In the recent past, homileticians have demanded that good biblical preaching should be expository—preachers open the Scriptures and let the Scriptures speak so that the sermon communicates to the audience the meaning of the text and why it matters. In this sense, expository goes beyond just a type of preaching as older preaching textbooks taught; it becomes a philosophy that guides the preachers. However, practically, some preachers maintained expository preaching as a type—characterized by finding three points or more from a pericope of Scripture and preaching that. The challenge with this understanding of expository is that books of the Bible, such as Proverbs and portions of Ecclesiastes, are not easily breakable into pericopes and do not necessarily lend themselves to three or four points. This misunderstanding of expository as a philosophy led some homileticians to coin the term ―text-driven preaching.‖ In this case, the sermon does not force a structure on the text; instead, the sermon is a re-presentation of the text based on its structure, substance and spirit. Preaching thus will vary the sermon as the text of the Scriptures was written with different genres. This article explore some of the complexities of Ecclesiastes, and suggest a text-driven methodology for preaching from the book of Ecclesiastes.