I'll read anything by Andrew Krepinevich, the fine strategic thinker who bears a strong resemblance to Dwight Eisenhower circa 1939. Right now my subway reading is a new essay he has done with Barry Watts titled "Regaining Strategic Competence."
I was especially intrigued by the list of 10 common strategic blunders they attribute to business strategy expert Richard Rumelt:
1. Failure to recognize or take seriously the scarcity of resources.
2. Mistaking strategic goals for strategy.
3. Failure to recognize or state the strategic problem.
4. Choosing poor or unattainable strategic goals.
5. Not defining the strategic challenge competitively.
6. Making false presumptions about one's own competence or the likely causal linkages between one's strategy and one's goals.
7. Insufficient focus on strategy due to such things as trying to satisfy too many different stakeholders or bureaucratic processes.
8. Inaccurately determining one's areas of comparative advantage relative to the opposition.
9. Failure to realize that few individuals possess the cognitive skills and mindset to be competent strategists.
10. Failure to understand the adversary.
There is a whole book of military history to be written just finding good illustrations of each of those mistakes. I think the United States was guilty of No. 2 and No. 10 in Iraq from 2003 through 2006. I'd say the British tripped on No. 3 during the American Revolution. I think Hitler committed No. 4 when he tackled Russia. No. 10 is probably the most common error.
I'd be interested in other examples that you see.