Recommended Reading

Here is a list of resources I put together to help someone get started with Stoicism. 
What is Stoicism? Stoicism is an applied philosophy for life; a practical framework for living a virtuous life in a way that you can look back on without regrets.
The classical texts are amazing, but they can be a challenging introduction if you don’t have any experience with Stoicism or a background in philosophy. I know I struggled with them a good bit. Based on my own experiences, here’s a list of resources that might be useful for others digging into Stoicism. Starting with a few modern introductions before diving into the classics can make it a lot easier to handle.
~5 Minute TED-Ed Video: “The philosophy of Stoicism”https://youtu.be/R9OCA6UFE-0
~18 Minute TEDx Talk: “Stoicism as a philosophy for an ordinary life”https://youtu.be/Yhn1Fe8cT0Q
Modern Books to Start with:
William B. Irvine, “A Guide to the Good Life: The Ancient Art of Stoic Joy” (https://amzn.to/2C9RqLt)This incredibly readable introduction to Stoicism is what got me hooked.  I read a review of it, found myself intrigued, and picked it up.  It isn’t a perfect book on Stoicism, but it’s probably the gentlest introduction for those of us without a philosophy background.  I still recommend it regularly.  An excellent starting point, but definitely don’t stop here.
Massimo Pigliucci, “How to Be a Stoic: Using Ancient Philosophy to Live a Modern Life” (https://amzn.to/2N2GWSv)This is a wonderful book on modern Stoicism.  It offers a great “middle ground” between Irvine’s gentle introduction, and Robertson’s more rigorous study (see next entry).
Donald Robertson, “Stoicism and the Art of Happiness” (https://amzn.to/2QKuokv)This book is something of a more serious study of modern Stoicism.  Robertson comes from a psychological background and explores the Stoicism and how it can help us navigate the modern world.  He even touches on how the highly regarded Cognitive Behavior Therapy (CBT) has its roots in Stoicism.  This is a book worth spending time with.
Ryan Holiday, “The Daily Stoic” (https://amzn.to/2wAUCtG)This is a great book to help start your day with a little of Stoicism.  Structured as a set of short, daily passages, it gives you a brief lesson or thought exercise from Stoicism every day for a year.
Ryan Holiday, “The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph” (http://amzn.to/2EUhaIv)A more business-focused introduction to Stoic concepts.  If you want a book on Stoicism that doesn’t feel like a book on philosophy, this is a great one.  It’s written in the style of modern business management books, and will be particularly approachable for people living in the corporate world.
Modern twists on the Classics:
Sharon Lebell, “Art of Living: The Classical Manual on Virtue, Happiness, and Effectiveness” (https://amzn.to/2LRxG0w)Lebell’s book is basically her take on Epictetus’s Handbook (The Enchiridion).  She thoroughly updates it and providers her take on it, in an amazingly well written and easy reading rendition (it’s more than a translation).
Ward Farnsworth, “The Practicing Stoic: A Philosophical User’s Manual” (https://amzn.to/2yzoICQ)This brilliant book is hard to classify.  It’s an amazing collection of quotes and excerpts from the classical Stoic authors, but intertwined with explanation, observations, and commentary in such a masterful way that it is immediately understandable and relatable to modern readers.  You’ll want to bring your highlighter for this one.
Frank Miles, “Get a Grip: A Humorous Look at Serious Wisdom Based on the Stoic Handbook by Epictetus” (https://amzn.to/2VrEINy)Frank does his own riff on the Stoic Handbook in a very original style.  This is a surprisingly entertaining mashup of Stoicism and well-written comedy.  Miles offers up the wisdom of Epictetus in a hip, modern vernacular complete with contemporary examples and jokes.  It’s very virtuous fun!
