How to Play Chess Against Yourself (and Learn)

Playing both sides teaches planning better than any puzzle — because you build the losing side yourself and finally feel why it loses. Here's how I do it.

I used to think playing both sides of a board was a party trick. Something you did on a train, moving one white piece, spinning the board in your head, moving one black piece back, keeping yourself company.

Then I noticed it was teaching me something a puzzle never had. When you play against yourself and you mean it, you're forced to argue against your own plan instead of only defending it. That's the whole thing. That's why it works.

Most of us learn planning backwards. We build an idea, we fall in love with it, and we defend it against imaginary weak resistance. Play both sides honestly and the resistance stops being imaginary. You have to find your own plan's worst enemy, because you're the one sitting in its chair.

Why I still play both sides of the board

A puzzle hands you a position and a question: white to move and win. You already know a win exists. Your job is to locate it. That's a real skill, but it's a narrow one, and it trains the wrong muscle for planning.

Planning isn't about finding the one move that wins. It's about carrying an idea across ten moves while someone actively tries to break it. Nobody hands you the losing side of that fight. You have to build it yourself.

When I play both colors, I build the losing side with real care. I look for black's best try the way black would, not the way white hopes black will. And somewhere in that, I finally understand why a plan loses — not as a fact I memorized, but as a pressure I felt.

If you're newer to this and the whole idea of "a plan" feels vague, your first game plan is a gentler place to start than a full solo game.

The Endgame Journal collects our writing on openings, tactics, endgames, and the habits that separate players who improve from players who plateau. Every article is written by people who teach chess, not by a content farm.

How to Play Chess Against Yourself (and Learn) | Endgame Society