One of the most important aspects to being successful and fulfilled is to be able to analyze and understand your past mistakes. After all, if you don’t learn from them, you are doomed for a re(or three)-peat. 

If you’re Type A and very self-critical (like me), the problem quickly becomes that dwelling on your past mistakes is like a recurring car crash dream: it sucks, it happens over and over again, and you are powerless to stop it. For example, even though it’s been many months since I shut down my last startup, rarely a day goes by that I don’t go over my mistakes from that period, trying to figure out what I can do better but beating myself up in the process.  

What I realized however was that all of my self-flagellation was treating my mistakes the same – the big ones, the small ones, and everything in between. They were all equally bad in my mind, and I would dwell on them with the same caustic energy.  For example, an overpriced office lease we signed and a couple of bad employee hires are equally disturbing. Every entrepreneur knows that the former sucks, but the latter can kill a company – so treating them the same serves little purpose but to hide an opportunity for future self-improvement. 

But failures and mistakes are not created equal. They of course vary by magnitude, but also in type and how we should respond to them. In order to determine the effort and correct response for not repeating our past mistakes, we have to treat them differently. 

Stanford’s famous “Designing Your Life” course has a section on analyzing past mistakes, and the creators have come up with a taxonomy that makes a lot of sense for thinking about failure. I’ve modified it slightly in order to accommodate some of the research I’ve been doing with corporate and individual clients and have distilled it to a framework you can use. 


The Mistake Matrix

The Mistake Matrix is a framework for analyzing your past mistakes, putting them into context, and creating concrete actions you can take moving forward (if appropriate). Most failures fit into one of the following four categories:

A/ Screw Ups (Minor, Ignore) 
B/ Weaknesses (Structural, Embrace) 
C/ Growth Opportunities (New Directions, Lean In)
D/ Terminal Failure (Outside Your Control, Accept) – note: this is a unique kind of failure that you cannot change and is final. For example, the death of a loved one. 

And those categories can be further categorized by proposed action to improve your future: 

How To Implement the Mistake Matrix

  1. Create a Table that looks something like this in your spreadsheet program of choice:

Then go back in time and list all past failures that come to mind. Do not fill in any other columns beyond the Failure Event (Column A) at first. If you’re highly self-critical this may be easy. If not, you may require more time to think through the various failures of significance. Either way, do only as many as come to you, and stop listing failures as soon as you’ve exhausted the main part of your brainstorm – you can always come back and add to the matrix later.

  1. Categorize Your Failures
    Use the list of failure categories from above (Screw Ups, Weaknesses, Growth, Terminal) and categorize each of the failures you listed in column A. 

  2. Review the Table
    How many of your failures are non-actionable types (Screw Ups and Terminal)? Many self-critical people have large lists of these which – upon reflection in this exercise – are not very important after all. Give yourself an opportunity to look at these unactionable failures and resolve not to invest any further energy in things that are not worth changing. Let them go, and you’ll have more resources to devote to the stuff that matters.
    Now, sort the table to bring the actionable categories (C&D) to the top. We are only going to spend time on these categories. Review the list and combine any failures that are similar or identical. 
  3. Identify Lessons Learned
    Think about the top 1-3 things that you learned for each of the C&D category failures, and write them down. Reflect on this list again, and consider how these lessons can be taken to heart.

  4. Write a Future Action
    Once you’re ready, distill your understanding of the failure, it’s category, the lessons and your current situation to identify one concrete action you can take to try and prevent future recurrences. 

Make an Action Plan from the List

Set aside some time each week for reflection on this list. Pick a concrete action and commit to working on it. Check in with yourself or a coach on regular progress against this list.

I know that putting so much attention on your failures may seem like a self-reinforcing criticism that can be awkward, frustrating or even negative. However, the experience has been that only by confronting failure head-on, by understanding it, analyzing it and reconstructing it for positive purpose, can we truly learn from our mistakes and move on. 

Hopefully the Mistake Matrix helps you start that journey, and remember to reach out anytime if I can be of help.


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