(started 3rd nov 2015)
Let’s start with a bit of skepticism. I’ve written about feeling guilty several times before, what makes this time any different? Well the main thing is that I’m not actually flooded with guilt right now, so it’s not like an escape mechanism. By escape mechanism I mean… I’m not talking about guilt to avoid addressing the foundations and fundamentals of said guilt. I’m not talking about it just to wash myself with good feels. That’s one of the patterns to watch out for, when you’ve defined yourself as a victim of some sort.
So we can start fresh by just approaching the whole thing with some calm, level-headed curiosity. What is the guilt, and where does it come from? Etymology is always a great hint, and it doesn’t fail me today either. The word guilt comes from Old English’s gylt: “crime, sin, moral defect, failure of duty.” And I have to say, “Failure of duty” captures it perfectly. The moral defect bit is sort of a package deal. 
Have written about this before. It’s far too easy to conflate different sorts of failure. Failure is an event, it is not who we are. We are bigger than our failures and our successes. A common response to that is “we will be judged by our successes and failures”, but even that is actually misleading. Because there are two kinds of judgement, and we often horribly conflate the two. The first is judgement as part of a sorting and/or selection process, like selecting somebody for a job interview. The second is the more iffy but massive ‘moral’ judgement, where we try to grasp at the fundamental value of a person. As I write these words I realize how odd that sounds. Paul Graham has a great post about this, and I’d defer to that: http://paulgraham.com/judgement.html
The important takeaway there is not to take optimal-set selection personally. If your teachers, etc don’t quite appreciate your oddball quirks, don’t take that personally. It’s not about you. Not everything is about you. Stop being so goddamn self-centered, bruh.
And I guess where it gets complicated is– the language we use doesn’t always make that distinction clear, so it’s quite understandable that people mess this up. I’m speaking in the general but all of this is really about me (wow, this vomit is a trainwreck). That is, I’m talking about my own experience. Let’s start over and clarify. I don’t want to go through my whole childhood story again, I’m bored of repeating that shit. The point is that I used to be competent at one set of t hings and incompetent at another, and I was excessively (IMHO) celebrated for the former and unecessarily (IMHO) chastized for the other. It’s easier to make the case that I over-celebrated as a kid, though maybe if I weren’t then I wouldn’t be who I am today, and I might regret that… though probably not, because I am always me, no matter which me I am.
It’s harder to be clear about the unnecessary chastizing part. Unnecessary for my personal growth and development and education, but that wasn’t what it was all about, that’s the part where it wasn’t all about me. It was about what was best for the broader system, for the whole, and I appreciate that that is a necessary thing. I appreciate the schools need to do the best with what they have to achieve what they can, and they aren’t exactly obligated to look out for weirdos like me. In the general sense, a case could be made that the weirdos need to be protected a little for make benefit of society, but life isn’t lived in the general sense. It’s every weirdo for himself.
(Continued 7 Feb 2016)
So let’s try to TLDR the above. Guilt is a feeling. It’s often a legitimate feeling, and it’s a signal from the mind/body that something is wrong. The signalling mechanism itself might be broken, which means it’s possible to feel either too little guilt or too much guilt. In both cases, we’re not deferring to some moral authority about what is an absolute, objectively appropriate amount of global guilt. Rather, we’re talking about guilt as a signalling mechanism for influencing behavior. If guilt makes you do things that are in your broad self-interest, it makes you a good person, father, husband, friend, colleague, and it drives you to do things that also make you satisfied and happy, then it’s probably a good thing and it should be a part of your life. If you just need to confess to a priest once a month or you need to have beers with a friend to deal with that, then so be it, that sounds like a legitimate coping mechanism. If having absolutely no guilt enables you to go on and create incredibly amazing things, like iPhones and Facebook, and millions of people are helped as a result, that’s pretty much great too.
And really, that’s looking at it from an outcome-centric POV. The person whose judgement you’ll have to bear is your own. That much seems rather inescapable, unless you’re really disassociative or are able to run away from your own mind. (I don’t think anybody’s ever really succeeded at this and I’m not sure it’s worth trying.) Beyond that, it’s partially up to you, and partially whatever you’ve inherited. If you believe or were raised to believe in a vengeful god, you might be worried about his or her judgement. Then there’s family and friends and peers and “others”. We’re often socialized to care about what other people think, and we seem to have some innate system for caring about others a priori, too. The two are interconnected.
But the point is, all of that is negotiable and navigable. Guilt begins when you feel that you have failed your duty– to yourself, to your family, to your peers, to society, to God. All of those things are really ideas, but sometimes ideas are backed up with violent force or threats– ie your parents might expect you to get certain grades or marry somebody of a certain type, and if you don’t do it, they might ostracize you, make you feel bad, withhold your inheritance, even be violent towards you, etc etc. Beyond that though, once you get into a position of strength, you get to renegotiate what your duty is– to yourself and to everyone else around you. So I think if you want to deal with guilt issues, that’s the sort of framework you have to work with. What is my duty to myself, first and foremost? How do I know if I’m honoring that duty? And then you work your way outwards.
Guilt is an unpleasant feeling, and nobody should feel crippled by guilt to the point where they can’t function, can’t get anything done, get driven to suicide, or simply live a miserable life. Life is just too short for that.