The problem with him was that he was an always regret boy. He regretted everything to the extent that he couldn’t enjoy anything anymore. The only real thing stopping him from depression was that he’d regret that as well. And that people expected him to not be depressed. But this always-regret psychology had ever-lasting repercussions on all that he did.
He was not sure when he started behaving this way. Was it because of some unaddressed insecurity? Or was it that he was not capable of rational thought – putting down the pros and cons and deciding on the basis of the maximization of pros? He ran the same arguments in his head, over and over again, and yet again, till his head metaphorically exploded, probably giving him an aneurysm.
He spent much of his time regretting, instead of constructive investments in studies, partying and the other usual things that people of his age did. He was more efficient, while not intelligent or street-smart in the strictest sense, he was capable of manipulating the environment to his liking without really being manipulative; this was a fortunate thing, because it meant that he actually did and achieved above-average in life.
But if he didn’t regret, and for once trusted his decisions, without second-guessing, stood up for them and just let the iterative (and often wrong, but that didn’t matter, everyone thinks wrong, most of the time) thinking machine in his head let go, he probably would have been a completely different person. Possibly more successful, and infinitely happier.
I wanted to put in some examples, but it just became too sad. 😦