Much less is there any room for the pulpiteers of today who like to exegete the latest movies, or preach on moral lessons drawn from television sitcoms, or build their sermons on themes borrowed from popular culture. You know what I mean: the kind of preachers who insist they are being "missional" when they are merely being worldly.
Still less is there any warrant for the celebrity rock-star pastor who continually makes himself the focus of his preaching. "For what we proclaim is not ourselves, but Jesus Christ as Lord, with ourselves as your servants for Jesus' sake" (2 Corinthians 4:5). "Necessity is laid upon me. Woe to me if I do not preach the gospel!" (1 Corinthians 9:16).
Paul's focus is extremely narrow—stiflingly narrow for the typical young-and-restless church planter for whom "style" is everything; and whose style (let's be honest) is conspicuously dictated by secular fashion rather than by the worldview Paul was exhorting Timothy to embrace.
"Preach the word." That's the centerpiece and the key to everything Paul tells Timothy about how to shepherd God's flock. That command is followed immediately by a second imperative that simply makes the first one more emphatic: "Be ready in season and out of season." The Greek verb means "stand by," and it does have the sense of readiness. (In fact, in radio, that is exactly what the expression "stand by" means: "Be ready." But the word Paul uses is richer and stronger than that.) It also carries the connotation of expressions like: "take a stand," "stand upon it," "stick to it," "stand up to it," or simply "carry on."
Paul is urging Timothy to be absolutely, unswervingly devoted to the truth of the Word and to the task of proclaiming it. "Stand firm, and stand ready. Keep at the task, no matter what." That's the idea. And the proof is in the rest of the phrase: "Be ready in season and out of season"—literally, "when it's timely and when it's untimely": when it's popular and when it's not.
Or to contextualize the phrase for the current crop of evangelical fashionistas: Preach the Word even when preaching the Word seems hopelessly uncool and unstylish.
The expression is ambiguous as to whether Timothy or his audience is the barometer declaring what's "in season [or] out of season." It doesn't matter. Regardless of how you or your audience—or anyone else—feels about it, keep preaching the Word.
Preach the word whether the timing seems opportune or awkward. Preach it whether it's convenient or inconvenient. Preach it whether you feel like it or not. Preach it whether the door is open or closed. Preach it no matter how much resistance you encounter. Preach it whether or not people say they want it. Preach it—and make it the heart and soul of your ministry strategy—no matter how many church-growth experts tell you otherwise.
Paul goes on to give several more imperatives, and all of them expand on or modify this initial command: "Preach the Word."