Let me start by saying that "troubled past" doesn't describe loss or grieving. Usually a person with a troubled past has had difficulties with the law, substance abuse, difficult childhood, or the like in his past.
I will assume that you are misusing the term troubled past and are actually referring to a person who is attempting to recover from a personal tragedy of some sort. Looking up "recovering" in a thesaurus gives several alternatives: getting over, picking up, perking up, picking up the pieces, feeling better, getting his life back together, coming along. In all these cases except getting over, you can say "He's had a personal tragedy, but he's [picking up/perking up/etc] now." With getting over, you'd have to say "he's getting over it now."
You may also say "He's recovering from a personal tragedy" or "He's getting over a personal tragedy." The others would work a bit differently: "He's getting his life back together after a personal tragedy", for example. You can use after in the same way with most of the others (you can use it with recover as well), but I wouldn't say "picking up after a personal tragedy" because it can easily be confused with the more literal sense of picking up: "picking up after a party" would mean gathering the trash. If I were going to use picking up, I would say "picking up after having had a personal tragedy". This sounds hopelessly stilted to me, so I wouldn't use it.
There are many words, which emphasize different meaning. Some are negative.
Pleasure aspect of doing whatever you want: bon vivant, hedonist, pleasure seeker.
Going wherever you want, possibly new places (metaphorically too): globetrotter, explorer, pioneer.
Free thought, defiance: maverick, liberal, free thinker, nonconformist.
Disregard for traditional social structures: bohemian, hippie, beatnik.
Disregard for manner and social grace: boor, barbarian, brute, philistine.
Ambition: doer, achiever.
Disregard for law: criminal, outlaw, gangster, robber, lawbreaker, desperado, etc.
Acting in self-interest without regard for trust: back-stabber, snitch, cheater, two-timer.
Acting in self-interest without regard for others: egoist, narcissist.
Best Answer
Perhaps you're looking for pedant:
In place of pretention there you could substitute pedantry.
TheFreeDictionary, Random House
Me, I've always tended to refer to such people as pompous asses.