Do Mistakes Get Easier the Better We Are At Something?

Oct 10, 2023 | Coaching, Leadership

I have recently realized that there is a deep irony in the fact that, the more experience and skilled I get in something, the less concerned I am about making mistakes and being right. If my expertise is questioned in an area where I think I am strong, my tendency is to get curious rather than defensive. To ask questions and see what is going on. This happened twice in the last month (probably more but these two stood out). Once, when a coaching client told me that the reflection I had given (that I had thought was really relevant) didn’t resonate or yield anything at all to them. And once during a facilitation, where an exercise fell completely flat. With the first, I realized that the insight I had been hoping the client might get, was not going to come from that particular approach and we changed course. With the second, we rolled up our sleeves as a group to figure out what went ‘wrong’ and that was the discussion that actually let the group to a breakthrough.

Historically, my tendency in either of these situations would have been to start explaining and justifying the reason behind my decisions and trying to get my client/s to see it from my point of view. It would have come from a desire to get them somewhere combined with my own sense of identity and fear of failure. What I’ve realized is that, in most of my own engagements with experts in their field, I want someone skilled and experienced but I don’t want or need perfection. I want someone who can offer new insights, knowledge or experience or even recommendations, but I want them to also be in relationship not only with me but with the dynamic emerging conversation. Clearly there are some, probably many, exceptions. I would prefer for my car mechanic or surgeon not to make mistakes. Or the chef not to mistakenly put meat (I’m vegetarian) on my pizza! But even then, I (and they) need to recognize that we are all human and make mistakes, or non optimal decisions, or even great decisions that just don’t work for me. And when they do, what I really want is for an honest conversation about where we go from there. Not a justification of why it was actually really right.

It sounds so obvious as I write it down. But our brains are wired to do a mental jiu jitsu to make us feel right at all times (read Mistakes Were Made, But Not By Me by Carol Tavris and Elliott Aronson for a brilliant explanation of cognitive dissonance and how it works). The carefully curated worlds of social media feed into this too –  at least for me.  Posts are all about successes, and even when someone posts about something that has gone wrong, it is often packaged into a success story in disguise. 

As I get more experienced and skilled in something, my identity doesn’t get so caught up in a sense of failure when one thing goes wrong. I can see it within the perspective of all the things that go right. The challenge is to catch this when I am working in areas that I feel less confident in and find strategies to counter my tendency to want to explain or rationalize or not be shown up as a fraud. (I’m sure there is an interesting intersect here with studies on imposter syndrome). My strategies involve staying connected to my own grounding practices (meditation, journaling, time to myself (and recently yoga where I am completely back in beginner mindset again!)) as well as finding ways to name what is going on and remind myself of three things:

  • That ‘failure’ is both inevitable if we are on our own learning edge. I can’t predict it but it will happen.  The skill is knowing how to recover and, where necessary, repair. 
  • That the concept of failure and mistakes is a relative one – I am deliberately using that word because I think we dance away from it too much. But I think back to the Chinese parable of the man whose horse ran away – we just don’t know in the long run what success/failure luck/bad luck is.
  • Building on this, ‘failure’ is a moment in time not a final destination – if I can stay open and in relationship we can use whatever went ‘wrong’ to keep exploring and moving forward.