The 45 Paradoxical Qualities of the Strategist


What qualities define the strategist? While some contemplate the best schools or best processes to “build” the best senior strategists—maybe the best way forward is to start with a simple set of characteristics that might best exemplify the strategist.

And if we were to take on such a task, these characteristics would have to follow in suit with the paradoxical logic of strategy itself, which Edward Luttwak described as a counterintuitive endeavor where a good road is a bad road because it is a good road (and so the enemy will likely attack there). Several similarly paradoxical statements have been widely expressed from other, perhaps better known quarters:

  • “Begin with the end in mind.” (Stephen Covey)
  • “Strong opinions, weakly held.” (Marc Andreeson)
  • The pen is mightier than the sword. (Unknown)
  • “In Israel, in order to be a realist you must believe in miracles.” (Israeli Prime Minister David Ben-Gurion)
  • Mission first, soldiers always. (Common US Army expression)
  • Escalate to deescalate. (current Russian nuclear doctrine)
  • “Be polite, be professional, but have a plan to kill everybody you meet.” (US Secretary of Defense James Mattis)

If the current US secretary of defense finds value in employing such a seemingly incongruent statement to describe military practitioners, then perhaps there’s some utility in trying to pin down a description of the strategist’s paradoxical qualities—temperament, attitudes, thoughts, ways of being—on the way to better understanding and developing future strategists. Of course, some below won’t fill the strict definition, but they all broadly meet the sentiment. Here goes:

  • The strategist is a loyal rebel.
  • The strategist practices admirational enmity.
  • The strategist knows the environment is unknowable.
  • The strategist sees strength in weakness, and weakness in strength.
  • The strategist exercises reckless, focused curiosity.
  • The strategist is a realist guided by ideals.
  • The strategist plots azimuth by looking equally rearward to history and forward to the future.
  • The strategist cares deeply about ideas but is not deeply committed to any idea.
  • The strategist sweats each syllable but takes no pride in authorship.
  • The strategist desperately wants to win but is the first to announce a loss.
  • The strategist seeks not the end but an edge.
  • The strategist flexibly considers any course but rigidly adheres to the best option.
  • The strategist religiously searches for truth while worshipping the tyranny of the deadline.
  • The strategist knows catastrophic success and triumphant failure.
  • The strategist spills gallons of blood but feels every drop.
  • The strategist loves each soldier and spends them by the battalion.
  • The strategist engages with the abstract while down in the dirty weeds.
  • The strategist is aware of true uncertainty and wary of false certainty.
  • The strategist sees the good in enemies and the bad in allies.
  • The strategist relies on data and numbers, but crafts strategy as applied artwork.
  • The strategist knows wars are won in the mind as much as the fist.
  • The strategist makes harmonious melody from a cacophony of chaos.
  • The strategist is always a participant, never a partisan in a political system.
  • The strategist is attuned to pinpoint details but never lets them obscure the broadly painted canvas.
  • The strategist thinks globally, plans regionally, executes locally.
  • The strategist privileges one answerable question over ten questionable answers.
  • The strategist wants to be wise and not smart.
  • The strategist pursues individuality of thought in an organization that values uniformity of action.
  • The strategist employs disciplined violence to kill for peace.
  • The strategist knows where the bureaucracy ends and the profession begins.
  • The strategist toes the impossible to find possibility’s edge.
  • The strategist knows tradition is meaningful and sacred cows provide the tastiest meat.
  • The strategist is certain the enemy’s mind is uncertain.
  • The strategist knows cannons can’t be shot from canoes, yet storms come from butterfly wings.
  • The strategist listens equally to the nine stating conventional wisdom as the crackpot armed with a solid point.
  • The strategist knows deterrence is nothing and deterrence is everything.
  • The strategist knows doctrine is nothing and doctrine is everything.
  • The strategist sees that the good fight and the right fight are not the same fight.
  • The strategist believes the battlefield cannot be fundamentally altered, yet changes constantly.
  • The strategist selects Q, Z, N/A, 59, or #, when asked to choose between A or B.
  • The strategist never confuses price with value.
  • The strategist’s math is defined by the equation 1 + 1 = apple.
  • The strategist’s behavior is marked by lazy ambition and productive sloth.
  • The strategist sees that geography is destiny, yet terrain is decisive.
  • The strategist believes hope is not a method, but hope always finds a way.

Do these characteristics fit you? Do they somehow make sense? If so, then keep at it—you might just be a budding strategist.


Note: This exercise was inspired by Steven Pressfield’s “Qualities of the Professional” in Turning Pro.  Also, the image was provided by Pathways.

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