Avoiding The Pain of Regret

I am the son of a pastor. During my dad’s forty years of ministry, he did many great things; he probably committed a few stupid acts; and he occasionally had to make unpopular decisions. He passed away almost twenty years ago.

The “Smith” family was originally supportive of my dad during his Detroit pastorate (from 1963 to 1975). And then they suddenly opposed him. The Smith’s used to smile; now they scowled. My dad was unsure what he had said or done (or not said or done).

A sketch of my church in Detroit

A sketch of my church in Detroit

He asked repeatedly what had happened. They denied, repeatedly, any hard feelings.

Pastor’s kids know almost everything that’s happening at church. I knew something was wrong. Mr. Smith had once mentored me. Then he began saying, “Sam, you son of a pastor.” But he slurred the last word to sound like, “Sam, you son of a bastard.”

He thought it was funny.

One day, when I was about twelve, a Frisbee landed on the roof of the sanctuary. The roof was probably twenty feet high, maybe more. I knew a secret access—pastor’s kids know every nook and cranny of their church—so I climbed up to retrieve it.

Mr. Smith happened to be on the ground right below me. He looked up and saw me. He sneered, “I dare you to jump.” Even as a kid I was shocked at his hostility.

I admit I was tempted, tempted to shout back, “Why the ‘F’ don’t you work this out with my dad?” But I was afraid of getting in trouble for cussing. Instead, I did what any bewildered twelve year-old boy would do. I simply stared at him.

And I jumped.          


I admit to experiencing a certain sinful pleasure as I watched his face blanch before I hit the ground. The future pain of the approaching ground paled as I saw the present pain of regret on his approaching face. It felt good.

God protects drunks and fools, and I was a twelve year-old boy. By definition, I was a fool. I escaped injury, not even a sprain. Not so for Mr. Smith. From that day forward, I think he lived under the pain of regret, the inner injury of what might have happened.

At least he never again questioned my lineage.

I wonder what Mr. Smith regretted specifically. Was it my potential injury; was it the witness of other kids; or was it the public unveiling of his bitterness? Maybe all three.

Whichever it was, I’m curious if he ever explored the regret beneath his regrets.

Our deeper regrets

Last week I heard an old quote,

There are two types of pain you will go through in life, the pain of discipline and the pain of regret. Discipline weighs ounces while regret weighs tons.

I asked myself what “tons of regret” weigh on me. So I made a list, bulleting every substantive regret I could remember. I listed words I’ve spoken, decisions I’ve made, actions I’ve taken, and relationships I’ve harmed (or not formed).

It took less than an hour to fill two pages. I regret never doing this before. (There’s another one for the list.)

Then I examined my list for underlying themes. What triggered each regretted action? Why had I said “X” inappropriately (or not said something needed)? Why did I act as I had? What were the common causes?

My themes of regret

The ache of regret arises when the pain of our action is paired with the painful disclosure of our self-deception. For some reason, we bowed in fear before Nebuchadnezzar’s idol, and we now stand alone in the furnace of an ugly self-revelation.

My deepest regrets are relational. Oh sure, I also made bad business decisions that cost money or prestige; but years later, that money or prestige matters little compared with the agony of relational hurts:

  • I never addressed a serious distress in my family when I was in High School.
  • I was silent about harmful practices in a large prayer group that I belonged to.
  • My marriage experienced deep adversity because of my passivity.

The biggest mistakes of my life would have been avoided—at least minimized—had I practiced the discipline of being real. I regret it. I bet your regrets have the same root. I wish that I had shared openly in my family, in that prayer group, and in my marriage. I regret not being real.

I don’t mean uncontrolled gushing of emotions. I mean disclosing my beliefs, questions, doubts, affirmations, and disagreements. I mean open expression; no more hiddenness.

I could have prevented terrible pain to my wife and kids; I could have protected dozens, maybe hundreds, of people in that prayer group; I could have forestalled relational shallowness with a sibling …

If I had only been real. But I cowardly kept quiet. And I regret it.

Mr. Smith’s regrets

Forty years later, I still see the fearful pain etched on Mr. Smith’s face. I wonder how that grown man could let his unspoken resentment fester; fester to the point he would bait an innocent preacher’s kid. If he had been real with my father—had he dissipated his bitterness through open expression—he would have saved a ton of regret.

(Okay, there’s no such thing as an innocent preacher’s kid. Just don’t tell anyone.)

I no longer wish to live with such regrets. This life without regret will take courage, a bit of self-disclosure, a sense of what’s happening in our own hearts, and a leap of faith; the leap that knows the pain of being real today is better than the pain of regret tomorrow.

Let’s jump. Shall we?


P. S. The wife of a friend wrote a book called, Groceries on a Saturday Morning. She openly shares her life without the pretense of tying up each story with a neat Christian bow. She’s real.

I rarely recommend a book. But if you get a chance, check it out, and read it with these questions in mind: How is she being real, and how can I be so too?

