Summary: The coming of winter imposes an urgency on our service to Christ. For someone we know, it is "winter, or never." Whatever we are to do, it must be now.
“Greet Prisca and Aquila, and the household of Onesiphorus. Erastus remained at Corinth, and I left Trophimus, who was ill, at Miletus. Do your best to come before winter. Eubulus sends greetings to you, as do Pudens and Linus and Claudia and all the brothers.
“The Lord be with your spirit. Grace be with you.” 
Paul is almost pleading when he writes, “Do your best to come to me soon” [2 TIMOTHY 4:9]. Now, in the text before us, he iterates this plea, expressing his concern that Timothy might never see him again in this life. Winter was coming; sea travel would become dangerous and overland journeys would be hindered by the onset of cold and snow. Timothy would lose precious time in travel if he failed to come immediately. The old man knew that he had but few days left before the sentence of death was carried out.
Though the Apostle had provided sufficient instruction concerning how one should conduct himself in the House of the Lord, there remained matters of a more personal nature that he no doubt felt compelled to communicate. Additionally, the old man longed for the personal comfort of a true friend that would make his final days somewhat more tolerable. The presence of the young theologue would be an encouragement, a source of comfort if only in the knowledge that Paul’s work of advancing the cause of Christ would continue through Timothy. It is a truism that any individual can stand against injustice and the unrighteous opposition many must face if only one somebody stands with him. Paul is facing death, and he longs for someone to come alongside to encourage him and lend him strength for the hard task he is facing.
Our lives, our very thoughts, are attuned to the annual seasons; and just as there are seasons to each year, so our lives are played out in a seasonal environment. You know that the normal life span is often compared to seasons. Birth and infancy are oft-times compared to spring, with the promise of all that lies ahead. Youth and young adulthood are seen as summer, when the vigour of youth and the vibrancy of life is pronounced. Middle age is viewed as the fall of life, when we are reaping, gathering, preparing for the dark future days. And our aged, final years are frequently spoken of as the winter of our lives. Winter is the signal that the cycle of life is nearly complete. Anything that will be accomplished for that year must be shortly completed with the onset of winter. Likewise, anything that will accomplished in a given life must soon be com¬pleted with the advent of our personal winter. As the grey hairs accumulate, as the bodily systems begin to weaken and fail, as we near our long home, our preparation for the inevitable assumes a new urgency. Anything that we would do must be accomplished very soon, and anything that others would do for us must be done quickly.
Reviewing this final letter to Timothy, I note an urgency that was previously unrecognised in the Apostle’s letters. It is not that Paul has been casual about the need for service, but he was confident that his work was not finished. Now, however, it is as though God has informed him that his service is nearly complete. In earlier missives his sentences are complex—they reflect the brilliance of his great mind as he rapidly moves from subject-to-subject. Now, his sentences are terse, sharp, pointed, urgent; they reveal a solemnity not previously noted and they assume a greater poignancy in light of his sense of finality.
Alone, facing the daunting prospect of beheading while isolated from beloved friends, the condemned prisoner carefully analyzed his untenable and unenviable situation. Winter was rapidly approaching, and winter meant the cessation of all travel on the tempestuous Aegean Sea. The war galleys, the great triremes, to say nothing of the small merchant barks which plied the seas to earn their masters' income, were kept within safe harbours during the winter months. You will recall the danger to sailing encountered by the ship and crew on which Paul was being transported to Rome. They knew they were sailing in the dangerous season, but they felt compelled to sail that they might reach “Phoenix,” a harbour in Crete which faced both southwest and northwest, “and spend the winter there.” The choice was necessitated because the harbour of Fair Havens, located near the town of Lasea, “was not suitable to spend the winter in” [see ACTS 27:9 12]. Travel by land was dangerous because of increased bandit activity, the brigands preying on hapless travelers forced to move by land by the winter conditions which halted sea traffic. For Timothy, it was truly winter, or never, if he would fulfill the hopes and expectations of the plea of loneliness.