There is much to like about this book. Ray Dalio examines his life in prose that is often honest and straightforward, often bordering on the conversational and vernacular. As you read this book, you feel as if you are talking with Ray in his office or in a restaurant. That gives the book some of its charm. For these reasons, we can comfortably situate this book with other autobiographies/life lesson books. Benjamin Franklin's autobiography and "Meditations" by Marcus Aurelius are other great examples. What these books lack in elegant prose, they more than makeup for in practical wisdom.
At the forefront of Dalio's approach is his practical scientist's approach to life and systems. Many pages are written about fundamental principles of life -- not all of them are as brief as they could be. This is fine. It should be kept in mind that this book is written by a practitioner, not a professional essayist or social scientist. In that case, the best style is raw honesty whenever possible. And it seems that Ray Dalio has stripped away at least some of his ego and status-seeking in order to tease out the themes of his life.
However, if I may attempt to bring a level of brevity and wit to Dalio's main messages, I would summarize his philosophy this way:
1) think in terms of systems
2) use painful moments as learning experiences
3) practice problem-solving through elegant design and
4) consistently and aggressively iterate.
These are timeless principles that have been written about in other books on start-ups and practical life success, but Dalio brings his own level-headedness and life experience to these themes. He doesn't often talk about systems, for example, but instead "machines" within "machines", which hurt the eyes and ears of this reader. Systems come in many forms: machines, ecosystems, and communities. Not all systems behave similarly and are as amenable to human manipulation. But one thing comes out crystal clear: learn to think in terms of systems.
Throughout his book, Dalio references other "great" people of his era. In doing so, he makes a mistake that is common to many who have studied great men or people: he samples on the dependent variables. (Here is one quick reference to explain sampling on the dependent variable: http://gabrielr.bol.ucla.edu/soc210a_f09/w9.pdf)
At several points in his book, he looks at the great people of our time -- the "shapers" -- and then works backward to understand what characteristics made them great. I doubt Dalio would have made the same mistake with investing. You don't look at the "winning" investments and then work backward without testing the principles you come up with against a complete sample of winners, losers, and somewhere in-betweeners. If he did have such a sample of human beings, he might find that many of the greatest shapers of history died before their time (because of sickness, war, or accident), were suppressed because of their gender or race, or were simply geographically or historically unlucky. These concepts are better explored in books such as Malcolm Gladwell's "Outliers" and the theoretical writings of Nicholas Nassim Taleb in his writing about "survivorship bias" ("Fooled by Randomness" and "Black Swan"). In fact, the concept of survivorships bias is so important (perhaps even more important than this book) that I feel compelled to include a link so that any reader of this book can explore it in depth.
Here is one quick article I found here: https://fs.blog/2019/12/survivorship-bias/
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Pure Writerly Moments 2 (Short Stories, Essays, Book Reviews, and More)
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