I happen to believe that there are certain mistake that will allow you to not only make mistake, but get you further from where you started and give you new perspectives on things that will allow you to better solve the initial problem you encounter.

These are great mistakes.

First issue: how can you spot a mistake if you don’t know that it’s the one you’re currently in?

Easy. A mistake will not happen without a prior action on your part. This means that if you can spot the type of action and its failure potentiality, you can probably predict how likely it is to be a mistake.

For example, if I’m building a house, doing things that are related to cooking (ie. bake a lasagna, brine a turkey) or programming (ie. GitHubbing, Ruby coding) are more likely to cause failure and result in a mistake than doing things related to architecture (ie. drawing a blueprint, divvying up rooms) or engineering (ie. putting up bricks, measuring woods.)

To put it simply, the rule to spotting a mistake is to ask yourself how far-fetched does the action that I am currently taking stray from the problem I am trying to solve? The further it is, the more likely you’ll make a mistake.

Second issue: could I identify and make great mistakes more often?

I think so; and I think that getting there involves asking yourself if I were…

For example: suppose that I asked you to cook dinner. There are three possible actions you cold take:

1. Do it right: follow a recipe book, consult a friend, get a caterer to deliver.
2. Make a good mistake: combine cooking methods, fuse Peruvian and Swahili cuisine, try exotic ingredients.
3. Make a great mistake by asking yourself: if I were the first human being who discovered fire, if I live in zero gravity, if I had a vacuum chamber, what would I cook for dinner?

Another example. Let’s say that I want to built a house. Again, I could do three things:

1. Do it right: commission an architect.
2. Make a good mistake: seek as much inspiration from outside your field of study, then blueprint it yourself.
3. Make a great mistake by asking yourself: if I were a horse, or a human who could live for 200 years, what kind of house would I make?

Note how, while both types of mistake—good and great—may lead to failure that you can learn from, asking if I were… allow you to see it from different points of view and recontextualize its content.

After you solved this question, you should then return to your original problem and incorporate the things you learn while you were reframing it. Doing this will help you think of singular solutions.

A good parallel to making a great mistake can be found in the Kōan, “a story, dialogue, question, or statement [...] generally containing aspects that are inaccessible to rational understanding, yet may be accessible to intuition.” A Kōan is designed to “confound the habit of discursive thought or shock the mind into awareness” rather than be answered.

In the same manner, a great mistake is designed to reimagine a problem rather than necessarily solve them. From reimagining, then naturally comes the solving.

And if I were you, I would start making great mistakes that produces more elegant, economic and game-changing solutions.