Intellectual weaknesses
For a while now I've been trying to think a bit about the way I think. When I get something wrong, fail to solve a problem, misunderstand something, or whatever, I try to look back on what went wrong, and I try to notice if it's the same thing that went wrong on other occasions. I now think I'm in a position to write down some of my most noticeable intellectual weaknesses. (At least, most noticeable to me. I expect other people probably notice different weaknesses about me from the ones I notice about myself.)
Neophobia. I often find that I'm extremely reluctant to get into a new piece of thought: picking up a new problem, or starting to learn about a new thing. Typically once I finally do get over that activation-
Too uninterested in the actual compared to the possible. To some extent this almost isn't a weakness –
Difficulty keeping track of many things. I much prefer to have a small number of problems to work on, each of which is complicated and fiddly, than a large number of problems each of which is in itself simple. I can handle complicated problems fine (or rather, I have at least as much of a fighting chance with them as anyone else), but keeping track of lots and lots of things without forgetting about one of them is much harder for me. Of course I can and do compensate by constant list-
Compartmentalisation. When I learn a fact in one context, I often find I've failed to apply it in another context, or failed to relate it to a fact I learned in another context which in combination with the first one would have told me something really useful. I seem to have a few mental compartments for thinking about different kinds of thing, and sometimes those compartments don't link up and talk to each other when they really ought to.
Insufficiently bold imagination. Quite a few times in the past couple of years I've tried to solve a problem by considering a lot of candidate solutions and then judging which of them are sensible or workable or likely. Often I've failed to solve the problem, and found out afterwards that this was because the real answer was completely outside the space of possibilities I'd considered –
I wonder what can be done about these. One feels that the neophobia ought to be dealable-

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However, that's probably annoying to hear rather than helpful, so I will try to come back and see if I have any positive suggestions how you (or I) might be able to improve on them...
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I could believe that compartmentalisation was a universal human cognitive bug, but I think most of the rest are things where it's possible to go too far the other way. (Of course it may well be that there is no actual happy medium between the two...)
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I don't think this is a universal bug. I suspect it of being a development/aquired skill issue. Sion and I run into this discussion a lot. Last night we were talking about the way each of our memories work so differently - and exactly HOW different we were to each other. Memory and compartmentalisation must be interelated very strongly. Exactly how must be where the action is.
It may be too easy to say that the way your mind works gives your brilliance you have in your fields of expertise and the way my mind works gives me solid capability in others, but I don't doubt that it's true.
For me, the way I break out of being unable to think laterally when it is critical that I must do (it's my job) is to hold the problem in my mind while exposing myself to a completely different environment. This can be as bizzare as walking round a garden centre while trying to work on a fundraising concept or flipping through a massive office supplies catalogue while thinking about trying to sell mortgages for building societies. You put these two seemingly random things together and suddenly become aware of connections that you didn't think of.
So I would say that as a person I have developed my lateral thinking over many years and am now quite good at it.
However - when I consider what people like you and Sion do for a living, the very idea gives me a headache. I guess that might also be because I haven't spent years training my brain to do it. But I suspect that we all need to have a small natural inclination and interest to develop skills to the point of excellence.
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For ages I've been meaning to write a more general discussion of the mental process involved in programming, with regard to the whole issue of many applicants being unable to write programs at interview. But my brain is fried now because I've spent two days tracing backwards in unfamiliar code in search of inconsistencies.
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I often find I'm intimidated getting started on something, I just imagine it will be tedious. What I think I need is to partly just recognise that, and partly get used to low-effort ways of getting started, reading a faq, trying some experiments, without worrying if it's not instantly obvious, as it usually becomes clear quickly. But I don't know what would apply to you.
as soon as I have to manage without a list it all goes pear-shaped.
Lots of simple things sounds exactly what lists are good at; delegating the "remembering" so you can concentrate on the "doing". Why DO you ever have to manage without a list?
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Oh, there's always some reason it works out that way. Somebody will tell me things I need to do in some inconvenient situation where I'm not next to a computer or piece of paper. Or lots of people will tell me things in different situations, so that I write them all down in different places and suddenly having to remember a list of the places I wrote them down isn't any easier than remembering all the things themselves. Or the list gradually grows from "too small to bother writing down" to "too large to cope without writing down" and I don't realise it until it's two items into the latter range. Or the list is a public one that other people can put things on (e.g. work bug tracker) and contains lots of stuff that's (for immediate practical purposes) ignorable drivel, but you have to remember which of the 130 things on there are not drivel and actually want sorting out. Or ...
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Lists work well when you're operating in 'pull' mode: you know you need something to do, so you go to the list, pick off the next thing, and make a start. When you finish that one, it's back to the list.
But in 'push' mode, when the various things I have to remember about all need to grab my attention in particular, different, confusingly overlapping sets of circumstances ... if I were to use a list to remember all of them then I'd have to consult the list all the time just in case there was something on it relevant to the current situation, and that would (a) be a huge expenditure of effort, and (b) not work anyway because after checking the list 99 times with no results my eyes would glaze over and I'd miss the thing I should have spotted the 100th time.
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I agree that's difficult and I don't have any good solution. The best I've done is to take a good guess when I'll be doing that and schedule it for then (sat: "if I go shopping, do X in town") or just accept I'll never remember it and make a special trip.
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Indeed, and other kinds of circumstance (next time I see a particular person, next time I'm scheduling a meeting, next time I write code that does a particular thing, next time I'm in the sort of general situation that I've just decided needs me to start list-making more proactively) are even harder. I have thought before that a GPS-based reminder system would be quite handy, but it wouldn't be the whole story even then – what I really need is a reminder system with read access to my thought processes, because it needs to respond to arbitrary semantic criteria on my current situation and the only thing that even works that out is my brain :-)
a separate TODO list for all the most common places
... the most obvious example of which is a shopping list, of course, which actually is the one list that I do carry everywhere with me.
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I agree that's what you really need, but it's also possible that maybe 90% of the time the problems can be fixed with something lesser, and then the amount to just remember may become actually manageable :)
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Do you respond to colour? Colour-coding the list items and notebook jottings could help (you have to do it when you collate the jottings, of course, but that adds another check). Sorry I can't offer anything more useful: instead, have a *hug* :)
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