Despite some initial warning signs (enumerated list, self help), the fantastic cover art and the fact that this book is about Montaigne drew me in. I've started reading his Essays several times and always bailed for one reason or another. I picked this up hoping it would give me some context and get me more excited to read, and maybe even finish the essays. It did. How to Live isn't just a biography of Montaigne, it's a history of Essays with a ton of rich context and interesting descriptions of the ways they have been influential throughout history. The 20 answers to the question of "how to live" don't define the book as much as give it some nice structure.Instead of urging constant improvement like a typical self help book would do, How to Live feels like it's written to give you permission to live a more examined life. Montaigne didn't go through life explicitly seeking improvement, instead he sought eudaimonia or "human flourishing." Often, finding that meant cutting back, spending more time alone, doing a good job but not a great job, focusing less on relationships and more on knowing and being comfortable with yourself. His essays, rather than preaching, are simply observations, mostly about his internal world.Knowing Montaigne a little better, I feel more free to abstain from having an opinion on anything and everything. Montaigne is famous for reviving the Pyrrhonian Stoicsm idea of epohke which means "I suspend judgement," or as Sextus put it more verbosely, "I now feel in such a way as neither to posit dogmatically nor to reject any of the things falling under this investigation." Epohke is different from the contemporary concept of open-mindedness. Today to be open-minded is to accept everything and everyone as they are. Epohke doesn't have a goal of acceptance, it is goalless. It's an approach that may not work all the time, but settling in to that mode of thought, even for a short period of time, can be incredibly freeing.Even in his stoicism Montaigne was not dogmatic. He summarized himself as "extremely idle, extremely independent, both by nature and by art." What he did he did because he wanted to. Honor played a part, civic-mindedness played a part, love of his friends and family played a part, but overall he was true to himself. It's hard for me to grasp this entirely, but How to Live gave me a good start and made me excited to read more. Shakespeare was influenced by Montaigne and on occasion heavily borrowed from his works. Nietzsche was influenced by him, Flaubert, Joyce, Rousseau, Descartes and Virginia Wolf were all very heavily influenced by Montaigne and after reading How to Live, I'm going to very humbly throw my name into that list too.