Strangely, it seems that the more competent or knowledgable I become, the more hesitant I am about the subject. Certainly, over the last two years I've become vastly more uncertain about myself, my thoughts, my core competences. So what's the limiting case? Is total competence an absolute freezeup? Or is the trend hyperbolic?

I think that knowing more makes it more difficult to make decisions for good simple reasons in some cases, and vastly easier in others. The deciding environmental factor appears to be whether the decision regards a finite deterministic plan, or a creative unbounded one. Creative tasks actually get harder the more information you're trying to include. Engineering gets easier because your bag of preset tricks is larger.

So what's the solution? If competence leads to problems in creativity, and anticompetence leads to issues with design, is it simply a two directional tradeoff, with no shortcuts?

Well, things aren't that simple. But one good way to keep yourself from becoming too competent, is to learn in new areas. increasing your total bag of tricks, whilst making you magically a rank newbie in some area. This doesn't solve the underlying problem, but it helps psychologically to have something you can do.

Real creativity is of course, out of the picture for humans. We are neural creatures, and our 'creativity' consists of misapplying pattern to object. We can't generate from principles, or come up with de novo patterns effectively. Perhaps there is some way around this, but that is why more information retards our creativity. A more aptly designed intelligence would not have this problem, I suspect.

Real design is more likely, but it has problems. Because our scientific method are so primitive, we have very few really solved design problems, we have preferred solutions, but few things have been optimized to a point where re-use is the simplest and best option. So design becomes a creative endeavor on some levels. So it's difficult to seperate too much, and not enough information. See above.

Psychologically the problem becomes even more complex, because in order to design and create well, we need confidence, attitudal differential , a sense of place, certain environmental factors must be invariant, etc. Providing yourself with a good working state can be more difficult than the work itself, sometimes. Which is frustrating, exaberating the problem.

unfortunately, this is another one of those areas where a few million years of development would come in handy. If we had more history, we might have optimized strategies for dealing with situations like this. But we're a young species, so you'll just have to work it out on your own. If you do, let me know, and we'll try and get the word out. On how NOT to do it, if nothing else.