One of the unexpected consequences of thinking seriously about the years ahead is that it makes us see the years behind us differently. Once we acknowledge that our time is limited, we naturally begin to examine how we have used the time already given to us. That reflection can produce gratitude as we recognize God’s faithfulness, but it can also awaken memories we would rather leave buried.
There are things most of us would do differently if we could. With the benefit of experience, we look back on decisions that once seemed reasonable and wonder what we were thinking. We remember opportunities we let slip, relationships we neglected, arguments that now seem embarrassingly unimportant, and years when our priorities were badly out of order. Sometimes the memories involve mistakes in judgment. Other times, if we’re honest, they involve sin.
If we aren’t careful, growing perspective can become a source of discouragement rather than of wisdom. Instead of using the past as a teacher, we can turn it into a courtroom where we repeatedly put ourselves on trial. We replay conversations, reconsider decisions, and imagine different outcomes. What if I had spent more time with my children? What if I had listened to my wife? What if I had managed my money differently or had followed Jesus more faithfully when I was younger?
There is value in examining those questions, but we need to consider where they are leading us. The past can teach, humble, and correct us. It cannot become the place where we live. A rearview mirror is useful precisely because it shows us what is behind us. No wise driver would remove it just because the road behind no longer matters. Sometimes we need to look back before changing direction. But the rearview mirror was never meant to be the driver’s primary field of vision. Our past deserves an honest look. It does not deserve to control our future.
What Regret Can Do
Regret is not always the enemy. In fact, the capacity to regret can be evidence that God has changed us. A decision once deemed acceptable may trouble us now because our character has matured. Something once justified may now seem selfish. Words once defended may now sound cruel. Priorities once considered normal may now seem misplaced.
Paul wrote to the Corinthians that “the sorrow that is according to the will of God produces a repentance without regret, leading to salvation” (2 Corinthians 7:10, NASB 2020). He rejoiced not merely that they had felt pain, but that their sorrow had led them to repentance. Godly sorrow takes us somewhere. It leads us to turn from sin toward God and to respond differently.
That distinction matters because regret can pull us in very different directions. We can tell the truth about what happened, accept responsibility, seek forgiveness, and change course. Or we can keep returning to the same failure, as though rehearsing it one more time would somehow alter what happened. The question is whether our reflection helps us respond to God or keeps us preoccupied with a verdict against ourselves.
This does not mean a painful memory should vanish the moment we repent. We may grieve the harm we caused long after we have received forgiveness. Sorrow that returns is not, in itself, evidence that our repentance was insincere. We need room to bring that sorrow to the Lord as we learn to trust His words about His grace.
Not Every Regret Is a Sin
We can also make the mistake of treating every disappointing outcome as evidence of moral failure. Not everything that went wrong was a sin. Sometimes we made the best decision we could with the information available to us. We accepted the job because it seemed right, trusted someone because we had no reason yet to doubt him, or moved our family somewhere that didn’t turn out as we expected. Those experiences may hold lessons, but they don’t all call for repentance.
Other things do. There were times when we knew what was right yet chose otherwise. Pride influenced us, and anger controlled us. We were selfish toward someone we claimed to love. We neglected responsibilities or ignored what God had clearly shown us in His Word. Christian maturity requires enough honesty to distinguish those choices from the limitations of human nature. We shouldn’t excuse what God calls sin, but neither should we condemn ourselves merely because we could not foresee how a decision would turn out.
Hindsight is remarkably confident. The failed business now seems obviously risky. The warning signs in a relationship seem impossible to miss. An opportunity we rejected became enormously successful for someone else. But we did not make those decisions with hindsight. We made them with whatever information, circumstances, counsel, and understanding we had at the time.
That doesn’t mean we refuse to learn from poor judgment. Wisdom requires us to examine why we made decisions, including whether we ignored counsel we should have heeded. But there is a meaningful difference between saying, “I would choose differently today,” and saying, “I sinned by making that choice.” Sometimes faithful decisions lead through difficult circumstances, while foolish ones may seem to work wonderfully for a season. An outcome alone cannot tell us whether a choice was faithful.
