“The enemy of a good plan is the dream of a perfect plan.” – Carl von Clausewitz

It was, without a doubt, the longest single year in my career. It began with the chief of staff derisively referring to his new planners as “Clausewitz” while subsequently informing us that we would all receive center of mass evaluations because he had no room in his profile for us. All the while, we were expected to remain focused, motivated, and provide the type of analysis and thinking expected by our near-legendary division commander. After a year in purgatory as a planner, I added a cynical comment to my Officer Evaluation Report Support Form: “Planned the invasion of 42 countries on three separate continents.” The comment was only half in jest – it was actually 47.

It was a long year.

The year began with a series of planning conferences for the annual Korean theater exercise Ulchi Focus Lens, rolled into the terrorist attacks of 9/11 and the deployment of the first conventional forces into Afghanistan, mounted a false summit with a division warfighter exercise, reached a crescendo with the initial planning for the invasion of Iraq, and finished with another summer of conferences for Ulchi Focus Lens. Between the peaks and valleys, there were any number of “what if” drills that involved detailed plans for everything from anti-piracy efforts along the coast of Somalia to operations deep into the heart of regions unfriendly and inhospitable.

Yeah, it was a long year. A very, very long year.

Looking back, I can see now that it was an unparalleled learning experience. Everything we discussed in the School of Advanced Military Studies proved true. The hours spent with Sun Tzu, Thucydides, Clausewitz, Corbett, and Douhet were reflected again and again in our work. We became masters of our craft, journeymen in the operational art of war. We earned the title “Jedi Knights,” first bestowed upon our predecessors during the Gulf War.

Along the way, I found the dry sarcasm and gallows humor common to planners. Let’s face it: a year locked in the basement of a secure facility will do that to you. That, and not seeing the sun. PX pizza, leftover bags of Cheetos, stale coffee, Girl Scout cookies sold during the Reagan Administration. The glamorous life of a war planner is anything but. Those long days – and longer nights – also produced planning “truisms.” Not exactly the type you would find in On War, but something more reminiscent of “Murphy’s Law.”

It was a very, very long year. But I learned more than I could have imagined:

  1. Friends may come and go, but enemies accumulate: Everything comes down to how you seal the deal. Inside the beltway, the people in expensive suits call it “conflict termination.” We call it “imposing your will on the enemy.” If you don’t break the will of other guy, you’re going to have to fight him again. And again. And again.
  2. Nothing spurs adaptability like a genuine lack of planning: Your plan won’t survive first contact. No plan does. Planning is like yoga: the greater the flexibility, the better. The more time you spend building excessive detail into a plan, the less time you have to think through the problem, and the more pain you impose on your subordinate headquarters. Sometimes, commander’s intent, planning guidance, and a clear mission statement is enough to get the ball moving.
  3. The facts, while interesting, are irrelevant: It’s not what you know that matters, it’s what you don’t know. And it’s what you don’t know that tends to get people killed. Let the battle staff sweat the detailed lists of facts and assumptions. Spend that time playing “Battlefield Clue” with the enemy’s possible courses of action. What do they know that you don’t? What do they see that you can’t? What do you have that they want?
  4. The effective delivery of terror is a form of strategic communication: This is something our enemies tend to understand far better than us. The violent execution of a plan will send a message your enemy will recognize and respect: “Be afraid, be very afraid.” Fear is the expressway to human will. If you want to break the will of your opponent, instill fear so deeply into their psyche that the mention of your forces results in an uncontrollable nervous twitch.
  5. All things being equal, hashtags look like waffles: Senior leaders love to wax eloquently about “reducing footprint” or “cutting tooth-to-tail.” Ignore them. Whatever you’re planning for sustainment requirements probably needs to be doubled. Once the balloon goes up, the logisticians determine how fast, how far, and for how long the fight can continue. You can’t afford to be cheap when hot steel is flying.
  6. Planning assumptions are an admission that you really don’t know what’s going on: The more assumptions you list, the more clueless you appear. If you’re that short on facts, you’ve got problems. Big problems.
  7. One decent course of action is better than three crappy ones: Use the extra time you spend developing (and wargaming) throwaway courses of action to build flexibility into one really good plan. Provide a menu of options. Use some originality. Think outside the box. Bring the heat in ways no one expects.
  8. There is always one more idiot in the group than you planned for: When developing your epic plan, keep in mind Occam’s razor. The more complicated the plan, the more likely Murphy’s Law will strike. Part of assessing the risk in a plan is gauging the likelihood someone will pivot right when you’re executing a left hook or cross the line of departure at 1700 instead of 0500. When all else fails, remember that simplicity is a principle of war.
  9. Those who live by the sword tend to get shot by those who don’t: Never forget the Powell Doctrine. If you’re in, go all in. Leave the soft skills for actions on the objective. Your enemies won’t cut you any slack, so anything less than overwhelming force is a recipe for failure. See #1 and #4.
  10. No plan is sufficiently foolproof when executed by the right fool: In the hands of the right fool, even the best plan can fail. Always remember who you’re developing the plan for, and how they’ll execute it. The time to admit that someone has been promoted above their ability is not AFTER you hand them your brilliant plan.

A long year? Sure, but worth every minute of it.


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Steve Leonard is a former senior military strategist and the creative force behind the defense microblog, Doctrine Man!!. A career writer and speaker with a passion for developing and mentoring the next generation of thought leaders, he is a senior fellow at the Modern War Institute; the co-founder of the national security blog, Divergent Options, and the podcast, The Smell of Victory; co-founder and former board member of the Military Writers Guild; and a member of the editorial review board of the Arthur D. Simons Center’s Interagency Journal. He is the author of five books, numerous professional articles, countless blog posts, and is a prolific military cartoonist.