Down economies are toxic to creativity. Thinking broadly is for the fat times...and for spare time, of which we now have so little now. In times like these we feel we cannot afford to fail; so we tend to stick to what we know, stowing our creative juices in deference to a full-frontal assault on the challenges before us.

This is dangerous. Any developer will tell you that messing with a stored procedure can produce unexpected collateral damage. In this sense, the same creative juices that fuel innovation (that risky, hyperbolous endeavor) also feed our ability to solve problems and to recognize less-than-obvious opportunities. Thus, in challenging times, we should strive to be more creative, not less.

This effort is a discipline. Creativity is hard. We all struggle to recognize the thought unthunk; whether in assessing risk, defungling a procedure, or convincing our managers to show us a little budgetary love. In practicality, the struggle often boils down to seeing the unseen, remembering the forgotting, and deducing the unrecognized. Some people are better at it than others, but we can all learn to be at least a little better at it, period. I say learn because creativity (read: innovation and problem solving) is a product of both nature and nurture. Our brains work a certain way, but we can somewhat influence the wiring.

The scope of our contextualization is limited by both what we know and don't know. Redressing either limitation will likely improve creativity, and addressing both will increase the value of improving either independently.  Obviously, it helps to increase our information intake. But we also need to train ourselves to seek or build non-obvious connections in that new information.

How do we do this? First, it helps to recognize why we don't think of things. In general, we forget information we can't easily contextualize (one of the reasons rote learning is inefficient). We also tend to stop seeking meaning for something once we find a comfortable way to think about it. We can push these boundaries. The trick is to learn to associate new information in non-obvious ways to knowledge we already retain. It's not just about relating one thing to another, though. By plugging new bits of information into your existing knowledge as liberally as possibly, you'll probably find those new bits also relate to each other in unexpected ways.

This is where the discipline part comes in. Contextualization can be methodological: you can train your brain to some degree to seek new connections. And once you've acquired a process for it, you'll probably find it kicks in reflexively whenever you encounter new information, a problem, an opportunity, or a choice.

Of course, we all learn different ways, but the following are the top five ways I've found to learn to see the big picture, the flip side of the coin, and the other guy's perspective—all just flavors of contextualization:

1. Feed the machine. Read everything you can, even stuff you think is unrelated (because very little is really unrelated). Even fiction. Even travel writing. Even the newpaper...yes, the paper kind, since it it will expose you to information you're not intentionally seeking.
2. Map your blind spots. Take Sun Tzu's The Art of War. Or anything written by Dave Barry. Or bash.org (warning: not for delicate natures). When you read funny or revelationary ideas, don't just laugh or hmm. Ask yourself why they strike you as novel or funny. Your answers are the mental barriers you'll need to break down to expand your own creative scope. Creative-thinking exercise books help some people...although I think the New York Times Sunday Crossword Puzzle Omnibus offers more practical training.
3. Mine metaphors. If one of these things is somewhat like the other, the implications might be broader than you think. Overlaying one body of knowledge on another can take you unexpected places. You could ponder biological metaphors for computing systems for years. Geopolitical history as a metaphor for business management. Urban planning as information architecture. Where disciplines largely or even generally align, you can look to one to solve problems in the other...or to find opportunities for innovation. So many brilliant innovations boil down to just providing something that's missing. You'd think it would be easy, but human brains are actually terrible at recognizing what's not there. (Simple demo: name the seven dwarves.) Metaphors can act as templates, revealing gaps.
4. Free associate rigorously. Think: What does this remind you of, and what does that remind you of? Often we know much more than we know, but we have to build the links to access that knowledge. One of the best guides Ive found for learning by association is the coincidentally enjoyable Prisoner of Tribekistan by Bob Harris. The main theme is to pick any idea as a starting point and push your mind to find connections (not out loud, unless you want coworkers to pummel you). Bonus: Practicing free association in meetings makes them go much faster.
5. Let your love flow. We retain information that we associate with emotions: especially fear, arousal, anger, and affection. These emotions are a connection between those apparently unrelated ideas. And in many cases, the emotional triggers themselves are also related. Does some bit of knowledge remind you of someone? Why? Why did you like them? What else did they say? How are those ideas connected? These emotional triggers, which often go unrecognized, can be creative connections in themselves.

Of course, these are just my observations. I'd like to hear your thoughts, too. How do you approach a problem? Are you the go-to guru for brainstorming? Does this mean you're creative or uncreative? Why or why not?