These are Nassim Taleb's favorite literary works.

My picks, some of which have already been mentioned. I would classify these all as "viewquake" books for someone who hasn't encountered the concepts in them before.

1. Godel, Escher, Bach - gets a huge credit for sending me down the rabbit hole of "what your brain is actually doing", though like others I'm not sure if I would like it as much on a second reading.

2. Meditations by Marcus Aurelius - Stoicism at its best, I count this as the most motivational book I've ever read.

3. The Sciences of the Artificial by Herbert Simon - retreads topics that are probably already somewhat familiar to LW readers, but still has one of the highest insights/page ratios I've ever seen.

4. 48 Laws of Power by Robert Greene - instrumental rationality in the social arena.

And one dis-recommendation:

1. A Pattern Language by Christopher Alexander - the concept of "design patterns" which gets quite a bit of mention nowadays got its start here, but this book is a mess. The support Alexander uses to back up his choice of patterns is laughably sparse, often completely wrong and picked to support his somewhat warped sense of eco-morality. Avoid.

I have using Rationale from Austhink back when I was taking Philosophy classes. It was actually pretty good compared to what others offer but unfortunately limited to Windows. Ever since that time I have been thinking on and of about what software could be developed to both share ideas and refine our collective thinking in a better way. While there are tons of projects attempting such things most are either horribly designed or targeted at a non existing market.

I've read through the discussion above and I wonder why a semantic web approach wasn't mentioned. I think the SemWeb can play an important role in these kind of applications. For example RDF statements could be used as part of the argumentation schema. This kind of approach would also allow us to publish in a more decentralized manner, which is where the power of the web lies.

Although semantic web technology hasn't seen a broad adoption yet, I think in the next two years this will finally change. The lack of adoption comes mainly from a cold start problem but over the last year the need for this kind of tech seems to be increasing. Search engines like Google are beginning to leverage the SemWeb to improve their search results since they seem to be losing the war on spam at the moment. Tim Berners-Lee's Linked Data format is gaining ground in the public sector as the standard format for governments to publish open data. I think this is the first time we are starting to see interest in the SemWeb from outside the academic world, which to me is a sign that we are finally gonna see some widespread use.

Anyway I can see this being the way forward in online communication.

We used Rationale in the philosophy classes at school. It's an argument mapping tool. Too bad it's Windows only :-(. I would really like to see a platform independent or online version.

http://rationale.austhink.com/

I read it last year (for the first time) and enjoyed it thoroughly. It has some classic articles from the field, which if you haven't read already, you should when they're all in one place.

If you've never read Dennett's Where Am I, you shoud click the link and do so now.