On Friedrich Nietzsche’s Thus Spoke Zarathustra, books 1 and 2 (1883).
What is wisdom? In Nietzsche's most famous book, he gives us his own Socrates, his own avatar to engage the foolish populace, though instead of asking them questions, Zarathustra tends to preach, and the whole book has a very Biblical tone, except more cagey. You see, this is a book "for all and none," meaning that Nietzsche doesn't think most of you will understand when he has Zarathustra state that man is something that shall be overcome or mentions in passing that God is dead, and he's not going to patiently explain it to you either.
This is definitely a book of ethics, but the principles enumerated are very general and can be hard to translate into practical action: "be faithful to the earth," "love with a great contempt," "listen to the voice of the healthy body," "where one can no longer love, there one should pass by," "become hard!" Also, since Nietzsche is a virtue ethicist, he can use the trick of just saying what the Overman (his ethical ideal) does, without necessarily implying that YOU can become that ideal and so "give birth to a dancing star."
What also complicates this is that, unlike Aristotle, Nietzsche does not think that human virtue is just one thing, a fulfillment of our inborn, common human nature whose development is amenable to common methods of training. Instead, we get psychological insights that serve as general advice: For instance, be sure to have friends (and enemies!) that challenge you. Don't get wrapped up in other people's misfortune such that you neglect yourself. Definitely don't tie yourself (like through marriage) to someone who is vapid. Respect your idiosyncrasies, your personal passions, and nurture these into virtues. Don't seek joy, but seek challenge and hardship, and joy will come.
Each person's creative journey of self-overcoming will be individual, and a lot of what we see in the book is the general pattern of Nietzsche's own moodiness: He needs to be alone, then he needs other people to talk to. He needs to wander, but then needs to come back home. He needs to soar creative heights, but then needs to sleep for days at a time.
These two books contain a lot of trenchant critique, though almost never with actual names attached. He accuses his (former) fellow professors of being sterile: unable to create. He calls priests "prisoners of false values and deluded words." He criticizes pessimists, i.e., the "preachers of death" who declare that "life is refuted" when they see "a sick man or an old man or a corpse" as seeing only one face of existence. He criticizes metaphysicians (the "afterworldly") who want to "reach the ultimate with one leap" as displaying "a poor ignorant weariness that does not want to want any more," declaring that "this created all gods and afterworlds." He criticizes "blockheads" who see values as fixed components of nature (the mistake of the historical Zarathustra).
A particularly fruitful negative image to come out of the book is the "Last Man," who is perhaps the natural consequence of the seemingly commendable desire to figure out and address human suffering. If there is a definable teleological goal—i.e. happiness—that all people share, we should be able to figure out what stands in the way of this and engineer society to maximize this, so that individuals no longer have to do any work in achieving it, and can just rest easy in their virtue and reasonableness. This seems to highlight the difference between utilitarianism and Nietzsche's ethics, but only if the "happiness" that utilitarianism is trying to maximize is clearly defined, e.g., in terms of pleasure. If you instead interpret happiness as "flourishing" and admit Nietzsche's point that this will vary to some degree between individuals, and that it necessarily involves creativity, including and especially creativity regarding values, then it may still be sensible to try to intentionally construct a society that maximizes the opportunity for as many people as possible to pursue self-actualization in this way, instead of declaring that "the earth is full of the superfluous" and focusing only on exceptionally bright and hardy individuals.
Mark, Wes, Seth, and Dylan join here to make our way slowly through the Prelude of the book, where we meet the Overman, Last Man, the tightrope walker that represents the seeker as bridge between man and Overman, the jester that leaps over the tightrope walker, an old hermit in the woods, gravediggers, and more.
For episode 214, we'll finish the work (reading books 3 and 4) and discuss his explicit guidance on how to do this: embrace the notion of eternal recurrence.
You can also listen to the book in full, albeit in an older translation. Given Nietzsche's intended tone, the older, King-James-Bible sort of style does actually make sense.
For a good secondary source, try Douglas Burhnam's Nietzsche's Thus Spoke Zarathustra: An Edinburgh Philosophical Guide (Edinburgh Philosophical Guides).
Epicurus picture by Genevieve Arnold.