We do not have to rewrite history until every outcome makes sense. We can learn what we can, repent where needed, and entrust to God what was never ours to control. Grace enables us to be truthful about it all.
The Night Peter Failed
Peter’s story gives us a place to see what grace does with a failure that cannot be explained away. By the night Jesus was arrested, Peter had spent years with Him, witnessing His works and hearing His teaching. He was among the men closest to Jesus and was confident in his loyalty. When Jesus told the disciples they would fall away, Peter insisted, “Even if I have to die with You, I will not deny You!” (Matthew 26:35, NASB 2020).
I don’t think Peter was pretending. I believe he meant what he said. Most of us have probably made promises with equal sincerity, only to discover later that our character was not as strong as our intentions. Within hours, the situation Peter had described so confidently turned dangerous and immediate. Jesus was arrested, and Peter followed at a distance. When people identified him as associated with Jesus, he denied it. He did so three times, just as Jesus had warned him he would.
Then the rooster crowed. Luke includes a detail that makes the scene painfully personal: “And then the Lord turned and looked at Peter” (Luke 22:61, NASB 2020). I have often wondered what Peter saw in that look. Scripture doesn’t tell us, so we shouldn’t pretend to know. But we do know what happened next. Peter remembered what Jesus had told him, went out, and wept bitterly (Luke 22:54–62).
Peter couldn’t take back his words. He couldn’t retract his first denial or go back and answer differently. His fear did not change the fact that he had denied the One he had promised to stand beside. The failure was real, and Peter knew it. What happened afterward reveals something essential about Jesus’s character.
Breakfast with Jesus
After the resurrection, John tells us that several of the disciples went fishing. They caught nothing all night. At daybreak, Jesus stood on the shore, though they did not yet recognize Him, and told them to cast the net on the right side of the boat. The catch was so large that they could not haul it in. The disciple whom Jesus loved recognized Him and said to Peter, “It is the Lord!” Peter threw himself into the sea, while the others brought the boat to shore (John 21:1–8, NASB 2020).
When the disciples reached the shore, they found a charcoal fire with fish and bread on it. Jesus served them breakfast. The charcoal fire recalls another scene in John’s Gospel: Peter warming himself in the courtyard on the night of his denials (John 18:18; 21:9–13). The resemblance is striking, though John does not tell us what Peter thought or felt upon seeing the fire on the shore.
After breakfast, Jesus addressed Peter. He did not pretend that nothing had happened. Grace does not require pretending. Jesus asked Peter three times whether he loved Him, and each time Peter affirmed his love. Each time, Jesus directed Peter to the people He was entrusting to his care: “Tend My lambs,” “Shepherd My sheep,” and “Tend My sheep” (John 21:15–17, NASB 2020).
There is something deeply encouraging about that conversation. Jesus had known Peter’s failure before it happened. He knew the man who had spoken so confidently and then denied Him. Yet He still entrusted Peter with responsibility. Peter’s failure was not minimized, nor was he reduced to it. Jesus restored him and called him to follow Him (John 21:19).
What Grace Does with Failure
We sometimes misunderstand grace, thinking the alternatives are either condemnation or pretending that what happened doesn’t matter. The gospel gives us a reason to tell the truth. If we sinned, we don’t have to reframe it as a mistake or explain it away because of our circumstances. If we hurt someone, we don’t have to rewrite the story until we become the victim. If pride, selfishness, anger, lust, greed, or the need for approval directed our decisions, we can admit it. A Christian can afford to tell the truth about his failure because his hope does not depend on proving he has never failed. Our hope is in Jesus Christ.
Paul states the reality plainly:
“Therefore there is now no condemnation at all for those who are in Christ Jesus.” — Romans 8:1 (NASB 2020)
That verse does not say our actions no longer matter. It does not remove consequences, eliminate God’s correction, or excuse deliberate disobedience. It assures those in Christ that they are not under condemnation. Our confidence rests in what God has done through His Son, not in our ability to punish ourselves enough to make up for the past.
