EP 61: How to Handle Deep Regrets in Parenting & Life

We’ve all said or done things that we later regret, sometimes profoundly so. But where does regret come from, and how are we supposed to handle this tangle of negative emotions that wants to seize control of our thoughts and side-track our focus on more important matters? That’s our topic for this week’s episode of Loving Life at Home. I hope you’ll listen in!

How to Handle Profound Regret

Episode 61 – Full transcript

Hello, friend.

Thanks so much for joining me again on Loving Life at Home. This week’s episode is all about regret. I meant to publish it last week, but regret to say I didn’t get it ready on time! And I’m posting it even later than I intended this week. But I’ve had a lot of other responsibilities demanding my attention, so the podcast had to be put on the back burner.

One of the things that piled up in the meantime, though, was the messages in my inbox, many of them asking for a biblical perspective on dealing with regrets—which is why that’s our topic for this week.

The first letter I’d like to respond to is from a listener who writes:

The writer goes on to explain that she and her husband have a lot of children, whom they’ve homeschooled from the beginning. And while she feels good about those decisions, she admits that, over time, she lost her focus on those primary callings of marriage and motherhood and instead became involved in a business opportunity that initially sounded like a good idea but that she now views as a huge mistake.

It promised to provide more family time together, if only she would give it her full focus for just a few years. Unfortunately, that promise never panned out. The business ended up stealing her time, energy, and passion for far too long, and now she’s sad she ever let such a venture deceive and derail her in the first place, especially when she sees the ill effects it had on her kids and family relationships. She continues:

Well I sent this sweet, side-tracked mama a brief response just as soon as I read her letter, to let her know that, yes, I did receive her message and that, no, I hadn’t addressed the topic on any of my prior episodes but would do so as soon as I could – which turned out to be today!

I think her question is a good one and will likely resonate with a lot of listeners. In fact, I know it will, because within days of that first message landing in my inbox, I received several messages from other listeners and subscribers on topics that are closely related.

One listener wrote in response to my episode on forgiveness (which I’ll link in the show notes) that she’s realized she not only struggles to forgive others, but also to forgive herself, and wondered if I could share some prayers or verses or other tips that might help her stop beating herself up over past mistakes. She writes:

Another listener wrote to ask if I’d make a prayer guide for dealing with grief, which I’m working on right now. While I realize grief and regret aren’t exactly the same thing, they often do go hand-in-hand.

Still another reader wrote to me about a difficult situation with her husband’s parents. An accident many years ago left her father-in-law in need of daily care, which fell largely to her husband to provide. But it meant that for most of their marriage – even as they were trying to establish their own family and raise their own children — their lives revolved around caring for demanding and sometimes domineering parents. And now she’s wondering, did they make the right call? She’s suffering from yet another kind of regret—the kind that comes when your life doesn’t play out as you’d envisioned.

Well, all these messages and letters serve as a good reminder to mothers everywhere of our desperate and overwhelming need for an outpouring of God’s grace and wisdom. Because no matter how many children you have, or how you choose to educate them, or whether you work inside or outside the home, or whether your life goes according to plan or throws you repeated curve balls, the truth is, there are no perfect parents. And we must all deal with regrets of one form or another.

I think the majority of regrets fall into four basic categories.

Four Categories of Regrets

1-Careless Mistakes

The first category is something I’d call careless mistakes:  There’s not really anything morally wrong with these actions; they’re just accidents. They’re the kind of things we do without thinking, but that sometimes lead to far-reaching and potentially devastating consequences.

They’re split-second decisions that go awry, like swerving your car to avoid hitting a dog and plowing into a telephone pole instead. Or forgetting to blow out the votive candle you had burning in an upstairs bathroom before leaving for church. Or diving into water that was shallower than you realized.

Then when your car is totaled or the person in your passenger seat is killed or your house burns down or you wake up paralyzed from the neck down and have to spend the rest of your life in a wheelchair, then you find yourself locked in a spiral of “IF-ONLY”s and “WHY-DIDN’T-I”s and deep, overwhelming, relentless regret that constantly cycles through your conscience in a never-ending loop, like a scratched vinyl record that gets stuck playing the same tired measure over and over and over again.

