Those who believe in Jesus are to approach God with a boldness that includes both confidence and courage (Eph 3:12, AB-1987). For Christians, this boldness is a result of having a close relationship with Christ (Acts 4:13) and being filled with (or directed by) the Holy Spirit (Acts 4:31). Abraham’s prayer for Sodom is an example of boldness with God (Gen 18:22-33).
In human warfare, the bold approach is generally the better approach. Yet, it is not foolish boldness that is commended. Rather, it is calculated risk-taking and boldness. Boldness does not make up for poor reconnaissance or poor planning or inadequate resources. For instance, in the Seven Days’ battles, Lee, though outnumbered by Union troops, attacked because he knew that timid Union General McClellan would assume he was outnumbered by the Confederates (McPherson, Battle Cry of Freedom, p 464). On the other hand, an example of foolish boldness is seen at the Battle of Beneventum where Pyrrhus, the Greek commander, attacked a heavily stockaded Roman camp because he took the view that the boldest course is usually the safest. He was soundly defeated (Pratt, Battles That Changed History, p 51-52). In spiritual warfare, when the Holy Spirit emboldens us to carry out a certain course of action, that is what we should confidently and courageously do (Eph 6:10-18 cf. Phil 3:3, GW).
In our social relationships (spouse, friends etc.), are there times that beg for calculated boldness on our parts? Undoubtedly. We ought to pray (1 Tim 2:1), do our best to prepare (Mt 25:12, CW), and determine a good time to act (Eccl 8:5-6). Yet, having done all, when action is called for, let us be lovingly bold: “The righteous are bold as a lion!” (Prov 28:1 with 1 Cor 16:14).
Instead of being timid, learn to be appropriately bold.