19Jesus saw that they wanted to ask him about this, so he said to them, “Are you asking one another what I meant when I said, ‘In a little while you will see me no more, and then after a little while you will see me’? 20I tell you the truth, you will weep and mourn while the world rejoices. You will grieve, but your grief will turn to joy. 21A woman giving birth to a child has pain because her time has come; but when her baby is born she forgets the anguish because of her joy that a child is born into the world. 22So with you: Now is your time of grief, but I will see you again and you will rejoice, and no one will take away your joy. 23In that day you will no longer ask me anything. I tell you the truth, my Father will give you whatever you ask in my name. 24Until now you have not asked for anything in my name. Ask and you will receive, and your joy will be complete.
Is it speaking to the fact that we know they are in heaven. I think Mary grieved because she saw the terrible physical punishment her son underwent.
I ran across a scripture that I think sheds light on this. John 11, verse 33-35. In the text of the scripture Christ is “deeply moved” and even weeps at the death of Lazarus. But the commentary I was reading says that “deeply moved” is the translation of the Greek word meaning literally the snort of a warhorse or a horse in a race. It is a different feeling than grief alone, as I picture it, it encompasses anger and energy and impatience, outrage. The dead rise in a relationship with Christ and death is an outrage. I believe Christ weeps for all of sin and death, with us, as well as beyond for it is frustrating and unnecessary, not what God wishes for us, for there to be death and grief at all. In another sense, to weep is unecessary because we live in Christ (and it is this sense that I think Thomas a Kempis means for his devotional here) and yet the deepest and most profound sadness is warranted for the barrier of sin and death that Christ overcomes. The frustration or impatience exists because it is inevitable that there is grief in a world with sin, even for believers. So the snort of the warhorse. We don’t dare ignore or minimize the grief in others when we face it because it is love and must be respected, but balancing this is hope and faith. Perhaps even joy.