Judgement and Empathy

This is SO NOT "Christmasy."
Christians think quite a bit about the afterlife. I'm teaching "Intro to Judaism" right now and we've had a lot of conversations about the Jewish perspective. Most of my students can't comprehend the idea that Jews are frequently agnostic or not that concerned about the afterlife. In addition, Christians mostly think about the afterlife exclusively in terms of heaven and hell. The Bible actually talks a lot more about judgement. It's not clear. God is portrayed as the supreme judge, but Paul also implies that humans may act as subsidiary judges. Also, while the criteria for "salvation" is faith, the judgement is generally described in terms of what one has done, or hasn't done (see Matthew 25, Romans 2). Now, I know Christians have lots of different ways of reconciling all this but I'm less interested in that. C.S. Lewis wrote a little novelette about heaven and hell called The Great Divorce. Lewis was clear that he didn't want it to be taken "literally" but it should also be clear that it wasn't intended to be frivolous or meaningless.
I write the following imagination of judgement with the same intent.

I imagine the experience of judgement to be something like the experience of 20/20 hindsight portrayed at the end of Schindler's List. If you watch that scene, you see Oscar Schindler, a man who rescued many Jews from the fate of the concentration camps come to some tangible realizations about his life. The simple idea is: "I could have done more." Oscar Schindler was a hero, but he didn't do everything he could've done, even knowing that lives were on the line. He stares at a host of people he saved and is broken by the realization that he could very easily have saved more.
What if judgement is like 20/20 and 360 degree hindsight and empathy? I suddenly arrive at a sweeping and accurate assessment of my whole life. It life flashes before my eyes. I see, not only the things that I did and didn't do, but their actual effects on other people, the created world, society... For instance, I don't just see the time I was rude or said something inconsiderate to someone in 7th grade (let's call him Joe), but I see the ripple effect of that on Joe's interaction with his little brother, friends and parents. What if judgement involves receiving the curse of retroactive empathy for everyone I could have had a positive effect on and didn't. What if I could feel what that student felt when he was anxious, lonely and needed someone to give a crap and I didn't. What if I could feel what the panhandler felt when I was the 1000th person to ignore him that morning in Center City.
Will anyone escape judgement? I'm not talking about hell now. I'm talking about judgement.
I don't know. I imagine if I could feel what I describe above for even a brief moment right now, after 35 years of life, it would feel like an eternity of anguish. Maybe on some level this would be a gift, preparing me to experience the deepest mercy and grace and to freely live the life that God has in store for us. Maybe there is a deeper mercy too.

"God humbles the proud, but gives grace to the humble"

Maybe the judgement I recieve will correspond to the manner in which I present my life to God.
Perhaps if I have learned the lessons of empathy and humility now, I will present my life (as I understand it) to God as a paltry thing and God will show me the opposite.
Or maybe God presents it all to us, like a performance appraisal.

Suppose we are given a box and the truth of our life can be seen glowing inside it.
The proud one is thrilled, imagining the rewarding experience it will be to open the box and see all that they have accomplished. They firmly and confidently lift the lid and breathe deeply before wilting, curling up into fetal position, gasping and weeping as they are emotionally and psychologically dismantled by the magnitude of their deficiencies.
The humble ones shake and stutters.
"No. I know what's in there. Please just take it away. I can't bear it."
Perhaps to these, God still responds, "You must open it."
They brace themselves and tear it open with gritted teeth, like ripping off a band-aid, but in their humility, their contribution to life is what shines forth. They experience empathy with those who were blessed by their kindness, however small.

I know some people will try to fit all this in to their theological boxes, and others will dismiss it as pious drivel. That's fine I suppose and yes, following Jesus is at the heart of this for me. But my point is that if the heroic Oscar Schindler could take a "do over" he might... I'd like to try it myself. Maybe I'll start now...