On the Risk of Fighting on a Battlefield You Cannot Win — Courage Charges In, Strategy Chooses the Ground

Part One asked what a business stands on. Vision, money, contact points, fortune — things that look like foundations but can’t hold a business up for long. In Part Two the question changes. Once you’ve found ground to stand on, how do you lead the organization from there?

The first of those questions concerns the earliest decision a leader makes: where to fight. In the previous post we looked at the risk of mistaking growth the market lifted for capability of your own. So where, exactly, do luck and capability each sit? That’s where this post begins.

The Organization That Grinds It Out on Unwinnable Ground

For a founder, grit is a virtue. The experience of forcing impossible things to work is what built today’s company, so most founders believe that the sheer volume of effort ultimately produces the result. But when that belief is aimed at the wrong target, the same virtue becomes what wears an organization down.

There’s a familiar scene. A company charges head-on into a market where a dominant player has already entrenched itself, trying to close the gap with more marketing spend and longer hours. Or it pushes harder in a category where demand itself is structurally drying up, convinced the problem isn’t the market but its own execution. In these moments the organization is unmistakably working hard, and the founder has every reason to be proud of the effort. The trouble is that the effort is being spent on ground that was never designed to be won. This is the courage of the common man — brave enough to charge in, but never asking where.

The Romans Did Not Postpone Their Wars

In The Prince, Machiavelli reports the Roman way like this: the Romans never postponed a war to avoid a conflict in front of them. They knew that a war is not avoided but only deferred, and that the side which benefits from the delay is always the other one. So the Romans chose to fight at a time and on ground favorable to themselves, before things could turn against them.

The point here isn’t that the Romans were unafraid to fight. It’s that they chose when and where they would fight. Being brave and fighting anywhere are not the same thing. Roman strength lay not in the grit of never backing down, but in the judgment that pulled the conditions of the fight over to their own side.

The Battlefield Is Set by Luck; the Fight Is Waged by Skill

There’s a saying: seven parts luck, three parts skill. Read as fatalism, it leaves you with nothing to do. But once you separate where the luck sits from where the skill sits, the same saying turns into practical guidance.

Which battlefield you end up on — which market opens, whether that market’s structure favors a newcomer, whether the timing lines up — is largely a matter of luck. No amount of striving lets a founder conjure demand that isn’t there or overturn a market structure that has already set. How you fight once you’re on that battlefield, though — what you concentrate resources on, in what order you move, where you pull back — is a matter of skill. This is where capability actually does its work.

Two postures split apart at this distinction. The courage of the common man pours skill into a losing battlefield. Believing that structurally unfavorable ground can be overturned by effort, it feeds its most precious resources — time and people — into a fight it cannot win. Cold strategy moves the other way. It first works out, without flinching, which battlefield is one that can be won, and then concentrates its skill there. The same skill vanishes without a trace on a losing battlefield and becomes the decisive difference on a winning one.

How to Recognize a Battlefield You Can Win

So how do you tell a winnable battlefield from a losing one? A few questions help.

First, is this market’s structure on your side or not? Does this market have examples of a latecomer overturning an incumbent, or is it one where the order, once set, rarely changes? In a market where network effects or switching costs already run strong, structure protects your rival no matter how well you play. Second, does the variable that decides the fight overlap with what you happen to be especially good at? If the ability that matters most for winning this market is precisely your strength, the ground is favorable; if your weak spot is where the fight is decided, it isn’t. Third, is the fight decided by the sheer volume of effort, or by structure? Some fights you win by working harder — but in others, structure has already fixed the outcome no matter how hard you work.

Answer these honestly and it becomes clear whether the ground you’re standing on is a battlefield that effort can open, or one you should have chosen differently from the start. A sobering answer doesn’t mean you did something wrong; a large share of choosing the battlefield was luck to begin with. But the moment you avoid that answer, it becomes entirely the leader’s responsibility.

A Retreat Is Not a Defeat

None of this means you should avoid every hard fight. Every good battlefield looks difficult at first, and the easy ground usually already has a crowd on it. The point is to distinguish the kinds of difficulty. Difficulty you can clear through execution is not the same as difficulty manufactured by structure. The former is something to fight with skill; the latter is a signal to move the battlefield.

That’s why strategy includes retreat and repositioning. In startups we usually call it a pivot. Pulling out of a losing battlefield to move onto one you can win comes not from a lack of grit but from knowing where to spend it. Just as the Romans chose a favorable moment to fight, a leader chooses ground that can be won and gathers the organization’s strength there. Courage charges in; strategy chooses.

Once you’ve chosen the battlefield, the next question is how to get people to move on it. The next post takes up the difference between leading an organization and dominating it — why, when a leader extracts obedience through the power of the office, that organization moves only while the leader is watching.