"Confidence in the flesh" generally means confidence in human things, whether it be our own strength and abilities, our heritage, or any aspect of our humanity. Here Paul specifically means confidence in his Jewish ancestry and adherence to the Jewish Law. He had been circumcised on the eighth day, had impeccable ancestry. He had been a Pharisee, the most zealous sect for keeping the Law, and he had even persecuted the church. If the Law provided a basis for righteousness then Paul was in ahead of practically every other Jew. Paul could not be accused of becoming a Christian because he was a "failed Jew". The only logical reason he had for following Christ was that the Law did not work as a means of being righteous, and he fully believed that following Christ did work. And this was the case.
Paul considered all his Jewish heritage as garbage. Now this does not mean he considered them absolutely worthless, but he considered them useless as a means of gaining righteousness. Knowing Christ is all that counts. The Jewish heritage and the Law were valuable if they are given their proper place, namely as pointing ahead to Christ, and Paul makes copious use of the Old Testament in his letters.
Righteousness is obtained by faith in Christ. Faith in what Jesus did on the cross is the source of our assurance. Moreover, Paul wanted to know the power of the resurrection and to share in Christ's sufferings. Believing in Christ is not just a matter of being forgiven, but a matter also of obtaining new life and sharing in the life of Christ. And sharing in Christ's sufferings is all part of this.
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