I’ve definitely experienced that kind of regret (though with far milder consequences than the true accounts of others I just related). I shared a few such regrets in my episode on miscarriage, which I’ll link in the show notes. But what has helped me avoid that continual mental barrage of negativity is the knowledge that “God causes all things to work together for good to those who love Him, to those who are called according to His purpose,” as we are told in Romans 8:28.

Notice that verse says ALL things, which includes even life-changing accidents and our own careless mistakes. God can take the sometimes-devastating results of a bad judgement call and use even THAT for our good, our growth, and His glory. He can use even our blunders to build character and conform us to the image of His blessed Son, Jesus Christ.  Isn’t that a comforting and encouraging thought?

We also need to remember that whatever Satan intends for evil, God will ultimately use for good. During one particularly difficult season, I wrote a poem (which I’ll link in the show notes, as well) about how this truth should serve to strengthen and encourage believers even amid the bleakest of circumstances.

2-Questionable Decisions

The second kind of regret comes when we do something that seems entirely reasonable at the time, but then later start to question if it were all a huge mistake.

Such regrets are especially common among parents, because we all want the best for our kids. We want to train them up “in the way they should go,” trusting that when they are old, they will not depart from them,” just as Proverbs 22:6 tells us to do.

So we do whatever seems right and fitting and best in the moment. But then, if those methods don’t produce the results we were hoping for, we begin to question our parenting decisions. Would a different approach have served us better? Would an alternate way have led to better results? We become plagued by doubts and regrets and a steady stream of WHAT IFs? — like the mom from that first message I read today who let a business opportunity distract her from the important work of managing her household and educating her children.  

But, like so many of us, she was doing something that seemed good at the time. I wouldn’t classify these decisions as willful disobedience or rebellion, but more as misdirected energies.

Even there, it’s sometimes hard to know. Proverbs 31:10-31 describes the virtuous woman as being both an excellent homemaker and a prudent business woman. I love the way those verses read in the Amplified Version:

“She considers a [new] field before she buys or accepts it [expanding prudently and not courting neglect of her present duties by assuming other duties]; with her savings [of time and strength] she plants fruitful vines in her vineyard. She girds herself with strength [spiritual, mental, and physical fitness for her God-given task] and makes her arms strong and firm…. She lays her hands to the spindle, and her hands hold the distaff…. She makes fine linen garments and leads others to buy them; she delivers to the merchants girdles [or sashes that free one up for service]. 

That was verses 16-17, 19, 24, but the entire chapter is inspiring.

And when you read such an account, you can understand how a wife and mother could feel torn between those two worlds. I’ve been involved in lots of work-at-home endeavors over the years myself:

• Back when I was in college, I sold needlework kits and taught groups of women how to do crewel embroidery, lace-net darning, candlewicking, chicken-scratch, trapunto, and lots of other long-forgotten needle arts
• When my husband and I were newly married, I had a weekly radio program called “Schooling with Software” that allowed me to get free copies of all the latest and greatest educational computer programs to review on air
• For a while, I hosted Bible studies for young moms in my neighborhood and, years later, our family opened our home for worship services and fellowship dinners which were attended by 100+ people every Sunday
• When we first moved to Tyler, I edited a weekly, online newsletter called Moms-Connect for local homeschoolers and also coordinated monthly Moms-Night-Out meetings where local women could come have dinner and listen to speakers address topics of interest
• I’ve written and published over 30 books, having done the bulk of that writing in the wee hours of the morning while my family slept (I’ll put a link in the show notes in case you’re interested)
• Later, I penned a weekly column for the newspaper called Family Matters. The editors let me write about whatever I wanted, and I received wonderfully positive feedback from the community about my chosen topics
• And, of course — for now — I’m still blogging and podcasting and teaching weekly classes at our local homeschool co-op (Algebra 1, Algebra 2, Woodburning and Leatherworking, plus I lead a women’s group there. How’s that for a fun but full Monday?)

My point is, all these things seemed like reasonable investments of time when I first started them — and many of them actually were a great fit for a season — but I eventually had to lay most of these endeavors aside in order to focus my attention on more pressing matters.

