For those of you who have never read the book, Siddhartha, it's a slight parallel to the Buddha's life. A young man is trained to be a meditator in his early adult life and then later gets attracted to a woman, a courtesan, I think, which was a higher class prostitute. He is attracted to her, falls in love, he gets involved with her and then starts becoming like an average person. Yet even worse. He gets involved with gambling and becomes rich as a business person. Because of falling in love with her, he goes into a complete mess. Then he wakes up out of it, realizes his young adulthood had benefits that he had forgotten about runs away. Then he lives basically alone for awhile and supposedly, I say supposedly, maybe gets enlightened.
Now the way that this relates to the Buddha's life was that the Buddha lived in riches. Growing up, his father tried to make absolutely certain that the Buddha never ever experienced any Dukkha, even so much that the King kept his son, the Prince, in palaces totally separated from town. He would never be allowed to go to the town, and everything in the palace was kept perfect. If a leaf was dying on a tree, the servants would climb up the tree and take the leaf off so he wouldn't even see a dead leaf.
Everything was kept that way, so he lived in riches, although he was not extreme like Siddhartha the book. He was never a gambler, he never did all the bad stuff, but he did live a very affluent spoiled life. Then he "woke up" and he actually did go to town one day. He saw death, he saw decay, he saw old age and disease. Yet he also saw a wandering monk and it inspired him to then leave his riches and go search for enlightenment, which he found. So there was that parallel to the book Siddhatha.
Now as to whether we have to experience all those easy desires, the indulgence of the rich life of the Buddha as a young man or the gambling rich life of Siddhartha in that book. Whether we have to experience it in order to find a way out, no we don't. All we have to do is listen to wise advice. All we have to do is look at our life already and see what Dukkha has come already in order to walk the way out.
There was a quote in the Bangkok paper 2 months back I happened to see from a past United States Chief Justice, Earl Warren. Coming from a person who had watched life in the courtroom for about 70 years - he had watched people do all sorts of dumb things, anything that could be, he had watched it all. This is a quote from him, his own words "The only thing we learn from history is that we don't learn."
Now, what he's saying here? Is that most people do not pay any attention to the wisdom that they're getting taught. What do they end up doing? They end up doing exactly what Siddhartha did in his book. He didn't listen to his teachers well enough, so he went and created all the pain all over again before he could find a way out that the teachers were giving him in the very beginning. So if we listen very well to the advice of wise people, reflect deeply about it, then we may be able to prevent Dukkha from arising and don't have to experience this same type of Dukkha again.