The Familiar Essay is a mode of non-fiction creative writing in which the authorial voice looms large. Hence we are concerned with a highly personal and subjective, often revealing, moving, humorous or otherwise distinctly idiosyncratic genre of composition.
So, the “familiar” aspect in questions pertains to the intimate nature of the prose. It is as if the author is addressing a close friend, someone familiar to them.
As an example, here is the very famous opening line of (perhaps the greatest Familiar Essay writer of them all) George Orwell's reflection on boarding school life, “Such, Such Were the Joys”:
Soon after I arrived at St Cyprian's (not immediately, but after a week or two, just when I seemed to be settling into the routine of school life) I began wetting my bed.
This is a very candid opener indeed, and, as will be immediately apparent, quite outside the remit of traditional academic writing. Orwell goes on to paint quite the vividly unpleasant picture of his pained school-days, thus rendering the repeated “Joys” of the title ironical.
Much of the essay focuses on Orwell own emotional and intellectual experience, employing language that would be out of place in more formal writing. Hence it is in keeping with the genre when Orwell states, in idiomatic style, that:
St Cyprian's was an expensive and snobbish school which was in process of becoming more snobbish, and, I imagine, more expensive.
Note, also, that Orwell uses the phrase, “I imagine”, a very loose kind of term but one which sits well in the above, faintly humorous construction.
Due to the extremely personal nature of the Familiar Essay, the kind of content will depend very much on the author's experience and intention. You are not analysing a problem nor are you engaged in exposition as such; however, you will almost certainly have some kind of point, even if this is discerned only obliquely.
For instance, Orwell by talking about his own miserable experience is, by extension, offering a fairly scathing critique of the boarding school system of his day. In other words, he has a very clear central theme; only, he addresses this theme through the lens of childhood reflections.
As for structure, again, the subjective nature of the work lends itself to a great many different approaches. Whatever best services the theme will dictate the form. Just be sure to have a clear sense of what you are trying to say and the best way of saying it should follow.
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