Invert, always invert

I recently finished Poor Charlie’s Almanack, a collection of eleven talks by Charlie Munger. When Stripe Press published a brand new edition of it with their usual beautiful type setting and cover design, I couldn’t resist.

For those unfamiliar to Charlie, he is worth getting to know. While his notoriety stemmed from being one of the greatest investors of his generation, he was also a prolific speaker and writer, and was an advocate of cross-disciplinary thinking and application of mental models. He excelled in taking ideas from mathematics, philosophy, and psychology in order to think about the world in a new way.

In this month’s article, we’re going to be looking at one of the mental models I learned from Charlie and how it can help us as engineering leaders think, plan, and execute better by avoiding failure.

Software engineering is tough. No matter how hard we try and how hard we plan, we always end up missing simple things which cause a whole bunch of problems down the line.

This can range from missing features and functionality (“how did we not think of that?”), to edge cases that we haven’t thought about (“how did we not see that coming?”), to poorly conceived rollouts and