Book Review: Uncanny Valley: A Memoir by Anna Wiener

Book Review: Uncanny Valley: A Memoir by Anna Wiener
Uncanny Valley: A Memoir
Genre: Management

EBook | 288 pp. | MCD | | 1st Edition
Buy on Amazon
4.0 rating

Uncanny Valley is a memoir novel by Anna Wiener, currently a writer for The New Yorker, but that experienced first person the culture of Silicon Valley of the 2010s, through various experiences that led her to move from Brooklyn to San Francisco, where she still lives. So, why am I reviewing this book here? The reason is simple: the book offers a rare glimpse into what many have continuously been defining “The Future of Work”. Her angle, however, is genuinely disillusioned. She’s not a technology fanatics (or what we would call a “nerd”). She fails to believe in the slogans of the start-up world. She grasps the concerns of a portion of the economy where financials are the real drivers (“The driving values of venture capital were growth, acceleration, and fast returns, and they could be transformative.”), and innovation is probably a by-side product. And she offers a genuinely pessimistic view on the role that workers play into this environment: far from being the masters of their destiny, they end up playing the roles of machine parts, precisely like Charlie Chaplin did in Modern Times, with much higher salaries, but in a city where costs have been rising so much that truly embracing a vibrant lifestyle continues to be a blurry goal for most.

I decided to write this review, also because I ended up taking so many notes on this book. The style is crisp, descriptive. Probably the most repeated phrase in Uncanny Valley is “I Didn’t Know,” outlining her role as an outsider in the world of technology start-ups. She started from a new app that was promising to be The Netflix of Books, but she failed to fall in love for the mostly technology spirit of the venture, clarifying from the beginning that this world is about the medium, not the content. The CEO dropped a note in a company chat once: “She’s too interested in learning, not doing,” It was the end of her first experience in this world. But she still did feel the appeal of a world that seemed so shiny and exceptional from the outside. She moved into an Analytics Start-Up where she solidifies an experience in Customer Support, one of the rare roles that impose human contact. “In a text-based industry, speaking on the phone was surprisingly intimate.” She finally transitions into an open-source start-up, where she experimented with a different type of setting. “Half the workforce was remote, and digital nomadism was considered banal.” This is the part where we also find the most significant commitment for the cause represented by the Open Source concept. But then, the realization came. “The startup’s early techno-utopianism did not scale—though not for lack of trying.”

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.

Anna Wiener, Uncanny Valley, page 259

Which led her to leave the industry. “Leaving a remote workplace was anticlimactic.” An exciting conclusion of what many things would be a life-changing experience, but that left mostly a bitter taste in the author’s knowledge.

As this is not a traditional book in terms of review, I have chosen to pick a few quotes from the book itself, mostly on topics that I have been covering elsewhere, organised around these.

On Work

Most of the book is written on her experience deriving from work. It emerges a much different perspective versus the typical narrative of the Future of Work, something that I have already tried to pick up in my post on Reinventing Work.

For example, the trend that many see as the fantastic opportunity of Job Crafting, is seen in reality as “hustling”.

The mark of a hustler, a true entrepreneurial spirit, was creating the job that you wanted and making it look indispensable, even if it was institutionally unnecessary.

Anna Wiener, Uncanny Valley, page 21

In Silicon Valley Work is perceived as holistically expanding in every part of the experience, and focus on productivity is a must. The result, however, is Overload, as we have already seen.

Research showed little correlation between productivity and extended working hours, but the tech industry thrived on the idea of its own exceptionalism; the data did not apply to us.

Anna Wiener, Uncanny Valley, page 64

Something that, however, is very much linked to the way start-ups cultures where working on, trying to embed a true mission for everyone.

Work had wedged its way into our identities. We were the company; the company was us.

Anna Wiener, Uncanny Valley, page 65

A lot was also linked to the Value of Work, and how we can better define it. A perception severely challenged by the skyrocketing salaries of that industry.

I had trouble seeing why writing support emails for a venture-funded startup should offer more economic stability and reward than creative work or civic contributions.

Anna Wiener, Uncanny Valley, page 194

There are hopeful glimpses towards the end of the book, where she describes the discussions that some programmers, engineers, and such were having about having more rights, better representation, the possibility of unionizing. Also, here, however, the reality was of disillusionment.

They were developing theoretical frameworks on the internet; they were beginning to identify with the Worker. They talked about universal basic income over free cocktails at the company bar.

Anna Wiener, Uncanny Valley, page 248

On Women at Work

Some of the most valuable content of this memoir comes on the first-hand perspective on how women are considered in the technology workplace. One sentence crystallises perfectly this perception.

After all, his work was seen as strategy, while my work was interpreted as love.

Anna Wiener, Uncanny Valley, page 139

Many of the elements that where intending to overcome the limits of traditional companies, ended being better suited for white male role-models, rather than for true diversity.

The infamous name-your-own-salary policy had resulted in a pay gap so severe that a number of women had recently received corrective increases of close to forty thousand dollars.

Anna Wiener, Uncanny Valley, page 174

And the author view is that this is not just an unintended consequence.

Flat structure, meritocracy, non-nonnegotiable offers. Systems do work as designed.

Anna Wiener, Uncanny Valley, page 273

On what a person really wants from Work

The most significant aspect that is missing from the discussion of the Future of Work is a thorough analysis of what workers want. Most of the literature concentrates on BS generational analysis, that always keeps painting a dream of performance, productivity and purpose alignment towards innovation. I suspect that the reality is much nearer to what is described here.

