It is important to grieve losses. Grieving was so important to Jews that they took an entire week after loss to mourn. There was to be such a focus on going through the process of grieving that they were not allowed to make love, study the Bible, or work (Jn 20:11, IVPBBC note). They realized that weeping could help ease their emotional pain (Eccl 7:3, Berkeley) if it was done with the Lord’s help or if it led to repentance, when that was needed (2 Cor 7:10, TNT note).
God grieved about the condition of the human race (Gen 6:6, Septuagint). Jesus wept (Jn 11:35). The Holy Spirit experiences grief, too (Eph 4:30). It is not surprising, therefore, that the trinity has told believers they are to keep rejoicing with those who are rejoicing and to keep weeping with those who are weeping (Rom 12:15). This helps to create unity via shared emotional experiences. Our appropriately expressing both joy and sorrow are valuable to the Lord.
Hardships can compel us to a response of sorrow (1 Pet 1:6, Weymouth) but our grief need not lead to depression. God’s desire is that we move on from appropriate, cleansing, life-enhancing grief to joy (Isa 61:3, GW). We go through grief with His help and, thus, it is used to draw us closer to Him. Even our prayers, which are to be offered with thanksgiving (Phil 4:5-6), can be full of grief (Ps 55:17, BB). Yet, we move from a lot of grief with perhaps perfunctory thanksgiving to relief and joy. We need to neither deny ourselves the chance to grieve nor stay stuck in grief. Abraham wept when his wife, Sarah, died (Gen 23:2). Jacob wept when he thought his son, Joseph, had died (Gen 37:35). Bitter weeping was made for children who died (Jer 31:15). Christian widows wept when their friend and patron, Tabitha, died (Acts 9:39). Mourning over loss is appropriate.
Instead of being timid, learn to be appropriately bold.