Location 145:

no amount of studying or open-mindedness can genuinely recreate the power of fear and uncertainty.

Location 197:

Every decision people make with money is justified by taking the information they have at the moment and plugging it into their unique mental model of how the world works.

Location 252:

Luck and risk are siblings. They are both the reality that every outcome in life is guided by forces other than individual effort.

Location 294:

the world is too complex to allow 100% of your actions to dictate 100% of your outcomes.

Location 296:

The accidental impact of actions outside of your control can be more consequential than the ones you consciously take.

Location 440:

To make money they didn’t have and didn’t need, they risked what they did have and did need. And that’s foolish.

Location 442:

There is no reason to risk what you have and need for what you don’t have and don’t need.

Location 467:

“Enough” is realizing that the opposite—an insatiable appetite for more—will push you to the point of regret.

Location 472:

the inability to deny a potential dollar will eventually catch up to you.

Location 563:

the counterintuitiveness of compounding may be responsible for the majority of disappointing trades, bad strategies, and successful investing attempts.

Location 652:

Merely good returns sustained uninterrupted for the longest period of time—especially in times of chaos and havoc—will always win.

Location 659:

A plan is only useful if it can survive reality. And a future filled with unknowns is everyone’s reality.

Location 691:

A mindset that can be paranoid and optimistic at the same time is hard to maintain, because seeing things as black or white takes less effort than accepting nuance. But you need short-term paranoia to keep you alive long enough to exploit long-term optimism.

Location 727:

Anything that is huge, profitable, famous, or influential is the result of a tail event—an outlying one-in-thousands or millions event. And most of our attention goes to things that are huge, profitable, famous, or influential. When most of what we pay attention to is the result of a tail, it’s easy to underestimate how rare and powerful they are.

Location 839:

Having a strong sense of controlling one’s life is a more dependable predictor of positive feelings of wellbeing than any of the objective conditions of life we have considered.

Location 859:

doing something you love on a schedule you can’t control can feel the same as doing something you hate.

Location 860:

There is a name for this feeling. Psychologists call it reactance.

Location 919:

Controlling your time is the highest dividend money pays.

Location 927:

people tend to want wealth to signal to others that they should be liked and admired. But in reality those other people often bypass admiring you, not because they don’t think wealth is admirable, but because they use your wealth as a benchmark for their own desire to be liked and admired.

Location 978:

The problem for many of us is that it is easy to find rich role models. It’s harder to find wealthy ones because by definition their success is more hidden.

Location 1054:

Every bit of savings is like taking a point in the future that would have been owned by someone else and giving it back to yourself.

Location 1132:

Investing has a social component that’s often ignored when viewed through a strictly financial lens.

Location 1138:

What’s often overlooked in finance is that something can be technically true but contextually nonsense.

Location 1156:

Anything that keeps you in the game has a quantifiable advantage.

Location 1157:

If you view “do what you love” as a guide to a happier life, it sounds like empty fortune cookie advice. If you view it as the thing providing the endurance necessary to put the quantifiable odds of success in your favor, you realize it should be the most important part of any financial strategy.

Location 1185:

“historians as prophets” fallacy: An overreliance on past data as a signal to future conditions in a field where innovation and change are the lifeblood of progress.

Location 1196:

The most important driver of anything tied to money is the stories people tell themselves and the preferences they have for goods and services. Those things don’t tend to sit still. They change with culture and generation. They’re always changing and always will.

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Location 1198:

The mental trick we play on ourselves here is an over-admiration of people who have been there, done that, when it comes to money.

Location 1241:

Realizing the future might not look anything like the past is a special kind of skill that is not generally looked highly upon by the financial forecasting community.

Location 1247:

The correct lesson to learn from surprises is that the world is surprising. Not that we should use past surprises as a guide to future boundaries; that we should use past surprises as an admission that we have no idea what might happen next.

Location 1312:

The further back in history you look, the more general your takeaways should be.

Location 1414:

You can plan for every risk except the things that are too crazy to cross your mind. And those crazy things can do the most harm, because they happen more often than you think and you have no plan for how to deal with them.

Location 1440:

the most important part of every plan is planning on your plan not going according to plan.

Location 1494:

when you consider our tendency to change who we are over time, balance at every point in your life becomes a strategy to avoid future regret and encourage endurance.

Location 1525:

Every job looks easy when you’re not the one doing it because the challenges faced by someone in the arena are often invisible to those in the crowd.

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Location 1697:

Optimism is the best bet for most people because the world tends to get better for most people most of the time. But pessimism holds a special place in our hearts. Pessimism isn’t just more common than optimism. It also sounds smarter. It’s intellectually captivating, and it’s paid more attention than optimism, which is often viewed as being oblivious to risk.