I find myself agonizing over selective mistakes for a various amounts of time. As far as "carrying" them, well, I will remember them for the longest time. As far as feeling agony, I feel more agony for longer amounts of time if I had made a social mistake. I look back on all the stupid things I've said without knowing what I was really saying. There would be things I would say to other people thinking I was going to get a good reaction just to find out they would despise me for it.
Social incidents come up on occasion and I would feel like an asshole for a brief moment, but then I would totally forget about it until 8 months to a year would go by and I would remember again.
As far as mistakes that have to do with just me, I rarely remember them. At the moment it is hard for me to think of a mistake that I have made that has cost me something, except for a time when I was a child riding my bicycle to the local library. I forgot my lock at home but had the chain, so I wrapped the chain around a light post and my bicycle to give the impression it was locked up, just to realize 10 minutes later my bicycle was gone. This type of mistake only comes up when I am in a situation that is very similar to the one I was in when I made the mistake. I do not feel any agony when the thought arises though, unlike the social mistakes I have made.
I don't think it is just me, but social mistakes last a hell of a lot longer than mistakes that just include me. Now that I think about it, I am sure it is a given with anybody.

My own mistakes: Appx. 4 years.

Social Mistakes: I feel an asshole for about 6 to 10 seconds upon remembering the incident. The feeling subsides the older the incident, but I think I will always feel like an asshole, even it it is just a very tiny bit.

For me the length I carry a mistake seems to me proportional to its size.
The bigger the mistake the longer I carry it with me.
However, I think there are two ways of carrying a mistake.
One way, the past mistake is a learning lesson but also paralyzing.
The other way, the mistake is a learning lesson and a stepping stone to success.
Any mistake can be seen both ways, in fact most mistakes may go though both scenarios. First regret, then empowerment. It is really important to learn to teach your mind to make the most of a mistake.
In Seth Godin terms, never let your mistakes be fuel to your lizard brain, but fuel to your motivation to become a better person, to get closer to your goals.
I think making mistakes is a beautiful and necessary art. We are born knowing nothing and bound to screw up from day one, and only our memory allow us not to trip over he same stone twice.
There is a huge range and flavors of mistakes, from the little ones to the mortal ones.
Taking risks is necessary to learn and succeed, but when we take risks we are bound to make mistakes. If you are not making mistakes, then you are not taking enough risks, and therefore your are postponing any kind of success in your life.
I think, we should never forget the biggest mistakes in our lives.
My biggest mistake was when I was 6 years old, and my sister 3. For some stupid reason, even at that young age, I loved experimentation, and I decided to experiment with my sister, in a very bad way. Both of us were pretending to jump from the sofa onto the carpet and pretend to swim. One of the times, when my sister was not looking, I placed a needle pointing up in the carpet. She jumped on top and the needle went inside my sister's left knee and broke into two pieces.
My parents took her to the hospital, I never told them what it was, she was a little 3 year old in excruciating pain. It took two 6 hours operations to find the needle inside her little knee. The Doctor worked with extreme care to avoid damaging crucial ligaments that would have left my little sister with a life long limp.
The Doctor succeeded, but 27 years later, my sister has to huge surgery scars on her knee as a souvenir from her older brother's stupidity.
Do you think I will ever forget that mistake? do you think the terrible regret stopped haunting me even decades after?
Like I say, there are many flavours and serveries of mistakes. There are mistakes you want and need to make to mature and gain invaluable experience.
But there are mistakes you don't wish anyone would ever make, specially the ones that can affect other people's life, including yours, in very bad ways.
There is a very typical mistake many of us have made, drinking and driving, there is nothing great to be learned from a car accident. There are mistakes that are better left unexplored.
My advice, just make sure that in life you make just enough mistakes to learn which mistakes you should never make.

Personally, I'm bothered by past mistakes insofar as I'm still prone to making them. Examples of such mistakes are having a big argument with a family member, or getting scammed because of not aggressively pushing your agenda (and instead "letting it slide").

