An undergraduate recently asked me how to get started with philosophy. I was embarrassed to be taken aback by this question. How does one get started with philosophy? In the end, this is (most of) what I wrote in response:
One fruitful thing to do is to find some burning questions: questions that you think anyone should be able to answer because they’re very important. Then ask experts, such as your GTF and the philosophy faculty here at the university, what you should read to help you grapple with these questions. Read those texts, always with an eye to formulating objections. It’s the highest sign of respect that you can pay someone to object to their theory. It shows that you take the idea seriously enough that you care whether it’s right or wrong. After you’ve formulated your objections, try to respond to them on behalf of the author. Imagine what she or he would say in response to these objections. This is the essence of philosophy. Sometimes we call it “dialectic,” meaning that it’s a constant back-and-forth about an important question. If you learn to do this well, you will be an expert philosopher.