Whenever you start thinking deep about something, there is a certain merit in remaining detached, observing carefully, and clarifying even the most subtle detail. Almost every question of relevance is complex; in real life, there's usually a multitude of factors that play a role. So whenever you get into deep thinking about something, there's something to say for a dispassionate, neutral, and detail-loving stance: not taking sides regarding a certain question; not having an emotional preference but carefully observing in a detached way; paying attention to all the details and connections which transpire.
This also applies to thinking about what matters most: how you want to live your life, what kind of person you want to be. When we start comparing different answers to those questions, when we evaluate the various approaches, examine the arguments for and against them, and try to find criteria by which we regard them as better or worse — in a word, when we start doing philosophy —, then it helps to remain open and neutral, not closing off roads just because of some judgment taken previously (or prematurely); it's good to be aware of all the details, options, the arguments pro and contra all the sides; and it's a helpful skill to be acute in making distinctions, and in making connections.
Of course, this must not be taken too far, or otherwise there would never be any action at all. It's not enough just to think, we also have to live the answers to these questions. In fact, we already do so, and it's probably fair to say that in most cases, the answers that we do live aren't the best ones we're actually capable of — capable of giving, and living. Whenever we make some progress, we have to update both our views and our actions.
If we don't, there is a danger that sophistication itself is made the goal, a l'art pour l'art of the intellect. And there is ample occasion for observing this danger coming true in today's intellectual institutions, where sophistication in argument, hunting for nuances in subtly different views, and compulsive quibbling frequently enough double up for any real goal or real direction. The phrase "it's an academic question" has become proverbial for this kind of talk. An 'academic' question is one without real relevance, one that can be left to those who play the self-contained game of debating it comprehensively, in all the minutest detail, just for the sake of debating nuances. There is a difference between theoretical skill and excellence on the one hand and this kind of self-absorbed sophistication on the other. Unless you want to start an academic career and measure up to others who also are intent on conquering that institutional path, thought and talk of that latter kind are not for you. It's philosophy that is valued for its own sake, not academic subtlety; for philosophy is ultimately a way of living your life in an examined way, informed by the best critical and theoretical thinking there is. As such (as an activity), philosophy must translate into action; and not much action flows from sophisticated talk that is primarily directed at, well: being sophisticated.
When sophistication in an area becomes a self-contained game, it's often difficult to recognize that this is what's going on; it tends to happen in a group or community which shares and mutually supports that sophistication, and so it will be difficult to tell from genuine admiration you receive when you're living a good life. The dangerous slip here is to make a community of similar-doers into an external standard for quality and worthiness, something that doesn't come from a connection to a real, personal quest for a goal in your life any more. (Of course, the connection doesn't have to be direct and explicit all the time, but it must be there somewhere.) In other words, when you get drawn to tendencies of sophistication you'll least notice it from the attitudes of encouragement or discouragement in those around you. With respect to philosophy, self-absorbed scholasticism is the result, a professionalization of intellectual debate that becomes separated not just from real goals, but even from real intellectual questions.
Philosophy is often about conceptual distinctions, and their good and correct use. Philosophical education is in many ways a process of getting trained to find and apply them. But then again, handling them should not be just a goal in itself. They are part of exercising rationality, but they must be anchored in real goals, and those include the improvement of character: working towards the elimination of false emotions, building a consistent view of the world, guiding practical decisions, and promoting excellence in yourself and others. If they don't, if sophistication becomes a habit and a goal in itself, it only drains our energies and diverts our focus from the things that really matter; for sophistication, even though it may look admirable at times, is not among the things that really matter. Take care.