The first is when you double down and defend the status quo. When, despite the available evidence (increased competition, fee compression, technological disruption), you spend too much of your time, energy and money defending a hill you will die on, willing but failing, to keep things the way they are forever.
This is the story of Kodak, Blockbuster and Toys R Us, and we both know this list could go on for pages.
The second is the mistake you make while you are pursuing or inventing the future, ideas or experiments that don’t quite work out the way you had hoped. Everyone, including me, has a long list of these Frankenstein ideas that have trashed the lab.
This is the story of Apple, FedEx and Airbnb.
You are almost never hurt badly by the second kind of mistake; yet you probably make the first mistake over and over again because it seems less risky to try to keep things the way they are than it does to redefine the future.
You might regret that.