Velorien comments on [FINAL CHAPTER] Harry Potter and the Methods of Rationality discussion thread, March 2015, chapter 122 - Less Wrong
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It seems that the problem with Tom "Voldemort" Riddle is that, although he was ambitious, he had no ambition. He was Sorted into Slytherin, and was driven by fear and cleverness to grasp at any opportunity for advancement which he could imagine. But there was no great ambition that he was driven to accomplish - at best he could grasp his way upward into the role of a hero, or a Dark Lord, or into personal immortality, or some other position of merely personal success, never breaking the bounds of his own lonely existence.
True ambition was the power that he knew not, and his downfall.
Let's not forget this:
I think a good way of describing Voldemort's ambition or lack thereof is that he has no preferences about worlds that do not contain him, whereas Harry Potter does.