These are books (and not-books) that had some lasting impact on me long after first reading them.
They're not all good books. Some of them are terrible books with one good idea, or weird books that just happened to come at the right time to complete some link in my head. But they all lasted, and that's rare.
In no particular order...
The Rock Warrior's Way
While notionally a book about climbing, it's really about what the author calls 'personal power' - the ability to act effectively in the world - and all the ways that that power can be drained by ego, fear, comfort-seeking, and even poor definitions of success and failure.
'I wish this hold was more positive' has no action quality to it. By wishing, you try to decrease your discomfort by escaping into a fantasy. This is a dreadful waste of power. Not only do you have power going into passive behavior, but you also cloud reality, impairing your ability to problem-solve. Remember that learning is the warrior's goal. The holds are what they are. You need to think actively so that deliberate, effective actions follow. Instead of wasting power by wishing the hold was more positive, use that power to determine how to use the hold in the best way possible.
If you find yourself becoming frustrated, take it as a symptom that you are out of alignment with your goals. If you really want an easy success, find an easier climb. If you want a real challenge, you've found it. If the Ego is asking for a trophy to use in its externally oriented game of self-worth, look the Ego dragon in the eye and draw your sword. Then pay attention, give your best, and enjoy the ride.
When you love the challenge, you freely give your attention to it. You are in tune with the flow of the experience. You aren't fighting it, avoiding it, or wanting to end it.
The safety, comfort, and security we crave aren't objective states. They are subjective feelings that come through increasing our understanding of our world and our capabilities. In short, we gain comfort and security by expanding our comfort zones, and we expand our comfort zones by venturing into the risk zone. We make ourselves uncomfortable and insecure for a short time in order to learn what we're capable of.
If you are settling in to a rigid comfort zone, then you are dying - slowly, but still dying.
It's easy to read these as obvious truisms. In any other context the same advice might just have washed over me. But the nice thing about climbing is that the mistakes are so visible and play out over such a short timescale that I can't avoid seeing them every fucking week. It's much easier to actually learn with such short sharp feedback loops. Only much later did I start noticing the same patterns everywhere else.
I also love Espresso Lessons, although it's much more climbing-specific.
You cannot effectively deal with a situation until you accept it as it is.
The World Beyond Your Head
This is a rambling and confusing book. I didn't like it much the first time I read it and I don't remember why I ever read it again. It's groping towards some kind of philosophy of agency and autonomy but it doesn't quite get there in any coherent fashion. And yet the things that it is groping towards feel important to me, even if I can't articulate them properly either.
Part of the argument is contrasting his ideas against enlightenment/liberatarian ideals of autonomy as being completely free of any constraints and influences:
If you have children, you know that the will of a toddler has a kind of purity to it: he wants what he wants, and refuses what he refuses, without reference to any fact that might inconvenience his will. It is freezing outside, but he doesn't want to wear shoes to the park.
Being an adult involves learning to accept limits imposed by a world that doesn't fully answer to our needs; to fail at this is to remain infantile...
The enlightenment/liberatarian promise that you can build up your own values from scratch is a trap. People don't exist in isolation but as part of a community and culture, whose norms and values affect the choices that you see open to yourself. By not recognizing the existence of choice architectures, we lose the opportunity to own them and instead leave ourselves vulnerable to manipulation:
...the Enlightenment legacy of autonomy talk, persisting as a cultural reflex, can neutralize our critical response to various ways in which our attention gets manipulated. This became most clear in the case of machine gambling, where we found that the gambling industry and its apologists rely on a notion of the sovereign individual to forestall criticism and regulation, even while pursuing 'addiction by design' as a social engineering project.
...how the built environment of our shared spaces may contribute to this flattening. When they are saturated with mass media, our attention is appropriated in such a way that the Public - an abstraction - comes to stand in for concrete others, and it becomes harder for us to show up for one another as individuals.
...choosing (from a menu of ready-made solutions) replaces doing, and it follows that such a person should be more pliable to the choice architectures presented to us in mass culture.
