The Unlikely Advocate: On Writing for Your Future Enemy

There’s a piece of advice so common it has become a reflex: know your audience. We’re told to build detailed avatars, to empathize with their desires, to speak directly to their pains and aspirations. The entire architecture of modern writing—from the headline to the call to action—is often built upon this foundation of targeted appeal. But what if this focus on a sympathetic, well-known reader is making our writing smaller, less resilient, and ultimately, less true?

I want to propose a different, more challenging exercise. Instead of writing for an idealized version of your biggest fan, try writing for your future enemy. Write for the person who is primed to misunderstand you, who holds an opposing worldview, who will pick apart your logic with glee. This is not an invitation to write combatively or defensively, but to write with such clarity, fairness, and foresight that your argument can withstand the coldest, most hostile scrutiny. When you write for a friend, you can rely on shared assumptions and goodwill. When you write for an adversary, you are forced to build a stronger case.

This approach fundamentally shifts the editorial craft. It moves you from persuasion through charm to persuasion through intellectual rigor. You can no longer lean on jargon that only your in-group understands. You must define your terms. You cannot rely on emotional appeals that resonate only with the already-converted. You must construct a logical pathway so sound that even someone starting from a different point might find it difficult to dismiss. It forces you to anticipate counterarguments not as annoying obstacles, but as integral parts of your own construction. You are building a pier, and you must account for the tides that will try to tear it down, not just the calm water of a sunny day.

The Alchemy of Antagonism

This practice has a curious alchemical effect on building an audience. Counterintuitively, writing for an enemy often earns you more respect from everyone, including the enemy. It demonstrates a command of your subject that transcends tribal allegiances. It signals confidence. A reader who stumbles upon your work, perhaps even disagreeing with your conclusion, might still recognize the integrity of the process. They may not become a convert, but they may become a thoughtful critic instead of a dismissive troll. This is how you build a durable audience, not a fragile bubble of agreement.

This isn't about courting controversy for its own sake. It’s about embracing a higher standard of communication. The headline crafted for a friend might be a clever wink; the headline vetted by the specter of an enemy must be precise and substantive. The paragraph written for a fan might flow with pleasant assumptions; the paragraph written with a critic in mind is fortified with evidence and nuance. The goal is not to win a fight, but to create something so robust and well-considered that it earns a place in the discourse, even among those who view it with skepticism. In the end, by considering the worst possible reader, you might just create your best possible work.

Notes & further reading

A few pages I came back to while writing this: