“You’re 9 years old,” I say to my younger self. “What do you have to be sad about?”

The charcoal portrait, sketched in the shadow of the Sacré-Coeur, now hangs in my father’s front room. And I look heroically gloomy. Presumably the artist did his best to capture the merriment of a family vacation, but the face is so sodden with regret it near drags the paper from its frame.

This was no isolated moment of childhood melancholy. “Cheer up,” complete strangers would routinely say to me, “it might never happen.” (“Too late,” I would say under my breath, “it already has.”)

I suppose some of us tend that way naturally. We’re always trying to swim back upstream to the moment just before we think it all went wrong. Our minds, sadly, aren’t well-behaved libraries shelved with orderly memoirs. They’re gothic charnel houses piled high with gaudy carousels, furiously spinning out past moments, past conversations, past relationships. What if I had done things differently? What if I had said something else? What if I had been someone else? The linoleum is worn through with pacing. We rehearse and re-rehearse dialogue as if we’re preparing for opening night on Broadway, except there is no play, these conversations ended long ago, and many of the people who shared them with us are long gone. Regret, the barbed wire hula-hoop, loping heavily around the brow, lacerating the skull with each revolve. Regret, the malevolent halo.

“What’s done is done.” “That tree has fallen.” “Why regret things you can’t change?”

Miserable comforters all. They may as well tell someone to ignore an itch they can’t scratch. The unreachability is what makes it so impossible to disregard.

Apostle of Regret

He was, by his own account, “a blasphemer and a persecutor and a violent man” (1 Timothy 1:13). Paul hounded Christian men and women from their homes, had them incarcerated, voted to have them killed, and approved the stoning of Stephen, one of the early church’s most beloved and powerful leaders (Acts 8:1-3; Acts 26:10-11). At that time, Scripture says, Paul “began to destroy the church.”

How did he live with himself? Once he became a Christian, what did he do with all the sorrow and regret that must have coursed through him?

Paul explains in 2 Corinthians 7, “Godly sorrow brings repentance that leads to salvation and leaves no regret.”

Sorrow and regret are tightly bound. We might even paraphrase Paul by saying, “Godly regret . . . leaves no regret.” The apparent contradiction resolves itself when we understand that godly regret is a transitional stage. It’s godly because it is a means to an end—namely, repentance—and once that end has been achieved, godly regret becomes happily redundant.

Regret had done its job in Paul, and he no longer had any use for it. “Forgetting what is behind,” he writes in Philippians 3, “and straining forward to what lies ahead, I press on toward the goal for the prize of the upward call of God in Christ Jesus.”

Godly regret is a chrysalis. It enables us to leave behind the wriggling larva of sin, grow the bright wings of repentance, and so fly upwards toward our salvation. It is not meant to be carried with us, but discarded once its purpose has been met.

Worldly Regret

Paul is well aware that there is another species of regret. A deadly one. He continues in 2 Corinthians, “But worldly sorrow brings death.” Worldly regret “brings death” in that it elicits no repentance, and so leaves our sin to run its natural course unchecked.

The difference, then, between godly regret and worldly regret is partly one of duration. If your regret keeps you on your knees longer than the time it takes to repent, there is something amiss. Good regret pays a fleeting visit; bad regret, like the thoughtless party guest at 3 a.m., outstays its welcome. Good regret is a doorway; bad regret is a destination. Good regret makes us more preoccupied with Jesus; bad regret makes us more preoccupied with self. Good regret drives us to repentance; bad regret drives us to distraction.

Not many butterflies achieve escape velocity if they insist on carrying their previous home with them.

Why then, when we could fly, do we find it so hard to let go of our regret?

Deathless Regret

One possibility is that we believe a lie. We believe that to forget our past sins or mistakes (whether real or imaginary) would be to suggest that they were not significant or serious. To forget would be like laughing at the graveside, a failure to pay our respects. So each regret becomes a shrine before which we endlessly bow, like somber priests offering dutiful sacrifices, and knowing that there must never be an end to our sadness, because no amount of sacrificial sorrow can truly do justice to the mistakes we’ve made.

But our great high priest did not offer himself as a sacrifice in order that we might go on offering ours.

At the end of Luke 9, Jesus encounters two men in thrall to their past. The first man says that before accepting Jesus’ invitation to follow him, he must go and bury his father. Jesus responds, “Leave the dead to bury their own dead. But as for you, go and proclaim the kingdom of God.” The second man says he must go and say his goodbyes. But Jesus insists. “No one who puts his hand to the plow and looks back is fit for the kingdom of God.”

Whether we are troubled by past sins, or merely the past, Jesus’ words will make us truly free if we will live by them. Listen, he says. The past has no jurisdiction in the kingdom of God.

Not Just a Better Future

You know that Jesus gives you a better future. But do you know, Christian, that he also gives you a better past?

Think back over your history, no matter how motley. All the things you did or did not do. All those choices made in cowardice, carelessness, or foolishness. Whether through oversight, ignorance, or sin. Jesus says to you what Joseph said to his fearful, regretful brothers. Be of good cheer. God ordained that all of them would be for your own good, and for his own glory.

To paraphrase John Newton: everything was needful that he sent. Nothing was needful that he withheld. Yes, if you had your time over again, you would choose differently. But know this: Your Father, whose name is Love, would not.

If there is repenting to be done, repent. But then set the chrysalis aside. Look up. Take your place in wonder alongside Joseph’s brothers, and with the rest of God’s people. Know that you did not fall between the cracks of your own life. Nothing in your past, present, or future can separate you from the love of Christ.

Feel that fierce embrace, within which no worldly regret can draw breath.