There’s a moment in every hard problem where you stop moving. You’ve been staring at it for an hour, or a day, or a week, and the perfect path forward refuses to reveal itself. You want to solve it. You want to see the whole solution laid out clean and complete before you commit to anything. So you wait, and think, and wait some more.
I’ve come to believe this is often a mistake. Sometimes the goal isn’t to solve the problem but rather just to make progress toward an idea. The difference sounds small, but it changes everything about how you work.
When you’re trying to solve something, you’re holding out for certainty. You want the finished answer before you take the first step. When you’re just trying to make progress, you give yourself permission to move before you’re sure. You write the bad first draft. You sketch the rough version. You try the approach you already suspect is wrong, just to see what happens.
Here’s the thing that surprised me the first time I really understood it: action generates information. You learn more from a wrong attempt than from an hour of careful thinking, because the wrong attempt shows you where the real limits are. It reveals the constraints you couldn’t have predicted from mere theory. Pure analysis is smooth and frictionless, and that’s exactly its weakness. It never bumps into anything.
There’s a psychological gift here too. Perfectionism is a quiet kind of paralysis. The pressure to solve, to get it right, to not waste effort, can freeze you completely. Lowering the bar to “just make some progress today” is often the exact thing that gets you unstuck.
A Place to Be Wrong Cheaply
In the Army, we use tabletop exercises for exactly this reason. We walk a plan forward, step by step, so we can clarify the bad ideas and identify the good ones. Nobody has committed anything real yet. No fuel burned, no units moved, no lives risked. The whole point is to generate information before the cost of being wrong gets expensive. You surface the bad ideas in a sand table instead of in the field, which is the only sane place to surface them.
Notice what this does to the perfectionism trap. You don’t sit around waiting for the flawless plan before you talk it through. You put a rough plan on the table specifically so people can attack it, poke holes in it, and find the assumptions nobody questioned. The plan being imperfect is the feature, not the bug. It’s disposable by design. You keep the lessons and throw away the parts that broke.
It also forces you to bump into the walls. You can’t predict every friction point from pure analysis. But when you walk through “then what happens, and then what, and then what,” the step that looked fine in the plan and on the map turns out to depend on a bridge, or a timing window, or a unit that’s already committed somewhere else. You couldn’t have seen that by staring at the objective.
The Harder Discipline
So far this is all about moving. Start before you’re certain. Move in a space cheap enough to reverse. That part is a habit of action, and most people can learn it.
The second part is harder, because it fights against you. You have to make sure you are not so staunch and vested in an idea that you’re unwilling to give it up. And this is especially true if you’ve spent a significant amount of time planning it.
That last part is the real trap. The amount of time you’ve invested should be irrelevant to whether the idea is good. But it isn’t, because the more you’ve poured into something, the more you feel like it costs you to admit it was wrong. So the ideas you’ve spent the most time on are precisely the ones you defend hardest, which is exactly backwards. The effort should buy you knowledge, not loyalty.
It’s sneaky, because it disguises itself as diligence. You tell yourself you understand this idea better than anyone else in the room, and that’s often true. You’ve lived with it. You’ve worked the details. But that same depth becomes the reason you can’t see it clearly anymore. You’re no longer evaluating the idea. You’re defending your investment in it.
This is where the tabletop exercise earns its keep in a way that goes beyond finding good and bad plans. It makes it safe to kill your own idea. When the whole point is to walk plans forward and let people attack them, abandoning a plan stops being a personal failure and becomes the expected outcome. You built it knowing some of it would die. That framing gives people permission to let go, and permission is usually what’s missing. Most people don’t cling to bad ideas because they can’t see the flaws, they cling because giving up feels like losing.
Initiating Movement
So the discipline has three parts, and they build on each other.
Start moving before you’re sure. Initiate movement, because certainty rarely arrives on its own. Move in a space cheap enough to reverse, whether that’s a rough draft or a plan walked forward on a table. And hold the whole thing loosely enough that the time you spent becomes a lesson instead of a leash.
Most of the time, the problem that feels impossible isn’t waiting for a flash of insight. It’s waiting for you to start, to make one imperfect move, and then another, until the shape of the real answer finally comes into view. The trick is to keep walking forward without falling in love with any single step, so that when the ground shifts, you’re still free to change direction.
