There was some sort of prophesy about Timothy making him a bad comparison for general use. He wasn't the norm. Frankly we don't even know what he actually did besides travel with Paul. Considering that he traveled around as an assistant , he could not have been a teen. He was likely somewhere between 20-30. It says Timothy was young, it doesn't say he was a boy (under 20). By the time Timothy was sent to Ephesus, he was over 30. Timothy didn't feel inadequate, he was afraid. They were hunting and killing Christians.
As for freedom, the WT does its best to demean the word and concept because it wants people to be its slave. Freedom-bad, Slavery-good.