As a person that started by randomly reading different philosophical works, I'd actually start with general overviews. Like, you might be interested to know that the Tao Te Ching is a response to the strict rituals of Confucianism. Introduction to Classical Chinese Philosophy is an excellent book in this regard. It's like putting all these different Chinese philosophies side by side, seeing how they grew out of each other, and you get to decide which you agree with and why.

I think the context is important because you get an idea of why they said what they said. The Tao Te Ching kinda seems like it's own book, a unique ahistorical perspective of living. But, if you think that (as too many people do), then you don't understand its limitations and its strengths. So, if you don't know what problem Confucian rituals are trying to solve, then you won't really understand why the Tao Te Ching eschews rituals in favor of "living in accordance with nature". It'll just sound like some hippy nonsense (which is, admittedly, very attractive on its own).

You might do the same for Stoicism, though I don't know any resources like the above for stoicism.