We assign Categories only to Posts, not to Pages. Until a post is published with a Category assigned to it that Category will have nothing to display in a Categories widget.
Adding Categories via the Dashboard > http://en.support.wordpress.com/posts/categories/#adding-categories-via-the-dashboard
Adding Categories to Posts via the Categories Module > Adding Categories via the Categories Module
Categories Widget > http://en.support.wordpress.com/widgets/categories-widget/
If you are seeking to simply upload a document to your blog’s Media Library (no download link), you can check out Media -> Add New in your dashboard. http://support.wordpress.com/media/media-add-new/
If you want to embed the document itself into a post, then you will have to use a third party application like Scribd or Google Docs. Otherwise, the documents will appear as a download link.
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