This way of thinking, in which you consider the opposite of what you want, is known as inversion... Inversion is a powerful thinking tool because it puts a spotlight on errors and roadblocks that are not obvious at first glance. What if the opposite was true? What if I focused on a different side of this situation? Instead of asking how to do something, ask how to not do it.
Many great headlines and titles use the power of inversion to up-end common assumptions. As a personal example, two of my more popular articles, “Forget About Setting Goals” and “Motivation is Overvalued”, take common notions and turn them on their head.
You can learn just as much from identifying what doesn't work as you can from spotting what does. What are the mistakes, errors, and flubs that you want to avoid? Inversion is not about finding good advice, but rather about finding anti-advice. It teaches you what to avoid.
Inversion is counterintuitive. It is not obvious to spend time thinking about the opposite of what you want.
Inversion can be particularly useful for challenging your own beliefs. It forces you to treat your decisions like a court of law. In court, the jury has to listen to both sides of the argument before making up their mind. Inversion helps you do something similar. What if the evidence disconfirmed what you believe? What if you tried to destroy the views that you cherish? Inversion prevents you from making up your mind after your first conclusion. It is a way to counteract the gravitational pull of confirmation bias.
Inversion is an essential skill for leading a logical and rational life. It allows you to step outside your normal patterns of thought and see situations from a different angle. Whatever problem you are facing, always consider the opposite side of things.