What I wanted in a workplace was simple. I wanted to trust my manager. To receive fair and equal compensation. To not feel weirdly bullied by a twenty-five-year-old. To put some faith in a system—any system would do—for accountability. To take it all much less personally, and not get too close.

Anna Wiener, Uncanny Valley, page 151

On organisation

There are also a few interesting glimpses on Organisation Design that are deriving from the book. It’s interesting for example to notice the perceived relationship between culture, organisation and individual in such fast-growing environments.

We didn’t want to outgrow the company, but the company was outgrowing us.

Anna Wiener, Uncanny Valley, page 130

Remote work is experimented through her last experience, something that is described in detail as part of a different way of acting.

I liked watching everyone watch themselves while we pretended to watch one another, an act of infinite surveillance.

Anna Wiener, Uncanny Valley, page 170

But what I found more enlightening, is the by-products of this remote-first culture of operations.

People obsessively documented their work, meetings, and decision-making processes. All internal communications and projects were visible across the organization. Due to the nature of the product, every version of every file was preserved. The entire company could practically be reverse engineered.

Anna Wiener, Uncanny Valley, page 158

Last but not least, a truly great view on the idea that meritocracy (originally invented as a spoof term by British sociologist Michael Young).

“Meritocracy”: a word that had originated in social satire and was adopted in sincerity by an industry that could be its own best caricature.

Anna Wiener, Uncanny Valley, page 181

On HR Processes

The author frequently refers to HR as an almost invisible presence in that part of the world, often segregated into managing only aspects of the recruiting process, or trying to silence the next sexual harassment case.

No one had warned me that in San Francisco and Silicon Valley interviewing was effectively punitive, more like a hazing ritual than an airtight vetting system.

Anna Wiener, Uncanny Valley, page 30

Also interesting her view on the perks and benefits that the industry typically offers.

Job listings were an excellent place to get sprayed with HR’s idea of fun and a twenty-three-year-old’s idea of work-life balance.

Anna Wiener, Uncanny Valley, page 145

When she got a smart-watch that would also monitor her heart rhythm, she very soon realized the extend of what that ecosystem was building.

The ecosystem’s fetish for optimization culture and productivity hacking—distraction blockers, task timers, hermit mode, batch emailing, timeboxing—had expanded into biohacking.

Anna Wiener, Uncanny Valley, page 165

On Digital Experience and the Technology Industry.

Wiener has a very strong point of view on the industry from the beginning and some of the underlying concepts it represents. Her view on the “Experience Economy” made me truly reflect.

The CEO did not acknowledge that the reason millennials might be interested in experiences—like the experience of renting things they could never own—was related to student loan debt, or the recession, or the plummeting market value of cultural products in an age of digital distribution. There were no crises in this vision of the future. There were only opportunities.

Anna Wiener, Uncanny Valley, page 19

The other aspect put under question is the entire idea of customisation. The way Wiener sees the industry is almost the opposite. As she looks at the Direct To Consumer brands that send you regular subscription boxes for your apparel, or for your Sunday roast recipe, the reality is that they tend to spread homogeneity.

Homogeneity was a small price to pay for the erasure of decision fatigue. It liberated our minds to pursue other endeavors, like work.

Anna Wiener, Uncanny Valley, page 198


Being skilled at deconstruction is a disadvantage for a customer-support specialist hoping to find “meaning” in her work”, but is an advantage for the writer. Anna Wiener has been able to truly offer us an insightful glimpse in the way Silicon Valley works, almost opposite from the traditional narrative of innovation, self-made fortune and sparkling living that most have been listing. It also delivers an exceptional view on the fact that the start-ups of that world are organisations like all the others, with the same problems and issues (sometimes amplified by the way the VC funding is used: “lavishly”).

The personal trove of the author is also a great sociological insight on modern America, but I suspect, also in a big part of today’s society.

I understood my blind faith in ambitious, aggressive, arrogant young men from America’s soft suburbs as a personal pathology, but it wasn’t personal at all. It had become a global affliction.

Anna Wiener, Uncanny Valley, page 154

What we can also take away, is a perception of Silicon Valley not as a force of good, for the advancement of mankind like many, have painted in the past, but a simple cluster of consistent supporting mechanisms, for an industry that ultimately needs to deliver financial value to its founders and funders.

The tech industry was making me a perfect consumer of the world it was creating. It wasn’t just about leisure, the easy access to nice food and private transportation and abundant personal entertainment. It was the work culture, too: what Silicon Valley got right, how it felt to be there. The energy of being surrounded by people who so easily articulated, and satisfied, their desires. The feeling that everything was just within reach.

Anna Wiener, Uncanny Valley, page 195

All in all a truly good read, that will stimulate every organisation design professional around in reflecting on the easy mythology that circulates around the coolness factor of too many organisation.

Did you also read Uncanny Valley? How did you find it? Please share your views in the comment section below.

Sergio Caredda - Blog Signature
Uncanny Valley: A Memoir
Genre: Management | Rating: 4/5
By Anna Wiener
EBook | 288 pp. | MCD | 14/01/2020 | 1st Edition
ISBN: 9780374278014
Buy on Amazon

Uncanny Vallery reviews on Goodreads

Why not leaving a comment?

This site uses Akismet to reduce spam. Learn how your comment data is processed.

%d bloggers like this: