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I love this thread. I love risk-taking players. I love thinking about how to make people more comfortable with risk. I have a buncha thoughts, but I feel like @Tat and @Sockmonkey drilled into the heart of the problem, at least as I see it.
I honestly think at the end of the day this comes down to you (and your storytellers) knowing your players and your game, and understanding how to engage with that. That's going to look wildly different, depending on the game you're talking about -- not even just the TYPE of game, but the specific game. Because so much of a game's culture, IC and OOC, is the product of its community of individuals, and I feel like the culture of the game will always define expectations and tone, and therefore how things happen in practice. And it's cyclic, too. Your players generate your game's culture, which defines what kind of players like your game, and etc.
It's almost impossible to make a system that works for everybody when it comes to motivation. @Faraday and I have talked about this elsewhere, but: everybody rps for different reasons. What people get out of RP, what they find satisfying, it's always spread across a wide spectrum. You can lump people into broad categories like 'story-driven' or 'system-driven' in an effort to figure out how to create incentive for them, but that seems inadequate to me. There are self-motivated story-driven players and people who don't generate plot. Of those self-motivated players there are people who like (for instance) grey ethical areas of rp, and people who do not. Of the people who like grey ethical rp, some (like me) love to be surprised by curveballs in story, while others (like some dear friends of mine) are a little uncomfortable with that, and might actually be nervous having that come at them from a staff direction in particular. So not only can you not say, broadly and without thinking about an individual's interests, 'I'm going to reward risk-taking and failure by giving more story to story-driven players' -- because you've got some players who are more into running their own stuff than being GM'd for, or who may not share your interests in types of story -- you may actively deter some of them. And you've still got players who aren't going to be motivated by story, anyway, particularly if you have a crunchy stat/combat system. Probably that'll be true even if it's as lightweight and RP-supporting as FS3.
I think my main quibble in the thread is that I really don't like the idea that success ought to be paired with a negative consequence. I think the idea is actually really intriguing and fresh as a mechanical concept, but as a storyteller it feels a bit skeevy and railroady to me. Ideally, a storyteller's job is to make an arc challenging, presenting players with problems to solve en route to some desirable end. That challenge is what makes the victory (if it comes) satisfying for the players in the first place, so those things are the price of success and they're already built in to the story. Sometimes there are more, when the victory is not unqualified. Often, even. But it's not assumed. A good storyteller is already thinking about the players involved, their unique preferences, and the kinds of hurdles that will be interesting for them, so tacking on a victory tax or making it impossible to succeed without some additional penalty feels weird and forced to me. The karma system @Seraphim73 suggested -- credit from past failures permitting future victories -- cushions that a little and it's a good thought, but still feels artificial for me personally, and shifts things on-balance toward being a mechanic. ('I haven't had a lot of time to play lately, and I don't have a failure-generated point to use for a victory, so I just decide, hey -- I'm not gonna get involved in this plot that's happening while I'm actually around and able to play, because I would want to lead the charge and I know I can't, so I'll just save this point for later.')
Players come up with surprising, creative ways to beat the odds all the time, and I feel like storytellers should respect that when it happens. You don't want your risk-averse players to feel like they can never win at anything because they don't want to gamble in order to do that -- plus, you wind up in a situation where you now have to incentivize them to eat the cost of succeeding, whenever that's not enough on its own. You don't want your bold players to know, going into something, that there's a going exchange rate on success, and that they're going to have to buy a win somehow. And for players like me, who like to be surprised by organic developments in RP and are already not risk-averse, it kinda saps all of the interest for me -- this thought that I know something bad is going to happen because something good is going to happen. Or that something good can't happen unless something bad already did.
None of this accounts for PRPs, either, if you want people to run those. Do your player GMs now have to figure out a way to tax success? Should there be limits to what they require people to sacrifice..?
I'm way more about incentivizing the behavior you WANT to see, and I love this thread so hard for making that a subject of conversation, especially when it comes to players being comfortable with failure. I just think how you wind up doing that is going to depend on the players you have, and trying to build a specific model, while it's interesting as an exercise, is probably not possible. It's still hugely useful to think about, granted, because your preferences there (do you want to reward with story, xp, karma, some combination of the above?) are probably going to play a big part in defining what kind of game culture you try to create.
There was an exchange early in the thread with @Ganymede and @Faraday about whether or how it's possible to make failure more appealing than success. I think it's true you can't do that for every player with one system...and you'll probably get a player or two whose needs you're not willing to cater to. All you can do is try to curate a game culture that draws/retains players with what you feel is a reasonable threshold of willingness to take risks when you offer them 'x' kind of incentive, and the others will just kinda weed themselves out. Then you stay consistent, and with time and experiences that don't leave people feeling burned, I think they gradually acclimate. But if you have a game, particularly a small game, where the bulk of players don't care about the incentive you want to offer them and you just try to ram that into practice, it's never going to work. It has to start as something based on what you have, and move toward being what you want to have.