There are a number of articles and books that have been key in shaping my thinking about technology, I've selected a few of the key ones here:
- Worse is Better. Actually entitled Lisp: Good News, Bad News, How to Win Big, but better known for this catchy line. Richard Gabriel's classic attempt to answer the question: why do technically worse solutions often win out over better-engineered ones? Richard re-thought this several times, but the original premise is pretty thought-provoking: "The lesson to be learned from this is that it is often undesirable to go for the right thing first. It is better to get half of the right thing available so that it spreads like a virus. Once people are hooked on it, take the time to improve it to 90% of the right thing."
- Metacrap. Cory Doctrow's analysis of why metadata is so unreliable. Lots of conclusions you can draw from this, chiefly, that we say what we wish were true, and not what necessarily is true. See also: The Problem With Metadata.
- On Semantics and Markup. Tim Bray's 2003 essay, summed up in the line "To oversimplify, XML is winning and ASN.1 is losing. There are a variety of reasons for this, but one of them is that it seems to be more important to know what something is called than what data type it is."
- Neurotransmitters. Sam Ruby on the future of distributed computing, modeled as an organism.
- Beating the Averages. Paul Graham on producing a successful startup. A bit of a counterpoint to Worse is Better.
- The Long Tail. Chris Anderson's original article on the concept, now a weblog and a book. Some of the original conclusions were flawed, but the original premise, turning Pareto's rule on its head, really appealed to me and turns out to have surprising practical applications.
Other technical books that I like a great deal:

- This is the way to write a book to teach programming languages. I don't think I've seen a better book in this genre.

- A very idiosyncratic format, but it works well. It's quite high level, it's more of a book to change the way you think about programming.

- Another book that will completely change the way you think about programming.

- Pretty much the definitive book on how to architect web services, or web sites in general, for that matter.