The simple answer is that life is obscure, complicated and confusing, but I don’t believe this suffices as an adequate response. Perhaps a better way to describe why philosophers tend to make simple questions complicated is due to life’s multifariousness. Life is multifaceted, diverse and often perplexing, which is why it often leads to multiplicity within answers and dissimilar ideologies amongst philosophers. Human beings obviously differ incredulously, and so do their opinions. And although many philosophers have sought to better human knowledge, amongst valid opinions often has been concealed innuendos, hidden agendas and inflated egos.
As Albert Einstein said, ‘things should be simpler but not simple’, and as far as philosophy goes, this often is adhered to. Just because a question is easy doesn’t necessarily mean the answer should or will be alike. Human reasoning is complex to say the least, just because a question is short and sweet doesn’t mean that a response is akin. Take for instance the question “who are you?” From this three worded question are you able to formulate a ‘sweet’ three worded answer?
Expressing oneself astutely, stalwartly and unmistakably is an awkward challenge. This is why simple questions can often appear obscure, complicated and confusing, which is why philosophers are often beleaguered and ridiculed as crass, rather than appreciated, as they indeed sometimes should be.