If You’re Rolling Then You’ve Already Lost: Imagination and Randomization in TTRPGs

A knight fights a skeleton in a woodcut.

I was reading a thread on Reddit and someone referenced an idea that made quite an impression on me.

I’ve run into an idea in PbtA [Powered by the Apocalypse] games where characters can get XP or progress towards stat increases when they fail a roll. … On the other hand, it goes against the OSR idea that “if you’re rolling you’ve already lost”—it doesn’t reward problem solving that avoids rolls.

– u/chocolatedessert on r/osr

“If you’re rolling you’ve already lost.” I’ve been thinking this way for decades, but I’ve never seen it put into words.

In PbtA games, there’s a mechanic where characters can gain XP or progress towards stat increases when they fail a roll. This makes sense, especially with stats. Failing to lift a large stone is still exercise, and still works towards giving you bigger muscles. Failing to solve a puzzle is a workout for your mind that you might learn from. It also works for experience—losing a fight can make you a better fighter later on. Failure is experience, a part of character development.

This also encourages the players to take risks. They know that even if they fail, they’ll get something out of it. And risk taking is, at the very least, entertaining.

In old school and OSR games, there is often an incentive to avoid rolling the dice altogether. Rolling is an abrogation of control, a decision to leave things to fate. One could always fumble or critically miss. A great idea can go wrong. This isn’t a flaw—the world often works this way. But players, who care about their characters, can see it as a risk not worth taking.

Rolling for combat and actions is unavoidable, even desirable, in an RPG. But the best players find ways to creatively avoid rolling—not avoiding taking chances, because they don’t know how I’m going to rule, but avoiding the cold, hard contingency of an unlikely die roll and instead trying to convince me they’re being clever and entertaining. (In my games, any really good, entertaining, or funny idea tends to automatically work, even if I pretend to roll the dice. This isn’t a hard rule, it’s a tendency—and I have to like the idea quite a bit.)

TTRPGs are, amongst many other things, puzzle solving games. In real life, you can solve a puzzle box, or you can smash it. But smashing it can fail, or damage the contents. In a game, you can brute force your way out of a situation, or you can finesse it. And if the latter is an option, it’s usually the better one.

When players overcome a challenge without resorting to die rolls, it feels like a significant achievement. It demonstrates their ability to think outside the box, and to use their characters’ skills and abilities in innovative ways. This kind of problem-solving allows players to engage with the game world on a deeper level, and feel a sense of accomplishment that goes beyond simply rolling a high number on a die.

Rolling well on dice does not make you a good player. (I have known people who played old school D&D who thought it did!) Successful strategy, and well-chosen tactics, make you a good player (as well as improvisational ability, cunning, and humor).

I shouldn’t have to say that a well-run game combines both clever thinking and some randomization. But while TTRPGs like D&D evolved from wargaming, they are not wargaming. They are not games of numbers and calculations and rulers. They are games of imagination. And in the end, experience should be awarded for imagination, and not so much for rolling well.

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