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What do YOU think?

26 thoughts on “Avoiding The Pain of Regret

  1. “The biggest mistakes of my life would have been avoided—at least minimized—had I practiced the discipline of being real. I regret it.” I have the opposite issue a life being too open, too unafraid too speak my mind, too battle, for I have been a fighter all my life. A life that does not often consider the words coming out before it’s too late. A friend once said that he and his wife were taking one of those animal personality tests. The kind where you pick an animal that best represents your personality.

    He said when they were discussing the lion and think of someone who fits that mold, silently they both thought of me. With that lion comes the roar. The roar that is too quick too roar, too quick too jump, too quick to deal with others not with grace but by how they are responding. Defend the weak from the bullies and point out the error teaching of others.

    So Sam there is another side. Just when I think I got all the issues licked they come roaring their heads up again. That is why no one has to convince me that we do not get better by focusing on our improvements because every time we make some, we discover ones we thought were conquered come rushing back. That s why I am glad that we are already qualified, already secured and we grow from the inside out by focusing on the perfect obedience of one because, Lord knows if he held my outbursts and tongue lashings and roars against me I could not stand even now in HIM. I am so thankful for grace that comes new every moment.

    I’m going through something today as a result of those issues and needed to be reminded that IT IS FINISHED!

    Thanks Sam

    • Hi Patrick,

      Well, I probably have a split personality; sometimes I talk too late and sometimes I talk too quickly.

      I think both are partly affected by too low a value of being real. Of course my quietness is an example (thus this blog). But sometimes my outburts are caused by not having releases inner pressures through day-to-day being real (sort of like the infamous Mr. Smith of this article).

      But I also think few of us really want to create an environment around us that allows for being real. One of the reasons I sometimes speak too quickly is my desire to “give advice” rather than fostering an environment in which I just ask questions and let the other person think, be real, and come to their own conclusions.

      In other words, how can we help them become real? As well as ourselves.

      Thanks as always,


      • “One of the reasons I sometimes speak too quickly is my desire to “give advice” rather than fostering an environment in which I just ask questions and let the other person think, be real, and come to their own conclusions.” SLAP!!!!!!!!!!!!!!! OH that felt good,do it again! Sam get out of my head! LOL!

  2. Hi Sam,
    Thanks for sharing. Oh yes, I can so easily go down that path too. I praise God that
    his blood covers those sins and I can move on with life as I face the pain for healing.
    Dot and I have found it interesting that your dad said he no regrets in life. I think maybe the reason he said that is because he was able to experience healing from our lord and savior Jesus.
    Bill English

  3. Sam,
    I’m a roof jumper too, egged on by “friends” to jump after retrieving a wiffle ball from a roof in the 1960s. It was a dare and challenge to my “manhood.” It hurt badly…body and spirit. Another time is was a baseball on a clubhouse roof at a local park. I loved to climb, and I hoisted another kid behind me to check out the view–where we were met by a volley of rocks from the cowards below. I ended up with stitches.
    The latter story did have a humorous side though. As I walked home from the park, blood pouring from just above my eye, a couple of teenagers smooching in a parked car took a breather from their lip lock just in time to look up and see my blood-drenched face. The change in their expression was priceless. They went from hormones to horror in .5 seconds. I laughed uproariously through my tears.
    Thanks be to God for loving us, that we can move from being shame-based to being real.

  4. I used to say to myself often “Live life without regrets” and I generally lived by this, seeking God’s wisdom in my choices, taking risks for Him, speaking my mind. Then suddenly I became “an adult” and my choices started to have huge consequences, my risks started to actually be dangerous and speaking my mind could land me in a load of, um… mess. For now, living without regrets seems to mean asking God what His vision is of my life and living that, rather than seeing the vision and thinking, “Oh, that’s a nice vision, God.” But not doing anything. My husband often says that there is a big difference between knowing and doing. Many of us know, but don’t do. I think James is talking about that when he says “For if anyone is a hearer of the word and not a doer, he is like a man who looks intently at his natural face in a mirror. For he looks at himself and goes away and at once forgets what he was like. But the one who looks into the perfect law, the law of liberty, and perseveres, being no hearer who forgets but a doer who acts, he will be blessed in his doing.” I feel like one of the keys to living without regret is being a hearer and a doer in Christ.

    • Hi Havs,

      Excellent response. Thank you for nuancing the issue.

      I would love for all of us to be able to be real all of the time. But we DO have to be careful. The person we are speaking with may not have the time, energy, or maturity to hear this right now. We can be speaking unwisely simply because we are not sensitive to God, his Holy Spirit, … or even to common sense.

      I honor and long for relationships in which I can be real. But not every relationship is deep enough or close enough for me to be real. I want to be real; I also DON’T want to be one of the people who vomit their opinions and emotions at the slightest provocation.

      We need God for the courage and wisdom of being real.


