In the tech world, 2023 was a year of pure chaos.

There was the artificial intelligence boom that breathed life into an industry in dire want of its next big thing, delivering a torrent of new startups, investment and hype. There was also the collapse of Silicon Valley Bank, the fraud conviction of crypto titan Sam Bankman-Fried, the implosion of Twitter and downward spiral of Elon Musk, who capped his year by telling advertisers fleeing his platform to “go f— yourself” on a very public stage. Google lost an antitrust lawsuit to Epic Games, and the future and shape of the web seem uncertain as ever.

Like I said: pure chaos.

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Now, with some of the dust settling, and an all-too-brief holiday respite upon us, it’s a fine time to reflect on where we are and what’s coming next, and to try to make some sense of that chaos — maybe with a book or two. Fortunately, there were a lot of books about tech this year, and quite a few that I’d consider required reading for Understanding This Moment. In fact, I think it calls for that most hallowed of year-end content traditions, the best-of list.

I was especially drawn to those that explored the wide-ranging social impacts and unexamined histories of technological power — perhaps because my own book, “Blood in the Machine,” which I naturally refrained from placing on this list yet very cleverly managed to plug right here, attempted this too.

I’d recommend skipping right past most of the “big” tech books of the year — especially “Elon Musk” by Walter Isaacson and “Going Infinite” by Michael Lewis, both of which sadly succumb to the kind of tech-founder hero worship that’s increasingly outmoded and often embarrassing. Especially when there are so many books that take a hard, nuanced look at the ways tech is affecting society — and are just so much more fun to read.

So without further ado, here are 10 of my favorite books about technology, power, AI and Silicon Valley this year:

The big-picture books

DOPPELGANGER by Naomi Klein

What begins with a hook that might seem a little thin — online, people keep confusing radical author and activist Naomi Klein with feminist-turned-conspiracist Naomi Wolf — quickly blooms into an engrossing exploration of the online and offline self, and why it is that our once-shared reality is fracturing into what Klein calls the “Mirror World.”

You know the place: It’s where your uncle, who always used to be such a hoot at Thanksgiving, now resides, posting QAnon links on Facebook. Where ex-journalists post breathless videos about COVID conspiracy theories on off-brand video streaming platforms. Where no amount of “but actually”-ing can draw its residents, who’ve all “done their own research,” back from the den of anger, resentment and truth-shaped lies that threaten to curdle into full-on fascism.

It’s the closest I’ve seen anyone come to offering a unified theory — involving the conquering force of the “personal brand,” the real intrusion of big tech into our lives, the exploitation of the subsequent unease and paranoia by savvy political operators, and the failures of the state to provide the basic supports necessary to keep people satisfactorily moored in reality — of the terrible and technologized political predicament we’re in. Klein’s narrative is also mordant and often wildly relatable, even as she draws us to deeper and darker planes.

One of my good friends had in recent years been dabbling in parts of the Mirror World — she had “only glanced into the looking glass here and there,” as Klein puts it in the text, rather than “stepped all the way through” — and reading Klein’s book made her resolve to shatter it and return to the real one for good. I can’t think of a more resounding endorsement than that.

PALO ALTO by Malcolm Harris

If you want to understand what truly makes Silicon Valley tick — the politics encrusted just under the surface (not too deep, though), the mechanisms that govern our biggest tech giants and the driving forces behind the world’s most storied purveyor of innovation (hint: One is the perennial pursuit of defense contracts) — I’d suggest you read Malcolm Harris’ “Palo Alto.”

Harris grew up there, and this year, he published the most comprehensive — and incendiary — history of the place that we’re ever likely to get. A sweeping and unsparing critique, it’s also well written, frequently surprising and, because history tends to rhyme, increasingly urgent. You may never think about Stanford, iconic tech companies like Hewlett Packard or, indeed, the Valley itself the same way again. I won’t.

The AI books

YOUR FACE BELONGS TO US by Kashmir Hill

A brisk and momentous nonfiction tale that follows New York Times reporter Kashmir Hill’s quest to get the scoop on Clearview AI, a shadowy startup that promised to “end privacy as we know it,” as Hill once put it, by building an enormous facial recognition database. Lots of reviews noted that reading “Your Face” is like real-life cyberpunk, and by dint of the subject matter, it is — but it’s also more than that. Hill devotes chapters to ensuring readers understand the wider context of facial recognition technology, exploring, for example, its sordid eugenicist origins. Citizens alarmed by the intrusive tech have been able to successfully resist it in a number of cases — its use by police is banned in a number of cities already, among them San Francisco — and understanding it is more crucial than ever as we move into a new age of AI.

UNMASKING AI by Joy Buolamwini

Most of the discourse around AI this year was stuck on grandiose questions of whether AI was good for humanity or would destroy us all. A fun parlor debate, but one that quite intentionally allows the Silicon Valley companies that stand to profit by selling the tech to evade questions more pertinent right now. Such as, will AI systematize or even exacerbate racial bias and discrimination? Buolamwini’s compelling and accessible memoir follows the MIT computer scientist’s path to investigating those questions — and to exposing the racism and inequity in the systems built and propagated by some of the biggest tech companies. The fight’s just begun, but “Unmasking AI” is a good place to get onboard.

