I read this as a follow-up to Lewis' earlier work, The Problem of Pain for an alternative look at theodicy. My understanding of the history of these two books was that Problem was writing prior to Lewis' wife dying and that Grief was written afterwards, after Lewis was unable to find comfort in his own words. I am also of the understanding that Grief was initially published under a pseudonym and Lewis only revealed himself as the author after a number of friends had recommended the book to him.
My own reasons for reading this now, as hinted at in my look at Problem, was that a close relative of mine died recently. This was a few weeks ago now, and we have had the funeral, ready to move on with our own lives now. A Grief Observed is a book that is often recommended as one to read during such a period of loss.
It has to be said that the book is extremely short (only 59 pages, fact). It is probably appropriate to state what the book is not, as much as what it is. It is not a detailed product of careful study or a complete thesis on the subject of dealing with grief. Lewis was merely trying to gather his thoughts into some semblance that would make sense. His extraordinary erudition and lucidity are what make it a great book. I found myself at many times reading in print thoughts that had been half-articulated in my own mind.
At such an extreme time of emotional stress, Lewis does what is only natural, and that is to question all that he believes in. Rather than throw all his beliefs out, he not only asks the questions but searches his soul for the answers. What results is one of the most honest of writings, where Lewis shows us a glimpse of his true soul. It is a level of honesty and openness that very few people ever dare to write publically, and one that I could only aspire to.
In spite of its brevity, it is an immensely rich book and incredibly thought-provoking. It is not a huge time-investment to read it, and the payoff is worth it. I would have no hesitation is recommending to anyone, whether in a time of grief or not.