Thanks for sharing your experience!

In case you or any other LWers would find these interesting, here are some resources I've enjoyed:

• Dan Carlin's Hardcore History podcast This is what got me hooked on history in the first place. [Edit: I see you mentioned this in the comments! Well ... seconded!]
• Philip Tetlock's Expert Political Judgment book Really anything that Tetlock has done (I think some LWers are involved in his Good Judgment Project). For my money, this is the steelman against using geopolitical insight for forecasting purposes.

I personally worry about moving from "reading history for insight" to "reading history for insight porn". What actions do you take to push back against that tendency?

Finally, FWIW, this sentence jumped off the page when I read it:

I don't read much fiction any more, because most fiction can't compete with the sheer weight, drama, and insightfulness of history.

There was a time in my life when I would have emphatically agreed. These days I have to disagree, though. I've taken to reading history for the experience of viewing the same events from multiple conflicting perspectives. I feel like it widens my set of available reference classes for common issues. Since shifting to view history as a "reference class generator" I've picked up literature as a "way of being in the world generator".

Note: Here's what I'm not saying. I'm not saying you or anybody else should have the same experience I do. I am saying to watch out for mind-projection at "most fiction can't compete with ... history". It's more accurate to say that your experience of most fiction can't compete with your experience of history ... which isn't really the same thing at all. Especially since you can probably change both experiences, either with some effort or just by waiting a while.