Game success, life failure
As was noted a few columns back, there's a disconnect between the arc of character progress and the arc that most roleplaying chracters follow. Your character keeps gaining levels, power, prestige, what-have-you... but personal problems keep accumulating, and quite often, keep getting worse. So how do you keep your character from feeling like failure incarnate?
Well, that's part of the answer right there. Clearly, if in game terms you're at the apex of your power, it's hard to argue that you can't do anything right. On the one hand, this might seem like it would undercut the carefully crafted setbacks you're putting in your character's path. The issue is that failure is less of a boolean operation. Having a level 85 Shaman sporting top-end gear and the adulation of every nation in the game doesn't matter if all she wants to do is find someone who loves her back. As long as she can't achieve that goal, she's going to feel fairly helpless, even amidst all of her other successes. She keeps succeeding at important tasks, but not the ones that personally drive her.
Now, even in this situation, someone with a constantly ruined personal life is going to eventually get a tad tedious. But at least it gives you a point to start with. A character's life can still be full of failures while also being full of successes; even if the character doesn't necessarily see the balance herself, others very well may. (There's nothing like having someone else be jealous of your character's prowess in combat when she herself actively dislikes it.)
The half-life of failures
If there's a single reason players (and people in general) get bored to tears of the perpetually gloomy character, it's probably less a matter of failure and more a matter of complaining while nothing changes. The character who's lovelorn just sits and whines about how much he wishes that character X returned his affection. The character who wants to be rich sits and whines about her lack of money. And yet these characters keep making the same mistakes, the same choices, and so after a while it starts getting searingly annoying.
Of course you're still going to be poor if you keep blowing your money on trinkets. Of course she's not going to date you if you just sit around and mope and make saucer eyes at her all the time. These plans haven't worked before, so why would they start working now?
You want your characters to suffer repeated setbacks, yeah. You might even want to make, say, a character who wants to be rich be perpetually poor instead. But you can milk that failure for a lot more if she starts out saving a lot of money, then has to spend it on something more important (say, another character). Then she builds up again and starts trying to invest, only to have that fall out from underneath her. She starts a business that fails. She marries a millionaire who goes broke. You get the idea. Why are people still amused with Wile E. Coyote and his perpetual inability to catch a single bird? Because he never goes about it quite the same way twice. He screws up each time, but he's always getting back up and trying something else. If you want your character to be perpetually unable to achieve something, don't keep it a one-note lamentation. Let her try and fail, try something else and fail, and so forth. Keep it moving -- I'd say that depending on playtime, two weeks to a month is the longest you want to linger on one note. That's enough time to rise, fall, and get back up without feeling rushed. But as it turns out, you might not actually fall again after all.
Picking a point of success
Let's say you spend a month with your perpetually poor character, building up her efforts to try to make money. You've been through this cycle many times, and you know she's on the verge of screwing up all over again and losing everything. Except... this time around, you're actually liking the fact that she has money at her disposal. You find her an interesting character to play despite the fact that one of her central, persistent failures isn't present any longer.
At that point, the best thing you can do is decide that she's not going to fail. You're moving on forward with her having finally succeeded at her goal, and you're going to play with the long-term implications of that success rather than subject her to another disappointment.
Haven't I been saying the whole time that failure is more dramatic than success? Yes, and it's entirely true. But above all else, the balance you're trying to strike is the sense that failure is never the only option. Your character can do things other than fail. If you can't think of a way to keep a failure interesting after a few go-rounds, it's time to have the character either discard that goal or actually succeed. Maybe she finally decides that she has enough money to accomplish what she really wants. Maybe he decides to stop pining for a woman who doesn't care about him. You move on, you find new things to strive for, and you keep going.
When do you stop failing and start succeeding? When failure is a foregone conclusion. If you absolutely need a better rule of thumb, go for the three-beat. Your character tries and fails, tries again even harder and fails, tries a third time and either succeeds or goes off in a different direction. And never underestimate the third option; a lot of character growth happens when instead of pursuing a goal to the bitter end, the character opts to sidestep the goal and reach for something better. But the short version is that your character should never be failing to the point that it's rote and boring. And as is often the case, I probably could have just said that and gotten half the point across right away.
As always, feedback is welcome in the comments or via mail to firstname.lastname@example.org. Next week, I'm going to talk about character goals -- and I'm going to get astonishingly meta in doing so.
Every Friday, Eliot Lefebvre fills a column up with excellent advice on investing money, writing award-winning novels, and being elected to public office. Then he removes all of that, and you're left with Storyboard, which focuses on roleplaying in MMOs. It won't help you get elected, but it will help you pretend you did.