Repentance is Hard

27 June 2026  Lamentations 2:2,10-14,18-19

“Your prophets have seen for you false and deceptive visions; they have not exposed your iniquity to restore your fortunes….” (Lamentations 2:14)

The shock of a cringe-worthy moment is not discovering that it is inconsistent with who you really are. The shock is finding that it is totally consistent. Cringe-worthy moments don’t come out of nowhere. Nobody makes mistakes that are sudden, wild departures from character. The cringey thing is the real you.

Another striking feature of cringe-worthy moments is that they are always retrospective events. We never cringe “in the moment,” we never anticipate cringing. It is only when we look back that we say, “What was I thinking?”

That is the nature of all mistakes – we don’t see them as mistakes until we are free of them, which is why we always need moral teachers who shine bright lights on the things that we do and point out loudly errors of reasoning and behavior. The wrong path never tells you it’s the wrong path.

That is the nature of all mistakes – we don’t see them as mistakes until we are free of them, which is why we always need moral teachers who shine bright lights on the things that we do and point out loudly errors of reasoning and behavior. The wrong path never tells you it’s the wrong path. Teachers and prophets are doing their job when they warn us about the things we will cringe about later if we’re not careful.

The Israelites weren’t careful, which is how they got the Exile, and we got the book of Lamentations, a loud, long, teeth-grinding, soul-grinding, keening wail: “What were we thinking?” Preachers are often reluctant to preach on the book of Lamentations because the ache in it is so palpable and deep. In fact, however, Lamentations is what Good News looks like in the beginning. No one recognizes the wrongness of a wrong path by staying on it. If they do recognize the wrongness, that can only be because they are no longer on the wrong path. There was a jolt that moved them, and that jolt was an act of Grace. Grace always precedes every revelation. Grace is revelation. Grace is repentance.

Of course, the new path is no picnic. At the start it is all uphill and feels like walking on broken glass in bare feet. The struggle is not something we go through before we repent, but simply what repentance feels like in the beginning. C.S. Lews says that repentance is no fun at all:

It means unlearning all the self-conceit and self-will that we have been training ourselves into for thousands of years. It means killing a part of yourself, undergoing a kind of death…. This willing submission to humiliation and a kind of death is not something God demands of you before He will take you back, and which He could let you off if He chose: it is simply a description of what going back to Him is like. If you ask God to take you back without it, you are really asking Him to let you go back without going back. It cannot happen. (Mere Christianity, p. 55)

The rightness of the right path tells you it won’t always be uphill and broken glass, so it is worthwhile to keep going – something the wrong path never says.

Good News is recognizable as good only with repentance. It is why Jesus mentions it first: “The time is fulfilled and the Kingdom of God is at hand. Repent and believe in the gospel” (Mark 1:15). Repentance is nothing to be afraid of. It is mercy just getting started.