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The Dead Weight of Regret

The experience of aging is full of surprises. Or it has been for me—maybe I’m more naïve than others in my stage of life. There are pleasant surprises for sure: I never anticipated how amazing it would be to have grandchildren. I love my grandpeople so much! And along with that is the sweetness of having adult children who live according to convictions they have developed on their own.

On the other hand, I’m surprised at how strong is the pull toward regret. I find myself regretting (or at least wondering if I should regret) a wide variety of things. I wish I had done certain things differently as a parent, that I had spent more time in some activities and less in others, that I hadn’t stayed in a fundamentalist environment as long as I did, that I had taken certain educational or financial steps differently, and so on. Some are relatively trivial, others involve major chunks of the life I’ve already lived and can’t redo.

It’s also a little surprising how ill-prepared I felt to deal with regret. I’ve had some really good times of pondering this with the Lord and a few close friends. I’m no expert on dealing with regret (I haven’t read any books on the topic), but I’ve been encouraged in the battle and thought it might be helpful to work out some of these thoughts into a form that might help others.

One dictionary definition of regret is, “a feeling of sorrow or remorse for a fault, act, loss, disappointment, etc.” That’s good as far as it goes, but I’ve found that a unique facet of regret is wishing you had done something differently. But you can’t go back and change the past, and this causes tension, stress, and/or frustration. Regret can hang like dead weight on your soul.

How Regret Feels

In my experience, regret has to do with two basic feelings: embarrassment and guilt. (Yes, I know the difference between guilt-as-feeling and guilt-as-fact. Keep reading.) First, I feel embarrassment about all sorts of things from my past, all the way back to adolescence. I’m aware of how arrogant I was, how I enjoyed impressing people with knowledge or skill (or the appearance of them). More heavily, I feel embarrassment about spiritual immaturities I manifested at various points in my adult life (one example: for a time, I was a fan of the book I Kissed Dating Goodbye). I feel my cheeks burn when I remember certain ministry missteps that I made out of ignorance, inadequacy, and lack of training.

The second major type of emotion I associate with regret is guilt. Especially in cases where I sinned against, hurt, or misled other people, I feel guilty. I remember moments when I spoke carelessly or counseled recklessly. When I chose self-gratification rather than self-sacrifice with my family or ministry. And I wonder how things might have turned out differently if I had made a different choice.

These emotions make regret particularly unpleasant. It can be mildly distracting, like a paper cut that keeps reminding you it’s there as you type, but it can easily progress to the spiritual equivalent of a back injury that restricts your movement and disrupts your whole life. What does the road of resolution look like when I’m feeling the pull into regret?

Embarrassment is for Humility

First, the Lord is teaching me (why have I been so slow to learn?) to let the embarrassment do the soul-enriching work of humbling. A sheepish, rueful grin with an admission like, “I was such an idiot” is not a bad thing—it can be freeing, because the recognition of immaturity is a sign of growth. Accept the humbling realization that you should have done differently. Be grateful that you’ve gained a more seasoned perspective. The embarrassment itself is evidence that you’ve grown since you did or said that really dumb thing!

But stay on guard against letting embarrassment turn into shame that can trap and debilitate. Apart from living in God’s grace, “I was such an idiot” turns into “I’ll never be anything other than an idiot.” But your Heavenly Father knows you, and he has provided better for you in Jesus. Let embarrassment for past mistakes lead you to a fresh gratitude for God’s kindness to you. Let his kindness toward you cultivate patience with others and peace with your past.

Grace is for Guilt

What about feeling guilty? All who struggle with guilty feelings must learn to discern the difference between guilt-as-feeling and guilt-as-fact. Prayerfully consider for any given regret: did I sin, or was it a mistake caused by some kind of weakness? Think about a few examples, and you’ll see the importance of this:

  • I regret specific things I did as a parent because in an effort to modify my kid’s behavior I did or said things that were unkind. That was sinful, and my guilt is both a feeling and a fact.
  • I regret one or two major financial decisions—what was an iffy plan to begin with turned out to hurt us badly due to broader economic forces that we could not anticipate or control. I don’t think this was a sin, but it was a result of a combination of weaknesses (taking risks we didn’t need to take, not knowing what was about to happen to the economy). My guilt here is feeling but not fact—it wasn’t a sin as far as I can tell.
  • I regret moments where I gave in to fear and uncertainty and acted quickly or impulsively instead of waiting on the Lord and taking a more patient approach. As I ponder moments like this in my life, I’m honestly not sure whether this was weakness or sin or a combination of the two.

