I suffer from a terrible curiosity about many, many things, almost to the point of distraction – let me just say that FOMO (Fear Of Missing Out) is real, folks.
If I were forced to identify the origin of this curiosity, I’d blame the insertion of key ideas and questions in my mind that, as I ruminated on them, either became core values for me, or acted as cautionary tales to avoid. Ironically, as tech-obsessed as I am, many of the most potent ideas that personally drive me came from the following books, so I thought it might be illuminating to share these troublemakers with you.
I’m kicking off with science fiction – because why not? – but I’ll be expanding this list to encompass a variety of other worthy genres. In the meantime, hit the jump to see the stories that stayed with me long after I turned the last page.
choose a book:
Ishmael, by Daniel Quinn
The Last Question, by Isaac Asimov
Jonathan Livingston Seagull, by Richard Bach
Watchmen, by Alan Moore
The Metamorphosis of Prime Intellect, by Roger Williams (probably my fave of all)
Fiction & Sci-Fi
Ishmael, by Daniel Quinn
The narrator’s expectations as to what will happen next are shattered, starting with his first encounter with the teacher who placed the ad: the titular Ishmael, a telepathic and infinitely wise gorilla (you heard me), with a talent for destroying long-held assumptions, and an urgent message that all mankind must hear.
Why you should read Ishmael
What if Mankind and Nature sat down for an honest come-to-Jesus conversation, aiming to reconcile what’s happened in the past, and frankly discuss their shared future?
That’s the hypothesis behind Daniel Quinn’s engaging and uniquely surprising story – at once both fantastical, and yet full of solemnly meaningful allegory – which dared me to ask myself some of the really hard questions about the sacrifices we make to further human civilization, and the potential futures that lie before us, in a collective decision of cosmic significance to mankind.
If that sounds grand in scope, it is. Ishmael takes on an intentionally challenging topic, and transforms it into an engaging, earnest and thought-provoking exploration of the path humanity has followed up to now, and what lies in front of it – all framed within the story of a man and a talking gorilla, and the bond they build while trying to save mankind from itself.
The thing that made Ishmael so indelible to me is the titular character’s relentless and uncompromising teaching style that led – almost forced – me to ponder really foundational questions about modern society, and their real implications for the future – like ‘How did society come to be the way it is?’ and ‘What hope is there for humanity’s long-term survival?’.
“Ishmael is like a swedish deep-tissue massage for your assumptions, to work out the knots”
Throughout the course of this book, Ishmael’s force of argument drilled down hard on some of my most bedrock subconscious beliefs (the idea of Man being above Nature and an individual’s responsibility in the face of impending crisis, to name a couple). Living vicariously through the relatable narrator, I frequently found myself squirming beneath Ishmael’s incisive questions, and the implications behind their answers. But it’s like a good hurt – a swedish deep-tissue massage for your assumptions that helps you work out the most troublesome knots in your thinking, and leaves you mentally limber and ready to tackle some big, hairy, 800 lb gorilla-type ideas.
Buy Ishmael on AmazonThe Last Question, by isaac asimov
In this short story – his professed favorite of all his writings – Asimov chases the answer to this fundamental question as it’s posed again and again, by various forms of Man through different evolutionary ages far in the past through the distant future, and at scales ranging from ordinary to colossal. Each setting somehow retains the common thread of boundless human curiosity, always wanting to know what cannot currently be known.
Why you should read The Last Question
Although short and sweet, this little story (which you can get here for free) covers an absolutely vast timeline, charting the various evolutionary incarnations of Man. All of which is interesting and all, but this isn’t the reason it’s a must-recommend for me: it’s the ending.
“…with one simple, well-known phrase, [The Last Question] manages to pay off and legitimize trillions of years of struggle”
The Last Question has one of the best twist endings I’ve ever read in any sci-fi story – hell, any story period. Of course, no spoilers, but it’s a remarkably elegant ending that with one simple, well-known phrase, manages to pay off and legitimize trillions of years of struggle in search of an answer to the unanswerable question.
Read it, and be awed.
Buy The Last Question on AmazonJonathan Livingston Seagull, by Richard Bach
One day, Jonathan’s passionate pursuit of perfect flight leads to tragedy – but far from being a conclusive end, it proves to be merely a transition into something far greater.
Why you should read Jonathan Livingston Seagull
If you’ve ever experienced Flow, or being “in the zone”, you’ll know exactly what drives the titular character of this charming and yet deeply meaningful story. Jonathan skips meals, loses old friendships and endures humiliating slings and arrows from his flock, all in the name of chasing his innocent curiosity, and his relentless quest to hone his flying skills will deeply resonate with any solo entrepreneur who sees potential and burns with the desire to realize it – at the risk of sacrificing everything else in their lives.
