The first column asks the question, "What is a philosopher?" Good way to start!
Here's my first take at an answer: a philosopher is someone who realizes how incredibly stupid it is to ask a question like "What is a philosopher?" because there are a million different answers, almost all equally meaningless.
Here's my second take at an answer: a philosopher is someone who can't resist trying to answer the question "What is a philosopher?" because his or her answer might be that one-in-a-million answer that is the most interesting and not entirely meaningless. Not "right," because in philosophy, there is no "right" answer, just more or less interesting ones. An "interesting" answer to a question, at least by philosopher standards, is one that provokes the listener into thinking more about both the question and the answer.
Here's my third take at an answer. This is a paraphrase of a quote from Franklin Roosevelt. He used the world "radical," not philosopher, but it's a fun take on it nonetheless: "A philosopher is someone with both feet planted firmly in the clouds."
Here's my fourth take. This one is rather cynical: A philosopher is someone who is paid to be professionally confused for years at a time.
Here's my fifth take, again rather cynical: A philosopher is someone who is professionally uninterested in making decisions.
Actually, four and five are not great answers, because it is entirely possible that someone could meet either or both of those criteria and not be anything close to a philosopher. But it was fun to write those sentences.
Sixth take. There are limits to questions. There are limits to what can be known merely by thinking. A philosopher is someone who is aware that these limits exist, and may even be vaguely aware of where they are, and completely ignores them.
Here's my final attempt to answer the question "What is a philosopher?": a philosopher is someone who understands this analogy: doing philosophy (not necessarily "studying" philosophy) is like driving a Ferrari: 99 times out of 100, it's either largely pointless, not worth the extra effort/cost, or potentially fatal. But that 1% of the time, there is nothing like it in the world.