• The needlework classes were especially short-lived. I had to quit teaching those when my college coursework became too heavy to do much more than study
• I quit evaluating educational software when our kids started fighting over who got the next turn on the computer — and instead shifted to a literature-based curriculum with living books we could read outside in the fresh air and sunshine
• I took what I thought would be a short break from writing my newspaper column when we went to Europe in January of 2020, but then COVID hit, quickly followed by some family crises that demanded my full attention, and I ended up never going back to it.
• We even took an extended, 7-year-long break from our homeschool co-op when one of our sons developed severe respiratory problems and we thought he was going to die every time he got the sniffles, which happened all too frequently when we were attending weekly classes with a couple hundred homeschooling friends during the peak of cold and flu season

That’s the way it goes for all of us, though. Sometimes we try new things and they’re wonderful. Sometimes we give something a go and it fizzles. If that first mom’s business opportunity had been all it was cracked up to be, bringing in extra income while simultaneously increasing the time she had to devote to her family, then she likely wouldn’t have been plagued with regrets at all.

A lot of times, you won’t know until you try whether some new business venture or educational endeavor or extracurricular activity or pastime or hobby will be a good fit for your family or not. When you realize something isn’t working, then do your best to ditch that plan and try something different. Or enjoy the extra margin that comes from pruning the non-essentials from your life and schedule.

My husband and I re-evaluate the things our family is involved in at least once or twice a year to decide whether the returns on our time investments justify our continued participation. Is it worth it to keep doing what we’re doing?

I don’t mean monetarily worth it. Lots of the things being re-examined don’t bring in any money at all, but rather cost money. But we want to be sure the things we devote our time and energy to are actually helping us accomplish primary goals.

Of course, making such decisions for yourself sounds fine and good, but what if you aren’t in a position to choose?

3-Dashed Hopes

That brings me to a third kind of regret: When plans don’t pan out. When your dreams don’t come true. When nothing looks like you envisioned. Or when life takes a turn you weren’t counting on, like the wife who found her entire existence revolving around the care of ailing in-laws.

I’ve experienced those kinds of turns, as well. As I’ve mentioned before, we have three sons with Type 1 diabetes: one was diagnosed at age 14, another at age 6, and our firstborn before he even turned 2. 

And while I wouldn’t say our lives have completely revolved around all the daily blood tests and shots and carb counting and keytone checking and glucometers and transmitters and insulin perscriptions associated with their care, it certainly seemed that way in the beginning and continues to be something we must routinely take into consideration.

And I think it’s okay to acknowledge the struggle in cases like that. It’s okay to feel sad about the fact your child has a disease for which there is no known cure. Or to long for a baby when you’re infertile. Or to pray for a spouse when you are single and lonely. Or to consider ways to increase the bottom line when you’re struggling financially.

Proverbs 13:12 tells us, “Hope deferred makes the heart sick, but a longing fulfilled is a tree of life.” We all long to be in the second half of that verse, don’t we? With all of our deepest desires fully realized? But we often have to live much of life in the first part of the verse, with hopes that keep getting popped each time they begin to bubble.

I don’t remember where, but I do remember reading something once that had been written by a parent of a severely disabled child in which she discussed the grieving process she and her husband had to go through.

Naturally, they love their baby fiercely and are so grateful to God for the opportunity to raise her, but each time they saw their friends’ children pass milestones they knew their child would never reach – taking first steps, riding a bike, playing team sports, graduating college, getting married, having babies – they had to take a moment to grieve and process and bury that hope for their own child and to lay all those tangled emotions at the foot of the cross and look to God for the grace and wisdom and strength they needed to “run with endurance the race” that was set before them—which looked so very different than the races their friend’s families were running – but they were determined to keep their eyes on Jesus, the author and finisher of their faith,” as Hebrews 12:1-2 encourages all of us to do.

I love the scene in The Lord of the Rings where Frodo is talking to Gandalf about the return of Sauron and the discovery of the ring and the need to destroy it, and Frodo laments, “I wish it need not have happened in my time.”

To which Gandalf replies, “So do I, and so do all who live to see such times. But that is not for them to decide. All we have to decide is what to do with the time that is given us.”

The same is true for you and me. Most of the time, we don’t get to pick the life circumstances we find ourselves dealing with. But we do get to choose how we’ll respond to them.

