Common parental regrets (and what to do before it's too late)

A friend of mine told me something last year that I haven't been able to shake. His daughter had just turned eighteen, and he was helping her pack for college. She held up a stuffed elephant he didn't recognize and said, "This is Ellie. She was my best friend in third grade." He had no memory of Ellie. Not the name, not the elephant, not whatever phase of his daughter's life that toy represented. He'd been there, technically. But he'd also been answering emails on his phone at the dinner table, flying to conferences on weekends, and assuming there'd always be more time to catch up on the details.

"I was in the house," he told me. "But I wasn't in her life. Not the way she needed me to be."

That conversation started something. I began asking other parents, mostly friends, a few strangers who were willing to be honest: what are your parental regrets? What do you wish you'd done differently? The answers came fast, and they came heavy. Not abstract theories about child psychology. Real, specific moments they can't get back.

Here's what they told me.

The dad who was always at the office

Mike is a financial advisor in his fifties. His kids are grown now, both out of the house, and he describes his relationship with them as "fine." That word, fine, is the one he keeps coming back to. Not close. Not strained. Just fine.

When his sons were young, Mike worked sixty-hour weeks. He told himself he was doing it for them. Better schools, a bigger house, vacations they'd remember. He missed most of their Little League games. He missed the science fair where his oldest won second place with a volcano that actually erupted. He missed bedtime more nights than not.

"I thought I was being a good dad by providing," Mike said. "And I was providing. But my kids didn't need a bigger house. They needed me to show up at their games and act like it mattered. Because it did matter. It mattered to them."

His youngest son once told him, years later, that he used to scan the bleachers before every game. He'd look for Mike's face. And the times he wasn't there, the game felt different. Not ruined, but dimmer. Like playing with the volume turned down.

If this hits close to home, you're not alone. The tension between work and presence is one of the most common parental regrets, and one of the hardest to recognize while you're in the middle of it. You can't bill for the hours you spend watching your kid strike out at T-ball. But those hours are worth more than anything you'll ever invoice.

The phone during bath time

Sarah is a marketing director and a mother of two. When I asked her about regrets, she didn't hesitate: "My phone. My stupid phone."

She described a specific night that still bothers her. Her daughter was maybe four years old, splashing around in the bathtub, making up a song about a mermaid who was afraid of fish. It was one of those magical, ridiculous kid moments that you can't manufacture. And Sarah was sitting on the bathroom floor next to the tub, scrolling through work emails.

"She was singing this whole elaborate song, and she kept looking at me to see if I was listening. And I wasn't. I was reading an email from my boss about a meeting that didn't matter, about a project I can't even remember now."

Sarah says she eventually looked up and her daughter had stopped singing. She was just sitting in the water, quiet, playing with a cup.

"That image wrecks me. She gave up trying to get my attention. A four-year-old gave up. How many times did that happen that I didn't even notice?"

The thing about distraction is that it feels harmless in the moment. You're still in the room. You're still technically available. But kids don't measure your presence by proximity. They measure it by your eyes, your reactions, whether you laugh at the funny part. Being physically present but mentally absent is its own kind of absence, and kids feel it even when they can't name it.

The parent who chose the "practical" path

David and his daughter Emily had their worst fight when she was seventeen. Emily wanted to study illustration. She'd been drawing since she could hold a pencil, filling sketchbooks with characters she invented, worlds she built from scratch. She was good. Her art teacher thought she was exceptional.

David told her to study something practical. Business, maybe, or pre-law. Something with a clear career path. He wasn't trying to crush her dreams. He genuinely believed he was protecting her from financial struggle, from the uncertainty he'd experienced in his own twenties.

Emily went to college for business administration. She graduated, got a job at a consulting firm, and by twenty-five she was in therapy for anxiety and depression. She told her therapist she felt like she was living someone else's life.

"She showed me one of her old sketchbooks last Christmas," David told me, his voice careful. "I sat there looking at these drawings she did when she was fifteen, and they were beautiful. Really beautiful. And I thought, what did I do? Why did I think I knew better than she did about who she was supposed to become?"

Emily is thirty-one now. She left consulting two years ago and is taking illustration classes at night. She and David are closer than they've been in years, but he carries the weight of those lost years. The decade she spent doing work that made her miserable because he was afraid.

Pushing your kids toward safety instead of supporting their actual interests is one of those parental regrets that feels responsible at the time. But there's a difference between guidance and redirection. You can help your child think clearly about their choices without overwriting their identity with your fears.

