Let’s be honest—there’s no such thing as a perfect parent.
We all do the best we can with the tools, knowledge, and energy we’ve got at the time.
But when I sat down with fifty men and women from my generation and asked them what they wish they’d done differently with their kids, I was struck by how often the same themes cropped up.
These weren’t small things either.
They were big, emotional regrets—choices they’d replay if given another chance.
And while hindsight may be 20/20, their honesty offers us a kind of roadmap.
So, if you’re raising children now, or even if your kids are already grown and you’re hoping to be a better grandparent, here are the eight regrets that boomers admitted to most often.
1) Not spending enough time with them
This was the number one answer, and by a mile.
Many told me they were so wrapped up in building careers, paying bills, or just “getting through the week” that they often missed the everyday moments that truly mattered.
Sure, they provided for their kids materially—but emotionally, they sometimes weren’t present.
I remember one father in particular saying, “I gave my son a Nintendo when he was twelve because I felt guilty about never being home. I thought toys could replace me. They didn’t.”
It’s not about grand trips or expensive outings. The regret was missing simple things: bedtime stories, school concerts, Sunday afternoon board games.
If you’re a parent reading this, it’s worth asking yourself: Am I giving my kids my presence, or just my presents?
2) Being too strict
Discipline came up a lot. Many boomers grew up in households where “spare the rod, spoil the child” was practically gospel. Naturally, they carried some of that into their own parenting.
But looking back, they felt they’d pushed too hard—on grades, on behavior, on “fitting in.” Some admitted they enforced rules that, in hindsight, didn’t really matter.
One woman told me, “I grounded my daughter for dyeing her hair pink. It seemed so important at the time, but now I realize I crushed her self-expression for no good reason.”
Boundaries are important, of course, but several said they wish they’d chosen their battles more wisely. Kids remember how you made them feel, not how perfectly they cleaned their rooms.
3) Not saying “I love you” enough
This one made me pause.
A surprising number of people admitted they rarely expressed affection out loud, even though they felt it deeply. Their excuse? “My kids knew how I felt.”
But the reality is, kids don’t always know. And if they do, they still need to hear it. Again and again.
One grandfather said something that’s stayed with me: “I thought providing a roof over their heads was love enough. But my son told me years later that he spent his whole childhood wondering if I actually liked him.”
If there’s one takeaway here, it’s this: don’t assume love is obvious. Say it. Show it. You’ll never regret telling your children too many times that you love them.
4) Pushing them toward the wrong dreams
Quite a few admitted they had tried to steer their kids into careers or lifestyles that looked “safe” or “respectable” rather than supporting what the child truly wanted.
Sometimes it came from fear: “Art doesn’t pay the bills, study accounting instead.” Sometimes it came from ego: “I didn’t make it as a doctor, but you will.”
But almost everyone who mentioned this told me the same thing—they realized later their child had their own path, and forcing them into another one created distance, resentment, or years spent in jobs that didn’t fit.
As one dad put it, “I wanted my son to be successful. I didn’t realize success meant something very different to him than it did to me.”
5) Not listening enough
It’s easy to nod along while your kid is talking but not really listen.
Between long workdays, financial stress, and the constant busyness of life, many parents admitted they tuned out their children more often than they’d like to admit.
One boomer told me he’d give anything to go back and really listen to his daughter’s long, rambling stories at the dinner table.
At the time, he brushed them off as “kid nonsense.” Years later, she told him those were the moments she most wanted to feel close to him.
Kids don’t just want advice—they want to feel heard. And sometimes, listening is the best way to love.
6) Comparing them to others
Another big regret was the habit of comparing kids to siblings, cousins, or classmates. “Why can’t you be more like your brother?” or “Your cousin got straight As—what happened with you?”
At the time, many parents thought they were motivating their kids. In reality, they were planting seeds of inadequacy.
A grandmother admitted through tears, “I thought I was pushing my daughter to be better. Instead, I made her feel like she was never enough. She’s 45 now and still struggles with that.”
Every child has their own pace, their own strengths, their own path. Comparisons rarely build confidence—they just chip away at it.
7) Not apologizing when they were wrong
This one surprised me, but it makes so much sense.
Parents make mistakes—losing their temper, making unfair assumptions, punishing too harshly. But back then, many boomers believed apologizing to a child was a sign of weakness.
Now, they see it differently. “I thought saying sorry would make me look less authoritative,” one man confessed. “But all it did was teach my son that pride mattered more than relationships.”
Apologizing to a child doesn’t lower your authority—it models humility and respect. And respect is a two-way street.
8) Worrying too much about the small stuff
Finally, many admitted they wasted energy on things that, in the long run, simply didn’t matter. Messy bedrooms. Mismatched outfits. Eating too much candy at a party.
One grandmother chuckled as she told me, “I nearly lost my mind over muddy footprints on the carpet. Do you think my kids remember the carpet? No. They remember me yelling.”
The older we get, the more we realize what’s truly important—good health, kindness, connection. The little things fade away. The big things stick.
Closing thoughts
What struck me most in these conversations wasn’t the mistakes themselves—it was the longing. The “if only.”
The sense that those moments, once gone, can’t be rewound.
But here’s the good news: if you’re in the middle of raising kids now, you still have time.
Time to choose presence over perfection. Time to listen more, to love more, to apologize when needed.
And if your kids are already grown?
It’s never too late to pick up the phone, send a message, or start fresh.
Relationships can be healed at any age.
So let me leave you with this question: years from now, when you look back, what do you want to remember?
The clean carpets—or the laughter echoing across them?
