For though we have let Christ into our lives and pretty believe that He died and rose again, and have the confidence that in Him, even when we die, because He rose from the dead, we have the precious opportunity to live again, not many would carry on with such confidence as did Paul. Why was he so confident of where he was going?
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Aside from the factors mentioned in the other answers, I think that a major reason for Paul's confidence was the special revelation that God had provided to him during his three years in the desert after he had fled from Damascus following his conversion (Acts 9:23-25; Galatians 1:17-18), in which (as Paul -- speaking of himself in the third person -- notes in 2 Corinthians 12) he was either physically or spiritually caught up to the "third heaven" (that is, the abode of God Himself), and allowed to see things that were so wonderful that they could not be described. (It was to keep Paul from becoming proud because of what he had experienced that God had afflicted him with the unspecified "thorn in the flesh" that Paul mentions in 2 Corinthians 12:7-9.)
Paul, after he was visited by the LORD, is a man to be admired by any purposeful Christian. He talks strongly of his new found life. How he is written about in the Acts of the Apostles, and how he writes his letters makes you envisage his love for God and for the ministry, and for God's people. For all the passion with which he had hated the church, most evidenced in the cheering of the stoning to death of Stephen (Acts 7:54-60), God turned it into the passion to love and serve the LORD. When he attempted to grumble before the LORD for his sufferings, the LORD told him; "....my grace is sufficient for you" (2 Cor 12:9) For at first, Paul had been known as Saul. He only assumed the name Paul after he was visited by the LORD (Acts 9). The name Paul means the least, for he was taken to be the least of all the Apostles, having not been one of the twelve and having been formerly a persecutor turned into an Apostle of the LORD. For he testifies of being the least of all the Apostles in 1 Cor 15:9. Just as was said by the LORD, Paul thought by persecuting the church, he was doing a service to God (John 16:2). But upon the LORD's appearance to him, he became the total opposite of what he was. There are a number of reasons why Paul must have spoken so confidently about his life after death among which are the following; 1) He had accepted and allowed Christ into his life 2) He had lived a transformed life 3) He had witnessed for Christ He had accepted and allowed Christ into his life: For the LORD'S appearance to Paul on the way to Damascus gave him confidence in all of the LORD's promises (Philippians 1:21-22). Thus in 2 Timothy 4:7-8, Paul speaks confidently of his reward for his labors after this earthly life. For Jesus gives us unprecedented promises and assurances of hope of life after death (John 6:47), (John 5:24), (John 3:36), (John 11:25), (John 3:16), (John 14:1-10). Our LORD Jesus goes on to not only assure us of life after death, but He becoming the first man to have died and rose again from the dead as is witnessed in Mark 16:9 and Luke 9. On account of the above, Paul was pretty sure that having given himself and submitted to the Lordship of Christ, he could have never gone wrong. Equally so, every Christian will if they are steadfast in their faith. He had lived a transformed life: When Paul gave his life to Christ, he never looked back. For he was totally transformed from a formerly known persecutor of the church to a preacher of the gospel. His personal life too had been transformed. For the sake of Christ, he had given up his status as a Jew from the tribe of Benjamin, an expert in the law and the zeal to keep it (Philippians 3:3-8). Paul had denied himself the freedom of the pleasures of this world (1 Cor 9:27). With such evidence of a purely transformed life, Paul was pretty sure that there was surely a reward for him after this earthly life. He had witnessed for Christ: Paul surely witnessed for Christ, for he preached the gospel with passion. For the sake of the gospel, Paul denied himself all the freedom he could have had (1 Corinthians 9:19-22). His passion for the gospel is further evidenced in 1 Corinthians 9:16 and Romans 1:16. Paul was right fulfilling the word of God as is said in Rev 12:11. Paul kept on making sure he testifies for the LORD, whether he had an opportunity or not, he would speak out no matter what. For the sake of the gospel, Paul feared nobody. In Acts 26, he fearlessly witnessed for Christ before the king Agrippa. Paul and the gospel were always identified with each other. In conclusive terms, though it is surely undeniable that the fear of death is with everyone. And as one who had put on human flesh, Jesus had equally feared it (Matthew 26:39). But if we live our lives after the pattern that Paul did live it, we surely stand to reduce this fear by very significant degrees. For our hope is in the reappearance of our LORD, not in this perishable earth.
Why did Paul speak so confidently of his life after death? Where could the confidence have been coming from? Paul like Abraham believed everything God had promised to those that are His. He had no doubt that he would be in the resurrection of life at the return of the lord Jesus and would at that time co-rule and co-inherit with him all things. God's righteousness can be defined as His faithfulness to the covenant promises He made to Abraham, and will be fulfilled in the "seed" of Abraham who is the lord Jesus as Paul makes plain in Galatians. James 2:23 And the scripture was fulfilled which saith, Abraham believed God, and it was imputed unto him for righteousness: and he was called the Friend of God. Galatians 3:16 Now to Abraham and his seed were the promises made. He saith not, And to seeds, as of many; but as of one, And to thy seed, which is Christ - His anointed one.
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