We’ve been walking through the problem (and I do think it is a problem) of bullet-point style preaching. You can catch up in the conversation here, here, and here. I know that for many preachers bullet-points are preferable. The reason they cite is “clarity.” I want to address this issue.
The pressing question is this, Were the teachings of Jesus clear? You’re right, it’s a trick question. Some of the Lord’s teachings are clear. Take for instance Matthew 5:23-24, “Therefore, if you are bringing an offering to God and you remember that your brother is angry at you or holds a grudge against you, then leave your gift before the altar, go to your brother, repent and forgive one another, be reconciled, and then return to the altar to offer your gift to God.” The fact that this teaching is clear hasn’t stopped it from being almost universally ignored. There is no connection between the clarity of the teaching and the application of what has been taught. Preachers, let’s loose the illusions that clarity necessarily produces obedience.

At the same time, Jesus frequently ends other teachings with words like “let those with ears to hear, hear the word of God.” And perhaps most puzzling is the exchange between Jesus and His disciples after the Parable of the Sower in Matthew 13:
Disciples: Why do You speak to the people in parables?
Jesus: The knowledge of the secrets of heaven has been given to you, but it has not been given to them. Those who have something will be given more—and they will have abundance. Those who have nothing will lose what they have—they will be destitute. I teach in parables so the people may look but not see, listen but not hear or understand.
There is a deliberate lack of clarity in Jesus’ teaching. We can confidently draw from this that Jesus actually wants folks to not only wrestle to do His teachings but to wrestle to understand them. As any psychologist will tell you, it takes information about one’s self and the wrestling to understand that information to produce lasting change. It’s not just that the hearer “get it” (clarity), but that the hearer works to get it. It’s the wrestling that produces the change not the information.
Putting the two texts in dialogue – both from Matthew, mind you – we see that Jesus taught both to reveal and conceal. And He did them both without bullet-style checklist. Therefore, we can conclude two things: (1) You don’t need bullet-points to be clear and (2) You don’t always want to be clear.
There is a danger to overwhelming clarity. What is it? The shuttering of missional imagination.
I had a professor in grad school whose tests were relatively easy as long as you knew to only parrot what he had said. When he asked about a particular biblical text, the only appropriate answer was the one he had given in class. He had given us the bullet-point and our job was to give it back. But everyone who has taught or preached any texts knows that there is typically a field of meaning and application. In another circumstance, I knew a minister who subscribed to the formerly popular notion that all parables only had 1 point. That means that as soon as someone gleaned something other than that 1 point, they had missed the point. I bet if I asked 15 Christians the meaning of the Parable of the Sower, I’d get at least 1o different meanings. Why? Because we all know that there is more there. The Scriptures are deep and wide and Jesus intends for us to struggle with His word, to work through it and work it out – individually and communally. As soon as I say “In text X, God is teaching us 1, 2, and 3,” I have been clear but curtailed the imagination of the hearer. This is a great way for preachers and theologians to stay employed. We can be the church’s Bible answer men, but we may not be serving the church.
Now, someone will certainly say, “Sean, you’re calling for uncertainty and confused teaching.” Not really. What I’m calling for is the embrace of Jesus-style preaching in the contemporary church. When Jesus describes the Kingdom of God it is like…a seed…a man who…a net…new and old treasures…etc….Get the point? The teaching of Jesus expands the imagination. It paints pictures. There is a stark difference between Van Gogh and my 5-year old’s connect the dots. Guess what? The connect the dots is much clearer. I know what it is and how she got there without any thinking, analysis, or struggle. But is is also rudimentary and, quite frankly, disposable.
Just in case what I’ve posited in not clear, here’s a similar word from Eugene Peterson:

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