I've spent a lot of time studying stoicism in the past, but have only recently given any serious thought towards the Buddhist teachings. I would like to see how eastern and western philosophies tie together more. They have roots planted on opposite sides of the planet but seem to have so much in common. The more I look it seems that many on both sides have said the same things but in different ways and this baffles me because if they had never interacted at the time then it is all natural conclusion.

Thank you, I will most certainly be looking into the Five Levels of Attachment, it sounds very much in tune with what I'm looking for. It's funny, I came to the conclusions that I did by relaxing and letting things come and go without effort but the way you worded this made it apparent that I'm trying to force these things to happen. I think I may have been approaching this in a counterproductive manner.

Do you have any insight as to how the ego/attachments play with optimism and pessimism? I have often worried that feeding one feeds the other and that a person could only make themselves miserable by trying to see positive in all events. When I see an optimist I feel they enjoy life more but when something hard enough comes along to break through it, they're beyond devastated. And as someone who had been lost in pessimism for many years, I handled tragedy and loss well but dulled myself from feeling any joy at all. They both seem like kinds of distortions to me, and I am curious to know if anyone has managed to balance the two(if they can be balanced, or if they're the same thing) as opposed to attempting to deny them entirely. I would still prefer to limit them as much as I can, but i believe that that will require the same type of control that a person would have to have to manage them.