Why doesn’t every kid come with an instruction manual? I keep thinking that after parenting one, I should have a clue with the next one. But no—what works for one totally backfires on the other. It’s like trying to fix an iPhone with Android instructions—nothing translates, and eventually, you just want to throw the whole thing out the window.

And just when I start feeling confident, my kids find new and creative ways to prove I have no idea what I’m doing. One moment, I think I’m teaching resilience, and the next, I’m wondering if I’m being too harsh. Other times, I step in to help, only to realize I might be making things too easy.

So I keep asking myself: How much do I step in, and how much do I let them struggle?

I know a certain amount of pain and struggle helps kids grow into strong, independent, well-rounded adults. But I also know too much struggle can make them bitter, angry, or overwhelmed. And too little? That breeds entitlement, laziness, and people who expect everything while working for nothing.

So where’s the line? What’s just enough struggle? And how do I, as a parent, learn to let it happen?

The Struggle Is the Point—But It’s Hard to Watch

I’ve always liked Jocko Willink’s “Good” mindset—the idea that hardship isn’t a setback but an opportunity for growth. If you haven’t heard it, his philosophy goes something like this:

  • Didn’t get the job? Good. More time to improve.
  • Failed the test? Good. Now you know what to work on.
  • Got injured? Good. You’ll come back stronger.

Saying “Good” about your own struggles is one thing. Watching your kid struggle and resisting the urge to fix it? That’s a whole different challenge.

I don’t want them to struggle or fail. But I know they need to. In the moment, my instinct is to step in, solve the problem, and make life easier for them. But then I hear people talk about what actually makes someone strong and capable, and the answer is never “an easy life.” It’s always some version of struggle, discomfort, and learning how to push through.

So how do I let my kids experience enough challenge to grow without pushing them too far?

The “Broken Arm or Broken Back?” Rule

Between my wife and me, I tend to be the more cautious one. I see my kid climbing a tree, and my brain immediately flashes to an ER visit. But at some point, I realized that most of my fears weren’t really about my kids’ well-being—they were about my own discomfort in watching them take risks.

So I started using a simple question to check myself:
Is this a broken arm or a broken back?

If it’s a broken back risk—something truly life-altering—I step in, no hesitation. But if it’s just a broken arm risk, I let them go. Because if they never test their own limits, they’ll never actually know them.

I’ve started applying this beyond just physical risks. If my kid has a problem with a friend or a classmate, I ask myself:

  • Is this something that will actually hurt them long-term?
  • Or is it just an uncomfortable experience that will help them grow?

If they’re in real trouble, I’ll step in. But if it’s just a tough moment, I try to let them work through it on their own. And later, when the dust settles, I’ll be there to help them process what happened.

Figuring It Out as I Go

I’d love to say I have this all figured out, but I don’t. Every time I watch my kids struggle—whether it’s a physical challenge, a friendship issue, or a failure—I feel that pull to step in. But I’m working on resisting it. I’m trying to remind myself that my job isn’t to eliminate struggle; it’s to help them learn how to handle it.

So I keep asking myself:

  • Am I stepping in because they need it, or because I don’t want to watch them struggle?
  • Will this problem make them stronger if they work through it?
  • Is this a broken arm or a broken back?

Because if I can figure out this balance—if I can get more comfortable letting them struggle in the right ways—then maybe, just maybe, they’ll grow up strong enough to handle whatever life throws at them.

And when that happens? Good. (Still hard to watch, though.)

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