The Paradoxical Strategist

42 ways to find strength and wisdom in opposing ideas

In early 2006, an interview between two bespeckled academics on the subject of strategy captivated me. Harry Kreisler asked the questions, Stephen Biddle answered them, pertaining to his then-recent book about military power. They also veered into strategy. Both the video and transcript are still available, and on second glance they’re chock full of gold bricks.

Kreisler asked about the tension between two goals in a strategy. Biddle responded:

“Inherent in the idea of strategy is the idea that your goals are always in some degree of tension. People don’t like that, and military people and strategists don’t like it either, but at the end of the day, there are always goals in tension. In this particular problem [we’ve been discussing], the goal of prosecuting the war on terror and prosecuting the delay of the rise of a superpower challenger are in tension in a variety of ways.”

Both X and Y can be “correct” paths forward at the same time. There is no 1 + 1 = 2 in strategy. What’s fascinating is the way Biddle acknowledged the strategist’s limitation in solving for the “X or Y, which way forward” dilemma:

“I think all of these positions are defensible. In fact, not only do I think they’re all defensible, I think a choice among them ultimately rests on value judgments that analyst folk like me can’t resolve. The question of risk preference, for example: rollback might solve the problem but it’s very risky. Containment is less risky in the short term but can’t solve the problem, at least not anytime soon. It’s like the difference between swinging for the fences and trying to get a home run but risking a strikeout, as opposed to someone who swings for contact, hits only singles, but rarely strikes out. No analyst can tell you that swinging for the fences is the wrong thing to do. It’s a function of how risk-tolerant we are as a people…I’m trying to lay bare the choices and illuminate the costs and benefits of them each, and to show where the value judgment lies as a way of facilitate a political debate that I can’t, at the end of the day, resolve about what are our values.”

Kreisler and Biddle were on to something. Strategists are paradoxical. Their job demands they hold onto seemingly contradictory ideas, all at once. 

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In the military sphere, Edward Luttwak has described strategy as having a   paradoxical logic, a counterintuitive endeavor where a good road becomes a bad road because it is a good road (and so the enemy will likely attack there). The business community’s come on board as well, and some even consider a “paradox mindset” the key to success.

The grand-daddy comes from literature. F. Scott Fitzgerald: “The test of a first-rate intelligence is the ability to hold two opposed ideas in mind at the same time and still retain the ability to function.” 

These gems are all over, hidden in plain sight. Stephen Covey’s comment to “begin with the end in mind.” Marc Andreeson’s personal rule to keep “strong opinions, weakly held.” David Ben-Gurion’s statement that, “in Israel, in order to be a realist you must believe in miracles.” Or the lines in Mahatma Gandhi’s 1931 speech: “I can see that in the midst of death life persists, in the midst of untruth truth persists, in the midst of darkness light persists.”

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The wise arm themselves with paradoxical ideas. Why must the strategist?

Strategy is always an orientation toward success in a complex competition against a hostile enemy or a harmful environment. The strategist must always think in constant tension with the adversary, and so must keep “two opposed ideas in mind at the same time,” all the time (in line with Mr. Fitzgerald). It’s never-ending, interactive thinking.

But it’s more than that. There are qualities, temperaments, attitudes, thoughts, ways of being, and they manifest themselves in millions of ways. 

Below are a few of those qualities (42 to be exact), in no particular order, that loosely describe the paradoxical endeavor that defines being a strategist.   

  • The strategist seeks not the end but an edge.

  • The strategist is a loyal rebel.

  • 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 looks equally rearward to history and forward to the future.

  • The strategist cares deeply about ideas but never commits to a single 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 flexibly considers every 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 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 figures and data, but crafts strategy as applied artwork.

  • The strategist knows wars are won in the mind as much as by 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 uses disciplined violence to kill for peace. (military specific)

  • The strategist knows where the bureaucracy ends and the profession begins.

  • The strategist touches the impossible to find possibility’s edge.

  • The strategist knows tradition matters and that some sacred cows must be slaughtered.

  • 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 both the nine staffers regurgitating received conventional wisdom, as well as the crackpot armed with a solid point.

  • 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.

  • When asked to choose A or B, the strategist selects Q, Z, N/A, 43, or nothing at all.

  • 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 you’re already a strategist, or a budding strategist-to-be. 

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“Escalate to deescalate.” (Tagline expressing current Russian nuclear doctrine

“Be polite, be professional, but have a plan to kill everybody you meet.” (Former US defense secretary and retired Marine general James Mattis)

*Editor’s Note:  Readers, thanks for your feedback—next week I’ll finally get after meaningful risk versus calculated risk.

What do you think about today’s topic? Please let me know with a comment, and, if you enjoyed this, forward Strategy Notes on to anyone you think might benefit or find it of interest. Your word-of-mouth mention to another person means everything to this community’s continued growth. 

All the very best & see you next week, Matt