Sermon Illustrations on Regret


Grace & Regrets

It is a simple fact of nature that once the leaves are off the tree, you cannot put them back again. Once you have uttered words, you cannot rip them out of another’s hearing. Once you have acted on a choice, you cannot relive that moment again. Once you have behaved in a certain way at a certain time, you cannot ask for a redo. You and I just don’t have the option of reliving our past to try to do better any more than we have the power to glue the leaves back on the tree and make them live once again. What’s done is done and cannot be redone.

We all wish we could live certain moments and certain decisions over again. If you’re at all humble and able to look back on your past with a degree of accuracy, you experience regret. None of us has always desired the right thing. None of us has always made the best decision. None of us has always been humble, kind, and loving. We haven’t always jumped to serve and forgive.

None of us has always spoken the truth. None of us has been free of anger, envy, or vengeance. None of us has walked through life with unblemished nobility. None of us. So all of us have reason for remorse and regret. All of us are left with the sadness of what has been done and can’t be undone. That’s why all of us should daily celebrate the grace that frees us from the regret of the past. This freedom is not the freedom of retraction or denial. It’s not the freedom of rewriting our history. No, it’s the freedom of forgiving and transforming grace.

Taken from New Morning Mercies by Paul David Tripp, © 2014. Used by permission of Crossway, a publishing ministry of Good News Publishers, Wheaton, IL 60187,

Madonna Struggles with Insecurity and Regret

It’s rare when celebrities acknowledge anything but the carefully crafted image that’s on view to the public. But this excerpt by the singer Madonna reveals that all of us, even celebrities struggle with insecurities. Sadly for Madonna, what has made her successful is also what causes pain and suffering in her life: her fear that she will only be “mediocre,” which to her appears to be a death sentence.

I have so many [regrets] … and I have none. I wish I hadn’t done a lot of things, but, on the other hand, if I hadn’t I wouldn’t be here. But, then again, nobody works the way I work. I have an iron will. And all of my will has always been to conquer some horrible feeling of inadequacy. I’m always struggling with that fear. I push past one spell of it and discover myself as a special human being and then I get to another stage and think I’m mediocre and uninteresting. And I find a way to get myself out of that. Again and again. My drive in life is from this horrible fear of being mediocre. And that’s always pushing me, pushing me. Because even though I’ve become Somebody. I still have to prove that Somebody. My struggle has never ended and it probably never will.

 Lynn Hirshberg, “The Misfit,” Vanity Fair, April 1991, 167.

Shifting Our Focus

By shifting the focus away from myself and onto Christ and his love for me, I have noticed that everything comes into view. When Martin Luther was suffering under the weight of guilt, his spiritual director, Johannes Staupitz, said, “Martin, quit looking at your sin and start looking at Jesus.”

James Bryan Smith, Embracing the Love of God: The Path and Promise of Christian Life, HarperCollins, 2010.


“I Don’t Remember”

In A Forgiving God in an Unforgiving World, Ron Lee Davis shares a powerful story of forgiveness about a priest from the Philippines. The clergyman had carried the weight of one particular sin that plagued his conscience for years. Though he had repented multiple times, he couldn’t shake the feeling he was still to be punished by God. At one point in his ministry, there was a deeply religious woman in his parish that loved God and claimed to have visions in which she spoke face-to-face with Jesus. The priest was initially skeptical. So he decided to test her by saying, 

“The next time you speak with Christ, I want you to ask him what sin your priest committed while he was in seminary.” The woman agreed.

A few days later the priest asked, “Well, did Christ visit you in your dreams?”

“Yes, he did,” she replied.

“And did you ask him what sin I committed in seminary?”


“Well, what did he say?”

“He said, ‘I don’t remember’“

What God forgives, He forgets.

Ron Lee Davis, A Forgiving God in an Unforgiving World.


The Sand Trap of the Soul

Sister Joan Chittister writes about regret in the context of aging, though I think most of us can identify with this personification of Mr. R.:

Regret…comes upon us one day dressed up like wisdom, looking profound and serious, sensible and responsible. It prods us to begin to look back. It presses us to question everything we’ve ever done: I should have listened to my mother . . .; I should have stayed in school . . .; I should have waited to get married . . .; I should have majored in something else . . .; I should have changed jobs . . .; I should have spent more time with the children, with the family, at home . . .; I should have gone away from this place, this town, this dull, or wild, or confining life, it whispers.

The exercise is an exhausting one. It is also a dangerous one. 

It nibbles around the edges of the mind, and we feel the weariness that comes with it…Worst of all, regret demands to know why I did what I did in the first place. And I don’t know. Regret claims to be insight. But how can it be spiritual insight to deny the good of what has been for the sake of what was not? No, regret is not insight. It is, in fact, the sand trap of the soul. It fails to understand that there are many ways to fullness of life, all of them different, all of them unique.

Joan Chittister, The Gift of Years: Growing Older Gracefully 

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