As much as you’re able, discern what kind of guilt your dealing with: feeling, fact, or both? Once you’ve honestly admitted to the reality behind your guilt feelings, you can respond accordingly. In short: preach the gospel to yourself again. Go back to the cross and see the love God has poured out for sinners through Jesus Christ. Go to the empty tomb and remember that sin’s defeat has been confirmed. Where you have sinned, God has forgiveness and new life for you in Christ. If you’ve sinned, repent and revisit God’s generous grace and thank him for it again. Don’t allow shame or condemnation to rob you of the joy of forgiveness.

If it’s clear that you haven’t sinned but you regret living in your earlier weakness, remember that it is in your weakness that the power of Christ comes through most clearly (2 Corinthians 12:9-10), and again, thank him for that. Yield to his transforming grace that is renewing you from the inside out, and let go of the guilty feelings that may turn into shame and hold you back from drawing near to God in Christ.

Did Paul Have Regret?

As I was pondering my own regrets in the recent past, I asked myself if Paul must have felt regret. I mean, he oversaw the violent persecution of the early church, then became one of its most prominent leaders. Did he ever, as he experienced the extraordinary list of hardships in 2 Corinthians 11, stop and think, “I used to do this and worse to Christians myself”? How did he deal with the regrets that surely welled up in his heart? I think he gave us clues.

Many of us have heard 1 Timothy 1:15 quoted by people either jokingly or in false humility, admitting to being “the chief of sinners.” But listen to Paul in context:

“This saying is trustworthy and deserving of full acceptance: ‘Christ Jesus came into the world to save sinners’—and I am the worst of them. But I received mercy for this reason, so that in me, the worst of them, Christ Jesus might demonstrate his extraordinary patience as an example to those who would believe in him for eternal life.” 1 Timothy 1:15–16 (CSB)

Do you hear Paul preaching the gospel to himself? “Yes, I feel like the worst sinner that’s ever lived. But I received mercy so that Jesus could show the world that he can save the worst of sinners!” He didn’t allow shame to pull him down into degradation and ineffectiveness. Instead he acknowledged—no, rejoiced in—the fact that his sordid past provided an ideal canvas for a portrait of Christ the merciful Savior. He made it about Jesus instead of himself.

In Philippians 3 Paul again rehearses his self-righteous and oppressive past, this time as something that others might expect him to brag about. But he declares that it was all worse than useless: “I consider everything to be a loss in view of the surpassing value of knowing Christ Jesus my Lord. Because of him I have suffered the loss of all things and consider them as dung, so that I may gain Christ and be found in him” Philippians 3:8–9 (CSB).

Paul’s life as a religious Jew was full of accomplishments that amounted to a pile of garbage—excrement, even. Why such harsh valuation? Because his respectable religiosity kept him from Christ. And with that reevaluation of his life before Christ—much of which he must have regretted—he presented this strategy for moving forward a few verses later:

“But one thing I do: Forgetting what is behind and reaching forward to what is ahead, I pursue as my goal the prize promised by God’s heavenly call in Christ Jesus.”

Obviously Paul couldn’t literally forget—as in wipe clean from his memory—the evil things he did in the past. But he didn’t let his regrettable past dictate his future efforts. On the one hand, he didn’t let regret of the past sap his energy for the future, and on the other hand he didn’t he treat the future as a way of making up for his regrettable past. He simply wanted to know, obey, and eventually be with Jesus. He determined to turn away from his past and use it only as a springboard into the future Jesus had for him.

Regret dissipates as we embrace God’s grace in Jesus Christ. Where I’ve sinned, his forgiving grace overflows to reassure me that if I’m in Christ, I’m right with God. And where I’ve been weak or immature, his transforming grace comforts me and reminds me that he is gradually making me more like his Son, even though, yeah, sometimes I’m an idiot. The goal of confronting regret is not to think better about myself but to more deeply embrace the sufficiency of Christ. To live actively in the gospel every day. To gratefully press into the life I have with him, wherever he may lead me.

Forget what lies behind, and stretch forward to what is ahead.

By
Andy Snider
August 7, 2023

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