Here's a collection of strategies for generating ideas and challenging you thinking. If you don't know where to start, almost any of these might get you on your way:

Phrase Your Lack of Understanding as a Question:
When you encounter something you don't get and respond by saying either "I don't understand," or "This doesn't make sense," or "This is dumb," that’s a dead end for thinking. None of these responses are useful, because none lead anywhere. Instead of saying, "I don't understand Holden," trying framing a question instead." Being able to ask the right question puts you well on the way toward an answer. And sometimes, the best questions don't have a single answer, or, for that matter, any answer, but the questions are still worth asking because of the thought processes they engender.

Question-Based Strategic Thinking: Having come up with a good question, consider as many answers as you can think of, even if they initially look like dead ends: A1, A2, A3, A4...A27. Once the list is out there, you can select, or, if necessary, invent a way of rank-ordering the answers based on whatever criteria are relevant: evidence, adequacy, simplicity (other things being equal, simple answers trump complicated answers).

Assess Your Current Situation: Three powerful questions that are relevant in any situation are: "Where am I now? Where am I trying to get to? How might I get there?" Whether you're writing an essay or reading a poem or considering where your relationship with your significant other is headed, these questions are worth visiting, and re-visiting.

The Sideways Move: Good thinkers have the ability to shift their point of view. The trigger for the move is some set of words like "Everything we've said so far is true, but there's another way of looking at it." Then consider—or invent—one.

Balance Generalizations with Specifics: The writer's cliché is "Show, Don't Tell." Much student thinking, like most of what passes for thinking in matters of public discourse, consists of what I have come to call BUGs—Big Unsupported Generalities. Like the sentence I just wrote. The next move, for balance, might begin with, "For example..." No one can be specific all the time. But it's useful for students you should make an effort to be aware of when you are generalizing and when you are being specific. "Life is just a bowl of cherries.” is a big, familiar generalization, and as such it’s just not very interesting, as opposed to a sentence like this” (from Richard Ford’s The Lay of the Land:) "The white-capped bay surface reveals, at a distance, only a single wet-suited jet-skier plowing and bucking along, clinging to his devil machine as it plunges, wave into steely wave."

Write Your Way Through It: I've come to believe that writing is perhaps the single most powerful self-instructional tool we possess. Most students assume that in order to write you have to first know what you have to say. Sometimes you do. But writing can also be a way to generate thought. Five-minute or ten-minute freewrites allow half-formed thoughts and hunches begin to evolve a form. Writing makes thinking hold still. Writing out your first thoughts makes it possible to arrive at second thoughts.

Converse: With others, yes, but with yourself, if necessary. One powerful way to generate solid thinking is to interview yourself: ask the questions you have, and give the answers that you can come up with. You will in all likelihood surprise yourself.

K-I-Q: What do you know for sure? What are some things that you may not know for sure, but that you are reasonably certain are good inferences? And finally, what do you need to figure out, what is still open to question?

Analogy: How does the situation you are looking at compare to anything else you may be familiar with? Explain situation A by drawing an analogy to situation B.

Juxtaposition: This is a slightly different take on analogy: take two things that may look dissimilar and think through their interconnections. One traditional form of this exercise is simply to do a comparison/contrast analysis.

Visualization: Often it's true that a picture equals a thousand words. Draw a picture or a diagram that captures the essence of you idea, and then either annotate it or try to translate into words.

Reflection: When you finish off a project or an process, think about how it went. What did you do well? What would you do differently if you were to start again? What did you learn that you didn’t expect to learn?