Let's see, obstacles are something else. They present themselves as problems for us to solve, regardless of our actual current capacity to do that, to overcome them. We have various options while dealing with them, like storming towards them by brute force, maybe analizing them and reflect upon the set of possible consecuences that the «difficult thing» may bring, ignore it or to look for help. Philosophy may really be of help in here, since no philosopher is exent of showing us new problems as they go developing their thoughts. Kant's Ethics, Nietzsche's willpower, Russell's life's values, Buda's understanding, stoics's disposition, epicureo's calmness and virtues as the prudency of Aristotles, even the rational faith of the Saints as Aquino and Agustine. All of that are proper tools for dealing with our lack of luck or sync between our desires of prosperity and the course of the nature of human events. I personally like both of the options as long as there is some proper feeling of fairness when I perceive them. Like a just challenge and that, kind of stuff, since I tend a bit to be affected strongly by the notion of being a failure.
I hope everyone has a nice day.