This page is an annotated compilation of media that is educating, enlightening, or uplifting in some substantial way. I’ll try to keep it separated into sections based on the types of wisdom it has to offer, but I don’t promise to keep it alphabetized. I’ll add more entries over time in no particular order as I discover, remember, or get around to annotating them.
It should be noted that I’m almost certainly not doing these works justice in my hasty blurbs of them. Regardless of whether my description of it sounds trite, if a work appears on this page it’s because I think you are likely to get great value out of it, and not just entertainment value (though there is plenty of that, too).
Also, just because I post something here doesn’t automatically mean I endorse it in full. That’s okay, though, because that’s not the point of recommended reading. I will never post anything here with the expectation that people accept it at face value. What I post is food for thought, to inspire you to form ideas that work for you. If the work has an explicit message (and not all of them do), it may not always be relevant or even good advice, but it will hopefully be interesting and help expand your perspective in a useful way.
General Ideas and Food for Thought
Wait But Why: This blog by Tim Urban has long but easy-to-follow articles (punctuated by helpful stick-figure diagrams) which give overviews on diverse subjects, starting from the very basics and building a big-picture understanding. His articles span applied philosophy and psychology (e.g. life choices, procrastination, perspective, and religion), technology (e.g. artificial intelligence, cryonics, and the works of Elon Musk), and much more. While many of the articles are directly relevant to your life, some articles simply introduce ways of looking at the world that can help you appreciate it that much more. Check it out here.
Tailsteak’s works: My first exposure to Tailsteak (a.k.a. Mason Williams) was his existential webcomic 1/0 (“One Over Zero”), which takes place in a very simple universe in which most of the characters are created by Tailsteak as the author/deity and are very much aware of it. It explores the ways in which we find meaning in the world. I continued reading with his second webcomic Leftover Soup, with a more conventionally slice-of-life human setting with preternaturally thoughtful, multifaceted (somewhat wacky) characters and nuanced real-life (somewhat wacky) ethical issues. The commentaries below each page are just as intriguing as the comics themselves. Tailsteak’s current webcomic, Forward, explores the anxiety and isolation in the psyche of a millennial born a century and a half from now (so, not technically a millennial, I guess?), when technology has more or less eliminated the need to work. Finally, Tailsteak’s site has a collection of philosophical insights, fascinating half-finished webcomics and unrealized story ideas, alternating hilarious and gripping vignettes, and even scripts for movies that I personally would like to see. If you want to rifle through an attic full of creative ideas and unique thoughts, this would be a good place to start.
You’re More Powerful Than You Think: This book by Eric Liu is an excellent starting point for anyone who wants to democratize power and resources, but who doesn’t see a clear path towards that goal. Since reading it, I’ve noticed the vast array of opportunities I’ve been overlooking to empower others to spread positive change at all levels. For longer than I care to admit, I had failed to appreciate other people’s potential to contribute towards cultural change of their own volition, but now I realize that it’s okay that I can’t handle all the details myself, because I don’t need to. I can focus on my chosen role: consistently and proactively giving people the tools they need to understand the core concepts of any situation, to apply that understanding toward a constructive solution, and to spread what they’ve learned so others can help. There are more than enough people just a few mouseclicks away who can take it from there. I recommend checking it out as soon as possible, and posting what you learn from it. Chances are you’ll be hearing more from me thanks to this book.
The Black Swan: This book by Nassim Nicholas Taleb is book two of his Incerto series on risk and uncertainty. (The only reason I’m listing this book specifically and not the whole series is because I have yet to read the rest.) The Black Swan is a collection of mind-expanding concepts and stories relating to how we deal with risk and how we overlook it. It inspired me to rethink my mental of order and chaos, to define them not by any assumed objective rules or randomness in the world, but by our subjective knowledge and ignorance of what will happen.
Taleb identifies the concept of the ludic (“game”) fallacy, the assumption that we know all the possible outcomes of a situation. We engage in this fallacy when we take probabilities too seriously. Even though numbers and percentages look very impressive, they ultimately measure our own ignorance, and that doesn’t insulate us from unknown unknowns (the eponymous black swan events). The ludic fallacy is rampant in our everyday life, and it affects not only how we prepare ourselves for crises, but also what government policies we support.
If you’re looking to practice the virtue of exposure to deal with the fundamental liability of disaster, this book is one good place to understand the general concept. The rest of his books are on my enormous “to read” list, but I think the probability is very high that they are equally engaging and enlightening. (On an irrelevant topic, I find it a lovely coincidence that his books are published by Random House. What are the odds?)
Building Habits and Productivity
Psycho-Cybernetics: Despite the sci-fi/horror/New Age-sounding title, this book by Maxwell Maltz is actually very down-to-earth (the title literally just means “feedback systems of consciousness”). It’s essentially a guide to practicing cognitive-behavioral therapy on oneself. Having already changed my own behavior repeatedly by installing helpful paradigms, thought patterns, and mental triggers to replace harmful ones, I was greatly encouraged by reading this book, because it reinforced the idea that such practices would help other people as well.
Psycho-Cybernetics describes in detail the principles and methods of mindful thinking. Whether you accept a situation or change it, this book will show you how to fully commit to it, deliberately and with purpose. It takes practice and self-observation to change the way you think, but in my experience it is well worth the effort.
P.S. There are various editions of this book, so I just picked one to link to. Also, I linked to the Smile version of Amazon. If you’re not set up for Amazon Smile (which donates part of your purchase) then I’m not sure what happens, but you may need to go to the regular version.
Stephen Guise: Guise has much good advice on productivity and goals, particularly his concept of “mini-habits”, which build consistent habits by removing the intimidation factor, and which you to develop them further as you feel up to it. His perspective has helped me a great deal, so if you are anything like me in terms of procrastination, check out some of his articles. They don’t take long to read and are an excellent time investment.
Here’s a link to Stephen Guise’s blog, formerly known as Deep Existence. You can also subscribe to his newsletter updates which he sends out on Tuesdays. It often contains further thoughts on the concepts he describes.
Communication and Collaborative Truth-Seeking
Difficult Conversations: I know I said that I wouldn’t be automatically endorsing at face value the ideas in the material I link to, but in this case I endorse the ideas at face value 100%. In my arrogant opinion, this book or an equivalent should be required reading for every person. Why the strong statement?
Difficult Conversations (by Douglas Stone, Bruce Patton, and Sheila Heen) is a nuanced and comprehensive guide to collaborative truth-seeking and effective communication. It breaks down every aspect of the process of discussing an emotionally conflicted situation and provides examples to illustrate the techniques and their benefits, and to help people relate them to their own lives. For the sake of averting future strife and enhancing communication skills, it is well worth the time to read.
P.S. I linked to the Smile version of Amazon. If you’re not set up for Amazon Smile (which donates part of your purchase) then I’m not sure what happens, but you may need to go to the regular version.