Reddit reviews Meditations: with selected correspondence (Oxford World's Classics)

First of all, I want to say that it speaks very well of you that you are looking to use your time in prison to your advantage. Most people would see this as a catastrophe, but you see it as an opportunity. If you want to make this a full-time, in-depth study, this is the plan I recommend.

I would first start with a good introduction to the entire Stoic system. A great one is Stoicism by John Sellars.

Then I would start reading the source material. We are fortunate enough to have the lectures of one of the great teachers of Stoicism, Epictetus. I would go with Epictetus - Discourses, Fragments, Handbook translated by Robin Hard.

After reading Epictetus, you can move on to Marcus Aurelius, who was directly influenced by the Discourses. Robin Hard has also done a translation of the Meditations.

To fully appreciate the Meditations (and to better appreciate Epictetus), next read The Inner Citadel by Pierre Hadot. This is an incredible analysis of the Meditations which explains Epictetus' influence on Marcus Aurelius and his work.

Finally, you must of course read Seneca. Two good sources are this book of his essays and this book of his letters.

Between the footnotes in these translations and the detail given by Sellars and Hadot, you won't need Wikipedia to get clarification on any points. You'll have the expert knowledge in your hands.

I don't think it's necessary to read one of the modern how-to type books before you begin reading these, but if you think it would help to read something lighter first to become acquainted with the core concepts ahead of time, I recommend Stoicism and the Art of Happiness by Donald Robertson.

There are other sources, such as Musonius Rufus and Cicero, but these are the three most people start with and the three that I recommend first. You can look at the FAQ for more ideas if you'd like.

Find out how many books you are allowed to have at one time, as this may be an issue in prison.

As others have said, it's a very good idea to keep a journal of your thoughts, both on what you are reading and how you relate what you are reading to your life.

The most popular by far are the ones by Gregory Hays and by Robin Hard, and which you will prefer depends on exactly what you are looking for. The English of the Hays translation is beautiful, but the translation has a reputation for being loose. (Edit 3: Even the Hard, though, is very readable.)

For more discussion, reviews, references to previous discussions, and a list of other translations, see this question in the FAQ.

Edit: The Amazon site is very sloppy about linking to different translations as if they were different formats of the same one. Be careful!

Edit 2: Added links to kindle versions, fixed edit 1 to correct that.

Edit 4: Of the many older, public domain (in the US) translations, I find Chrystal's revision of the Hutcheson and Moor translation most readable complete translation. (The abridgement by Smith is similarly readable.) All of the modern translations I have had a chance to look at were easier to read than even these, though..

Have you considered the Robin Hard one? I like it better. The US Amazon has a Kindle copy, perhaps then the Canada one does to: http://www.amazon.com/Meditations-selected-correspondence-Oxford-Classics-ebook/dp/B006QV7YN8/