In season (2122) (eukairos from eu = good + kairos = season, opportune time, "window of opportunity") is an adverb modifying "preach" and means opportunely (the "right time") or conveniently. In short regarding preaching, some opportunities will be "In season" or opportune and some "opportunities" will be out of season! Chrysostom says eukairos in this context means... Having no defined season, letting all time be the season, not only in peace; not only in security; nor yet when sitting in the church only; even if thou be in perils, even if in prison (cp 2Ti 2:9), even if bound with a chain (cp 2Ti 1:16), even if being led out to die, at every such opportunity, convict and shrink not from rebuking: then then it is that rebuke is in season, when the conviction goes forward and the fact is demonstrated.... But if men continue in the same courses even after our exhortation, not even then must we abstain from counseling them. For fountains flow, even if no one draw from them: and rivers run, though no one drinks. So too the preacher ought, even if no one attend to him, to fulfill all his own duty; for our rule, who have taken in hand the ministry of the Word, is laid down by God the Lover of men, that His part is never to slacken, nor to be silent, whether men bear (with the Word preached) or pass by. The only other NT use is in Mark in a negative sense where we read of Judas Iscariot (Mk 14:10) willingness to betray Jesus presented himself to the Jewish religious leaders who... were glad when they heard this, and promised to give him money. And he began seeking how to betray Him at an opportune time. (Mark 14:11) There is one use in the apocryphal writings... Let nothing prevent your discharging a vow in good time, and do not wait till death to set matters right. (Sirach 18:22) The challenge of faithfully preaching the Word brings the believer into conflict with others. Some seasons will be immediately satisfying but others will not be so satisfying. In some seasons the fruit is evident, and in others the fruit seems invisible. Some seasons from a human perspective seem suitable for profitable proclamation but others seem not to be so well suited. It matters not what the preacher's perception is...the command remains to preach regardless of the response. Writing to the saints at Ephesus, Paul saying that they (and by default "we") should... make the most (exagorazo) of every opportunity (kairos), (Why?) because the days are evil. (Ep 5:16-note) To help understand Paul's use of eukairos it is important to understand that the main root word kairos [word study] refers to a fixed and definite time, a period possessed of certain characteristics (e.g., in context Paul has alluded to the characteristics of the "last days" - cp 2Ti 3:1, 2ff-note. Kairos does not emphasize a point of time but rather a "time space", a segment of time, filled with all kinds of possibilities/oppurtunities. An ancient Greek statue depicted a man with wings on his feet, a large lock of hair on the front of his head, and no hair at all on the back. Beneath was the inscription: Who made thee? Lysippus made me. What is thy name? My name is Opportunity. Why hast thou wings on thy feet? That I may fly away swiftly. Why hast thou a great forelock? That men may seize me when I come. Why art thou bald in back? That when I am gone by, none can lay hold of me. Shakespeare although not using the specific Greek word, alludes to the idea inherent in the word kairos... There is a tide in the affairs of men, which, taken at the flood, leads on to fortune. Omitted, all the voyage of their life Is bound in shallows and in miseries. (Julius Caesar, 4.3.217) Napoleon said, There is in the midst of every great battle a ten to fifteen minute period that is the crucial point. (cf "Kairos") Take that period and you win the battle; lose it and you will be defeated. And - Note that "and" is added by the translators but is not present in the Greek. More literally the text should read "Be ready in season, out of season." Stephen Olford explains the importance noting that... In season suggests the traditional and prearranged opportunities that come along in the normal program of the church. A preacher can be so conformed to and bound by the great machinery of Christendom that he can lose his inspiration and vision, his sense of freedom and anointing. The minister is to save himself from that. He is not only to take the opportunities given him, but also to make opportunities. (Recommended reading - Anointed Expository Preaching - Broadman & Holman Publishers [hardcover] or Logos Software or Wordsearch Software)