Does your website fit any of the following? Then your web site’s design is outdated for sure. Either you or your web designer is living in a cave 
* Never disappearing Under construction clip art sign. Mostly with a nice hammer and nail.
* Home page says Click here to enter for no reason (Except for adult sites)
* Ever loading home page flash screen with a skip flash button.
* Site full of frames.
* Site optimized for Internet Explorer 6.
* The whole site is an image map.
* Non Unicode sites with “find-me-where” download font links.
Related post: Things I hate in web design
Can you think of more clues? Let me know in comments.
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Self hosted word press at own domain without using any plugins nor updated to latest version
Well, not using plugins is not that bad. Even Matt Mullenweg (WP founder) uses just two plugins. Many geeks actually prefer to do things non-plugin way. But not having an updated CMS is definitely bad. At least it is not good for site security.
Sites ending with .asp