I understand grieving over what is lost or feeling profound disappointment over unfulfilled dreams, but you simply cannot remain there. At some point — hopefully sooner rather than later — you’ve got to dry your eyes, pick yourself up, dust yourself off, and start doing what you can to make the best of whatever situation you find yourself in. “…each one should lead the life that the Lord has assigned to him and to which God has called him,” as Paul prescribes in 1 Corinthians 7:17.

• If you’re single when you’d rather be married, commit those years to God and pray that He would give you meaningful ways to invest in the lives of those around you to encourage and uplift them. Work on developing the same kind of character qualities as a single that would serve you well as a spouse: integrity, patience, industry, understanding, purity of both thought and action, love, joy, peace, and all the other fruit of the Spirit. And trust in God’s good plan for your life, even if that plan isn’t unfolding anything like you hoped it would.
• By the same token, if you are married but unhappily so, don’t start thinking the grass is greener on the other side. Do what you can to infuse joy back into the marriage you’ve got. Focus on your spouse’s good qualities and build him up. Pray. I have several free printable prayer guides to help you do this, which I’ll link in today’s show notes. And my husband and I both have free 30-day challenges on loving your wife and respecting your husband that I’ll link as well.
• Perhaps you are crowded into a tiny house or apartment that seems way too small for your rapidly growing family. I remember how it felt to be busting at the seams that way. My advice to you: Do what you can to make your current place feel more like home. Keep it as neat and tidy as you can and fill it with as many happy, warm memories as it can possibly hold, all the while praying and trusting that God has you right where He wants you and will move you to something bigger and better in His perfect timing, if that is truly what you need.

My goal – and I recommend it to you, too — is to adopt Paul’s mindset by learning to be content in whatever circumstances I find myself, as he describes in Philippians 4:11-13:

“I know how to live humbly, and I know how to abound. I am accustomed to any and every situation—to being filled and being hungry, to having plenty and having need.  I can do all things through Christ who gives me strength.”

Wherever you find yourself today, I hope you won’t waste any more precious time in fretting over things beyond your control, but instead will lay all of your regrets at the foot of the cross and move forward in the strength Christ provides.

Accept the invitation He offers, first of salvation and forgiveness: “If you confess with your mouth, “Jesus is Lord,” and believe in your heart that God raised him from the dead, you will be saved” (as we read in Romans 10:9).

And then, accept Christ’s promise for rest and relief from life’s burdens: “Come unto Me, all who are weary and heavy-laden, and I will give you rest. Take My yoke upon you, and learn from Me, for I am gentle and humble in heart; and YOU SHALL FIND REST FOR YOUR SOULS. For My yoke is easy and My burden is light.”

4-Intentional Sin

Finally, I won’t do this topic justice unless I address a final source of regret — and that is willful sin or intentional rebellion against God.

That’s what happens when we start to question His Word. When we entertain the same question the serpent posed to Eve, “Hath God really said…” When we ignore or twist or otherwise go against God’s clear direction and design.

I imagine Adam and Eve had some serious regrets when they were cast out of the Garden of Eden in penalty for their willful sin and rebellion against God’s clear command. And the fact is, any of those three prior categories of regret can serve as a gateway to sin, depending on how we respond to them.

We will do well if we “count it all joy when we encounter various trials, knowing that the testing of our faith produces endurance,” as James 1:2-3 tells us to do, and proclaim with Job, “The LORD gave and the LORD has taken away. Blessed be the name of the LORD.” (Job 1:21 ) “Shall we indeed accept good from God and not accept adversity?” (Job 2:10)

But our regrets will only be compounded if we respond to careless mistakes, uncertain decisions, and dashed hopes by doing things that the Bible tells us to avoid, such as:

