I raced to finish Uncanny Valley this past weekend and not just because we’re two months into the year and I’ve gotta keep on track with my reading goal. My friend Kim Scott invited me to a dinner with the author, Anna Wiener, and as an author myself, I know how it feels to talk to a room of folks who haven’t quite gotten around to reading your book yet. 

I have to admit this was not a book on my to-read list. It’s the story of a 20-something woman who leaves her limited options in the publishing industry to work for a startup. My general sense of the book before reading it was that it was another of those “I had no idea!” gradual exposés of the evils of an industry.

Don’t get me wrong: There are so amazing, even timeless stories that fit into this genre, including Michael Lewis’ Liar’s Poker and Flash Boys as well as Lauren Weisberger’s The Devil Wears Prada.

These stories can be salacious reads when you aren’t in the industry—a window into a whole different world from the point of view of the naive 20-something you once were while you’re going into your own vocation, perhaps. The trouble for me is reading one about the industry I’m already in, have spent more than 20 years reporting on, know quite a bit about, and have PTSD from exposing a lot of those same “evils.” 

It didn’t feel like the book was for me. And, I’m still not totally sure it was. But I enjoyed the book a great deal, and definitely recommend it to everyone who hasn’t OD’d on tech for several decades. (And maybe also those of you who have.)

Even for me, there were some interesting takeaways. I moved here in the dot-com bubble and was accelerating my career into its best years as the Web 2.0 movement took off. Like it or not, I belong to a different era of the Valley. In the bro era I became cynical and jaded. One of the many reasons I decided to leave journalism was that I felt like the Valley today needed to be reported by fresher eyes. Ones that don’t see the same old patterns, good and bad, ones that can believe again, but also be horrified anew when things go wrong. Anna is the first great and meaningful new set of those eyes I’ve come across, and I, for one, am glad she left tech to write about it. 

I’ve spent most of the 2000s arguing why whatever year we are in isn’t “just like 1999.” The internet was in its infancy then and so much of the speculation was driven by wonder and an entire new world that it would (and did) open up. That also precipitated the crash: Many of those bets were simply too early to justify the hype and the valuations. 

Whatever era (bro-nicorns?) we’ve just lived through was wholly different than that. You can make that argument from the outside: Talking about the global nature of the web, the monetization patterns that are in place, the fact that companies arguably wait too late to go public not rush things out too early, the global slug of billions and billions from emerging markets that are driving a unicorn era unlike anything the industry has seen before. 

But Wiener makes that argument from the inside out of these companies. Reading her, I could easily see the cultural contrasts between the dot-com era, the revenge of the hoodie geek era, and the brogrammer era. How each sucked in naive and hopeful talent, and jaded them all in different ways. 

The tone of the book is interesting. She both felt too judgemental at times, but also not judgemental enough at other times. And that might be the most authentic and relatable aspect of the book if you have worked in this industry, been inspired by it but also became disillusioned with it. You seem to always be rooting for the best in people, maybe turning a blind eye at times, and then at other times, railing at the whole establishment as much because of your naive complicity as anything else. 

Wiener never takes the easy path as the author, as much as she beats herself up for taking the easy path of making a big paycheck for limited skills and little accountability for so many years. 

Mostly you should read it because the writing is excellent and that’s frequently not the case in 20-something “tell-alls” where the shock is supposed to be enough to carry it.

Today’s new questions on Chairman Mom:

* * * *