On Mistakes

There’s a natural tension when we talk about mistakes.

  1. We want to avoid mistakes naturally because they are costly and painful
  2. Yet we know mistakes is one of the best sources for learning and growth

The first part is so embedded in us, that most writings on mistakes focus on the second part. No surprise a significant amount of fortune-cookie social media post talks about how we should make them in order to learn.

An example of an idiotic fortune-cookie saying "Don't make the mistake of being afraid to make mistakes"
Another idiotic, insincere fortune-cookie on social media

Mistakes != Learning

Another often overlooked detail when talking about mistakes: they do NOT automatically lead to learning. Take for example, if you’re constantly fixing an error your colleague Mallory makes repeatedly, you would rightly conclude (and also rightly frustrated) your colleague Mallory is not learning at all.

The opposite of that example but with the same outcome of non-learning is when you never try again after a mistake.

For example, you experiment with a new technique at work and an error was made. But you falsely conclude that new technique was not worth it and never experiment again. Not even with any adjustments from the original approach. If I were to ask you why the new technique didn’t work, and you cannot go beyond “it simply doesn’t work”, can you safely say that you learn anything useful from that one experiment? Can you safely say you draw the right lessons from that one fault?

Make NEW mistakes

There’s a way to square the circle when it comes to mistakes. First, let’s revisit the original dilemma.

  1. We want to avoid mistakes naturally because they are costly and painful
  2. Yet we know mistakes is one of the best sources for learning and growth

And if I add to that list with a couple more points, we get

  1. We want to avoid mistakes naturally because they are costly and painful
  2. Yet we know mistakes is one of the best sources for learning and growth
  3. But if we make the same ones repeatedly, we are obviously not learning either
  4. We can draw wrong conclusions from our erroneous ways

The best take I have seen that takes into account everything on the list and summarize it in a pithy way is: make new mistakes. I recall coming across this idea on the internet though I cannot recall from where exactly. It would be great, if I can attribute the canonical source, so let me know.

Analysis of Make NEW mistakes

If you only consider point 1 and 2, one logical rule would be “make the smallest number of mistakes”.

Point 3 raises a loophole with that rule. Someone making the same error repeatedly clearly satisfies the rule but is not learning as in the case for Point 3. Point 4 simply points out the tenuous link between errors and learning.

The “make new mistakes” rule addresses the first 3 points directly and the 4th point indirectly. It exhorts us to still make errors but in a thoughtful way. Furthermore, there’s an implicit emphasis on learning from your previous faults via the word “new”.

Regarding the 4th point, there’s no guaranteed way of drawing good conclusions from our past errors. But if we can continuously make new (and hopefully better) mistakes, that’s a definite sign of learning.

Finally, let’s stress test the “make new mistakes” idea and try to find a loophole with that one.

Suppose you need to make a decision and one option has the possibility of the ultimate catastrophe — losing your life. And obviously up to that point in time in your life, that error would be brand new. Wouldn’t “make new mistakes” push you towards that dreadful option?

Caveat: Be Careful with One-Way Doors

Jeff Bezos of Amazon divides decisions into two types: type 1 where you cannot walk back and reverse and type 2 where you can. He cleverly likens them to doors.

Type 1 decisions are one-way doors. Once you enter one-way doors, you cannot come out the other way. Type 2 decisions are two-way doors which you can come out the other way.

On the surface, “make new mistakes” can lead you to treat both types of decisions equally. Therefore, you might want to tweak it into “make new mistakes especially when it’s a two-way door situation”. My ego also would like to share this needlessly complex version: “make new mistakes in a way you can continue to make new mistakes in the future”.

Given that Bezos himself points out most decisions are Type-2, “make new mistakes” is good enough most of the time. To end off, I leave you with this how-to list on treating mistakes. I intend to update this article whenever I get new information. For now, this is my current best attempt after considering factors such as completeness and easy-to-recall:

  1. Make new mistakes
  2. Preferably better ones than the past
  3. Go slow when it’s a one-way door
  4. Don’t die

Featured image is a photo by Estée Janssens on Unsplash

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