A couple RAND reports come to mind. I have not read either yet myself, would be interested to hear your thoughts if you do!
Shaping the Next 100 Years: https://www.rand.org/content/dam/rand/pubs/monograph_reports/2007/MR1626.pdf
Speed and Security: https://www.rand.org/pubs/perspectives/PE274.html
+1, @Buck I also would be interested in your thoughts about how to improve one's judgment, or recommendations of other writing on this topic. Would probably merit a separate post as it seems potentially quite relevant for people in "standard" EA careers as well.