Oct 12, 2026
On difficulty of learning from books:
Let's say you want to learn about leadership so you pick up biographies of great leaders. Maybe Caesar, Washington, Napoleon, FDR, Churchill. I'm not one to ever discourage people from reading, you'll probably be much better off reading these than not. But I think this is a pretty bad curriculum, let me give you an example why.
Somewhere early in Ron Chernow's George Washington bio Chernow tells us that Washington worked as a surveyor in his teens, exploring and fixing tracts of land on the frontier. He'd ride for weeks at a time, sleep in his cloak by the campfire, and starting 18 he'd pick out and buy good tracts for himself. By age 20 he owned about 2000 acres. (He was supposed to survey for other people but used the opportunity to snipe the best plots of land for himself, which seems kinda shady but whatever.) Then Washington gets a patronage adjutancy post and we move on to his early military career.
But what did we learn about this early period in his life *really*? What does a surveyor do exactly, and how? How do you "fix" tracts of land? Have you ever driven past a stretch of land without Google Maps and try to make sense of it? It's impossible! How would they mark off the borders? Did he have to bring paperwork back and deposit it somewhere? How did they keep people from just using the land? What makes good and bad land? What does it feel like for a 16yo to sleep on the ground in the middle of a forest on the frontier? Could you try it for a day? How about every day for a fortnight? Also, how do you ride a horse through a forest, and how much land is 2000 acres?
Surveying was supposed to be this big formative experience for Washington that taught him to read terrain and endure the hardships of the frontier. But even a basic interrogation reveals we barely have any idea what surveying actually means. As we proceed through the bio and start learning about his early battles we won't understand those either for all the same reasons, nor will we understand his later big battles, and so on. (For example, why is it easier to defend a wooded hill than to attack it? Line of sight is bidirectional, isn't it? And why is flanking such a big deal? You supposedly know, but do you really?)
You could argue all this doesn't matter, you're just getting a feel for Washington and what you're learning is his higher-level/strategic decisions. I'm very skeptical of this argument. Every chess or Go player knows you can endlessly study strategy, then trivially get ripped apart by a bright middle school student. You can't learn math by only studying "higher level" stuff, or programming, or cooking, or jazz piano, or really much of anything. The only obvious difference is that in all these cases you get immediate feedback, but with reading you can tell yourself you've learned something without ever validating it one way or the other.
Another difficulty is that authors have to move the plot along, so without deliberate effort you never get to immerse yourself in the character's emotional state or decision-making fog, even for turning point events. For example, Chernow spends a chapter on the Delaware crossing (and the chapter before that is on Washington's indecision running up to the event). New York is lost, the Continental Army is down to ~3k men (from the peak of ~28k), enlistments are about to expire by year's end. Washington's own officers are circling him like piranhas-- Charles Lee is stalling reinforcements, Horatio Gates is lobbying Congress for Washington's replacement, Joseph Reed is conspiring with Lee. Washington is a hair's breadth away from political ruin. He deliberates for days, then decides to roll a hard six on Christmas night, and miraculously wins.
Maybe I lack theatrical imagination but if I read these chapters on autopilot I mostly just think “wow that’s a bad situation, let’s see what happens!” Then, since humans naturally identify with the protagonist, I think “of course, obviously I’d also do this same thing and also win in that situation,” then move on to the next chapter. To *really* learn from all this I'd have to understand the tactical situation in depth, try to generate and evaluate other options, somehow try to approach Washington's despair. All of which is time-consuming, difficult, and impossible to do on your own.
After you read a great book like Chernow's, the next thing to do is experiential, not intellectual. It is not to read another book, this time on Napoleon. Spend that time visiting historical sites, talk to museum curators, go see a play and talk to the theater troupe, ask army vets questions. If you're really dedicated go on an ultralight backpacking trip through Virginia backcountry.
(On Washington specifically, I've only done some of these things myself. But this is a general principle, not a revolutionary war nerd thing. If you're learning about Sun Microsystems go see one in a museum and talk to old employees, if you're learning about music talk to musicians and maybe take a music lesson, etc.)