Hand-picked quotes about luck from the best non-fiction books

We tend to be overly optimistic when we map out timelines, goals, targets, and other horizons. We look at the best-case scenario instead of using the past to determine what a more realistic scenario would look like.

The biggest single point of failure with money is a sole reliance on a paycheck to fund short-term spending needs, with no savings to create a gap between what you think your expenses are and what they might be in the future.

But if something has 95% odds of being right, the 5% odds of being wrong means you will almost certainly experience the downside at some point in your life. And if the cost of the downside is ruin, the upside the other 95% of the time likely isn’t worth the risk, no matter how appealing it looks.

Many bets fail not because they were wrong, but because they were mostly right in a situation that required things to be exactly right.

Things that have never happened before happen all the time.

A good rule of thumb for a lot of things in life is that everything that can break will eventually break.

If a VC makes 50 investments they likely expect half of them to fail, 10 to do pretty well, and one or two to be bonanzas that drive 100% of the fund’s returns.

The more you overestimate your own skill relative to luck, the less you learn from what the environment was trying to tell you, and the worse your decisions become.

We need to train ourselves to see the world in a probabilistic light - and even then, we often ignore the numbers in favor of our own experience. We believe what we want to see, not what research shows.

“It’s not whether you’re right or wrong that’s important,” George Soros once said, “but how much money you make when you’re right and how much you lose when you’re wrong.” You can be wrong half the time and still make a fortune.

Perhaps 99% of the works someone like Berggruen acquired in his life turned out to be of little value. But that doesn’t particularly matter if the other 1% turn out to be the work of someone like Picasso.

Successful investing demands a price. But its currency is not dollars and cents. It’s volatility, fear, doubt, uncertainty, and regret—all of which are easy to overlook until you’re dealing with them in real time.

Luck and risk are both the reality that every outcome in life is guided by forces other than individual effort. They are so similar that you can’t believe in one without equally respecting the other.

You did what worked in the past, or what you had decided would work - and failed to grasp that the circumstances had shifted so that a previously successful strategy was no longer so.

You’re not lucky because more good things are actually happening; you’re lucky because you’re alert to them when they do.

The difficulty in identifying what is luck, what is skill, and what is risk is one of the biggest problems we face when trying to learn about the best way to manage money.