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Nassim Nicholas Taleb is a really good writer on this subject, especially with regards to the financial markets. You can either read the Black Swan or Fooled by Randomness (or both, but there is a lot of overlap, personally I think Fooled by Randomness is a better read, although the ideas in the Black Swan are a little more developed).
If you want to get technical, my textbook: Jay Devore, Probability and Statistics for the Engineering and Sciences is an excellent treatment of the subject and begins at the most basic level and covers many advance subjects. I think any econometrics textbook is good too, as the skills you learn apply not just to economic time series but in general when thinking about how to synthesize observed data into a descriptive model.