“We are very good at predicting the future – except for the surprises – which tend to be all that matter.”

Iteration: At some point, it may be better to focus on the likelihood and impact of surprises instead of trying to improve my base-case model by a fraction of a percentage. 

“Invest in preparedness, not prediction.”

“People don’t really communicate on social media so much as they perform for one another.”

Iteration: View social media posts as performance art instead of non-fiction.

“With a large enough sample, any outrageous thing is apt to happen. That’s part of why the world seems so crazy, and why once-in-a-lifetime events seem to happen regularly.

…if an event has a one-in-a-million chance of occurring every day, it should happen to 8,000 people a day, or 2.9 million times a year.

Iteration: Another reminder of how bad we (humans) are at processing large numbers. The 24-hour news cycle now exposes us to more one-in-a-million chance events than ever. The world is not crazier than ever – its exposure has changed. As Housel put it a few pages later, “We just see more of the bad stuff that’s always happened than we ever saw before.”

“The best story wins. When a topic is complex, stories are leverage. Guiding people’s attention to a single point is one of the most powerful life skills.”

Some of the most important questions to ask yourself are: Who has the right answer, but I ignore it because they’re inarticulate? And what do I believe is true but is actually just good marketing.”

Iteration: Replace inarticulate with disliked, new, unknown, or any other bias. The best answer is often unfamiliar, unknown, or uncomfortable. 

Bezos once said, “The thing I have noticed is when the anecdotes and the data disagree, the anecdotes are usually right. There’s something wrong with the way you are measuring it.”

Iteration: I remember the day I told my boss I had data available to help him win whichever side of his argument he wanted to be on. He replied, “Congratulations, you just became a real analyst.” We love data and quantification, but it can be bent, abused, and manipulated. The real skill is peeling back the details of the data and providing thought. Data interpretation is the more impressive skill. 

“Most things have a natural size and speed and backfire quickly when you push them beyond that.”

Iteration: Sitting in a room and applying simple math or hurried thoughts on how to double a measurable item or event is easy. Experience teaches you that doing such a thing is more likely to be exponential than linear.