2:1–3 In verse 1 we find the Preacher in dialogue with himself, commanding his heart to enjoy itself (cf. comment on 1:16–17). The emotional component of our human nature typically needs little encouragement to seek enjoyment. However, a more intellectual or cerebral type of person, such as the Preacher, could need to encourage his rational faculties not to overlook the possibility that pleasure might hold the key to the meaning of human existence. It should be noted that 2:1 is not necessarily as hedonistic as it might initially sound, for the word translated “pleasure” in verses 1–2 (Hb. simkhah) most often means “joy, gladness, mirth.” Even though the Preacher will say in verse 10 that he kept his heart from no “pleasure” (Hb. simkhah), verse 3 mentions only the specific example of enjoying wine (the word translated “concubines” in v. 8 is very uncertain; cf. comment on 2:7–8). Moreover, he insists that, even while he was finding enjoyment in wine, his heart was “still guiding me with wisdom.” Clearly, then, he did not engage in a completely uninhibited use of alcohol to the point of losing control of his faculties (cf. 10:16–17). The basic point of 2:1–3 is simply that the Preacher directed his heart to adopt a carefree, happy-go-lucky approach to life focused on “joy/pleasure” (Hb. simkhah) and “laughter” (Hb. sekhoq), as opposed to a more rigorously ascetic and somber outlook. As he continues his observations of mankind and the fallen state of the world, however, his desire for a blissful life will be appropriately tempered by reality. In the end, he is too careful an observer of reality to be able to maintain a “don’t worry, be happy” approach to the world for long. On his attempt to “lay hold on folly” (2:3) cf. comment on 1:16–17.

2:4–6 Finding that the pursuit of constant enjoyment proved to be ultimately unsatisfying, the Preacher consequently sought to discover whether meaning in life could be found in great achievements. Verses 4–6 mention a variety of large-scale building projects and public works that he undertook. While any of these enterprises could have been perfectly legitimate in its own right, the crucial feature of these and the following verses (vv. 7–8) is the Preacher’s focus on himself. The phrase “(for) myself” (Hb. li) occurs at least once in every verse in verses 4–8 (and twice in vv. 4, 7, 8). The repetition of this phrase reveals a certain degree of self-centeredness in his achievements and acquisitions, if not a hubristic sense of self-reliance and self-sufficiency. It is not so surprising, then, that in verse 11 he will speak of “all that my hands had done,” suggesting that for the moment he is concerned with seeking first his own kingdom rather than the kingdom of God (Matt. 6:33). As such, it is inevitable that eventually the vanity of all these things will be revealed. Like all things, impressive achievements and great possessions fulfill their ultimate purpose only when directed toward the glory of God and the good of others.

2:7–8 Just as the Preacher attempted great works for himself, so also he accumulated great possessions for himself. Much of this wealth consisted of commodities frequently mentioned as valuable in the Bible, including material goods (silver, gold, treasure), livestock, and human beings (male and female slaves and singers). The word translated “concubines” in Ecclesiastes 2:8 is very uncertain and occurs nowhere else in ancient Hebrew texts. Perhaps the best ancient testimony to its meaning is that of the LXX and Peshitta, which render the word as “cupbearers.” It is clear in any event that the Preacher was intent on gathering up the things that are a “delight of the sons of man” (v. 8). Great wealth can be a sign of the Lord’s blessing, as it was with the patriarchs, for example, though this is not always the case. Regardless, one’s wealth must be used appropriately in the service of the God who gives it (cf. 5:19; 6:2). Again, the repeated references to the wealth he acquired “for himself” indicate a more self-serving motive.

2:9–11  In verse 9 the Preacher summarizes his career: he surpassed all his predecessors in Jerusalem in his pleasures, achievements, and acquisitions. On the implication of this statement for one’s understanding of the authorship of the book cf. Introduction: Author, Date, Occasion. Despite the element of self-centeredness noted in verses 4–8, the Preacher nevertheless continued to act with wisdom (v. 9). The purpose of this comment is to reassure the listener that his evaluation of his efforts will be accurate and fair. The reference to enjoying “whatever my eyes desired” could raise concerns (cf. comments on 6:7–9; 11:9–10). At this early juncture in the book, however, it serves merely to reinforce the notion that he did not refuse himself any “pleasure” or “joy” (cf. comment on 2:1–3). In other words, he was not a world-renouncing hermit or monk, whom one might expect to be predisposed to viewing the pleasures of the world with skepticism. In contrast, the Preacher gladly experienced the joys that life offers, and at the same time his heart “found pleasure” (Hb. verb samakh) in his work (2:10). Yet, as will later be seen (v. 18), the Preacher also came to “hate” his work. The Preacher, in dialogue with his heart (cf. comment on 1:16–17), is of a divided opinion on the value of work and perhaps for this reason will come back to it repeatedly throughout the book as he seeks to gain greater clarity on the matter.

The Preacher’s conclusion, at least in this section, is negative concerning the value of pleasures, achievements, and possessions. It is all “vanity” and a “striving after wind” and represents no “gain” under the sun. Ultimate meaning is not found in any of them.