I recently had a chance to pick the brains of my eldest daughter, Gretchen, and her husband, Ryan, who are both very technosavvy. We chatted about a few sites that might help me get a better understanding of what's happening out on the web. Here is where we "netted" out.
John Scalzi is an author who blogs on whatever strikes his fancy. Some times its politics, sometimes its about sci-fi writing, sometimes it's just random internet geekery. He's easy to read, and can give you a good baseline for blog style writing and some understanding of net culture.
Good all around software geekiness with some other lifehacks built in. Good for keeping up with Firefox extensions, Google updates, and what's happening in the tech world. Not too hardcore, and there's always some fun stuff mixed into the feed.
Boing boing: http://www.boingboing.net/
This is the original source of web geek culture. This will give you a good idea of what issues and trends are currently on the radar of global geeks.
Freelance Switch: http://freelanceswitch.com/
Mostly about the freelancing world, but it will help you get a good knowledge designing for the web and can clarify terms like Web 2.0
And this recommendation is mine -
Seth Godin: http://sethgodin.typepad.com/seths_blog/
The guy behind Squidoo and the author of Meatball Sundae, who's a Marketing Guru. His short posts are always a good read and his comments focus on industry trends and insights about the Internet and about marketing.