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If you find optimism in the thing you were pessimistic about before that’s ideal. But if you can’t, how do you switch to not caring about it and switch to something else that you can be optimistic about ? It’s hard to know when to quit.

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Yeah, that's all part of the technique; breaking down the issue, understanding why you're having negative emotional reactions to it, and deciding whether the problem is your emotional reaction (in which case, change that), or the outer-world situation (in which case, figure out the steps needed to change the situation).

It's taken a while to learn it (indeed I'm still learning it), but it's powerful the more it starts to click.

That sounds very interesting. Would you happen to have any pointers (i.e. books, links etc.) for anyone interested in learning more?

Not really any books - I think I'm going to have to write one! My approach comes from a variety of different sources - mostly in-person coaching from practitioners.

But you're welcome to email me (address in profile) and I can send you some links and suggestions.

This sounds a lot like what I learned going through the Headspace introductory meditations. I'd give them a look if you haven't already, it's a great program.

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