The life of a planner is far from glamorous. Despite the endless comparisons to the Jedi Knights, the reality is often closer to rescuing Princess Leia from the garbage compactor on the first Death Star than meeting in the Jedi Temple on Coruscant. It has its moments, but more often than not, you feel like your days—and nights, in many cases—are spent chained to Jabba the Hutt on his sail barge. After a while, the obscure references to Star Wars are as inescapable as the cold Domino’s Pizza and stale coffee. They define your very existence as a planner, as well as the life you lead.
BANISHED TO THE OUTER RIM
The allusions to Jedi Knights aside, I never hesitated for a moment when offered the opportunity to serve as a planner. I’m a problem solver at heart, and a planning assignment presented a chance to test that ability. A lot. After a year as a division-level planner in the wake of the attacks of 9/11, I joked that I had planned operations in 42 countries on three separate continents. Except it wasn’t a joke. And it was 47 countries on four continents. Gallows humor is, after all, a survival mechanism.
During that year, there were plenty of times I felt like a Jedi Knight. A Jedi Knight fighting for survival after Darth Sidious directed the execution of Order 66. That’s pretty much the norm for a year spent underground cranking out one plan after another, or multiple iterations of the same plan. All the while, those inescapable Star Wars references circulated like “Bye, Felicia” memes on Facebook. They were everywhere, from the first day on the job to the last.
WELCOME TO THE DARK SIDE
The memories of that first day as a planner are seared into my brain like a homemade brand: the sights, the sounds, the burning pain. Descending the narrow, dimly lit concrete stairs that led to the SCIF—Sensitive Compartmented Information Facility I stepped into a cavernous room filled with strange faces that looked back at me with a combination of indifference and disdain. It was like walking into the Mos Eisley cantina. The only thing missing was the cranky bartender.
1. “You will never find a more wretched hive of scum and villainy.”
From the persistent musty odor of the damp concrete walls to the weird specialist who screamed “RED BADGE!” at anyone who didn’t have a top-secret clearance, the SCIF—was as welcoming as a frontier settlement on Tatooine. As a new planner, you learned two quick lessons: one, never leave anything on your desk that you didn’t want to have “repatriated” by the Sand People (non-planners) and two, avoid engaging with people who spend most of their days staring into a computer monitor.
2. “No, I am your father.”
Forget what the Chief of Staff says, you work for the commander. If push comes to shove, set out some interesting picture books to keep the Chief of Staff occupied. Crayons are optional, of course.
3. “Never tell me the odds.”
This is the Star Wars equivalent to “This ain’t my first rodeo.” Any halfway decent planner possesses an innate sense of the viability of a course of action—what will work, what won’t, and why. While going to the trouble of conducting comparative analysis of several courses of action might seem necessary to some, a seasoned planner will want to skip to wargaming and, even then, will only want to test the critical pieces of the plan.
4. “You must unlearn what you have learned.”
No matter how much effort you expend on course of action analysis and wargaming, the commanding general will come up with their own course of action. With that knowledge in hand, make some fresh coffee, order a pizza, and create one really good course of action. Then, when the commanding general asks why you only have one course of action, tell them that their time is too important to waste on throwaway courses of action. It works. Trust me.
5. “I’ve got a bad feeling about this.”
It’s always darkest before the dawn. The same holds true for a plans briefing—the moments leading up to it are always the most stressful. That’s when you learn that no one saved the slides you’ve been working on for the past two days, someone decided to add a lot of animation that makes printing the slides an exercise in futility, or the intelligence planner arrives with an “updated” set of slides in a completely different format 30 seconds before the briefing is scheduled to start. Then you upload the briefing onto a new laptop only to learn that it needs a full Windows update to operate.
6. “It’s a trap.”
There’s nothing more dangerous than a quiet higher headquarters. Anytime planning is going really well, someone is about to unleash a Crazy Ivan—something so unexpected that it will relegate all your work to that point to the burn barrel. When your higher headquarters goes quiet, don’t bask in the silence. Call them before it’s too late.
7. “These aren’t the droids you’re looking for.”
Any plan is only as good as the buy-in you get from the subordinate organizations that have to execute that plan. Getting that buy-in is almost wholly dependent on the reliability of liaisons. And there’s one immutable fact about liaisons: like the keys to an old underground storage bunker, you can only find them when you’re not looking for them.
8. “I’m here to put you back on schedule.”
If there is one truism to planning, it’s that the commanding general will always arrive sooner than you expect. Worse yet, no one will give you any advance warning. None. And, if that isn’t bad enough, the weird specialist next to SCIF entrance will let out a blood-curdling, serial killer in the house scream the moment the commanding general is within sight.
9. “Fear is the path to the dark side. Fear leads to anger; anger leads to hate; hate leads to suffering. I sense much fear in you.”
Senior leaders are like dogs—they smell fear. Everybody gets a little nervous when they brief the boss. Just don’t allow that nervousness to ruin a good briefing.
10. “Do… or do not. There is no try.”
You’re going to earn your pay as a planner. Long hours are the norm, free nights are a luxury, and weekends are the stuff of fantasy. That cold pizza and stale coffee is what’s going to fuel your efforts, so get used to them. Maybe if you’re lucky someone will sneak some Starbucks past the screaming specialist once in a while. You can always hope.
A New Hope
In the years that followed, the wisdom of Yoda came to define existence as a planner: “Action. Excitement. A Jedi craves not these things.” The planner life lies somewhere on the spectrum between serving on a Roman trireme (“Row well and live.”) and an Imperial star destroyer (“I find your lack of faith disturbing.”). You spend your days in a desperate search for the exhaust port on the Death Star, hoping against hope that the force will be with you.