The things we never said out loud

Not every regret is about something a parent did. Some of the heaviest ones are about what they didn't say.

Terri raised three kids mostly on her own after her divorce. She worked hard, kept the household running, made sure everyone was fed and clothed and got to school on time. What she didn't do, she says, is tell her kids she loved them. Not often enough. Not in ways they could feel.

"I'm not a hugger. I'm not someone who says sweet things naturally. I grew up in a house where love was assumed, never stated. And I carried that into my own parenting without thinking about it."

Her middle child, her son James, told her during a difficult conversation in his late twenties that he'd spent most of his childhood wondering if she liked him. Not loved. Liked. He knew she'd sacrifice anything for him, but he didn't know if she actually enjoyed having him around.

"That broke my heart," Terri said. "Because I adored that kid. I adored all of them. But I never learned how to show it, and I never thought I needed to."

You might think your kids know how you feel about them. Maybe they do, on some level. But knowing and feeling are different things. Kids need to hear it. They need the words and the small, consistent signals that say: you matter to me, specifically. Not as a duty. As a joy.

The comparison trap

Rachel has two daughters, eighteen months apart. She describes them as "completely different humans who happen to share the same parents." One is athletic and outgoing. The other is quiet, bookish, and happy spending Saturday alone with a novel.

For years, Rachel held up her older daughter as the standard. She didn't do it consciously. She never said "why can't you be more like your sister?" But she said things that carried the same weight. "Your sister made the soccer team, maybe you should try out too." Or "your sister has so many friends, you should invite someone over."

Her younger daughter, Anna, internalized all of it. She grew up believing she was the lesser version, the rough draft. It wasn't until Anna was in college and stopped calling home that Rachel realized something had gone seriously wrong.

"She told me she'd spent her whole childhood feeling like a disappointment," Rachel said. "And the worst part is, she wasn't wrong. I was disappointed. Not in her, but she couldn't have known that. I was disappointed that she didn't fit into the version of childhood I understood. I didn't know what to do with a quiet kid. So I tried to make her louder. And she heard that as: who you are isn't enough."

Every child is their own person with their own wiring. Comparing siblings, even subtly, sends a message that love is conditional and approval has to be earned by being someone else. The conversations you have with your children about who they are, not who you want them to be, shape everything.

So what do you do with this?

If you're reading this and recognizing yourself in some of these stories, good. That recognition is the whole point. Not to pile on guilt, but to give you something these parents didn't have: the chance to change course while there's still time.

Parental regrets don't come from being terrible parents. They come from being human ones. From being tired, distracted, scared, or just running on the default settings you inherited from your own childhood. The parents who shared their stories with me aren't cautionary tales. They're honest people who did their best and can now see, with the clarity of hindsight, where their best fell short.

Here's what's worth remembering:

Put the phone down. Not forever. Just during the moments that matter. Bath time, dinner, the car ride home from school when your kid is actually talking. Those windows close fast and they don't announce themselves.

Show up. Physically, yes, but also emotionally. Your kids don't need you to be perfect. They need you to be paying attention. To notice the stuffed elephant. To remember the song about the mermaid.

Let them be who they are. Not who you were, not who you wanted to be, not who makes your life easier. Your job is to help them become more of themselves, not a version of you.

Say it out loud. I love you. I'm proud of you. I like spending time with you. I think you're funny. I noticed how hard you worked on that. These sentences take five seconds and they build something that lasts decades.

Forgive yourself for yesterday. You can't go back and uncheck the email during bath time. You can't un-miss the science fair. But you can be here now, fully, starting tonight.

The letter you haven't written yet

One thing that came up in almost every conversation I had with these parents was the wish that they'd written things down. Not just apologies or explanations, but the full picture: what they felt, what they noticed, what they'd want their kids to understand about the choices they made and the love that was always underneath, even when it didn't look like it.

A few of them have started doing exactly that. Writing letters to their kids. Not for a birthday or a graduation. Just honest accounts of what they see, what they feel, and what they hope.

If any of these stories stirred something in you, maybe that's worth considering. You don't need perfect words. You just need your real ones. When I Die Files was built for exactly this: a place to write the things that matter most and know they'll reach the people who need to hear them, even if you're not there to say it yourself.

Your kids don't need a perfect parent. They need one who showed up, paid attention, and left something behind that says: I saw you. I loved you. You were the best part of my life.