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1) Discourses (incl Enchiridion) by Epictetus, if you're interested in happiness and contentment.

1a) A Guide to the Good Life is an easier introduction to Stoic philosophy if you don't want to dive straight into Epictetus

2) The Black Swan by Taleb to change the way you think about risk

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I second Guide to the Good Life by William Irvine. It contains applicable techniques and a modern explanation of Stoicism. Stoic Serenity by Keith Seddon is very nice too, it is a guided introduction to Stoic concepts and to Seneca and Marcus Aurelius.

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