The internet and blogging has become the Agorà of the 21st century and, within such a context, regarded as a “recounting” technology with a double objective: “recounting about oneself to other people” and “recounting to oneself about oneself.” The “weblog” phenomenon accounts for the triumph of the principle of democracy in the Internet which is no longer considered as a “center” which provides information, but rather as a “many to many” branching system under which each user becomes at once the consumer and the producer of information, messages, and contents. This study demonstrates that weblogs are tools to account for an education opportunity since self-narration enables gives a form and a meaning to the continuity of one’s own life: an unrenouncable chance to uncover and make visible connections across the different “stances” of one’s soul. The authors present the case of an online diary with 224 posts (the blog of A.), analyzed with a set of linguistic and statistical software tools. Content analysis has been resorted to for assessing the narrative strategies used by A. to share his life experience with others through metaphors, punctuation marks, and syntactic structures. This demonstrates that the blog accounts for a training ground of the Self for people experiencing important and decisive times in their lives as it enhances the self-narrative skills of the internauts.