It wasn’t required that we wholeheartedly affirm that making cans of Campbell’s Soup was as important as going to the Moon. We could separate our real lives from our work lives and avoid the dread that comes with too closely identifying one with the other.

Yes, companies and individuals with purpose are more productive, innovative, and happy. But trying to graft on a culture and purpose from above is like creating Frankenstein’s monster. Rhetorically using hype to assert you have a purpose and culture is not just counterproductive, but creepy too.

From Napster to Uber: The Internet 15 years later

The year I started university was the year of Napster. All the computers in the dorm were networked, and we’d stay up all night browsing each other’s music directory. I’d already heard Rolling Stones on Psychedelic Sundays, and now here was their entire discography. Might as well as download everything. Most of my Led Zeppelin are still those original MP3s I nabbed from the university network. I discovered Radiohead really through Kid A when it was leaked completely on Napster.

Before YouTube, if you wanted to hear a song instantly you searched, waited 30 seconds, and then listened. Even with all the technological improvements the ease of playing a single song hasn’t evolved.

After studying Philosophy, I was preparing for graduation and first ran into Marshall McLuhan. It seemed like media was everything people were talking about. Copyright and Web 2.0 and bootleg Metallica and Google Book scanning. The great benefit of the Internet was that it was going to free everyone’s content and take production out of the hands of the gatekeepers. Information wanted to be free.


The little Coach House where McLuhan did his business. And where I studied with a former student.


With this interest in what Neil Postman called “media ecology“—the medium is the message—I started a Masters in Information. The department was the last shard of a legacy of McLuhan at the University of Toronto. I had a class in his Coach House. Sat on the couch where I am sure he must have slept. I read McLuhan and Postman, Walter Ong and Elizabeth Eisenstein. For me a lot of the cultural implications of print  culture were being undone, and copyright was one of them. Musicians at one time were roving entertainers. Then records were invented. And now that they were being uninvented musicians were becoming entertainers again.

Almost ten years later changes to media are the least interesting development of the computerization of everything. YouTube, iTunes, Spotify. These seem like obvious developments now. Sure, they were difficult to implement. But their logic goes back to those initial desires I had in 2000 to listen to any song and watch any movie anywhere I wanted. All the rest is logistics.

The real craziness seems to be happening completely outside of media, and even off of the Internet. It’s cars and banks and hotel rooms. Real people in the real world, not digital files. The Internet isn’t just communicating. It’s the global nervous system moving the human muscle.

Even more than products and services, culture and organizations themselves are adjusting. What is most fascinating to me now is not that books as objects are challenged, but that entire bureaucratic systems based on the efficiencies of paper are made redundant. 1


The global nervous system in 2005.


McLuhan’s perennial insights therefore are much more relevant when he is not talking about media. Everyone could see that television was becoming important and that the children were somehow “re-tribalizing.” But in 1964 no one could fully think through the implications of this:

In terms of the ways in which the machine altered our relations to one another and to ourselves, it mattered not in the least whether it turned out cornflakes or Cadillacs. The restructuring of human work and association was shaped by the technique of fragmentation that is the essence of machine technology. The essence of automation technology is the opposite. It is integral and decentralist in depth, just as the machine was fragmentary, centralist, and superficial in its patterning of human relationships.


Obsession with the older patterns of mechanical, one-way expansion from centers to margins is no longer relevant to our electric world. Electricity does not centralize, but decentralizes. It is like the difference between a railway system and an electric grid system….Electric power, equally available in the farmhouse and the Executive Suite, permits any place to be center, and does not require large aggregations.


In the the new electric Age of Information and programmed production, commodities themselves assume more and more the character of information. 2

The message isn’t the technology. It’s the change of scale, pace, or arrangement in they introduce in society. And it is not that information has become a commodity. Commodities are being “informationized,” vivified through connection and data.

I don’t care much about the Apple Watch. I care about what happens when I can carry a mobile, ever-connected, supercomputer to the top of Mount Everest.

And I don’t care much about startups or Slack’s 2.8 billion dollar valuation. I care about happens to organizations when I can have no boss and be on the beach and still file my TPS reports.3