Will an out-of-the-box yeshivah offer my son too much freedom?

My oldest son is an incredible kid. He has a sunny nature and loves people. He’s also extremely creative, super-talented musically, and an out-of-the-box thinker and mover. He’s organized his own band, together with three other like-minded boys, and they spend hours practicing in our garage.

In school, though, he often runs into issues with his slightly zany antics and his need to march to his own tune. But his rebbeim are great, and we have a terrific working relationship with the administration.

Now my son’s graduating eighth grade, and we’re faced with the challenge of finding him a good yeshivah high school for next year. On one hand, he’d do well with a slightly alternative setting, with rebbeim and principals who’ll understand him and give him space.

On the other hand, those types of schools often allow much more leeway in other areas — and that may drag him down spiritually or allow him friendships that could become problematic. Furthermore, by sending to a school that’s off the beaten track, we may be branding our younger sons when they try applying to the more standard yeshivos.