I know the basic rules for shiru and wakaru, but in this case I'm tempted to use 'wakaru' but 'shiru' might seem more correct. Which is more natural I wonder?
Maybe this is a question of nuance? In that case, which more expresses the idea of 'In 5 years time, I have no idea what I'll be doing, but I'd like to visit Toyko again'?
Or perhaps one is still correct and one is wrong, just that sometimes people are a little loose?
OK, I think that in certain cases 「分かる」 can be used in the sense of 「知る」(from looking up in several dictionaries) which explains why it can be used in this context.
My guess is that it is just a difference in nuance – 「知る」 put's more focus on the knowledge or lack of it, whereas 「分かる」 puts more focus on the *state* of not knowing. I'm no expert, but that's my intuitive feel.
The former 5年後何をしてるか、まったく分からない is more common for future. 知らない is usually used for the present state. Your example 羽ばたいて2年後何してるか知らないけど also refers to the present state. The person in the topic begun their career as a professional illustrator two years ago, and the writer don't know what they are doing now(= 2年後).
Notice that 分かる, 分からない, 分かっている, 分かっていない, 知る, 知らない, 知っている and 知っていない are all different.
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