The simple and short answer to this is: to make it easier to communicate his message (i.e. to make it easier for us, his "audience," to understand his teachings).
From Matthew 13:13: "Therefore I speak to them in parables; because while seeing they do not see, and while hearing they do not hear, nor do they understand."
Essentially Jesus spoke in parables so that his teachings are easier to understand. Sometimes, we have been ingrained with certain habits and beliefs that while we are able to "hear" of "new" teachings, we do not really "listen" or "understand" fully those new teachings.
One example I can give you is imagine you have a friend who participated in a certain sports competition and lost. You come up to him and then, what do you say?
Do you tell him, "You lost because you are not good enough. The other person is better and deserving to win!"?
Of course you do not tell him that, fact or not! It is very judgmental!
Instead as a loving friend, you might tell him, "That's alright, friend. Let's practice some more and maybe we can win next time! I'll help you out next time. Maybe we can do more of this certain exercise so that you can better your chances of winning!" Or you might tell him, "Good effort! But I'm sorry about the loss. Don't worry, I'm still your friend." Or something like that. Or, you might crack a joke, to cheer your friend up.
The thing is, your friend is at such an emotional state that he cannot be able to accept you telling him that he's "not good enough" directly. So the best thing to do is to say something to cheer him up (or not tell him anything at all, just be there and comfort him). Say something that indirectly communicates what you want to tell him, but at the same time it is a loving way to say it...
This is how Jesus spoke to many during that time because all that he was speaking of were "new" to them. They were used to taking a rest (even from doing good deeds) on the Sabbath. They were used to stoning adulterors to death. They were used to disowning prodigal sons who have returned. They were used to not loving their enemies.
But Jesus preached about turning back to God, and about love, and if he spoke in an unloving way, e.g. if he just told people "Repent for the end is near!", who are to believe him?
In this same way, I admire Bo Sanchez because he gives teachings that are very much relevant to his audience. He knows that we - the Philippines - are not economically well, and that many of us would want out of our current financial situations. So he teaches about how to make money - and adds that money is not evil, but it is a tool we can use to bless others. He encourages us to level up and become rich, so that we have more to share with others who are less fortunate than us!
In the same way, when you are a Christian and you are in a non-Christian city or country, you do not openly preach about Jesus and Christianity and so on. When you are a religious and prayerful Christian and you are around not-so-prayerful Christians, you do not just force them into praying, or talk about your prayer life! That is not the loving way - that is not how Jesus would do it! Instead you would first do acts of kindness and generosity out of love - as Jesus has taught us... thru parables!
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