Create a progression for developing a skill. You can use one or a combination of Levels, Phases, Stages, Seasons, Episodes, Acts and so on.
Here is an example of a big picture progression for developing a skill:
Literacy stage is about deconstructing the skill and being able to have a minimum language and understanding so that you can start practicing and self correcting.
Fluency stage is about becoming fluent (duh!) in that skill, embodying it as a reflex and doing it with success more often than not, in many contexts.
Mastery is when you have learned it and practiced it so well that, in your context, you are ready to teach it. At this stage you can see, extract and name patters and you have clear enough models of the skill that you can help other people learn it.
Art is the stage where your practice of a skill becomes an aesthetic experience, a unique form of your self-expression that has beauty and character.
This is just one way to imagine a progression. You can also divide the skill into sub-skills (Skill A, Skill B, Skill C, ….) and each skill divide it by levels: Skill A – Level 1, Skill A – Level 2, etc)
There are two tricks to this. (1) First, think of this leveling like building a staircase. If the steps are too small, you loose time and focus trying to step on each of them. If the steps are too high, you go up with difficulty or not at all. (2) Second, naming the levels other than (Level 1,2,3) can help you to grasp in one word where you are on the overall journey and have some fun using words like Noob, Ninja, or Grand Master Black Belt; Here is an example of a progression from a games forum.
Crippling (literally — you can’t live a normal life)
Poor (you can life a normal life, with care, but never be an adventurer)
Below Average (low side of able-bodied, probably the lowest an adventurer should ever have)
Average (most scores for most people)
Above Average (high side of able-bodied, probably a good average for adventurers)
Exceptional (highest you’ll likely meet on the street, above average for adventurers)
Amazing (highest you’ll likely see or hear about, strongly defines an adventurer)
Legendary (historical “bests” and remarkable fictional heroes)
Mythic (astounding even among great heroes in fiction and folklore)
Superhuman (off-limits to humans, barely suitable for great heroes, okay for deities)
