"...Now God, who has made us, knows what we are and that our happiness lies in Him. Yet we will not seek it in Him as long as He leaves us any other resort where it can even plausibly be looked for. While what we call 'our own life' remains agreeable we will not surrender it to Him. What then can God do in our interests but make 'our own life' less agreeable to us, and take away the plausible source of false happiness. It is just here where God's providence seems at first to be most cruel, that the Divine humility, the stooping down of the Highest, most deserves praise. ..."
I was not particularly happy to read this, as the idea of God deliberately inflicting pain to make a point makes me very uncomfortable. But was Lewis referring to the choices that we humans make that are at odds with God's will for our lives? Are those choices what result in pain? And if so, how do they fit into God's providence? A couple pages later in this chapter, Lewis has this to say (and this is what jolted me):
"...The dangers of apparent self-sufficiency explain why our Lord regards the vices of the feckless and dissipated so much more leniently that the vices that lead to worldly success. Prostitutes are in no danger of finding their present life so satisfactory that they cannot turn to God: The proud, the avaricious, the self-righteous are in that danger. ..."
The Roman Catholics include pride and avarice on the list of Seven Deadly Sins, and a case might be made for self-righteousness to be placed under pride. I wonder if Tolkien's Roman Catholic faith influenced Lewis here?
In any event, it seems to me that sin has consequences, and that such consequences cause pain. This is true whether the sinner feels the pain or victims feel the pain. Lewis makes a key point here that where sinners are aware that their lives leave much to be desired, that they can turn to God more easily. In contrast, those whose desire for material gain leaves a trail of hurting people, but whose lives are, superficially at least, what they want, have a far longer way to go before it even occurs to them to call on God.
Perhaps this is why the tears of the woman who anointed Jesus' feet with costly ointment (Luke 7:36-50) meant more to Jesus than the sorrow of the rich young man who just couldn't give up his wealth to follow the Lord (Matthew 19:16-30). Both the sinful woman and the rich man felt pain. Whose pain presented the opportunity to turn to God and repent?