Here's a simple trick -- well, not so simple, since it requires a lot of work -- for generating original insights: commit yourself to going deep in at least THREE different areas of expertise.
Here's why THREE is essential: If you pick two areas, it's virtually inevitable that there will be quite a number of other people reading and thinking across those two domains; but if you pick 3, especially 3 that are usually pretty distant from one another, you'll have an edge.
For me, the three fields I try to read in pretty broadly and deeply in, keeping up with the cutting edge arguments, are (1) intellectual history; (2) national security; and (3) technology.
Now, I'm hardly the smartest or deepest in any of these domains. But because hardly anyone else (that I know of, and I would know) is reading and cross-pollinating across all three of those fields, I often perceives things *across* them that others aren't even looking for.
I know lots of extremely smart people who are reading across any pair of the three pairs (Int.history+tech, tech+security, int.history+tech) and those are often among my favorite authors and thinkers. But hardly anyone I know works consistently across all three.
What this afford me is the ability, for example, to import insights and methods from intellectual history to the tech+security conversation. Or to think about the security implications of the intellectual history of tech. Etc.
What this "triple play" offers, in short, is a kind of a hack, or really an insurance policy, against my own lack of originality and insight in each individual field, narrowly construed. Put another way: it enables intellectual arbitrage.
Now, I'll be the first to admit that arbitrage is not the same thing as creating original value: heck, I edited a book where this was a key thesis. What arbitrage does do, however, is allow one to see opportunities for entrepreneurship that can generate returns.
