There's a page for each day of the year (so ideally you would read a page per day). Each page has a short quote from Seneca, Marcus Aurelius and others, together with an interpretation of Ryan Holiday. For me, this wa an easy way to get started with the whole topic of Stoicism and some of Senecas and Aurelius ideas.
[0] https://www.goodreads.com/book/show/29093292-the-daily-stoic
As a side note, my second reading was provoked by the movie "Silence of the Lambs", where Hannibal Lecter coaches Clarice to, "“First principles, Clarice. Simplicity. Read Marcus Aurelius." ;)
Remembered saying something that a man craves for what he sees.
Or you may read plenty of that sort of thing but just bounced off Aurelius. Still happens. I'd recommend Staniforth's translation as the best balance between easy-reading and fidelity to the text, if you want to try again. Probably don't need annotations—it's very straightforward by the standards of philosophy. If you'd like an overview of Stoicism to accompany a reading of Aurelius, and you plan to read more philosophy, it's hard to beat Russell's A History of Western Philosophy for a single volume treatment of the field's classics; people complain about its having a lot of opinion in it as if Russell were trying to trick them, but it's pretty explicit when he's describing something and when he's opining so I've never understood what the fuss is.
http://classics.mit.edu/Epictetus/epicench.html
I organised MA quotes by themes to make a narrative of what Stoicism stands for.
https://www.reddit.com/r/Stoicism/comments/a3d4ap/brief_desc...
I still perceive repetitive dumps of text too!