T.N.
Well I'm not sure if this is what you're looking for but here goes....
None of my kids went to a Montessori school. BUT, I actually have something of a "Montessori-Waldorf-esque" style of parenting. If you have to put a name to a thing, yes, I def subscribe to many of their theories.
All my kids started out in a tiny, extremely rigid neighborhood Catholic school. There they all thrived , despite my much more casual style of parenting.
Then, we built a house in the 'burbs, and moved them from that environment to an ENORMOUS public school system. And I was SICK with worry, MY GOD! WHAT HAVE I DONE!!!
They were 2nd grade, 5th grade 7th grade (OMG JR High), and miraculously
immediately excelled, immediately adjusted immediately embraced the differences.
My point is I guess, is that kids are WAY more rescilient to change than WE are, way more likely to shrug and move on to the next thing.
They are now 18, 16, 13, and honestly seem to be completely equipped to handle anything change that comes their way (me, not so much). And to be perfectly honest, I suspect the REASON for this is...
How do I put this?
Their REALITY, their CORE, is HOME, is ME, not school, not friends, not any other influence. Their homelife is their CONSTANT, and wherever that is, it hasn't EVER changed.
Tehehe, sorry so deep, anyway, based on MY experience, your fella will be just fine with the change!
Have a great weekend!!
:)