The business models of the web thrive by showing you more and more information that echoes exactly what you want to hear - because it's probably easier to sell you something that way. But one of the things we lose in an ever-more-personalized world is exposure to information and views that challenge our mental model of the world in a thoughtful way.
The ink-and-paper world is not immune to this - you can probably tell something about me by the fact that I subscribe to the Wall Street Journal and the Economist, and often pick up a copy of Harpers in airports. Those publications definitely have a certain bias that is reflected in the stories they run. At the same time, I rely on those editors to give me a certain slice of the world which I might not otherwise be exposed to.
For example, while I rarely would voluntarily click through to many of the WSJ stories, I love reading through the "What's News" section on the front page because I trust the Editor to give me their view of What's Important Today (actually, there are two reasons why I would rarely click through - (1) because not all of the stories are that interesting to me, and also (2) because I have different reading habits online and offline - something that the Kindle may one day change)
But no one likes taking bitter medicine. How do you get people to look outside their comfort zone? How do you get people to see the value in doing so? I always talk about wanting to read more about what republicans think, but I've never really gone out and done so. It's just hard to justify the time.
My gut feel is that you first have to bring people to a safe and comfortable environment, and then let them interact in a structured way with different people and views. It reminds me of a documentary about Mauritius that I saw a long time ago. I can't find the reference, but the following quote is related, as it captures the same metaphors I remember:
In the fruit salad, the components are clearly distinct; ethnic boundaries are intact, and reflexively "rooted" identites are secure and stable. In the fruit compote, on the other hand, the different fruits are squashed and mixed together with substantial use of force.
...
He himself therefore supports the fruit salad variety.... In order to have a dialogue, Souchon argues, one needs a firm position to conduct it from. ( Multiculturalism, individualism and human rights:Romanticism, Enlightenment and lessons from Mauritius, by Thomas Hylland Eriksen)
I'm currently working on an experiment to bring this, and some related ideas, to the web. I've been working with Jambool - creators of the Send Good Karma facebook application - and my first contribution has been a pair of politics apps : I Vote 4 Obama and I Vote 4 McCain.
They're still nascent, and we will be adding many more features over the coming weeks. However, they're the beginnings of an experiment to try to punch a few holes in the echo chambers on the web. I'm not going to give away any of the goodies just yet about how we're planning on doing that - but I encourage you to add one of the applications (depending on who you support) - and and use it at least a few times as we introduce new features.