Shane Parrish on the power of second-order thinking:

Second-order thinking is more deliberate. It is thinking in terms of interactions and time, understanding that despite our intentions our interventions often cause harm. Second order thinkers ask themselves the question “And then what?” This means thinking about the consequences of repeatedly eating a chocolate bar when you are hungry and using that to inform your decision. If you do this you’re more likely to eat something healthy.

Those that excel at second- or third-order thinking spend a lot more time running these simulations in their heads, playing out various scenarios and weighing costs/benefits of each unique pathway. It seems like an obvious thing to attempt with any decision; but I see cases regularly where it doesn’t appear that a person is playing out their chosen path beyond the next immediate step and likely outcome.

I’m reminded of the business concept of the “pre-mortem”, wherein a team sits down collectively to look ahead at a decision about to be made or a project about to be tackled, and attempts to predict the contents of the post-mortem saying why the project failed or succeeded.

See also Annie Duke’s Thinking in Bets, a whole book on orienting your critical decision-making capacity on thinking in probabilities.