      • That’s absolutely true and well put. It would be great if we could be the same level of “real” with everyone, but for some people we can apply the well known Malkovich quote “You can’t handle the truth!” That’s where the aspect of God’s sovereignty comes in to play. We should certainly do our part with the leading of the Holy Spirit, but we will never know how much of what happened depended on us and how much God was working things for His will, even our failures.

    • Hi Chuck,

      Thanks for your encouragement.

      I bet, in some ways, you have had some similar regrets.

      The good news, is God really does pursue us in the garden, even when we’ve put on fig leaves.


      • You’re doing better than me, my list would have been longer! And yes, God is always pursuing us, in every place, in every moment, no matter what we do or think or say, he is there inviting us to a deeper intimacy with Him.

        • Hi Chuck,

          I was writing tiny. But you’re right, a longer list is possible.

          I especially want to emphasize your closing line, “No matter what we do or think or say, he is there inviting us to a deeper intimacy with Him.”

          That is the secret, only it’s not a secret. We just keep forgetting it. God wants intimacy and he uses everything to help in his pursuit of us; no matter what we’ve done or not done, or said or not said..


  5. Sam, I have loved that “innocent” kid for a long, long time. Praise God for our regrets because that is where we know just how much we need His love, mercy and grace. Thank you for your honesty as we all can identify with regrets and know as Bill English said, we are covered by the blood. It’ all about God’s grace!

    • Hi Nancy,

      I agree. “Praise God for our regrets.” Too often we try to escape any pain of any sort. And, of course, a certain degree of wisdom will help us avoid a certain degree of pain. But more than wisdom, we simply need God.

      We need to learn a new response to pain, regret, low self-esteem, shame, and disappointment. We need to learn to let these drive us to God instead of to pity or numbness.

      It’s God that we need most of all.


  6. I thought about doing what you did, however for me I don’t think it would be good. Looking back at all of my regrets, would I believe evoke negative feelings for me and having a history of depression, I think it would bring me sadness and I would begin ruminating over it… I have a lot of regrets … For others it is probably a good thing… Diane

    • Hi Diane,

      It sounds like you are acting out of wisdom. You have an understanding of yourself, and you are avoiding an activity that would tug at your soul.

      Another approach is to remember Paul’s words, that “everything works out for the good.” There are times in our lives we can look back and see a bad event but recognize that God brought something good out of it. He may have humbled a bit of pride and we are now more gracious people; he may have protected us from a job that would have killed our hearts (or a relationship that would have sucked our soul); he may may have formed an inner resilience, a greater patience.

      Someday, maybe not now–you know your heart–someday you may be able to look back at your life and see God bringing victory out of the jaws of defeat.

      Because in the end, God always triumphs and evil always fails. It’s fun to look back as see God’s triumph.

      But there is a season for everything. Let’s turn to God to see what season we are in.

      As always, thank you for your great, personal sharing.


  7. Reminds me of another article I read recently entitled Existential Regret written by a young man who has struggled with regrets. His suggested remedy is to be authentic. Always act according to who you know yourself to be and in line with your values. That way you can look back at the choices you made and have peace, knowing you acted true to yourself and with sincerity of heart. My most painful regrets are those of inaction, that is, not what I did, but what I left undone. When I didn’t listen to what my conscience was telling me. Often, taking the easier path and not being disciplined to act authentically.

    • Great comment. Thanks.

      I wonder if we need a type of balance. I’ve met too many people who are insensitive jerks, claiming to just be authentic; and I’ve met too many overly sensitive doormats claiming to be nice.

      We need to learn the art–the virtue–of humble boldness and gracious courage.


  8. In my case it has to do with not living up to my ideals and values. I take the easy way out.

    Recently we protected our next door neighbor from her abusive husband when she came screaming at our door at 2am bleeding and brutalized. He was outside the house shooting a gun and the police ended up killing him in a long drawn out gunfight. It was all so traumatic. It was a 3 hour ordeal of us listening to the gunfire while being barricaded in a small room of our house. The police SWAT team evacuated the neighborhood except us since we were too close to the shooter. I had my wife and two daughters with me, my youngest being 4 months old. I had nothing to protect us that I could use if he had tried to come into our house. I felt very vulnerable. I asked the battered woman if we could pray with her, and so we asked God for his protection over our home and lives. I believe he protected us that night. We were all safe.

    My regret is we declined the tv interview or talking to the newspaper. I do not know why but it just felt wrong to do so at the time. I wanted to get it behind us. I may have thought I was protecting the privacy of my family, I don’t really know. My regret is I now see this as a missed opportunity to give God the credit and to share our testimony of the power of prayer to the tv viewers which would be a large majority if this small town. But we remained silent. The news report stated that the unnamed next door neighbor took the victim into their house at the risk of his own family’s safety. That is all.

    I can recall other significant events in my life when I chose to remain silent when I should have spoke up. It doesn’t align with my values. I am a Christian.

  9. My habit of being short-sighted and not realizing (at the time) how I can take something tragic and find something good to pull out of it.