Timothy was a faithful Christian, though he may have been vexed with anxiety. Paul spends a good deal of time encouraging Timothy to stay strong, to keep fighting, to remember why he is a minister of the gospel. This would seem unnecessary unless Timothy struggled with that sometimes. Paul wrote to the church in Corinth, telling them that if Timothy arrives, they are to take it easy on him, possibly because—unlike Paul—Timothy did not thrive on confrontation and debate.
If Timothy comes, see that he may be with you without fear: for he works the work of the Lord, as I also do. Therefore, let no man despise [belittle] him, but conduct him in peace that he may come to me (1 Corinthians 16:10-11).
In Ephesus, Timothy seemed to struggle with problems with the elders. This situation apparently was so stressful that he was having stomach ailments (many believe this is describing ulcers) and was frequently sick.
Against an elder do not receive an accusation, except before two or three witnesses. [But] them that sin, rebuke before all, so that others may fear. I charge you before God and the Lord Jesus Christ, and the elect angels, that you observe these things without preferring one before another, doing nothing by partiality. Lay hands [or, ordain] suddenly on no man, neither be a partaker of other men’s sins: keep yourself pure. Drink no longer water, but use a little wine for your stomach’s sake and your frequent sicknesses. Some men’s sins are open beforehand, going before unto judgment; and some men they follow after. Likewise also the good works of some are manifest beforehand; and they that are otherwise cannot be hid (1 Timothy 5:19-25).
The popular verse about “drink a little wine for your stomach’s sake” is contained in a discussion of dealing with elders who sinned and those who aren’t qualified trying to become elders. Timothy was making himself sick worrying about these problems. It says a lot about Timothy that he was so concerned about the spiritual condition of the church and her leaders that he would be physically sick because of it.
A work entitled the Acts of Timothy claims that Paul ordained Timothy as “Bishop” of Ephesus during the reign of Nero, and that Timothy remained there the rest of his life. In this apocryphal writing, a pagan festival called the Katagogia (the “bringing down”) was taking place in Ephesus, where men with masks on took sticks and clubs “assaulting without restraint free men and respectable women, perpetrating murders of no common sort and shedding endless blood in the best parts of the city, as if they were performing a religious duty.” Historians are divided on whether this was done in the name of Diana (the chief goddess of Ephesus) or Dionysius (the god of liquor and revelry). Timothy, according to the story, stood in front of the mob, pleading with them to stop, preaching peace in the name of Jesus, but was clubbed to death in the street. This was said to have happened in AD 97.