Support or Ruination

“I will not deny my child the privilege of failure.”  Shall I remind again of the deadline, or let it slide past?  Will building him up fool him or set him on a path?  Will allowing him to fail devastate to the point that reaching the  no longer seen as an option?  I fear the weight of failure might tethering him forever,  Fear never freed anyone.  How in God’s name do you free a child ?