“It is more preferable to be a youth who is poor and wise than an old king who is a fool and who cannot heed warnings any longer.”
There are various ways in which commentators have interpreted this verse and the ones immediately following it. It seems to me, though, that the plain reading is preferable, particularly in light of Solomon’s own history. As a young man he started out in his role as king in exactly the right way. He may have been poor in understanding, but his request of God for wisdom and discernment to govern the people of God showed not only insight, but a humble spirit that was willing to learn and to grow. And, in doing so, he gained the attention of the known world.
Yet, as Solomon grew older and his kingdom became established, he fell into the traps of the world, not only taking numerous wives and concubines to himself, but allowing them to continue their pagan worship within the kingdom. Truly his counselors must have spoken repeatedly to him on this matter. Indeed, if one goes back to Solomon’s earlier words, he truly knew better. Yet Solomon refused to listen to counsel and engaged in pagan sacrifice along with his many wives. And oh, how spiritually poor he became.
And thus, we have Solomon looking back on his life realizing that in almost every way, he was better off as the younger, more idealistic, and humble youth-king that leaned on God for everything he did. And the plain reading provides a principle that is no less true today than it was in Solomon’s time. It is a great advantage to be humble and teachable. Further, when you get to the point where you are no longer able or willing to learn from those around you, you will cease to be useful to society. The good news is that there is a solution to this stubborn pride: repentance. And in many ways, Ecclesiastes is Solomon’s repentance for the foolishness of his worldly pursuits.