Classic Texts:
“Meditations”, by Marcus Aurelius (the Hays translation)https://amzn.to/2LPyu4a
“The Enchiridion” (or “Handbook”), by Epictetushttps://amzn.to/2Sl9HcWhttp://classics.mit.edu/Epictetus/epicench.htmlhttps://www.gutenberg.org/files/45109/45109-h/45109-h.htmhttp://www.sacred-texts.com/cla/dep/dep102.htmhttps://librivox.org/the-enchiridion-by-epictetus-tr-elizabeth-carter/(audiobook)
Collected Writings on Stoicism from Senecahttp://www.openculture.com/2017/10/three-huge-volumes-of-stoic-writings-by-seneca-now-free-online-thanks-to-tim-ferriss.html
Seneca’s “Moral Letters to Lucilius”https://en.wikisource.org/wiki/Moral_letters_to_Lucilius
Modern Books to Continue Learning:
Brad Inwood, “Stoicism: A Very Short Introduction” (https://amzn.to/2TCxZ4l)This a small book, only 136 pages, but it is very well written to provide a concise overview of the development of Stoicism.  It is clear, quick, and a little gem of a book.
Donald Robertson, “How to Think Like a Roman Emperor: The Stoic Philosophy of Marcus Aurelius” (https://amzn.to/2LUoBF1)Acknowledgement: I haven’t actually read this one, yet.  It’s in my queue and I’ll be starting it shortly.  However, the reviews are glowing and it looks like a home run from someone who has already proven his chops in writing about Stoicism.
John Sellars, “Stoicism (Ancient Philosophies)” (https://amzn.to/3cZj7ET)Most of the modern books on this list are written for a lay audience.  This one is written with a stronger academic approach.  It is basically an introductory textbook on the history and evolution of Stoicism.  If you want to really understand the context of Stoicism, this book is an excellent aid.
Derren Brown, “Happy: Why More or Less Everything Is Fine” (https://amzn.to/2APAkCf)
William B. Irvine, “The Stoic Challenge: A Philosopher’s Guide to Becoming Tougher, Calmer, and More Resilient” (https://amzn.to/2Tx5uon)
Other Books:
Viktor Frankl, “Man’s Search for Meaning” (https://amzn.to/2UqJaPa)This is a book that sticks with you.  Frankl spent years in Nazi concentration camps, including Auschwitz  This is his account of that experience, and what he learned from it.  You’ll want to read it again after you’ve had time to digest it. 
Tom Wolfe, “A Man in Full” (https://amzn.to/2TAUIxE)A unique entry on this list, “A Man in Full” is not a book about philosophy; it is a work of fiction.  This book follows a man who finds Stoicism, and how it changes and shapes his life.  For those looking for a book on Stoicism to “read” as opposed to a book to “study”, this ought to fit the bill for you.
Video Resources:
Academy of Ideas Article and Video: “Introduction to Stoicism”https://academyofideas.com/2014/04/introduction-to-stoicism/https://www.youtube.com/watch?v=o0MzQZ_eFEY
Video: “Tim Ferriss on how to apply stoic philosophy to your life”https://www.youtube.com/watch?v=A0XxceO4qX0
Articles on Stoicism:
“What’s the difference between stoicism and Stoicism?”https://donaldrobertson.name/2018/01/03/whats-the-difference-between-stoicism-and-stoicism/
“Stoicism as a Philosophy of Life: My jargon-free guide to putting Stoicism into practice”https://medium.com/stoicism-philosophy-as-a-way-of-life/stoicism-as-a-philosophy-of-life-6f0a1d18d41
“What Is Stoicism? A Definition & 9 Stoic Exercises To Get You Started”https://dailystoic.com/what-is-stoicism-a-definition-3-stoic-exercises-to-get-you-started/
“Stoicism 101”https://howtobeastoic.wordpress.com/stoicism-101/
“Why You Need to Read Modern Books on Stoicism”https://medium.com/stoicism-philosophy-as-a-way-of-life/why-you-need-to-read-modern-books-on-stoicism-48c8c498b098
[Note: These books and URLs are recommended based on my own personal (positive) experience.  There are numerous other books, articles, and videos that I haven’t gotten to, so I haven’t listed them.  Please take this list with a grain of salt and enjoy your journey with Stoicism!]