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How to Healthfully Learn from My Mistakes

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Anonymous User at Taro Community10 months ago

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.



  • 5
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    Senior Software Engineer and Career Coach
    10 months ago

    Thanks for being open to sharing the habit you do to learn from your mistakes.

    I think whether its an unhealthy habit would depend on its impact on you.

    • Does it make you feel bad about yourself as a person?
    • Does it actually help you get better at these things?
    • Does it lower your self-esteem?

    Be cautious about it depending on the answers above.

    Regardless of what you do to help you learn from your mistakes, it's important to remember that none of us are perfect. We are far from it. It's completely normal to have things you want to get better at. So there's no sense in beating yourself up over it.

    With that said, if you're looking for other approaches, here are some that come to mind:

    • Identify a pattern or group of things you'd like to work on. Read a book on it, take highlights with Readwise, then set Readwise to give you highlights of that book every day. Try to apply some amount of the tips you read into your day-to-day. Check them off over time
    • Meditate. I personally can't commit to this but I know it is highly recommended. You could either do the "not thinking about anything" meditation or a more "reflective" meditation, where you just let yourself think about the different parts of the day that happened, what went well, and what you think could have gone better.
    • In general, reward yourself when you do things that show you are making progress. It can be getting a nice meal, dessert, a new video game, watching extra Netflix, getting a massage, anything like that. It will help reinforce your growth mindset and help your mind relax.

    Regardless of what you do, I recommend reading or watching an Atomic Habits summary. The one by Ali Abdaal is good: https://www.youtube.com/watch?v=YT7tQzmGRLA. Him and Clark Kegley have good videos about habits: https://www.youtube.com/results?search_query=clark+kegley+habits

    Best of luck!

  • 3
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    Principal Director at Capgemini
    10 months ago

    I think the overall practice of identifying and documenting 'mistakes' has a lot of benefits, as long as you don't tear yourself down in the process. This is essentially the underpinning of introspection, which greatly accelerates your growth because you are effectively squeezing more 'reps' out of a single experience and building self-awareness.

    However, I recommend reframing each 'mistake' as a 'mini-case study' instead and would extend your approach by doing 3 additional things:

    1. List out the lessons learned
    2. Document better way(s) to handle the situation if it happened again
    3. Share and teach others what you captured in #1, #2, which reinforces your learning even more while paying it forward
  • 3
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    Senior Software Engineer [L5] at Google
    10 months ago

    What a thought provoking question!

    This questions gets into the psychology of self-improvement and I'm not sure any of us are really experts or have degrees there. What I can share is what I've learned through my years of being w/ a coach, reading various books, and applying the advice/lessons I've been given. So do take all of these w/ a massive block of salt.

    And before I get started, Jordan and Casey has a list of amazing questions and resources. I would think hard about them.

    Specifically, "does this habit make me feel worse?" is an important question. If reading those email headings makes you feel like a failure or somehow inadequate, then I do believe this isn't healthy.

    Now, the second question is whether this behavior has actually achieve your goals. Have you taken more proactive behavior in social settings when you've seen those messages? If not, the habit is at best ineffective.

    If a habit makes you feel worse AND doesn't help you achieve your goals and/or become the person you wish to be, then it's likely self-destructive.

    From what I can tell, most of us have some level of self-destructive tendencies - for me, it's binge watching shows and binge gaming, and for some it's comparing themselves to others, etc.

    However, from my personal experience and reading other psychology books, there almost always is a good emotional reason we are engage in self-destructive behaviors, despite the fact we know it doesn't help us achieve our goals.

    A large part of that for a lot of us is the feeling of comfort. Loneliness, self-loathe, and other painful feelings are sometimes ingrained in us from our past experiences, and reminding us of these painful feelings can sometimes in turn help feel us feel more comfortable because they are familiar.

    So maybe the question to ask is what are you personally or emotionally gaining from this activity? We humans are very bad at doing things that give us no incentives. There must be something you are gaining from doing this that you need. Know this will help in the case you wish to replace this behavior - you would probably have satisfy the underlying emotional urge some other way.

    Lastly, resources!

    If this piqued your interest in psychology of our behaviors, I've found "Maybe you should talk to someone" very informative and great read.

    If you are looking for more proactive ways to become more proactive socially, there are actually social coaches for engineers out there. I've chatted with Myke but never taken any courses with him, but this might be something you want to look more into.

  • 0
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    Anonymous User [OP]
    Taro Community
    10 months ago

    Thanks Jordan, Casey, and Kuan. Very thoughtful and helpful responses.

    To address Kuan's point, the reason I do those behaviours is because it's hard doing something new and putting yourself in situations where you might fail and be embarrassed. Nothing novel here.

    To address Jordan's questions, I confess that I don't have good or hard data on how effective this habit is. Does it make me feel bad? I guess a little bit. More frustrated that I have an email in my inbox I can't archive.

    Thanks Casey for the practical questions.