Plato famously said that the ‘unexamined life is not worth living’ (Apology 38a). But what is an examined life in contrast? Normally, I suppose, when we live our lives we do not question our principles, values or beliefs. If we did so constantly, then we would not be able to live our lives at all. I imagine that this what most people think philosophers are. People who can’t live proper lives, who have their heads in the skies, who aren’t reasonable, serious people. This isn’t a new insult. It does right back to when there were first philosophers (because there haven’t always been such strange people). Plato tells the story of Thales, who was one of the first philosophers, who we know off, who was so distracted by the heavens that he fell into a hole. This is the passage in full:
Why take the case of Thales. While he was studying the stars and looking upwards, he fell into a pit, and a neat, witty, Thracian girl jeered at him, they say, because he was so eager to know the things in the sky that he could not see what was there before him at his very feet. The same jest applies to all who pass their lives in philosophy.
Well I don’t suppose such a thing really happened. It has the ring of a myth just because the metaphor is so telling. Isn’t studying philosophy just like falling into a hole, and doesn’t everyone laugh at philosophers because they don’t take life seriously enough. The joke, however, in the end is Thales’, because having spent so much time staring at the heavens, he was able to predict that the next olive harvest was going to be very good and thus he made a fortune. Perhaps it is not so useless being a philosopher at all.
I don’t think, though, that was the reason that Plato thought an examined life was better. I don’t think he was recommending philosophy as a way of making money (or getting a career as we might say nowadays). Though that might be a consequence of doing philosophy, that would be the reason that you chose to do philosophy. The reason that Plato recommended philosophy was that he thought that it would make you a better human being.
In this way he saw philosophy as a spiritual task that consumed the whole person and not just a skill that one could become better at. The word ‘spiritual’ has perhaps become an overused word in our culture and in that way might be redundant unless we give it a precise meaning. What I do not mean by spirituality is a pseudo-religious activity or practice, as when someone might say that they are spiritual but not religious. Still less do I mean the commercial side of spiritual activity, like faith healing, crystals and reincarnation. All these are a kind of watered down mysticism that is the opposite of what Plato means by an examined life.
At the end of another dialogue, The Symposium, Plato tells us a story about how philosophy was born from Poverty and Resource (203a). Someone who has everything and desires nothing cannot be a philosopher, but equally someone who has nothing and cannot desire anything will not be able either. The philosopher is someone who exists in between the two. She knows that there is truth but that she lacks it, and it is because she lacks it that she desires it. Wisdom, the love of wisdom, which is what philosophy means, is this continual search for the truth and Plato seems to suggest that this search is unending. The philosopher is always looking for the truth and is never certain that she has found it, whereas the non-philosophers are always those who know that they have found the truth and it everyone else that is wrong. The fundamentalist and the philosopher, then, would be two very different people.
Is all of this still too abstract? How would we apply Plato’s dictum to our own lives. Most of the time, I think, if we were to be honest we don’t think for ourselves. Rather we think like everyone else. We have the same opinions, the same likes and dislikes, and we act in the same way. It is when we question this common opinion that we begin to ask ourselves how could we be ourselves. Now this might seem to be the easiest thing of all to do of all. Since aren’t we all ‘selves’ aren’t we already born a ‘somebody’, an individual. Yet this self that everyone is isn’t the self that we are after, because we want to be uniquely ourselves. This isn’t something that we born to be. Rather it is something we have to accomplish throughout our whole lives, something it is very possible to fail at.
The courage to be oneself, the courage to just be, is very difficult indeed. To conform, to be like everyone else, is, in comparison, very easy and what we always tempted to do instead. Philosophy isn’t about learning about philosophy just for its own sake, though it can become like that in a university sometimes, but how one faces the question of one’s own existence and how one gives meaning to one’s own life. This means being able to look inside of yourself and reflect about what is important to you, what are you values and desires and from that be able to choose the best life for yourself (which might not be the same as what other people might think is the best life for you), and once you have chosen to have the strength and commitment to carry it through.
What might prevent you from doing so is always the opposite of philosophy, distraction and boredom. Most of the time we just fill our lives in with doing stuff, as though are time were endless and we could always put off making a decision. It’s a bit like how we think about our own deaths. We are always certain that our death is some way ahead (especially when we are young) so we don’t really have to concern ourselves with it. Of course that isn’t true, because in fact our deaths could happen at any time and we wouldn’t know at all. What would it mean to live with that realisation? It would mean that you would have to ask yourself if you were really to die in the next moment would you be wasting your time as you are doing now just drifting from one moment to the next. The American writer, Hubert Selby Jr., writes about a ‘spiritual experience’ that he had, which is close to what I am describing here. He says that one day at home, he suddenly had the realisation that he was going to die, and that if he did die, he would look back upon his whole life as a waste because he hadn’t done what he wanted to do. He hadn’t become the person he wished to be. In that very moment of wishing that he could live his life again and not waste it, he would die. This realisation terrified him. It was this terror that was his spiritual experience, though at the time, he says, he didn’t realise that, he was just terrified. It was at that very moment that he became a writer. Not that he had any skill, or any idea of what being a writer was, but he wanted to do something with his life (at the time he was on the dole and in between doing dead-end jobs) and writing seemed the best thing (of course it could have been something else, but it was doing something with his life and not regretting it that was the important thing). He has learnt to become a writer by writing but it was his ‘spiritual experience’ that made he do it and also made him commit to it, not just give up because it was difficult.
I think what Plato means by philosophy, by an ‘examined life’ as opposed to an ‘unexamined one’ is what Hubert Selby Jr. means by a ‘spiritual experience’. I am not sure that you can do philosophy if you haven’t had one (though you might be very clever about philosophy). Notice that this experience hasn’t got anything to do with being intellectual or knowing a lot of stuff. It’s about facing oneself honestly and about a commitment to a life without knowing how it might end up.
 From an interview with Hubert Selby Jr. that you can find here http://www.cunepress.com/cunemagazine/news/articles/selby.htm. He also described pretty much the same experience in an interview with the American actress Ellen Burstyn https://www.youtube.com/watch?v=y1Zcf1maJlE&feature=g-user-f&list=FLA11eaq9wA-dQezPhEv8IWQ.