I have wrestled with the question many times of what will make a child love Torah and love mitzvos and what will make a child reject and hate it. What will make a child grow up to attend shul and will those same actions (nudging, pushing) cause a future abhorrence.
The confusing thing seemed to me that if you ask people "what did your parents do that encouraged you to go to minyan" and if you ask people "what did your parents do that made you avoid minyan" you'll find an overlap. Sometimes the very same actions people say worked is exactly what other people say backfired.
Well, I'm pretty sure no one ever said "They made it fun and exciting and I swore I'd never do it again."
But I think you'll find divisiveness on "they were firm and pushed me to do it even though I objected" and equal divisiveness on "they let it go and were relaxed about it." (Though come to think of it, I'm not sure I ever heard an adult say "I dropped it because it didn't seem like it was a priority to my parents." I have heard others denounce parents and say "If you don't show your children it's a priority, they won't know and they won't do it.")
So I was all muddled about this for a while. It's especially confusing when I'm trying to decide if unschooling and trust the process is a good idea. Or if I'm abdicating responsibility and making a huge mistake.
But recently I've come to some conclusions. And it seems so obvious to me now, I wonder why I didn't always see it this way.
My children have very different personalities. I've found it useful when thinking about this area to look through the lens of Gretchen Rubin's Four Tendencies which frames what types of habit forming strategies work for different types of people.
Looking at my children through the above lens has allowed me to really carefully craft their "obligations" or "good for them activities" (i.e. "mitzvos") through strategies that speak to their tendencies. While one of my children may love structure and love accomplishing, another will shut down completely if there is a whiff of obligation.
In addition to that, there is also neurodiversity and learning style, which greatly affects whether someone is the type who can sit in the beis medrash or even sit through shacharis. And then there is the early riser vs. the night owl in terms of who is physically going to be really struggling with morning minyan.
There's a reason why we have different expectations from different children. Some children are social and if their friends do it, they'll be inclined to do it. Some children are upholders and are pretty driven and motivated. Some children are just going to go the opposite direction if you push them.
I just think a lot of this is personality and nature. I'm sure as parents we can do a lot of things to make things worse. But assuming we don't make things worse and can get out of the way, it seems like a lot of this comes down to personality. And that it's really important to factor personality into chinuch.
I know that an Eisav can be a Dovid HaMelech. But an Eisav is never going to be a Yaakov. As my children grow up, it just seems to me that for some children, gentle chinuch works beautifully. And for others, even Herculean efforts might be counter-productive and the best thing you can do is show love and support and shut up (which is a different but equally important Herculean effort). It seems the more I look at it, certain types of strategies are going to be a really bad idea for some kids and be at best indifferent for others. And other strategies will work really well--but it depends on the child's personality.
I'm reminded of Koheles perek 11:6
בַּבֹּ֙קֶר֙ זְרַ֣ע אֶת־זַרְעֶ֔ךָ וְלָעֶ֖רֶב אַל־תַּנַּ֣ח יָדֶ֑ךָ כִּי֩ אֵֽינְךָ֨ יוֹדֵ֜עַ אֵ֣י זֶ֤ה יִכְשָׁר֙ הֲזֶ֣ה אוֹ־זֶ֔ה וְאִם־שְׁנֵיהֶ֥ם כְּאֶחָ֖ד טוֹבִֽים׃
Chazal say have children or students both in your youth and in your old age. Because you have no idea what's going to work out.
It's kind of comforting to have Chazal shrug and say, "It's a numbers game."
(I have a feeling that this post can be VASTLY misinterpreted so I reserve the right to clarify in the future.)