I enjoyed the Black Swan (and being an 'analyst' doing a lot of 'synthetic' reasoning in my work, particularly liked his pointed barbs at analysts which were like IT types and Dilbert cartoons to me - over the top - but with enough truth to evoke a "laugh or cry" response) though Talebs "skeptical empiricsm" approach seems incomplete and could do with some more discussion relative to Popper and Peirce (and similar skeptics of empericism).

What is needed to my mind is more study of what is going on when we have "aha moments", "flashes of intuition", "moments of genius" or whatever you want to call it when concepts in our heads merge to form new wholes.

To bring this back to OODA loops - that is what is going on in the "orient" box of the OODA loop, which, when you zoom into it in boyds depiction almost makes you look for the box labeld "then a miracle occurs" rather than amass of arrows captioned "an interactive process of many-sided implicit cross-referencing projections, empathies, correlations and rejections".

This to me is where the "meat" of the OODA loop conceptualization is and its part most seem to miss to get to the "loopiness". "Getting inside your opponets OODA Loop is less about speed and more about geting inside his orientation process - understanding how he is constructing the context for what he is observing (which for organizations vice fighter pilots is effectively a continuum of data collection not a periodic "cockpit scan").

The reduction of this insightful framework of observation leading to action through a lens of contexual orientation that frames decision - and thus action to a mechanistic competition over information processing times, misses the point "its all about orientation" - properly understanding what you observe in context of what it is you are trying to accomplish. AND understanding that your adversaries are doing the same.

That we have reduced what Boyd characterizes as 'an evolving, open ended, far from equilibrium process of self-organization, emergence and natural selction" to "spinning our wheel faster" shows just how far ahead of his time Boyd was...(and may still be).