For Crawford, agency comes from skill - from being deeply attuned to some feature of the world outside your head, in a way that opens up new ways of seeing and exposes you to the values and judgements of a community of practice:
...this is precisely the condition of the narcissist: he treats objects as props for his fragile ego and has an uncertain grasp of them as having a reality of their own. The clearest contrast to the narcissist that I can think of is the repairman, who must subordinate himself to the broken washing machine, listen to it with patience, notice its symptoms, and then act accordingly. He cannot treat it abstractly; the kind of agency he exhibits is not at all magical.
...your skill set determines what possibilities for action you perceive in your environment... How we act is not determined in an isolated moment of choice; it is powerfully ordered by how we perceive the situation, how we are attuned to it, and this is very much a function of our previous history of shaping ourselves to the world in a particular way.
As embodied beings who use tools and prosthetics, the world shows up for us through its affordances; it is a world that we act in, not merely observe. And this means that when we acquire new skills, we come to see the world differently.
This strikes me as having a lot in common with Ilgner's notion of personal power above, and also with Alexander's arugment in The Globalization of Addiction that the root of many addictions is dislocation from community and culture.
There is a lot I disagree with in this book (not least his intense distaste for safety features in cars), but I feel there is something important in there somewhere.
Microadventures
This book congealed for me the idea that adventure is more an attitude or a habit than a circumstance. I'd experienced that before, especially in the parkour scene in London, but always in narrow contexts. Alastair convinced me to treat my whole life the same way.
When I phoned my friend Rob to invite him along he said, "That's a stupid idea. Let's do it!" And so we set out together to walk a lap of the M25 motorway.
A regular theme of this book is conjuring up arbitrary journeys simply to create a reason for heading out the front door.
...the hint of gentle madness and subversiveness is one of the bits I like best about microadventures.
Strangely, something about that gentle madness makes life feel a little more real. I think it's something abou the puncturing of automaticity - realizing that you are constantly faced with decisions and that at any moment you could wake up and actually make one.
A City Dreaming
Pretending to be urban fantasy, but really a love letter to New York and to unplanned adventures.
But the thing about good decisions is that making them exclusively turns out, curiously, to be to be the worse decision a person can make; it leads to ruination, to a business-casual existence, to eating take-out and watching network sitcoms. In short, a bad decision is required to even things out every so often, and M was feeling up for making one that afternoon.
And then just when you relax, it's really about the ennui caused by hiding behind detached cynicism.
"No one likes you, you know." "No?" "You're always laughing behind your hand at everyone." "Am I? Behind my hand, you say?"
The cool-quipping protagonist is afraid to be believe in anything and it's slowly killing him.
Some days, there seemed very little point in magic. Some days, there seemed very little point in anything at all, but M soldiered on just the same.
Uncontrolled
The 20th century saw huge advances in physics and chemistry. We found simple universal laws hiding beneath the apparent chaos of reality. We expected to quickly find the same for psychology, sociology, and politics. But as documented in Seeing like a state, whenever we tried to govern 'scientifically' it always seemed to lead to famine and genocide.
Uncontrolled argues that we didn't really learn the underlying lesson. We still research those fields as if we will be able to extract easily generalizable laws from short experiments on small numbers of people in artificial settings. But these fields have far too many variables and too many causal connections between those variables.
First, note that all of the inference is built on the purchase of a grand total of thirty-five jars of jam. Second, note that if the results of the jam experiment were valid and applicable with the kind of generality required to be relevant as the basis for economic or social policy, it would imply that many stores could eliminate 75 percent of their products and cause sales to increase by 900 percent. That would be a fairly astounding result and indicates that there may be a problem with the measurement.
[...] the researchers in the original experiment themselves were careful about their explicit claims of generalizability, and significant effort has been devoted to the exact question of finding conditions under which choice overload occurs consistently, but popularizers telescoped the conclusions derived from one coupon-plus-display promotion in one store on two Saturdays, up through assertions about the impact of product selection for jam for this store, to the impact of product selection for jam for all grocery stores in America, to claims about the impact of product selection for all retail products of any kind in every store, ultimately to fairly grandiose claims about the benefits of choice to society. But as we saw, testing this kind of claim in fifty experiments in different situations throws a lot of cold water on the assertion.
