The most painful lesson that was repeatedly hammered home is that you can never be sure of anything: There are always risks out there that can hurt you badly, even in the seemingly safest bets, so it’s always best to assume you’re missing something. This lesson changed my approach to decision making in ways that will reverberate throughout this book – and to which I attribute much of my success. But I would make many other mistakes before I fully changed my behavior.

— Ray Dalio

Ray Dalio Quotes

Everyone has weaknesses. They are generally revealed in the patterns of mistakes they make. Knowing what your weaknesses are and staring hard at them is the first step on the path to success.

— Ray Dalio

People typically feel bad about their mistakes because they think in a shortsighted way about the bad outcome and not about the evolutionary process of which mistakes are an integral part.

— Ray Dalio

Don’t let fears of what others think of you stand in your way. You must be willing to do things in the unique ways you think are best – and to open-mindedly reflect on the feedback that comes inevitably as a result of being that way.

— Ray Dalio

Imagine how many fewer misunderstandings we would have and how much more efficient the world would be – and how much closer we all would be to knowing what’s true – if instead of hiding what they think, people shared it openly. I’m not talking about everyone’s very personal inner secrets; I’m talking about people’s opinions of each other and of how the world works.

— Ray Dalio

Look to nature to learn how reality works. All the laws of reality were given to us by nature. Man didn’t create these laws, but by understanding them we can use them to foster our own evolution and achieve our goals.

— Ray Dalio

If you’re willing to confront reality, accept the pain that comes with doing so, and follow the 5-Step Process to drive yourself toward your goals, you’re on the path to success. Yet most people fail to do this because they hold on to bad opinions that could easily be rectified by going above themselves to objectively look down at their situation and weigh what they and others think about it. It’s for that reason I believe you must be radically open-minded.

— Ray Dalio

I believe that the need to have meaningful work is connected to man’s innate desire to improve.

— Ray Dalio

The word “philanthropy” doesn’t sit well with me in describing what we are doing. What we are doing is helping out with what we care about because of the joy it gives us – like the joy one gets from helping a friend.

— Ray Dalio

In retrospect, my crash was one of the best things that ever happened to me because it gave me the humility I needed to balance my aggressiveness. I learned a great fear of being wrong that shifted my mind-set from thinking “I’m right” to asking myself “How do I know I’m right?

— Ray Dalio

Looking back on getting fired from Apple in 1985, Steve Jobs said, “It was awful-tasting medicine, but I guess the patient needed it. Sometimes life hits you in the head with a brick. Don’t lose faith. I’m convinced that the only thing that kept me going was that I loved what I did.

— Ray Dalio

If you are disappointed because you can’t be the best person to do everything yourself, you are terribly naive. Nobody can do everything well. Would you want to have Einstein on your basketball team? When he fails to dribble and shoot well, would you think badly of him? Should he feel humiliated? Imagine all the areas in which Einstein was incompetent, and imagine how hard he struggled to excel even in the areas in which he was the best in the world.

— Ray Dalio

After seeing how much more effective it is to face the painful realities that are caused by your problems, mistakes, and weaknesses, I believe you won’t want to operate any other way. It’s just a matter of getting in the habit of doing it.

— Ray Dalio

In thoughtful disagreement, your goal is not to convince the other party that you are right – it is to find out which view is true and decide what to do about it.

— Ray Dalio

I learned that if you work hard and creatively, you can have just about anything you want, but not everything you want.

— Ray Dalio

As we move toward these goals, we encounter problems, make mistakes, and run up against our own personal weaknesses. We learn about ourselves and about reality and make new decisions. Over the course of our lives, we make millions and millions of decisions that are essentially bets, some large and some small. It pays to think about how we make them because they are what ultimately determine the quality of our lives.

— Ray Dalio

I’ve always been an independent thinker inclined to take risks in search of rewards – not just in the markets, but in most everything.

— Ray Dalio

Embrace tough love. In my own life, what I want to give to people, most importantly to people I love, is the power to deal with reality to get what they want. In pursuit of my goal to give them strength, I will often deny them what they “want” because that will give them.

— Ray Dalio

My plan was to step out as CEO while helping my replacements as a mentor, remain in my investment role, and take the time I gained from no longer managing the company to suck the marrow out of life while I still could.

— Ray Dalio

Our returns in 2010 were the best ever – nearly 45 and 28 percent in our two Pure Alpha funds and close to 18 percent in All Weather – almost exclusively because the systems we had programmed to take in information and process it were doing it superbly.

— Ray Dalio

As I studied history, I saw that it typically transpires via relatively well-defined life cycles, like those of organisms, that evolve as each generation transitions to the next.

— Ray Dalio
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