This is a great question to discuss! And it is not an easy one to answer.
The Bible tells us that Jesus wept (Gospel of John 11:35), and that Mary’s heart would be pierced with a sword of sorrow (Luke 2:35) (in fact one the titles we have given her is “Lady of Sorrows”).
St. Paul tells us “I have great sorrow and unceasing anguish in my heart” for the Jews’ rejection of the Bible (Romans 9:2), and then he exhorts us to “rejoice with those who rejoice and weep with those who weep” (Romans 12:15).
Then he tells us to “rejoice in the Lord always” (Philippians 4:4) and then, “I rejoice in my sufferings for your sake” (Colossians 1:24).
St. James tells us “Count it all joy, my brethren, when you meet various trials, for you know that the testing of your faith produces steadfastness” (1:2-3) and “As an example of suffering and patience, brethren, take the prophets who spoke in the name of the Lord. Behold, we call those happy who were steadfast. You have heard of the steadfastness of Job, and you have seen the purpose of the Lord, how the Lord is compassionate and merciful” (5:10-11).
Ecclesiastes 3:1,4,12-14,22: There is an appointed time for everything, and a time for every affair under the heavens. . . A time to weep, and a time to laugh; a time to mourn, and a time to dance. . . I recognized that there is nothing better than to be glad and to do well during life. For every man, moreover, to eat and drink and enjoy the fruit of all his labor is a gift of God. . . I recognized that whatever God does will endure forever; there is no adding to it, or taking from it. Thus has God done that he may be revered. . . And I saw that there is nothing better for a man than to rejoice in his work; for this is his lot. Who will let him see what is to come after him?
Book of Revelation 21:1-4 (about Heaven): Then I saw a new heaven and a new earth. The former heaven and the former earth had passed away, and the sea was no more. I also saw the holy city, a new Jerusalem, coming down out of heaven from God, prepared as a bride adorned for her husband. I heard a loud voice from the throne saying, “Behold, God’s dwelling is with the human race. He will dwell with them and they will be his people and God himself will always be with them (as their God). He will wipe every tear from their eyes, and there shall be no more death or mourning, wailing or pain, (for) the old order has passed away.”
And our Lord Himself reassured his disciples, and us: “Truly, truly, I say to you, you will weep and lament, but the world will rejoice; you will be sorrowful, but your sorrow will turn into joy. . . So you have sorrow now, but I will see you again and your hearts will rejoice, and no one will take your joy from you” (John 16:20,22).
Of course there are many other passages about grief, suffering, and joy. It is not easy to make a glib conclusion about “always be joyful”, in the context of what we are each trying to endure every day in our personal journeys of faith.
I have been blessed to know people who have suffered greatly, a few on their deathbed, while expressing intense and joyful love for the Lord. Because of witnessing the strength of their faith, their hope, and their love for God and others, I’m able to make some sense about this message to always be joyful. While being in union with the Lord we can suffer, we can mourn, we can cry, but simultaneously have hope, peace and joy, with the knowledge that our steadfastness in our suffering and in our faith have meaning and purpose. Our steadfastness will bear fruit. We know (but sometimes don’t remember) that our Lord is with us, helping us to be steadfast on our journey to Heaven.
So will I be joyful the next time I get a headache, spill my coffee, am treated with disrespect, get a flat tire on the freeway, or mourn with a friend who is suffering? I hope I will. I hope I’ll at least remember to pray, asking for help to remain joyful in the Lord in spite of the tiny or big ways I might suffer.
I’ve been trying to practice it, let joy in. Our Church does so many things to make our walk easier. I seriously missed the absence of the Alleluia during Lent…but didn’t figure that out until Easter vigil.