This is one of the places where the order we established at the beginning of this book is especially important:
Jesus > Others > Self
Regret can turn our attention almost entirely inward. We think about what we did, how badly we failed, what others must think of us, and how different our lives might have been. Even self- condemnation can become self-absorption when we spend so much time staring at ourselves that we stop looking at Christ or attending to those around us. We need to examine that possibility honestly, without dismissing every expression of grief as selfish.
Notice the direction of Jesus’ conversation with Peter. He asked about Peter’s love for Him and entrusted him with caring for His people. Peter’s future would involve following Jesus and loving those who belonged to Him. Grace gave him a path forward in obedience and service.
Peter’s restoration does not promise that every position or relationship damaged by our sin will return to what it was. Trust may need to be rebuilt, and some responsibilities may no longer be appropriate for us to hold. Yet forgiveness in Christ gives us a foundation for faithful living now. We can receive care, submit to wise counsel, and learn to love others without making service another attempt to earn the grace we have already received.
When the Past Still Requires Something from Us
There are times when moving forward requires us to honestly face what lies behind us. We should never use grace as an excuse to avoid responsibility. Jesus taught that a person who remembers a brother has something against him should leave his offering at the altar and first seek reconciliation (Matthew 5:23–24). Our worship does not give us permission to disregard someone we have wronged.
Perhaps someone deserves an apology. A real apology is both remarkably simple and surprisingly difficult. It doesn’t begin with an explanation of why we did what we did. It doesn’t say, “I’m sorry you felt that way,” or spend ten minutes proving the other person was also wrong. Sometimes the most Christlike thing we can say is, “I was wrong. I hurt you. Will you forgive me?” Then we need to listen, give the person room to respond, and be willing to change the behavior that caused the harm.
There may be other situations where restitution is appropriate, a promise needs to be honored, or the truth needs to be acknowledged. If something can still be made right, faithfulness may require us to make the effort. We should be specific about what is ours rather than settle for a vague sense that we ought to do better.
At the same time, reconciliation involves more than one person. Someone may refuse our apology. The person involved may no longer be alive. A relationship may have become unsafe, or renewed contact may violate a boundary the other person has rightly set. In complicated circumstances, mature counsel can help us determine what a responsible step would be. Moving forward does not require forcing contact or demanding that another person reassure us that everything is all right.
We cannot control another person’s response. We are responsible for our part, including respecting the time someone may need and the boundaries that remain necessary. Faithfulness and outcomes are not the same. We can obey God, acknowledge our actions, and trust Him with what follows.
When Regret Becomes Wisdom
There is another possibility for the experiences we wish had been different: what we learn from them may help someone else. A man who mishandled money for twenty years may possess hard- earned wisdom that could spare a younger man from repeating the same mistakes. A husband who allowed work to crowd out his marriage may recognize the warning signs when he sees someone else doing the same. Someone who spent years chasing approval may be able to recognize that hunger in another person before the younger man understands what is driving him.
This doesn’t make the original failure good. We should be careful with language that suggests sin becomes worthwhile because we learned from it. Peter’s denial was not good, and he did not need to deny Jesus to become useful. Yet Jesus was not defeated by Peter’s failure. At the breakfast on the shore, He entrusted Peter with caring for His people. The failure remained part of Peter’s story, but it did not become the final word.
Perhaps some of our deepest wisdom will come from places we once dismissed as failures. If so, that wisdom becomes another thing God has entrusted to us. We can share it humbly, without making ourselves the hero or exposing someone else’s private pain. Sometimes giving wisdom away means sharing part of our story. Other times, it means listening more closely, recognizing danger sooner, or offering encouragement we once needed.
Paul Remembered Without Remaining
Paul also knew what it meant to carry a painful past. In Philippians 3:6, he acknowledged that he had persecuted the church. In the same chapter, he considered the religious credentials he once trusted. His focus shifted from those credentials to knowing Christ and receiving righteousness through faith in Him (Philippians 3:4–11).
