Philemon 1:8

Therefore, although in [the fellowship of] Christ I have enough boldness to order you to do the proper thing,

Treasury of Scripture Knowledge

Summary

Wherefore, though I might be much bold in Christ to enjoin thee that which is convenient,

Bible References

Bold

2 Corinthians 3:12
Therefore, since we have such a hope [i.e., that the Gospel is much superior to the law], we speak with great boldness,
2 Corinthians 10:1
Now I Paul, who am humble [when speaking] face to face with you, but bold when I am away from you, urge you by the meekness and gentleness of Christ [Note: This means either Paul was imitating Christ's behavior or that the Corinthians were to do so]:
2 Corinthians 11:21
I am ashamed to say that we were [too] weak to do such things. [Note: Paul is probably saying, sarcastically, "We are too 'weak' to take financial advantage of people and mistreat them the way those 'super apostles' there in Corinth were doing"]. Yet, in whatever [matters] anyone [there] dares to boast about, (now I am really speaking foolishly), I will dare to boast also.
1 Thessalonians 2:2
But [even though] we had already suffered and been mistreated at Philippi [See Acts 16:19-24], as you people know, we had the boldness, [with help] from God, to tell you His message in spite of much struggle [i.e., opposition].

Enjoin

2 Corinthians 10:8
For even if I should boast too much about the authority the Lord gave us for building you people up [spiritually], and not tearing you down, I will not be ashamed of it.