| | Sven,
I'm responding to your initial post, where you were asking about questions to generate thought about philosophy, as opposed to memorizing. If someone here had a set of good questions that would be valuable, but you would be memorizing someone's questions. The greatest value is in learning to find your own questions. I have been delighted to find that it isn't that hard to do. The right kind of practice, some effort, and in time the mind learns to work at a new level significantly better than one would have hoped for.
When you talk about applying a philosophy to your life, that is a little bit different. Learning how to think about philosophy as a subject is an art in itself. Learning to think about your individual life is different. I'll adrress thinking about philosophy since it provides generalizable thinking skills, good mental discipline, and is often less prone to emotionalism... These skills will transfer across to working on personal goals.
There are different kinds of questions, or approaches that are helpful for me. Few are as productive as asking for a purpose. I learned this one from Rand. She would start explaining a concept by asking what would it's purpose be. E.g., "What is the purpose of a government?" It involves the trick of metadata - of stepping back from a statement or assertion or concept and seeing the key term or concept in its broader context, and from that perspective asking, "Why would we need it?" Or, "What good would it do?" Or, "How would it have arisen to start with?" And it never hurts to ask, "What is my purpose in examining this? What would I like to kind out or understand?"
If I get even a tiny bit serious about something, I start writing notes about it on the computer - I can go into Wikipedia and skim history, or summaries and look for differing views. Then I start revising, or rewriting based upon the power of the questions that come up.
Defining key terms and their synonyms is also very productive - and a kind of questioning... "What is the genus for this concept and what is the primary discriminate that separates it from all others in that genus? Why would that be - i.e., "What makes that essential as the defining term?"
I also like taking apart a sentence to look at the grammar. What is the subject, and what is being predicated of it - what is the assertion? Isolating the key terms makes it easier to look for an ambiguity. Two of the simplest questions are, "What is being asserted?" And, "Is it true?"
Another category of questions have to do with the area of knowledge involved - is this an issue of metaphysics, epistemology, ethics, politics, economics, etc.? Often an assertion will bridge two areas, and sometimes in a way that contains errors.
And there are layers of thought, a kind of genealogy of ideas. That is, some ideas are built into, and are required, for the understanding of their child-concepts). Looking at an idea in this way often produces good questions.
Looking for errors or sloppy wording is a kind of alertness that often leads me to ask questions that end up generating new understandings rather than just locating a fallacy.
I'm sure you are familiar with some of the questions Rand would often ask, like, "By what standard?" That takes you to a place where it is easy to ask, "How would one derive a standard for this?"
The best thing you can do is to be able to watch someone with an exceptional mind, see what their response is to something you are both looking at and then ask how did they process the experience of looking at that to arrive at that conclusion. The book, "Ayn Rand's Marginalia" by Robert Mayhew gives you a chance to do just that. You read the same page she was reading and then you read what she scribbled in the margin. Chris Matthew Sciabarra wrote at length on Rand's processes in "Ayn Rand: The Russian Radical" Trying to emulate the mental processing will get the message across to your mind that you expect it to do something other than memorize.
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