The Circle of Stubborn Wisdom

There’s a particular ache that comes with watching your child walk confidently toward a mistake you made yourself twenty years ago. You can see it coming like a slow-motion replay—the relationship that’s clearly wrong for them, the job they’re taking for all the superficial reasons, the money they’re about to waste, the friend who will inevitably let them down. You’ve been there. You know how this story ends.

And yet, you also know that nothing you say will change their course.

This is the paradox at the heart of parenting older children: we possess hard-won wisdom that feels worthless because it cannot be transferred, only earned. Our children must touch the same hot stoves we did, fall into the same potholes, and learn the same lessons that seemed so obvious in hindsight but were invisible in the moment.

The Rebellion We All Needed

I remember the conversation with my mother when I was eighteen and pregnant, explaining why I was staying in the state we were living while they (my parents and little sister) moved back to the state we were from. She didn’t yell. She didn’t forbid it. She just said quietly, “I hope it works out the way you think it will,” in a tone that clearly meant she knew it wouldn’t. I was furious at her skepticism. How dare she not believe in me? How dare she project her limited worldview onto my unique situation?

Years later, after it all fell apart exactly as she’d anticipated, all I could do was cry on her shoulder. She simply held me and didn’t say “I told you so,” which somehow made it worse.

Now, as I watch my son go live a life similar to the one I was living back then, selfish, irresponsible in some ways, muleheaded and stubborn, I want to shake him and tell him to stop. Well, I do tell him to stop, to reevaluate his priorities, but he listens as much as I listened.

Why We Need to Prove Them Wrong

But here’s what I’ve come to understand: I needed to prove my mother wrong, even though I ended up proving her right. That rebellion wasn’t pointless stubbornness—it was the necessary process of becoming myself.

When we’re young, our parents’ wisdom feels like a cage. Every “I know better because I’ve lived longer” sounds like “You are not capable of knowing anything yourself.” Every cautionary tale feels like a vote of no confidence in our judgment, our uniqueness, our ability to write a different story than the generation before us.

We need to test our own limits. We need to discover that yes, we really do need eight hours of sleep, that credit card debt actually does accumulate faster than we think, that the exciting job with the chaotic boss will burn us out, that we can’t change people who don’t want to change. We need to learn that our parents weren’t controlling oracles, but rather fellow humans who simply walked the path before us and noticed where the rocks were.

The rebellion isn’t about proving our parents wrong. It’s about proving to ourselves that we’re capable of learning, surviving, and becoming wise through our own experience.

The Wisdom We Can’t Give Away

As parents, we want to spare our children every pain we endured. We want to hand them our hard-earned insights like a cheat code for life. But wisdom doesn’t work that way. It’s not a gift that can be wrapped and presented. It’s a trophy that must be won through lived experience.

I can tell my son that heartbreak is survivable, but until his heart actually breaks and he discovers he can still get out of bed the next morning, the words are just sounds. I can explain that most things he’s anxious about won’t matter in five years, but until he lives through those five years and looks back, he won’t feel it in his bones.

The most valuable lessons are the ones we resist the hardest. Maybe that’s because deep down, we know they’re true, and we’re not ready to accept the limitations they imply about our control over the world.

Learning to Let Go

So what do we do with this knowledge? How do we parent adult children who are determined to learn everything the hard way?

We bear witness. We keep the door open. We offer advice when asked and sometimes when not, knowing it likely won’t be taken. We watch them struggle with problems we could solve in an instant, and we hold ourselves back because solving it for them would rob them of the growth that comes from solving it themselves.

We remember that every scraped knee of childhood was preparation for this—that we let them fall when they were learning to walk, and now we must let them fall while learning to live.

And when they do fall, when they come to us with the exact problem we warned them about, we don’t say “I told you so.” We make the tea. We listen. We let them arrive at their own conclusions. We watch them become wise.

The Long Game

Here’s the secret comfort: they will learn. Not on our timeline, not through our methods, but they will learn. And thirty years from now, they’ll be having tea with their own adult children, biting their tongue as they watch history repeat itself once more.

Everyone wants to exist—to be their own person, to make their own choices, to write their own story. Most people need to learn the hard way because the hard way is the only way that feels real, that creates lasting change, that transforms information into wisdom.

We don’t prove our parents wrong only to prove them right because we were being foolish. We do it because wisdom requires experience, and experience requires risk, and risk requires the freedom to fail.

Our job as parents isn’t to prevent our children from making mistakes. It’s to love them enough to let them make those mistakes, and to be there on the other side when the lesson has been learned.

That’s the long game. That’s the circle. That’s the hard, beautiful work of raising humans who will one day shake their heads at their own children and finally, fully understand.

What season of life are you currently in? This season of my life, four adult sons married and one with a family of his own, and four daughters still living at home…..it’s rough. And by rough I mean all the joys and all the heartbreaks wrapped up in hormones and stubbornness and love and frustrations and tempers and laughter and tears, and very not neatly. And now….now I want my parents’ wisdom that came flowing so freely back when I was 18. With parenting, there’s no rulebook. There’s hoping we raised them well enough to live a life in which they aren’t harboring anger and resentment….that they can give and accept love. And all the other stuff, too (productive members of society, etc, etc)