How to Play Chess Against Yourself (and Learn)

Playing both sides only works if you switch off your own plan. The board-turning trick I use to stay honest against myself at 1am — and what it can't teach.

It's 1am and nobody I want to play is online. The board is still set up from earlier. So I do the thing everyone half-knows how to do and half-suspects is pointless: I play myself.

The honest answer to how you play chess against yourself is that you make a move for White, then walk around the table, sit down, and make a move for Black. Simple. What nobody tells you is that the simple version teaches you almost nothing. You already know what White wanted. So when you sit down as Black, you're not defending — you're reading the ending of a book you wrote ten seconds ago.

That's the whole problem, and getting past it is the whole point.

Why I still play both sides at my own kitchen table

I keep coming back to solo chess for the same reason I sketch when there's no one to dress: I want to keep my hands moving. Playing a single player game against yourself isn't a substitute for a real opponent. It's closer to running scales. You feel out a structure, you test a move order, you watch what a plan actually looks like when it has to survive four more moves.

And it's free of stakes. When I'm the only one at the board, I'll try the sacrifice I'd never risk against a person. I'll push the pawn I'm not sure about and see what falls apart. That freedom is the gift of playing yourself. The curse is sitting right next to it.

The one problem with playing yourself, and how I get around it

Here is the curse: you cannot surprise yourself. When I set a trap as White, Black sees it coming, because Black is me and I just set it. So I sidestep it, and White never gets to learn whether the trap would have worked. I've rehearsed a script where both actors know the ending. That is not a game. It's a read-through.

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