You can read the entire story in a short car ride, and you’ll be a changed person by the time you arrive at your destination.
Buy Jonathan Livingston Seagull on AmazonWatchmen, by alan moore & dave gibbons
In New York, the brutal murder of The Comedian, one of the United States’ most decorated retired superheroes, sets off an investigation that forces his peers back into their costumes and back onto the streets. But their heydays are long behind them, and the world they return to is in the throes of desperate social decay. It isn’t long before their focus turns away from the murder, and more toward the terrible burden of heroism – and whether they actually made any difference in the first place.
It’s against this backdrop of fear, doubt and self-recrimination that our “heroes” follow the whodunnit-esque clues to a remote location, and find themselves facing a once-familiar foe, bent on a realizing a twisted plan to unite humanity – at a horrific cost.
Why you should read Watchmen
If you’re at all like me, it chafes you how the most popular superheroes get to inhabit these childish and superficial binary worlds of morality – things are black and white, good guys win and bad guys lose, and it’s always clear what’s right and what’s wrong. Yawn – it’s easy to be a hero when the choices are paint-by-numbers, with the outcomes known well in advance.
“…full of flawed characters who haul around their mental trauma and individual regrets like broken beasts of burden.”
Watchmen was the first graphic novel I encountered that explored a more realistic, amoral world, full of flawed characters who haul around their mental trauma and individual regrets like broken beasts of burden. That probably sounds like a real downer – and it was, but it was also fascinating to watch these former superhero idealists navigate their way around this far more complex and treacherous moral and physical landscape.
Seeing them wrestle to comprehend the consequences of their past antics, and struggle to reconcile the choices they’re forced to make, with becoming the people they once reviled, completely sucked me in – and if you’re at all interested in watching your heroes have to make difficult decisions, I think you’ll be along for the ride too.
Buy Watchmen on AmazonThe Metamorphosis of Prime Intellect, by Roger williams
What happens to humanity when all limitations – feasibility, access, of endurance, and morality – are permanently suspended? Do we even count as human anymore, when we can go anywhere, and do anything, and be anyone, on a whim?
Why you should read The Metamorphosis of Prime Intellect
Fair warning: this story will challenge you. It pulls zero punches, gives even fewer fucks and in a couple specific scenes, matter-of-factly describes detailed tableaus of brutal, almost gleeful depravity and sexual violence.
And you know what? That’s kind of the point.
With Intellect, Roger Williams explores the conflicting demons and better angels of the animal known as Man – but transplants this common topic into a setting where the social norms and physical limitations that typically keep our most extreme behaviors in check, no longer apply. I personally believe most people possess the capacity for astounding good at the same time as incalculable evil, and this story probes the edge of that moral envelope by stripping away all limitations from human desire, then allows the reader to peer in and see how we behave. It is, in turns, rapturous and horrifying.
I love how Williams balances a believable extrapolation of contemporary technological progress (especially in the areas of machine learning and artificial intelligence), with an intense focus on the humanity at the center of the story. He elegantly describes situations that seem impossibly bizarre to the reader on the outside, but to which humanity has become accustomed – almost like they’re numbed to all the fantastic sights and possibilities, centuries after their collective ascension to immortality. The undercurrent of resigned boredom and nondescript frustration that simmers below the skin of each of the main characters is hard to miss, and makes for sometimes hilarious reading.
“To call it all a wonderfully contradictory headtrip doesn’t do it justice.”
It’s simultaneously alien yet recognizable, as we watch the interactions between these irrevocably changed, but unmistakably human characters interact with each other. Hovering over every chapter like an overly-attentive nanny, there’s Prime Intellect, the godlike AI that simultaneously rules every atom in the entire universe, yet deferentially caters to every passing whim of the “people” under its purview. To call it all a wonderfully contradictory headtrip doesn’t do it justice.
This book will make you question everything you thought you knew about relationships, morality, and technology, and if I had to choose one book from this entire list, this would be it.
Buy The Metamorphosis of Prime Intellect on AmazonSome Closing Notes
- I hope to keep adding to this list over time, so help me out and send me your recommendations!
- It was only once I finished writing this post that I noticed all of these books were written by older white men. While this detracts nothing from the impact they’ve had on me personally, it is, perhaps, a sign I should be broadening my literary horizons and seeking new perspectives.
- My full best-of list of books was originally so long it’d take me forever to write, and no-one would read it – so I’ll be following up with the rest in separate posts that address their respective categories. There are some killer reads that I can’t wait to share with you. Subscribe to get notified!
For balance, a good story by a woman:
“The Word for World Is Forest” by Ursula Le Guin.
Le Guin has written several good stories, but this is my personal favorite mind-bender.