Needless to say Jesus said some very strange, confusing and profound things that really take some thinking about (and that is rather the point: think). One of the most confusing things He has ever said is that if you want to be His disciple, you have to hate your family, and even your life.
Like, wow Jesus! Never mind being contrary to basic human nature, You, Yourself, told us to love everyone, even our enemies, and your word also says that hatred is murder, so what gives? How can we possibly hate our families if we're supposed to love them?
In context, Jesus was not saying that you must literally hate your families. Rather, He was talking about counting the cost of Christianity before you become a Christian. He goes on to describe a tower, and how a builder will consider whether or not he can finish the tower before he builds it, and also to describe how a wise king will consider whether or not he can win a war before declaring it. The takeaway, therefore, is that before you become a Christian, you must consider what you might lose.
One thing to consider is that this was a much less civilised age. We in the Christianised West have grown somewhat accustomed to a multi-faith environment. If you don't believe what your family believes, it may cause a few arguments at the dinner table, but you can usually get on just fine. That's not always the case, of course, and in some places in the world, it's still very dangerous to be a Christian, but at least in the Western world, we no longer live in an environment where sharing a house necessitates sharing religious values. But in ancient Israel, it really did. Not only could you be shunned and cut off from your family, but they may even betray you to your death.
Although it's not commonplace in the Western World, I am reminded of a story I once heard about a Muslim who became a Christian. His mother, still a Muslim, not only disowned him, but actually hired a fellow Muslim to kill him. So the Muslim hitman approached the new convert in a shopping mall and pushed him over a barrier to the floor below. Thankfully, the Christian survived (though if memory serves he was paralysed from the waist down), yet in true Christian fashion, He forgave her.
Now, if this ex-Muslim had desired, he could have kept his mother's favour by maintaining his Islamic faith. But by becoming a Christian, he lost her. When Jesus says you must hate your family and your life to follow Him, He's not saying you must literally hate them, He's saying that if you become a Christian, you might lose them, but you have to consider this a worthy price to pay.
There's always going to be a cost of being a Christian. Sometimes it's a small cost. Ok, so you laugh at me. I'm not going to lose sleep over that. You call me names, I'm not going to cry into my pillow. But sometimes the cost is higher. Sometimes, we lose our careers. Sometimes, we lose our homes. Sometimes, we lose our family members. Sometimes, we lose our lives. Christianity is a dangerous faith to have, and throughout history, it always has been. When Jesus says to hate these things, He's saying if it comes down to the choice: Family or Jesus, choose Jesus.