I've been thinking about two different dramatic approaches to leveling up, and how to apply them to real life. (This post came out of a conversation with a friend, a lot of it was copied from my comments, but I wanted to give myself "credit" for doing the writing, since it is in fact actual writing.)
One is the training montage, which I think is basically equivalent to grinding for levels. You have a skill you want to work on, so you practice that skill, and then you get better. Wax-on wax-off is a related trope. Everyone theoretically knows how to do that, at least when you've already successfully decomposed whatever you want to accomplish into a bunch of discrete, simple skills.
The other is "breaking stronger", when an impossible task motivates you to learn the skills you need to do it on the fly. It seems like the latter requires less willpower, or at least less sustained willpower, so I should be thinking about which skills I want to develop, that would be well-developed by it.
Examples of "breaking stronger":
In real life, a math professor at Georgetown assigned me very computationally intensive problems, so that I just plain couldn't get them done by the deadline unless I thought really carefully about how to solve them efficiently. It didn't feel like the practice or working hard. What it felt like was just being really terrible at something for a long time and desperately flailing for solutions, until I looked back at some past problems and realized they all seemed really easy now.
In fiction, when Frodo and Sam get back to the Shire, all of the sudden they are tremendous badasses by comparison to everyone else, even though they never explicitly tried to become badass. But even barely surviving Mordor, they had to build those skills.
To be fair to explicit practice, there are techniques like "deliberate practice" that make it somewhat better. I'm practicing "deliberate practice" by practicing piano, where I can tell very easily if I'm doing it wrong and need more work on something. And there are probably a bunch of skills I could get a lot better at if I could just decompose them into simple practiceable skills, and then apply deliberate practice to one at a time.
For example, to get better at social interaction with strangers, I could break that down into approaches, probing for a topic of mutual interest, reading body language and other nonverbal cues, sending body language and other nonverbal cues, etc., and practice one at a time - but it's not clear how to do that. The best concentrated practice I've had so far was a few consecutive hours of rejection therapy at the first CFAR Minicamp. I highly, highly recommend it. I am not a particularly smooth or charming person to strangers, but I came up with some "reach" requests that would have actually been quite cool, like getting a random passerby to do a dramatic reading from the book he was carrying (he turned out to be a literature professor and was happy to oblige), and getting a stranger to go have tea with me (the conversation turned out to be quite nice).
But on the other hand, I have finite willpower, and if I can set myself up to break stronger, that would be a low-willpower-cost dramatic improvement. Some workouts, for example, are like that, and it's for this reason that I'm going to invest in a personal trainer or some kind of intense fitness classes like CrossFit - so someone can push me to the outside of my limits - without pushing me in a way that's likely to injure me.
The trick is finding a task that's not literally impossible, but seems like it. And to ratchet up the intensity of what's required from you, not to raise the stakes. What are some things like that, that I can do to improve ordinary life skills?