It is a common idea that we should learn from our mistakes. In practice though I see many people making the same mistakes repeatedly. I myself have found that it often takes me making the same mistake at least twice before I really learn from it. Leading a startup is about personal growth and mistakes are that opportunity for growth, so how come it is so difficult to do?

The framing of “learn from your mistakes” suggests that this is entirely about a rational process. It is too easy to think of the mistake as a failure of rational analysis. There were several options available and for some rational reason, I picked the wrong one. If I am good at analyzing that mistake after the fact and understand the reason, surely I will not repeat it.

But most important mistakes, especially when it comes to leadership, have a strong emotional component to them. That is the real source of the mistake wasn’t a rational error but rather an emotion such as fear, regret or maybe greed, made us view the situation in the wrong light. At a later point, without the emotion present, the mistake will seem rational and easily avoidable. But if a similar situation arises and we again are driven by the same emotion we are extremely likely to repeat the mistake.

We will then blame ourselves. How could I have been so stupid to make that same mistake again? I knew better. But it is not about knowing rationally, it is about identifying the source of the emotion and working on that.

Fear in particular stands in the way of leadership. For example, a common pattern are organizational changes that need to happen but will cause disruption. Many leaders will wait too long to make these. After the fact they will often say something like “I should have done that months ago.” They vow not to make this mistake again which at this points seems like a rational weighing of the pros and cons of solving the organizational problem. But what really drove the mistake was their own fear of something going wrong and so the downsides loomed so much larger than the benefits at the time when the decision had to be made.

So how does one do this? The key is to focus in on the emotional component of a decision and be willing to ask probing questions of oneself, in particular about sources of fear and regret. As a leader, any encounter with a problem that brings up emotions is an opportunity to learn about this. Even if you do not have children, I highly recommend Dr. Shefali Tsabary’s book “The Conscious Parent” (see prior post also). The same approach she describes can easily be transferred to relationships with others in our lives, including partners and employees. Once you understand the source of an emotion you can try to let go of it or at least be conscious of it in the future.

So the next time you make a big mistake, don’t look at it just through the lens of rational analysis. If you really want to learn from it you need to understand your emotions and where those came from.