It's a useful counterpoint to the modern idea that if your life is not Instagram/Pinboard material then you are a failure.
I always direct people to http://classics.mit.edu/Epictetus/goldsay.html for a taste of Stoicism. It is still tricky because what most Stoics thought of as "God" and what a modern reader would interpret as (the Christian) God are pretty different, but it is still easy reading. Other than that caveat it is pretty easy to understand.
As a sort of random aside, some of the most memorable sections of Epictetus for me are when he would referee to a pupil or discussion partner as a "slave". It always gave me a good chuckle. "My nose is running." "Why do you have hands, you slave?" e.g. quit complaining and wipe your nose. The color of comments like that really gives a feel for when the stoics think someone is being dense or wasting their mind. Some of the time now, when I am feeling particularly sorry for my self, Epictetus will pop up in my mind and call me a slave for complaining and it really helps me get over whatever random thing I was fixated on.
In terms of modern Stoic writing, I find Ryan Holiday's "The Ego is The Enemy" and "The Obstacle is the Way" (as well as his "Daily Stoic", although that's more of a daily devotional) to be very enjoyable and help to reframe the often hard-to-read writings of Aurelius, Seneca and Epictetus into actionable advice.
If someone has wronged you, and sending a corrective signal is in your power, than Stoicism would be favor of you fixing that problem.
But... if on your way to fixing that problem, it were to rain on you, Stoicism would be against you getting angry at the clouds.
what is this idea, and is it new?
A Guide to the Good Life by William Irvine
I also read The Obstacle is the Way by Ryan Holiday, which read too much like a self-help/business book to me. It might be to some people's tastes, but I found it lacked the substance of the two above. Ryan Holiday does have Daily Stoic email newsletter which is often interesting, though.
Edit: Also, the 2003 Hays translation of Meditations is a much more accessible version of the text. I wish it was still in print.
I also recently picked up The Daily Stoic book, which does help me get into a Stoic "mindset" (for lack of a better term) to start my day. Although with the way Meditations by Marcus Aurelius is written, you could almost just open up to a random page each morning, read a passage and reflect. But so far I've enjoyed this book.
This short essay by GILBERT MURRAY is the best introduction to Stoicism: http://ia600304.us.archive.org/13/items/thestoicphilosop00mu...
After that, you can dive into:
- EPICTETUS, Discourses, Fragments, Handbook (Oxford World's Classics. It features both Enchiridion and fragments)
- MARCUS AURELIUS, Meditations (Oxford World's Classics)
- Any collection of letters and essays written by SENECA
- PIERRE HADOT, The Inner Citadel (Harvard Press, Translated by Michael Chase)
Don't rush through the material, think deeply about every page you read. Don't forget to understand the life and history of each author. Context is extremely important. Don't let modern sensibilities fill the gaps. If you're looking for a solid introduction to traditional logic, I recommend you Socratic Logic, by Peter Kreeft. Lastly, the only way to truly understand Stoicism is to learn about Socrates and Plato as well.
[1] http://www.press.uchicago.edu/ucp/books/series/CWLAS.html