• giving place to anger, bitterness, resentment, unforgiveness, or thoughts of revenge, as Ephesians 4:31-32 warns us not to do
• or letting “the cares of this world and the deceitfulness of wealth and the desire for other things come in and choke the word and make it unfruitful,” as Mark 4:19 tells us so often happens
• or ignoring the clear promptings of the Holy Spirit to change course, as passages like Ephesians 4:30 and 1 Thessalonians 5:19 caution us against
• or engaging in malice, deceit, hypocrisy, envy, or slander — responses that are all forbidden by 1 Peter 2:1
• or trying to satisfy unfulfilled longings in unrighteous or forbidden ways (in defiance of Romans 6:12-13)
• or allowing fears, worries, and anxiety to fill your thoughts and steal your joy — the Bible repeatedly commands us to “be anxious for nothing” but to cast our worries at the foot of the cross through continual prayer (as Philippians 4:6 and 1 Peter 5:7 implore)
• or maligning God’s name or rejecting His Word when He doesn’t do what you want (Isaiah 29:16)
• or stubbornly clinging to selfish pursuits instead of lovingly serving others, as Galatians 5:13 and Philippians 2:3-4 tells us to do

As Proverbs 14:12 cautions us, “There is a way that seems right to a man, but its end is the way of death.” So if disobedience or defiance is at the root of any regret you’re presently dealing with, I have both good news and bad news for you.

The good news is that if you repent and turn away from your sin, you can find full forgiveness in Christ. As 1 John 1:9 assures us, “If we confess our sins, He is faithful and just to forgive us our sins and to cleanse us from all unrighteousness.”

God’s forgiveness won’t necessarily erase the earthly consequences of our sin – (I discussed this fact in my episode on forgiveness, which I’ll link in the show notes.  In other words, if I rob a bank, I may still go to prison, or if I get enough uncontested speeding tickets, I may still lose my license, despite the fact God separates my sin from me as far as the east is from the west (as Psalms 103:12 tells us He does).  

Yet, even though Christ’s forgiveness doesn’t automatically eradicate all temporal consequences, it WILL secure you an eternal home in heaven with Him and will also keep you from having to wallow in guilt for the rest of your life. As Romans 8:1 proclaims, “There is therefore now no condemnation for those who are in Christ Jesus.”

And surely, if God forgives us so fully and freely, we should follow His example and fully forgive ourselves, as well, which is my answer to the listener who wrote the second letter I read at the beginning of this episode—the one who’s been beating herself up for decades and doesn’t want to operate that way anymore.

If this describes you, too, then next time Satan tries to throw some past sin back in your face, remind him — and yourself – that that offense is under the blood. The payment has been made in full and you can stand before God clothed in the righteousness of Christ. (Philippians 3:9)

So that’s the good news: Full forgiveness. No condemnation.

The bad news is: If the extent of your regrets is that you merely feel sorry about how things TURNED OUT and are not truly remorseful that you chose to sin in the first place, then nothing else I say here will be of much help to you.  

This is especially true if you are deliberately choosing to persist in your sin and are simply shifting blame, or focusing anger and resentment toward somebody else instead of turning to God, taking ownership, and making necessary changes, no matter how difficult. Repentence is the first and necessary, crucial step for dealing with regret that arises from this source. Just feeling sorry for getting caught is insufficient.

Even so, beyond repenting of wrongdoing, and purposing, by God’s empowering grace, not to make those same mistakes going forward, I don’t think God wants us to waste time fretting over the past any more than He wants us to worry about the future.

Jesus says in Luke 12:26,

“Who of you by worrying can add a single hour to his life? So, if you cannot do such a small thing, why do you worry about the rest?”

This principle certainly applies to anxiety over the future. Jesus tells us in Matthew 6:25-30 not to “worry about your life, what you will eat or drink; or about your body, what you will wear. Is not life more than food, and the body more than clothes?” He says the same God who provides for the birds of the air and clothes the lilies of the field in such glorious splendor will take care of us, too, for we are of much more value to Him than flowering grass or feathered flocks.

But the ban on worrying doesn’t just cover what comes next. It also applies to what came before. We have to accept the fact that what is is. What happened happened. So don’t get caught up in that endless cycle of what ifs and wherefores. Fretting over the past will do nothing to change it but will only serve to further squander the present.

Thankfully, our God is able to restore what the locusts have eaten (as we read in Joel 2:25). What Satan meant for evil, God will use for good. (Genesis 50:20; Romans 8:28).

And when you turn to God and entrust your life and future to Him, He will give you the grace to forgive yourself and to recommit yourself to living in accordance with His Word. And when we make it our habit to walk by faith and live to God’s glory, we soon find that our regrets diminish in both size and number.