What does 2 Corinthians 1:14 mean?

Paul is defending himself against false charges: that he has not been straightforward or honest with the Corinthians. He insists the opposite is true both for himself and his co-workers. They operate with "simplicity," which here means the opposite of guile or trickery. Paul and his associates deal in integrity and openness. They use no falsehood: they are sincere. Paul's letters are the same as his personal conduct, he says; everything is out in the open. He writes what it means, and he means what he writes (2 Corinthians 1:12).

Earlier Paul wrote that he hoped the believers of Corinth would fully understand what he is writing to them, just as they did partially understand what he wrote to them in his previous letter. Paul will address the parts they did not understand or accept in the coming chapters.

When Paul speaks about "the day of our Lord Jesus," he means the day Christ returns to earth to make all things right. Paul's hope is that the Corinthians' spiritual knowledge, and their relationship to God, will be so well-developed that they will boast of Paul and his co-workers on the day of the Lord Jesus just as Paul hopes to boast of them.

This is not the self-centered, prideful "boasting," of course, but a celebration of what the Lord has done through the connection between Paul and the Corinthians. It's a gathering together at the finish line to say, "We could not have done it without the Lord working through Paul and Timothy and Titus and all of them." Or, "Look at those Corinthians! Our suffering in ministry was worth it all along."