Losing and Pure Punishment

Winning

I want to talk about winning. A lot of games, whether they be competitive or single-player, really prioritize winning. That feels natural; given a challenge, something in which you can win or lose, winning is the intended completion of that challenge. Failure has to be a part of that, though. If you only ever win in a challenge-based game, it's not typically very engaging. What is the role of failure, though? Is it just what you're trying to avoid? Is it a punishment? Does it have to be a strictly negative event? Maybe by better understanding the role of failure, designers can learn how to design more fulfilling games.

Punishment

To start, consider games with very clear win/loss conditions. If you fall in Mario, you lose. You start that level over, and any points you achieved, items you collected, etc. are gone. The game's only recognition of your previous journey through that level is the life you lost from it. The rest is lost to time. In this context, failure is, mechanically, solely a punishment. Conceivably, you've learned more about the level and the game. Through your experience, you've gotten better, and you apply that increased skill in the level again to perhaps come out victorious. The game doesn't measure that progress, though. It doesn't tell you that you've gotten any better. Mario uses failure as negative reinforcement: without it, winning would be meaningless, but it's meant to be avoided.

Many other games, like RPGs, won't mechanically punish you for failure, but only take your time. When you fail, that failure is not a part of your character's story, and it's only vaguely a part of yours, as a player. Suppose you're playing Final Fantasy. You fight through a dungeon to face a boss and reap your treasure. You fall in battle against that boss. You return to the title screen. You reload your save file. Everything that happened between this saved state and when you fell in battle is erased from history. Like Mario, the only difference is you, your skill. You'll play things differently this time, certainly. You know more about the enemies, and you can learn from those mistakes. 
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However, this pushes the player toward certain behaviors. Failure is purely a punishment, so you want to avoid it. There's a particular method in RPGs that helps with that: grinding. Frequently pointed to as a signifier of poorly balanced RPGs, grinding is when you perform a simple, easily achievable task repeatedly in order to make your characters numerically stronger. Grinding is antithetical to the entire point of the game, since an RPG's systems are entirely an exercise in resource management. If you simply dump tons of resources in your favor, there isn't much management to do. 
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Avoiding failure doesn't sound unexpected. Obviously, I'm going to try not to fall while playing Mario, because that's how I proceed to more content. However, if the game handed me a pair of wings that made losing almost impossible while simultaneously telling me to avoid failure at all costs, I'd probably take those wings. Games that even include grinding encourage grinding, because of how it affects one certain resource, time. The game is going to take your time either way. If you don't grind and then fall in battle, you've lost time and gained nothing. If you spend time grinding, you've lost time, but gained power.

Bask in my extremely detailed info-graphic.

Good Losing?

Not all games treat failure as a shameful event to be forgotten, however. Dungeons & Dragons gives essentially ultimate narrative freedom. Most game masters do not rewind time as video games do. If the players fail, time simply moves on. The story does not have to end, even if it means creating new characters to replace fallen ones. The game master can weave that failure into the fabric of the story. It's not even necessarily a bad thing. It could be tragic, but it can also mark new beginnings. It can be comical. It can be so spectacular a failure that you tell the story for years to come. This treatment of failure makes gameplay focus on the journey, not the destination. 

When failure isn't only a punishment, we tend to take greater risks. We focus more on our journey. A D&D player may choose a suboptimal, even downright destructive action in a given moment because it makes sense for their character in context. "In a fit of rage, my player disregards the party's request to keep our hostage alive and fires a crossbow bolt!" This decision is flawed, it's controversial, but it puts less pressure on winning. It's authentic to the story and the journey.

While D&D allows near infinite freedom with which to handle unexpected failures, digital games don't typically have that luxury. In a digital game, content is (mostly) finite, but can they still acknowledge your failures in a constructive way? Roguelike games, like Risk of Rain, are all-or-nothing in design. If you fail, you must start the entire game over, without any checkpoints. However, Risk of Rain recognizes everything you'd done. During gameplay, you can find and complete puzzles to unlock new characters. Even if you die immediately after, that new character remains unlocked. Ironically, in a game without checkpoints, failure is a relatively minor punishment. 
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How else can games weave failure into your story, rather than simply encourage a power fantasy where failure never happens? I think it's an important question to ask, because how we represent ourselves in games reflects how we represent ourselves in real life. A depiction of failure as so shameful it's not worth remembering is unhealthy. Failure is normal. In life, it's unavoidable. Maybe it shouldn't be rewarded, but we could do more to treat it less like the end of the world.

Want to Argue?

If you have any counterpoints, additional points, tangents, or other notable examples related to the topic of winning and games, come fight me on Twitter @kiefjerky. I'd love to hear other designers' and players' perspectives on the matter. (You don't actually have to fight me, it can be a kind exchange.)