So whenever I'm tempted to lecture said family member about some self-righteous opinion, or whenever I'm back in the situation where I sense something shoddy is going on with the salesperson I'm talking to, I remember those instances and my response is usually improved.

I know some who are bothered financial mistakes, and if the nature of the mistake is as above, then I think that's fine.

I'm definitely not bothered by mistakes that don't gel with my current identity. For example, I'm not bothered by any mistakes I made in High School. (I tend to laugh at them)

I think the same can probably be said for those who change professions. As a morally questionable example, some of my relatives who are civil servants seem not to be bothered by the mistakes made under a previous department (health) and move on to a new department (education) with a clean conscience.

Interesting, yeah, I know what you mean about social mistakes. It's no good to adversely affect someone else because of a blunder.

Thanks for the reply here Charlie, good to hear how other people think about this sort of thing. Most people don't talk about it very much, so cheers for the perspective.

I'm not yet very good at it, but I've been trying hard not to be bothered by past mistakes because I do not believe it to be very useful. To me it's just an easier but dangerous shortcut to achieve two fundamental goals: a) maintain an emotional contact with oneself and others; b) make a step toward what we consider a better way of doing things. Being bothered by a mistake is a powerful force because it acts at a subconscious level and as such is more likely to produce the wanted result: connect with the entity we wronged and act to avoid repeating that mistake. On the other hand not being bothered by a mistake is likely to cause one to detach from the world by reducing our empathy levels. It also makes unlikely that we will avoid repeating the same mistakes since there's no bad association with it. But the same force can negatively impact our mood and relationships and degenerate into something that drives us even deeper into the tunnel or hinders our learning.
An alternative I've been exploring is to focus on the wronged side and avoid altogether to be bothered by whatever mistake I've made. This has still a very strong emotional impact, but shifts the focus from oneself to an external source. I found that this drives me even harder to make the other side happy which in turns makes me happy and associate a positive sentiment to remedying (and avoiding) a mistake instead of a negative one with making a mistake. There are plenty possible problems with this approach too, but overall it seems to be working well for me.

All the best and thanks for writing this blog, it's always great food for thought.

This is a great way of putting it Spike:

> To me it’s just an easier but dangerous shortcut to achieve two fundamental goals: a) maintain an emotional contact with oneself and others; b) make a step toward what we consider a better way of doing things. Being bothered by a mistake is a powerful force because it acts at a subconscious level and as such is more likely to produce the wanted result: connect with the entity we wronged and act to avoid repeating that mistake. On the other hand not being bothered by a mistake is likely to cause one to detach from the world by reducing our empathy levels. It also makes unlikely that we will avoid repeating the same mistakes since there’s no bad association with it. But the same force can negatively impact our mood and relationships and degenerate into something that drives us even deeper into the tunnel or hinders our learning.

I re-read it a couple times for depth, good insight there. Cheers.

Good question. A couple things come to mind here:

1. Self-compassion. Think of how you would treat a friend if they came knocking on your door saying they made a mistake. You probably wouldn't chastise them. You might say "hey man, that really sucks, do you want to talk about it?" Then you may explore ways that they could act better in the future.

The risk here is, of course, you go too easy and repeat mistakes. But in my experiments with this self-compassion, I haven't found that yet to be the case. That may be because instead of just forgetting about the mistake, I explore it with a calm mind. Which leads me to #2

2. Think like Dalio. I saw you were reading Principles bay Ray Dalio; one of the themes I read in his work is that "problems" are to be expected 100% of the time, and the faster you get around them the better. He says "The most common source of pain is in exploring your mistakes and weaknesses. You will either react badly to the pain or react like a master problem solver. That is your choice. To figure out how to get around these problems you must be calm and analytical to accurately diagnose your problems."

So, some self-compassion to create a calm mind, and then put on your strategic hat for some master problem solving.