When the Commands of Jesus Make You Sad

In the book of Matthew, the man is called young. Luke makes clear that he was a ruler of some kind. And both point to the fact that he had great wealth. That’s why we call him “The Rich, Young Ruler.” The Bible tells us that crowds were following Jesus wherever He went in those days, and there must have been a sharp contrast between this guy and the crowd pressing in on Him. They were dirty; he was clean. They were poor; he was rich. They were shabby; he was finely dressed. He had a simple and straightforward question for Jesus: “What do I need to do to inherit eternal life?”

Jesus responded that he should keep the law. The man claimed that he was already doing that. Wasn’t there something more? And that’s when Jesus came with the zinger—“Sell it all. Become poor. Then you can follow Me.”

The Bible says that the man went away sad because he had great wealth (Matt. 19:22).

I wonder if you’ve ever felt the same way. Surely you have – surely you’ve been reading the Bible or listening to a message being preached and you run headlong into a command from Jesus. It might be, as it was for the rich, young, ruler, a command about money. But it might also be a command about sex or moral purity. A command about parenting. About marriage. About laziness or gluttony or a host of other things because the Bible is full of commands.

You are confronted with this command and you feel… sad.

Most of the time, if and when that happens to us, we either disregard that command or we look for some way to get around it. We search for some reason why either the Bible can’t really be saying what it seems to be saying, or else why the manner in which we are currently operating is an exception to that command. But if we can get past those initial reactions of denial and self-justification, perhaps we can ask ourselves just why it is that we are so sad to begin with.

Most likely the answer is pretty simple – it’s because we like whatever we are doing, and the thought of stopping it makes us sad.

But that’s not all there is. There is yet another level to the sadness, and it’s a level beyond the initial emotional reaction to that command. The deeper level is that of faith. Yes, this command of Jesus makes you sad, but at a deeper level, what do you believe to be true about Jesus? And that question – the question of faith – is what will ultimately determine how you respond to the commands of Jesus that make you sad.

The question of faith is whether you and I really believe that Jesus loves us and wants the best for us or not. Because if we truly believe that, even if His commands make us sad, we can move through the sadness into obedience, trusting that though the command might be painful in the moment to follow, it is ultimately for our own good.

This is the beautiful detail from the rich, young ruler’s own experience. Look back in Mark’s account of this story before Jesus gave the saddening command:

Looking at him, Jesus loved him and said to him, “You lack one thing: Go, sell all you have and give to the poor, and you will have treasure in heaven. Then come, follow me” (Mark 10:21).

Notice the order here, because the order is important.

Jesus looked at him and loved him…


Jesus gave him a command.

In other words, Jesus loved this man enough to tell Him to sell everything He had. The same thing is true for us. Jesus loves us enough to give us commands to follow. This is how we respond, by God’s grace, when the commands of Jesus make us sad:

We remember He loves us. Loves us enough to die for us. And so we follow Him, despite our temporary sadness, knowing that there will eventually be more joy for us on the other side.


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