Great post indeed! With increased longevity and the need to reinvent ourselves and take unfamiliar jobs more and more of the things we do will lack precedent and that increases the potential for surprises. In a post-scarcity future human motivation will be less about surviving and more about improving the world. Most people today are motivated by comfort and security. Few are even motivated by success, and fewer still by humanitarian ideals. No matter how much concerns about comfort and security are reduced many would have no interest in improving the world. In lower level discourse you might simply call them lazy, but it is more complicated than that and an important problem for the future!
As a general principle the right answer depends on the consequence of low quality and the balance of creativity versus practice. In medicine where the consequence of low quality (of a surgical operation for instance) may be death of the patient, there still is value to quantity and perfecting technique by frequent practice. Therefore simulations play a role. Ideally the surgeon makes use of much tacit knowledge in a successful operation, many instinctual elements that cannot be put into words. In many tasks like surgery, you want only intermittent creativity. Most efforts go into getting better and better at a task already mastered conceptually, not into improving the concept.
In a recent interview on Singularity One on One http://singularityblog.singularitysymposium.com/question-everything-max-more-on-singularity-1-on-1/ (first video) Max More, one of the founders of transhumanism talks about how important philosophy was as the starting point for the important things he has done. Philosophy provided an important vantage point from which he wrote the influential papers which started transhumanism. Philosophy is not something to give up or shun, you just need to know what parts of it to ignore in pursuing important objectives.
It may just be my physician's bias, but "diseased" seems like a very imprecise term. The title would be more informative and more widely quoted with another word choice. In medicine you would not find that word in an article title.
There needs to be more cross-talk between philosophy and science. It is not an "either or" choice; we need an amalgam of the two. As a scientist I object strongly to your statement "Second, if you want to contribute to cutting-edge problems, even ones that seem philosophical, it's far more productive to study math and science than it is to study philosophy." Combined approaches are what is needed, not abandonment of philosophy.
drethelin it is an easily solvable formula to determine whether you are right. How many books do you have, how often do you lend them and how many do you lend, how long does it take to read the title of each book, how good is your memory of where books are when randomly distributed? Only if you have a very large number of books or a very poor memory, or both, does it make sense to actually alphabetize etc. On the other hand leisure time activities are personal choice, not everything in life needs to be logical!
Cyan, you could make an analogy with cataloging and organizing the books you have on your shelves at home. It might make for interesting cocktail party conversation to say you had done that, but it would be of no practical value to you, just a waste of time, an expression of compulsive tendencies.
For many people overplanning things like which books to read that are usually spontaneous and unplanned is an example of trying to control more aspects of life than is desirable. We need to be free and unfettered in many parts of our lives. There is endless variation possible. For instance if a book is not fun for you, you may persist in reading it all if that fulfills a specific goal for you, or abandon it, or skip to the end etc. depending on the circumstance. Having a list of books to read and having books in front of you you plan to read are both good things, but from that point on anything that happens is fine. Serendipity plays a very positive role in life and trying too hard to organize things that are by nature somewhat disorganized does not enhance the marvelous accidental discoveries of serendipity.