As a practical business example, even a simplification of the causal mechanism that comprises a useful forward prediction rule is unlikely to be much like 'Renaming QwikMart stores to FastMart will cause sales to rise,' but will instead tend to be more like 'Renaming QwikMart stores to FastMart in high-income neighborhoods on high-traffic roads will cause sales to rise, as long as the store is closed for painting for no more than two days.' It is extremely unlikely that we would know all of the possible hidden conditionals before beginning testing, and be able to design and execute one test that discovers such a condition-laden rule.
Further, these causal relationships themselves can frequently change. For example, we discover that a specific sales promotion drives a net gain in profit versus no promotion in a test, but next year when a huge number of changes occurs - our competitors have innovated with new promotions, the overall economy has deteriorated, consumer traffic has shifted somewhat from malls to strip centers, and so on - this rule no longer holds true. To extend the prior metaphor, we are finding our way through our dark room by bumping our shins into furniture, while unobserved gremlins keep moving the furniture around on us. For these reasons, it is not enough to run an experiment, find a causal relationship, and assume that it is widely applicable. We must run tests and then measure the actual predictiveness of the rules developed from these tests in actual implementation.
They argue instead of a process of continuous widespread experimentation and monitoring. We will never find universal laws, but we can still find locally valid rules of thumb by running many small experiments, slowly scaling up anything that seems to work, and staying responsive to feedback and changing contexts.
I read this as a cognitive science post-grad and it perfectly captured my unease with the field.
Deep Work and Digital Minimalism
This is when I first started to notice how much of my experience of life is determined by where and how I direct my attention.
Spend enough time in a state of frenetic shallowness and you permanently reduce your capacity to perform deep work.
A workday driven by the shallow, from a neurological perspective, is likely to be a draining and upsetting day, even if most of the shallow things that capture your attention seem harmless or fun.
It also made me realize that there can be a huge amount of life satisfaction in mastery itself, even if the things I'm being paid to build seem frivolous or dull.
It connects to with Ilgner's ideas about shying away from improvement to protect your ego:
There's also an uneasiness that surrounds any effort to produce the best things you're capable of producing, as this forces you to confront the possibility that your best is not (yet) that good.
But the most powerful idea was that of mental solitude:
...a subjective state in which your mind is free from input from other minds.
They argue that daily solitude is necessary for emotional processing, and that being deprived of solitude by constant entertainment leads to anxiety and insomnia, your mind racing in bed as it tries to catch up with the work it missed. Nearly a decade after reading I'm thoroughly convinced by this theory.
Factfulness and Not the End of the World
What struck me the most about both of these was the strength and pervasiveness of the media bias towards negativity, and how fervently people want to continue believing in downfall of all that is good and the intrinsic evil of modernity, even when faced with clear evidence otherwise.
(Adam Mastroianni provides at least a partial explanation for this - if you indirectly ask people when the world started falling apart they generally put the date at around the time they were born. Personal memories of negative events hit harder than history books.)
It's scary because these worldviews are what drive policy. Slowly grinding improvements works but it's not as narratively satisfying as the inevitable triumph of original sin. We built systems that massively reduced human misery, and then we convinced ourselves that those systems made things worse, and now we want to burn it all down and start again because things were better back then.
More than anything, these books convinced me to work hard to avoid these negativity chambers entirely and aim to only hang out in spaces where people are trying to make things better, instead of delightedly bemoaning that everything is awful.
The Life Goals of Dead People
I won't summarize it - it's only a few minutes read. But I often catch myself being a dead person, and having a term for it has noticably improved my life.
Shallow Feedback Hollows You Out
Your fear of being called out will make you likely to hedge your true beliefs; conversely, your desire to get the group's attention encourages you to exaggerate or embellish a bit. Most devastating is that you will have thoughts that are more obvious and require less context and reader investment to understand. If you don't create a very unusual social context, you will subconsciously optimize your thoughts for the least-informed member of your group...
Regardless of its social value, suppose you don't want to lose your ability to think new thoughts and see new things. [...] The best remedy is to write to the single smartest person you know who cares a lot about your topic of interest.
I noticed this happening when my blog started getting popular and I read all the forum comments. My writing got more defensive, and then focused on litigating stupid arguments. It was incredibly freeing when I switched to deliberately writing for specific people and not even reading the internet comments.