Okay, I admit, the labels we use to talk about eggs is NOT the best analogy, but as my almost four year old son ventured out into the front yard to "look for fossils," I realized that my parenting has changed a lot in the last year.
When he was two years old, he looked and talked like he was three. On the playground he often saw kids, who talked and looked like him, do things that I wasn't sure he knew how to do yet (like jump from a certain height on the playground). So I hovered and helicoptered. I don't care what other parents say, I know the distance I need to be for us both to feel comfortable.
But over time, I noticed that he was venturing farther and farther away (not too far, of course) and we learned to "check back" (he uses his own internal clock to check in with me from time to time so I know he's safe), he learned to try stuff without me prodding or cringing, and eventually, I learned to see how much he trusted himself.
That was key, though. I needed to see how comfortable he felt with himself, not how comfortable I felt about him and his actions. For instance, he's really comfortable in the water. He wears a life jacket and has no problem jumping in, getting his face wet, belly-flopping, etc. I don't think I would have guessed it would happen so early (I was not a fan of face in the water swim methods as a child), but he's way into it. When he does get a mouthful of water, we're right there, NOT freaking out, and asking if he's okay. We aren't alarmists. Freaking out in the water always makes it worse. We see if he's okay and when he nods, we go back to what we were doing.
We still don't let him roam too far away, but we are in communication often. Cage free for chickens means that they aren't in cages but have no outdoor access (so the analogy isn't really accurate, we DO let K outside!) and free range is full access to outdoors, and ability to freely roam. We're not there yet (but we talk about when that might be a lot). But I like the idea that we are paying attention to what sort of freedom K needs. It's not simple enough to say that he can play on his own (he can't, he needs some eye contact every once in a while), but he doesn't need us around every moment, micro-managing. He needs to know where we are, so he can find us, and he needs to know we're paying attention. I believe that helps him trust himself and allows us to see how much he trusts himself. He's also free to tell us to go away. He needs that too (and so do we).
I don't want to undermine that. When he gets older, we'll have to do similar things. I was trustworthy but my parents were skeptical and that irritated me. While I did a few "teenage-y" things, I was relatively responsible. And had they been more trusting, I might have shared more.
Communication is 93% nonverbal and 7% verbal! So trust is one of those things that is probably mostly non-verbal. Saying we trust him is probably not what demonstrates trust. Letting him experiment, explore, play, and roam on his own is what shows that we trust him and he learns that he's trustworthy that way, too.
We're definitely not perfect at it (and sometimes even if he's "safe" I micromanage the use of crayons, pens, and staining things because I'm like that), but it helps to realize that we are in communication about it, even when we don't say a thing.