Is Sin Possible in Heaven? No, Not If You're Perfect

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This month we wondered about the possibility for free will and sinlessness to coexist in the context of heaven. Or, worded in a less obtuse manner, we asked, Is Sin Possible in Heaven?

Johannes Plenio

But rather than just tell you about it, here's a short excerpt from the piece:

To answer the question we turn back to Revelation. In the twenty-first chapter, right after the defeat of Satan and the final judgment, Scripture tells us that "[God] will wipe away every tear from [his people's] eyes, and death shall be no more, neither shall there be mourning, nor crying, nor pain anymore, for the former things have passed away" (Rev. 21:4).
This verse provides a definitive answer to our question: sin is an impossibility in heaven. Were sin possible, mourning and crying and pain would surely still take place. 
Therefore, we must ask, How? 
How is it possible for created, limited beings to have both free will and never sin? 
This answer is a bit murkier, but scripture does provide us with several clues and explanations. 
But before we dive in too deep though, I must confess something.

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Good News for Guttersnipes Like Us: Heaven Is Not a Meritocracy

Do you ever wonder what Jesus meant when he said, The last will be first, and the first last?

The statement sounds like typical rabbi-speak or else something Yoda would say were we to invert the wording a bit: First the last shall be, perhaps.

Jon Tyson

Nevertheless, Jesus didn't waste words. So the phrase, no doubt, points to some important truth. In fact, last month we explored one such meaning behind the phrase. That is, heaven's value system is often in opposition to that of this world's. The rich young man of Mark 10 and Matthew 19 found this out the hard way when Jesus told him to sell his possessions, give the proceeds to the poor, and follow Jesus.

The rich man, obsessed with firstness, could not do it.

And yet, if we probe deeper we uncover more layers behind the saying, The last will be first. These nuances are interesting and useful enough that I thought it would be worth spilling more digital ink in contemplation of the phrase.