Having therefore, brethren, boldness to enter into the holiest by the blood of Jesus, By a new and living way, which He hath consecrated for us, through the veil, that is to say, His flesh (Hebrews 10:19,20).
The words boldness and boldly are found three times in the Book of Hebrews, with each reference teaching a different spiritual truth. In none of these references does boldness ever mean brashness, but confidence and assurance. The believers absolute confidence is seen in the following areas.
Boldness concerning salvation. Once a year on the Day of Atonement, the high priest went within the veil into the Most Holy Place to sprinkle the blood on the mercy seat. It was a fearful experience. One small act of disobedience and he would die. (Leviticus 16:2,13).
For the New Testament believer entering into Gods holiest place (heaven) is not a fearful one because Christ has led the way through His shed blood. Boldness comes through the blood, not ourselves (see text).
Boldness concerning prayer. Let us therefore come boldly unto the throne of grace, that we may obtain mercy, and find grace to help in time of need (Hebrews 4:16). Due to the fact that Christ, as our Great High Priest, has ascended into heaven (v.14); that He is touched with the feeling of our infirmities (v.15); that He is keenly aware of our trials having been tested in all points like as we are (v.15). Therefore, all believers have boldness (confidence and assurance) to pray to Christ at the throne of grace, openly, freely, and frankly in order to receive mercy and grace.
Boldness to claim Gods promises. For He hath said, I will never leave thee, nor forsake thee. So that we may boldly say, The Lord is my helper, and I will not fear what man shall do unto me (Hebrews 13:5,6). Here, confidence and assurance rests on the fact of Gods omnipresence. NPS