I have read Siddhartha quite a few times in my life (every 4-5 years). Every time I align with a different character, or with Siddhartha in the various phases.

Timing is (almost) everything in life. I read 3-4 years ago "Though shall prosper" and "Half-time" and I could not have picked a better timing for both. I couldn't imagine appreciating either 20 years ago, and it would be "too late" reading them at my 70s.

So yes, timing matters.

But there is also 1984, which everytime I read it just hits the (same almost) spot!