This analogy seems like a stretch. An artist that has paint dripping from their strokes strikes me as sloppy. Is this analogy really tied to a single specific type of painting?
I believe the analogy is more a reference to the shape of paint drips as seen in the image on the page. The T model of skills has a single "descender" that represents deep knowledge in a single topic, whereas paint drips represent varying depths of knowledge in several areas.
It's a good enough analogy to go deeper than that. The T model is an intentional, planned descender. The paint drip thing implies that you don't know which drips are going to go where, or what will turn up. It's a more flexible approach that will be quicker to seize on underlying conditions people are just beginning to discover. The terrain defines what you end up doing, and if something takes off, the paint drip types are going to be all over it, even though it's not planned.
It's not that useful of an observation because you must then ask what you're going to do about it, but it is a valid observation all the same. This mode of being does exist. My career's based on being that, and also putting in the effort to finish things: otherwise it would be pure dilettantism.
Yeah but if you don't have attached article the first thing I'm gonna think about is "sloppy" or "this person is into boring tasks like watching paint dry"