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"We'll See"

How to play the long game

Jeff Bogdan's avatar
Jeff Bogdan
Apr 13, 2026
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Boy and horse discovery

I’m going to attempt to reference a political movie without making this a political post. Wish me luck. While the connections from this movie and the current Middle East events are obvious, I assure you that is not the motivation behind this post.

In Charlie Wilson’s War1, Gust Avrakotos is a CIA agent who partners with Charlie Wilson, a US Congressman representing Texas. The movie details how a small group of individuals in various circles join forces and leverage their influence to fund rebels who are fighting the Soviet army in Afghanistan in the early 80s. The final scene in the movie is at a party celebrating the rebels’ success in driving the Soviets out of their land. The movie closes with a private exchange between Charlie and Gust out on the balcony.

Gust: “Do you know the story about the Zen master and the little boy? …
There’s a little boy, and on his 14th birthday he gets a horse, and everyone in the village says,
‘How wonderful, the boy got a horse.’
And the Zen master says, ‘We’ll see.’
Two years later the boy falls off the horse and breaks his leg, and everyone in the village says, ‘How terrible.’
Then the Zen master says, ‘We’ll see.’
Then a war breaks out and all the young men have to go off to fight but the boy can’t because his leg’s all messed up, and everyone in the village says, ‘How wonderful.’”
Charlie: “Then the Zen master says, ‘We’ll see.’”
Gust: “So you get it.”
Charlie: “No … ‘cuz I’m stupid.”
Gust: “You’re not stupid, you’re just in Congress.”
Charlie: “Send ‘em money?”
Gust: “You’re gonna start with the roads, move on to the schools, factories. Restock the sheep herds, give ‘em jobs. Give ‘em hope.”
Charlie: “I’m trying.”
Gust: “Yeah well try harder.”
Charlie: “I’m fightin’ for every dollar. I took you from 5 million to a billion. I got a Democratic Congress in lock step behind a Republican president.”
Gust: “Well that’s not good enough, because I’m gonna hand you a covert classified NIA right now and it’s gonna tell you that the crazies have started rolling into Kandahar like it’s a f*cking bathtub drain.”
Charlie: “Jesus Gust, you could depress a bride on her wedding day.”
Gust: “Hey, listen to what I’m telling you.”
Charlie: “You did a hell of a job for the son of a soda pop maker.”
Gust: “We’ll see … Said the Zen master.”

This is great story about the importance of playing the long game2. Gust has been steadily raising Charlie’s awareness3 on the situation in Afghanistan. And at a moment when it seems that their work is done, Gust tries to create yet another moment of insight by telling the Zen master story.

You have certainly experienced your own Charlie moment, where you think your work is done, only to find that, as Gust says, it’s not good enough. The more complex the mission, the more likely you’re going to encounter this phase, perhaps even repeatedly, during the execution. This is the benefit of the iterative planning approach, where you keep yourself open to the suprises to come.

Let’s explore the components to a successful extended mission.

  • Define long-term success

  • Establish an initial best guess plan

  • Follow-up: Course correct regularly

  • Follow-through: Keep your eye on the prize and drive success

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