The bitcoin books

NUMBER GO UP by Zeke Faux

TOKENS by Rachel O’Dwyer

EASY MONEY by Jacob Silverman and Ben McKenzie

Reports of bitcoin’s death have been greatly exaggerated. Even after an interminable stream of scandals, crises and criminal fraud convictions, bitcoin, the cryptocurrency that has no real-world utility to speak of, is, as I write this, worth $43,000 a pop. There will be more booms, more busts. And in the interest of understanding why, and the specific texture and flavor of these busts and booms, not one but three great books about bitcoin were minted this year.

“Number Go Up” is a globe-trotting nonfiction picaresque that’s as much fun as you can have reading about financial malfeasance and blockchain scams. It’s a crisp primer that effortlessly ties the overinflated promise of bitcoin not just to the fraudsters like Sam Bankman-Fried who peddle it, but to the places in the Global South, like the Philippines and Cambodia, that are steamrolled by the fallout when that promise dies, often in spectacular fashion. It’s scathing; it made me snort rage chortles aloud as I read. I would have finished it in a single sitting if I didn’t have to sleep.

“Easy Money” zeroes in on many of the same subjects but drills in a bit deeper rather than going laterally; it lingers longer on the details, though it too is funny and plenty scathing.

Finally, “Tokens” deftly gives the basic concept that animates cryptocurrency — the titular token — the critical and historical treatment. It’s much-needed. “Tokens” is a book of theory, yes, but one that’s sharply written and readable; it peels back the onion of what we’re even talking about when we’re talking about a crypto “coin” or other digital commodity. Think of it as a field guide for understanding the weird digital future of money. And much as most of us wish we didn’t, we’re going to need it.

The future-of-the-internet books

SELLING THE AMERICAN PEOPLE by Lee McGuigan

When we talk about the internet, we don’t spend enough time talking about adtech. Yet advertising undergirds the commercial web as we know it, molding our digital commons to suit its incentive structures and bending online media to its needs. In his consistently illuminating book, Lee McGuigan shows both that A) the advertising industry’s project of selling tech that promises maximally effective ads — ads that now tinge every corner of the online experience — is nothing new, and in fact was many decades in the making, and B) that this is ultimately terrible for society. Surprise! Don’t let the fact that this is an academic book turn you off — it’s propulsive, compelling, even fiery. It’s ultimately a call to stop letting advertisers dictate the qualities of our public spaces, online and off.

EXTREMELY ONLINE by Taylor Lorenz

A crash course in how influencers took over the world, Taylor Lorenz’s tome collects and expands upon the kind of stories that have built her reputation as the web’s foremost internet culture reporter. It makes for a lively and vital account of how the web was won by a cadre of determined and talented bloggers, content creators and self-promoters. Few books will better prepare you to understand the cultural orientation of today‘s (and tomorrow’s) platform-laden and creator-driven internet.

THE INTERNET CON by Cory Doctorow

Cory Doctorow published three books this year, and I almost left him off this list out of authorly spite. No human should be so productive. Instead, I’m just putting him last.

While I’m enjoying his climate-fiction thriller “The Lost Cause,” it’s his nonfiction entry, “The Internet Con,” that I’m slotting in here. Doctorow popularized the term “enshittification” to describe what happens when tech monopolies control whole platforms and need to find new ways to squeeze more profits out of them — they lard them up with ads and bad automation, and cut corners, generally making everything online worse. “The Internet Con” explains how we got here, then makes the case for a solution: interoperability. Basically, making social networks and web infrastructure talk to each other the way email clients do, rather than locking everything in on each individual platform. It’s a compelling idea, and the book’s written in such a pithy and pleasurable way that, in spite of myself, I look forward to reading each of the half-dozen books Doctorow will undoubtedly drop in 2024.

Speculative fiction bonus round

These may not count as “tech” books,” but they are speculative works about the future, have deep resonances to today and are all great, so for some science fiction for the holidays, I recommend: “Chain Gang All Stars” by Nana Kwame Adjei-Brenyah; “Wrong Way” by Joanne McNeil; “After World” by Debbie Urbanski and “The Ascension” by Nicholas Binge.

Bonus bonus round

There were tons of great books that I wasn’t able get to yet, or to fit on the above list that deserve mention here: “Optimal Illusions” by Coco Krumme is a great consideration of the relentless drive toward optimization from a great mathematical thinker. “Disrupting D.C.,” by Katie J. Wells, Kafui Attoh and Declan Cullen, is a fantastic look at how and why Uber was able to conquer our cities. And I am looking forward to digging into “Against Techno-Ableism” by Ashley Shew, “Own This! How Platform Cooperatives Change the World” by R. Trebor Scholz, “The Palestine Laboratory” by Antony Loewenstein and “Making a Metaverse That Matters” by Wagner James Au.