Whenever I make a mistake that really upsets me, I send an email to myself about the mistake. By default, the email sits in my inbox for a week, after which I can archive it, but depending on how upset I am about the mistake, I might include in the subject "(2 weeks)", "(1 month)", "(3 months)". The whole point of this is because I don't like having emails in my inbox, I'm continually reminded of my mistake and will hopefully not repeat this in future.
A few people close to me have told me this seems like an unhealthy habit of negativity and that I am beating myself up too much.
For context, almost all the emails I send to myself involve chastizing myself for being too passive, e.g. "next time introduce myself to that exec/important person/girl at the gym, etc." I am naturally not assertive and would like to be a lot more confident and assertive, but am not sure if this is a system for getting there.
On the one hand, it is similar to journalling which is generally considered good. On the other hand, it works off of negative reinforcement. One idea is to just have all my mistakes in a separate doc, but I'm not forced to look at that doc the same way I am forced to look at my inbox. I guess I could have a habit of looking at that doc once a week. That might be the best solution.
Happy to hear anyone's thoughts.