1 Corinthians 16:5-6 After I go through Macedonia, I will come to you—for I will be going through Macedonia.Perhaps I will stay with you for a while, or even spend the winter, so that you can help me on my journey, wherever I go. 

Paul may have been in Ephesus when he wrote this letter to the Corinthian believers (see v. 8). He would have been on his second missionary journey described in Acts 16:23–20:38. He planned to go back to Corinth and visit. To get there, he would go over land through Macedonia, which would likely include stops in Philippi and Thessalonica. He evidently changed his plans because he takes up this issue of traveling to Macedonia and Corinth in 2 Corinthians. The Corinthians were upset that Paul never came to see them as he said here in this first letter, which led to their criticism of him. This is one of the reasons he wrote the second letter.

He planned to spend an extended time with the Corinthians, which would have been helpful for resolve some of the issues and help them grow spiritually. Spending the winter there would have been necessary because it was dangerous to travel during the winter, especially by ship. Paul was planning to return to Judea after that (2 Corinthians 1:16). Earlier in this letter, Paul boasted of not relying on the Corinthians 9. In this passage, however, he is anticipating the generosity of the Corinthians to support him in some way during his planned visit there. He wanted them to be a sending church, involved in the broader mission of preaching the gospel. Churches that are outward focused will grow. Churches that focus only on themselves will stagnate and have internal problems. The last phrase of v. 6 shows Paul’s openness to go wherever God would lead him. This leading would come from the Holy Spirit. The Acts of the Apostles records times when Paul followed the leading of the Holy Spirit for where he traveled.

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