Parents of Adults Share the Biggest Regrets From Their Early Parenting Days

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Mid-afternoon, on a particularly chaotic Tuesday during the dog days of summer, I took leave of my desk at work and meandered into a local Starbucks.

Partly for the caffeine, but mostly to exist in a space where neither my clients nor my children were asking me to do something.

I promptly ran into Kate, a co-worker of mine, I’d assumed there for the same reason I was. But as we got to talking, I realized that there was a significant differentiator dividing our stresses.

The topic of parenthood came up. And I joked about how packed my schedule was, noting that I was needed “from the minute I wake up, to the minute I fall asleep, and then again 10 minutes later.”

I brought it up to explain that, whether at home or at work, I was constantly in demand, always had someone knocking at the proverbial door. But a bit of sadness seemed to come over her face.

“Well, my daughter’s in San Francisco, and these days, she doesn’t seem to need me at all,” Kate said, with a half-hearted smile. It was in that moment when I realized, although I might often feel stretched beyond my means, there will come a day where I’ll actually miss that same stress I now lament over.

And as Kate and I continued talking, it became clear that, in essence, I wasn’t just talking to Kate; I was talking to myself in 15-20 years.

The conversation turned nostalgic, with Kate grinning proudly thinking of the little girl and boy she raised who are now a man and a woman. But I noticed the nostalgia was marked with a twinge of regret. And as any parent could imagine, it was regret around what she could have done differently when her children were in their formative years.

“I just wish….I wish I had brought them to each other’s sporting events and encouraged them to cheer and to be stronger advocates for each other,” Kate noted.

This got me thinking. Is regret an unfortunate, inevitable footnote to parenthood? Will I ever reach a point in my own process where I feel I’ve done enough?

With that in mind, I decided to seek out some older parents in my life and asked them one simple (yet divisive) question:

What is your biggest regret from your early days as a parent?

The respondents included co-workers, friends, and shall I say, someone involved very actively with yours truly’s childhood. What they had to say likely won’t shock you. But it may open your eyes to what you’re currently focusing on with your own children…

A co-worker, Sue, who has two adult children, had this to say:

“Frankly, I wish I had been a bit stricter with my kids. I was a bit too quick to give in rather than see something escalate into a larger argument. I only trained them to outlast me, undermining my own authority.”

It’s fair to say we’ve all given in a bit too quickly, especially at the end of an exhausting, stressful day when you’ll do anything to avoid more chaos.

My career mentor, Maureen, with two children in their 30s, brought up a regret that many of us are guilty of without realizing it:

“I wish I’d given my children the courage to consistently be more assertive, to not confuse being thoughtful, kind, and an overall good person with the need to always defer to others.”

How many of you have ever told your children, “Honey, let the other boy go first” or “Your cousin wants to play with that Batman toy that’s currently in your hands”? I think Maureen speaks to a general attitude many of us have toward parenting, where we’re so concerned with our children being perceived as unruly or selfish, that we push too far in the other direction, turning them passive.

A friend, Ron, whose daughter has just graduated college and entering the workforce, replied:

“As school and sports became the dominant responsibilities in my daughter’s life, we became lenient about her tasks at home. By supporting her through these stressful times, we also became enablers of lax behavior.

Also, I made it clear that the Beatles are holy, but I should have been more religious in practice. Her semester abroad, she sent back a picture of herself from Abbey Road, but she was crossing in the wrong direction.”

As a big music (and Beatles) fan, I wholeheartedly relate to this.

A family friend, Rachel, whose children’s ages range from 36-41, mostly holds regret about her physical presence.

“Even though I always worked very close to our house, I think that looking back, it was harder to be working outside the house when the kids were pre-teen and teenagers. That may sound silly, but it is a very impressionable time, and it made it harder to be sure they were staying on the right path. Sometimes I felt like a cop!” Rachel said.

In fairness, I think the vast majority of us feel like cops who are constantly one step behind whatever schemes our children are plotting.

My cousin Lucille, who raised her daughter until age 7 as a single mom, had this to say:

“Being a single mom, when Adrienne was between the ages of 2-7, I wish that I didn’t overcompensate for her not having a dad in her life. Now I realize we were a ‘force of two’ and I could have just been myself.”

I imagine Lucille isn’t the only single mom who ever thought at one point that they “weren’t enough.”

And the sixth person who participated in this mini-study was my own father, Joe DeProspero, Sr. I thought it’d be interesting to hear the regrets of one of the two parents who raised me, to see if it lined up with any feelings I personally had about my childhood.

“I always made it a point not to pressure my kids into anything they didn’t want to do,” he started. “But I really think that, if I had encouraged you to do track in high school, your whole social world would have been different. You could have been great. But you were the type of kid that needed that extra push.”

He’s right. I was the type who needed a push. But at the same time, I always respected and appreciated his lack of interference. Never once did he try to influence my career, or the sports I decided to play.

As long as I was a good kid, he let me blaze my own trail and didn’t try to force anything on me. I can attest to the fact that his decision to not be overly hands-on with my direction had much less negative impact than he feels it did.

And that’s the case with all of these regrets, I’d imagine. We stew over them. Even obsess over them to the point where they become a permanent fixture of doubt in our minds, convincing us we could’ve done it better…if we only had a second chance.

But here’s what I also know…

I personally know some of the adult children referenced in this study. And while I won’t pretend to have intimate knowledge of all of them, I do know that each of the parents who responded to this survey have strong, healthy relationship with their kids.

None of the children have ever been jailed (to my knowledge), they’re all successful in their own right, many with children of their own. Whatever regret their parents might have had about their upbringing, one thing is clear—it didn’t affect them in a meaningful way.

The bottom line is we all feel like we’re screwing up this parenting thing. And quite clearly, years later, we’re still going to look back and amplify our imperfections.

But I’ve also come to realize something else. I’ve come to realize that the best of the best parents feel like they’re screwing up. And the microscope we hold over ourselves might drive us mad at times. But it’s also that same diligence that yields balanced, happy adults to follow.

Thanks for reading, and go easy on yourself.

I can be contacted on Twitter @JoeDeProspero.