Uncanny Valley

by Anna Wiener

Here was a character flaw on parade, my industry origin story: I had always responded well to negging.

There had always been two sides to my personality. One side was sensible and organized, good at math; appreciative of order, achievement, authority, rules. The other side did everything it could to undermine the first.

A book-related startup held a small, sad library, the shelves half-empty, paperbacks and programming manuals sloping against one another. It reminded me of the people who dressed like Michael Jackson to attend Michael Jackson’s funeral.

In this respect, it was not unlike book publishing: talking about doing work for money felt like screaming the safe word. While perhaps not unique to tech—it may even have been endemic to a generation—the expectation was overbearing. Why did it feel so taboo, I asked, to approach work the way most people did, as a trade of my time and labor for money? Why did we have to pretend it was all so fun?

It seemed to me that whatever I had, that the men of Silicon Valley did not, was exactly what I had been trying to sublimate for the past four years. Working in tech had provided an escape from the side of my personality that was emotional, impractical, ambivalent, and inconvenient—the part of me that wanted to know everyone’s feelings, that wanted to be moved, that had no apparent market value.