It was in that setting that Paul wrote:
“Brothers and sisters, I do not regard myself as having taken hold of it yet; but one thing I do: forgetting what lies behind and reaching forward to what lies ahead, I press on toward the goal for the prize of the upward call of God in Christ Jesus.” — Philippians 3:13–14 (NASB 2020)
Paul had not erased his memory; he had simply written about his past. Neither his failures nor the credentials he once valued could replace his pursuit of Christ. His words give us more than permission to stop rehearsing regret. They also give us direction.
That is what I want for us. There are things behind us that deserve examination. Some require repentance or an apology. Some hold lessons we should never forget. Some reveal God’s faithfulness in ways we could not see at the time. We can remember them as we continue to follow Jesus today. The rearview mirror has a purpose. So does the windshield.
From Regret to Redemption
Before moving forward, take time to look back with a specific purpose. Choose one regret to start with, then consider one or two others if that would be helpful. You do not need to compile a list of everything you have ever done wrong. Use a notebook or document you will keep with your Remaining Years Plan, and write a separate response for each regret you choose.
What I regret. Describe what happened. Resist the temptation to minimize or exaggerate your responsibility. Distinguish what you know from what you now imagine might have happened if you had made a different choice.
What responsibility is mine? Was there sin that requires confession? Is an apology, restitution, or a change in behavior required? What was outside your control? If you are uncertain, identify the question you need help answering and find a mature, trustworthy person with whom you can discuss it.
What grace asks me to trust. Read Romans 8:1 and 1 John 1:9. Bring any sin honestly before God, and consider His promise of forgiveness and cleansing. Write down what you need to remember when regret returns. If the regret concerns a painful outcome rather than wrongdoing, name the burden you need to entrust to Him without labeling it a sin.
What I have learned. What do you understand today that you did not then? Consider your character, priorities, relationships, dependence on God, and need for grace. If you cannot yet identify a lesson, say so honestly. You do not have to explain every painful experience to bring it to Him.
How this can shape my love for others. Consider one way what you have learned could influence how you listen, encourage, serve, or share wisdom. You do not need to tell the whole story, especially if doing so would reveal another person’s private experience.
Take your time with this. Some things remain painful, and some consequences endure. Redemption does not require us to pretend otherwise. If something needs correction, address it. If you have gained wisdom, carry it forward. When an old accusation resurfaces, you can return to the truth of God’s grace without reopening the question of whether you can earn His forgiveness.
One Thing
Review what you have written and identify one faithful response you can make now. It may involve another person: a conversation, an apology, or a step toward restitution. If renewed contact would be unsafe, unwise, or unwelcome, begin by seeking mature counsel on how to take responsibility appropriately.
There may be nothing left to repair externally. Your response may be to express regret to God in prayer, reread what Scripture says about forgiveness, or talk honestly with a trusted pastor or mature believer about a burden you have been carrying alone. The purpose is to take a faithful step, not to produce a particular feeling by a deadline.
The regret or unfinished matter I am addressing is:
The next faithful action within my responsibility is:
I will take that action on: ____________________
If this is the action you identified in Chapter 1, keep the same commitment and make the next step clearer. You do not need to create another task just because you have completed another chapter.
Your Remaining Years Plan
What I’m Leaving Behind and Carrying Forward
You now have the material for the second piece of your Remaining Years Plan. Keep your reflections and the following summary together under What I’m Leaving Behind and Carrying Forward. Leaving something behind does not mean forgetting it, evading responsibility, or demanding that grief end. It means identifying what you no longer want to govern your response to Jesus today.
What I’m leaving behind: Name an excuse, a pattern of self-condemnation, or a demand to control what never belonged to you.
What I’m carrying forward: Name a truth about God’s grace, a lesson to remember, or a responsibility you’re ready to honor.
How this will help me love Jesus and others more faithfully:
My next faithful action and the date I will take it:
I will review this part of my plan on: ____________________
You can use the review date you chose in Chapter 1. When you return, consider whether you took the step you identified, whether any further responsibility remains, and what you are learning to entrust to God. The past may still bring sorrow, but it need not fill the space ahead. There are people to love and opportunities to be faithful today, and you can meet them as a man whose hope rests in Jesus Christ.