The most interesting thing about the story of the Buddha’s life is, I think, that he started off as a prince. He first experienced the finest pleasure that life had to offer in his time and place, before he let go of the world. If you imagine the milieux he entered into when he left the palace behind, it seems like it would be very difficult to convince anyone that you had discovered something deep and important. It seems likely that there would have been any number of wild-eyed ascetics who were claiming that they had seen all there was to see. There certainly are these days, and our culture doesn’t respond in the way it did to Shakyamuni.
I would find that compelling, as a poor and suffering old man gone to the forest to look for a freedom that the grind of life had not afforded me. Here was a fresh faced young person who had experienced every joy that the world had denied me, but who had found no real happiness in it. And here he was saying that he had found something that didn’t require material comforts to be totally satisfied. I think that would be quite compelling.
I also think it’s interesting that, as the story goes, he hesitated for a week after attaining complete enlightenment before deciding to hang around and teach. As the logic of the story goes, he was already as wise as a being can get – and yet it wasn’t immediately obvious that he should spend his time trying to help others. He was so ok with everything that not helping was apparently almost (but not quite) as ok as spending a few decades showing thousands of others how to be completely happy.
If that indicates anything, it’s that the key thing is to find an interesting path to liberation. What made the buddha worth listening to amongst the quite serious seekers that surrounded him was the route he had taken. The straight and standard path will only make you free – but a life that stands as a parable can resonate across millennia.