Planning vs Iteration
Every time I've walked into a quarterly or annual planning cycle, I've heard some version of the same pushback: "We're agile. Don't we only need to plan the current sprint?"
Contrary to that instinct, I've found that the question isn't whether to plan — it's what kind of goal you're planning toward.
The skateboard metaphor is one of the most useful things agile gave us. Instead of building a wheel, then a frame, then an engine, then a car, you build a skateboard: something that works now, even if it isn't the final thing. You iterate from there. Skateboard to scooter to bicycle to motorcycle to car. At every step, you have something functional. At every step, you can course-correct.
It's a good metaphor. For a specific kind of goal.
There are two types of goals here, and the skateboard metaphor only works for one of them. "Go faster" is the first type. Every iteration optimizes for "moves efficiently." The decisions are locally reasonable at each step. You might end up with a car. You might end up with a boat. Both are coherent answers to that question.
But what if your goal is "get to the moon"? That's an entirely different type of goal. You might be able to iterate from a skateboard to a rocket. But without longer-term planning, you're just as likely to end up with a submarine.
Some goals require planning. Not instead of iteration, but to give it direction. A longer-term plan tells you what to optimize for at each sprint, and that's rarely the same thing at every stage. You might be proving a concept in month one and building for reliability in month six. Without that plan, every sprint defaults to optimizing for whatever feels most urgent. Agile is a method for how you build, not a substitute for deciding what you're building or why. "We're agile" is not a strategy. And it's not an excuse for skipping the work of figuring out where you're actually trying to go.
The teams I've seen struggle most with this aren't the ones who iterate too slowly. They're the ones who iterate confidently in the wrong direction, sprint after sprint, because no one ever pointed at the moon.
