Word of Wisdom: Regret

“Make the most of your regrets…” Henry David Thoreau

“Not a day goes by I don't feel regret.” So begins Red’s answer to the parole board’s inquiry as to whether he’s been “rehabilitated” at the end of The Shawshank Redemption.

Many of us can relate. We may not have spent the past forty years in prison, yet we inhabit a cell of regrets, our heart and mind confined and limited by the things we wish we had—or hadn’t—done.

And it is indeed a confinement. Places of joy in the present and fields of hope in the future are cut off, made inaccessible to us by the regrets that, though seemingly rooted in the past, actually creep into the here and now, even covering and hiding healthy pathways into the days ahead.

I’ve thought about this much lately, particularly as I’ve walked with brothers expressing regrets—about misdeeds, missed deeds, and even mistimed deeds in response. I’ve searched out my own regrets, and been forced to examine them. And, as such examen is wont to do, it’s led to discovery.

First, the clarity of what regret is not. It isn’t simply missing someone, or some place. It is not a forlorn wonder about what might have been. It’s not a nostalgic longing for something that is no more—even if we were the one to leave it.

No, regret is a grief, a profound sense of loss or absence that we—the one regretting—cannot now lose or avoid the presence of. It is a fixture in our consciousness, and, hence, a thing that takes up space…even casting a shadow.

But this leads to the second discovery. Because it is a grief—and because grief is not always evil—there must be something particular about the grief of regret that requires attention.

I think the nature of the word itself reveals the answer.

Our English term regret originated in the fourteenth century, meaning “to look back with distress or sorrow”, from Old French meaning “to bewail or lament”. Its Germanic source was literally “to weep”, or, specifically, “to grieve”.

The sense, however, is of a grief that is continually looked back to, repetitively. It is a grief that is not fully grieved. To regret, it seems, is to “re-grieve”…again, and again, and again, without closure. Without progress.

It is, in that sense, a prison indeed. But one for which there exists a key; one that is simple in concept, though not always easy in application: to grieve fully.

Because grief is foundational to the mortal human experience, it is one that not only will be experienced, but also must be directly addressed for health and flourishing to follow.

The problem is that we don’t tend to grieve well…because we rarely invest in grieving fully.

The time and energy required to grieve change is not insignificant. That’s the first challenge. The second challenge is perceiving the moments in life that deserve grieving—and not just instances of loss. Even positive, celebratory change that marks an exciting beginning is at the same time the end of something—of the previous season that is now passing.

And if we do not grieve them fully, we will find ourselves re-grieving them.

How to grieve fully? There are variations of “the stages of grief” or “the grief cycle”, but denial, anger, bargaining, and depression are commonly identified parts of the process. And they are common stages that regret keeps us stuck in.

“I should have/shouldn’t have done that thing.” “I should have/shouldn’t have married that person.” “I should have/shouldn’t have left that place.” “I could have/should have prevented that incident.” When we don’t fully grieve those transitions in our journey, we re-grieve them repeatedly, and we find ourselves locked in anger. Or denial. Or bargaining and scheming. Or in depression.

It is only when the fullness of our grief emerges that we escape regret, and we arrive at the final stage of grieving (and the first stage of what is new and next): acceptance. This is when things that “could have” or “shouldn’t have” happened are released, in exchange for what “did” happen.

We accept reality, instead of avoiding it. Put another way, we face what is real. What is true.

And we begin to see more clearly the One who is True.

That One is a good Father to his sons, One who compassionately tends our grief. He guides us in our grieving, and leads us from there to joy.

He does that by tenderly helping us accept reality: “Moses my servant is dead.”

Only then can we receive his covering, his strength to stand and go, to believe that he will not leave us or forsake us. That he will make us strong and courageous for the mission he has for us.

So that as sons, we can walk straight ahead, with no regret.


“For godly grief produces a repentance that leads to salvation without regret, but worldly grief produces death.” II Corinthians 7:10

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Why We Need: Understanding