Which books should I read first? If you’ve ever found yourself wanting to study a particular subject (e.g. theology, philosophy, politics, science, data analytics), whether it was for preparation for school or a new/hopeful job or just a hobby, you’ve likely asked yourself that question. Where to begin? As King Solomon once said, “the writing of many books is endless, and excessive devotion to books is wearying to the body” (Ecclesiastes 12:12, NASB). If that was true of his day, it’s certainly true of ours. As a general rule of thumb, applied to all the steps below, focus on the well-known and/or well-rated books. You only have so much time to read and you don’t want to waste it reading a less-than-noteworthy book. On this note, don’t be afraid to stop reading a book, even if you’re halfway through, if you find it to be uninteresting or unhelpful. Count it as a sunk cost and move on.
What follows is a simple guide based on my own experience of reading on particular subjects. An important truth to keep in mind is that learning is an iterative process. You’re not going to grasp everything the first time through; but with each pass, your comprehension will increase, along with your ability to read and engage with more advanced material. This reality undergirds the below steps.
1. Read introductory or overview books. At this point, you don’t know very much on the subject; you’re a novice. For this reason, you don’t want to jump right away (or straight away, as the English would say) into the deep end. You’re likely to drown in the depths of knowledge and specialized vocabulary. If you start reading a book on the subject and your experience is nothing but perplexity and frustration, you’re drowning. Get out of the deep end and wade in the shallows a little bit.
Allow me to provide an example. Let’s say you’re wanting to study politics. You don’t want to go right to Plato, Aristotle, Augustine, Locke, and the like. Not only is the style of writing different, but there’s historical contexts and specialized vocabulary that you’re not yet acquainted with. Rather, you should read a good book that provides an overview of political thought throughout history, which would undoubtedly summarize the key views and writings of the previously mentioned political philosophers, more or less. What this does is it allows you to become acquainted with the primary contributors, perspectives, writings, and vocabulary within the subject area. It creates a framework of the subject matter for you, allowing you to more easily construct an edifice of knowledge and thought, making it your own, as you move throughout the next steps.
2. Read important original authors. Now that you have a general knowledge of the subject, you can start building upon your knowledge by doing more specialized reading. Sticking with the example of politics, you may want to read Plato’s Republic and Aristotle’s Politics, two classic examples. Since you’re already somewhat acquainted with the subject, the dots will be more easily connected as you make your way through these original authors. It’s also good to read both older/ancient and contemporary authors, as this can give you insight into the development of thought over time.
3. Read authors from differing perspectives. This will likely occur naturally as you go through step 2, but it’s important to make this explicit. Recognize the differences in thought and argument as you read these authors. Compare and contrast. Note strengths and weaknesses. Ask yourself where you tend to lie on the spectrum. Sometimes you can find books that are specifically written from this angle. A good example in the area of politics would be The Great Debate: Edmund Burke, Thomas Paine, and the Birth of Right and Left by Yuval Levin.
4. Branch out and read related subjects. When you get to this point things can get really exciting. Not that the previous steps aren’t exciting, but you know what I mean. At this point, you’re ready to read more broadly, allowing you to see how other subjects relate to and strengthen your particular field of study. For example, philosophy, theology, and history are strongly related to politics. As a Christian, I recognize that the Bible has much to say in the areas of politics and ethics, and much of politics surrounds ethical issues. History takes place in the context of political regimes rising and falling, and so historical readings can provide greater context within which political theories were developed. An example would be the book, Elihu Washburne: The Diary and Letters of America’s Minister to France During the Siege and Commune of Paris, by Mike Hill, an old friend of mine. The point is that branching out into reading books from other genres or subjects provide greater context into your particular subject of choice. On this point I am reminded of a related comment by F.A. Hayek:
It may well be that the chemist or physiologist is right when he decides that he will become a better chemist or physiologist if he concentrates on his subject at the expense of his general education. But in the study of society exclusive concentration on a speciality has a peculiarly baneful effect: it will not merely prevent us from being attractive company or good citizens but may impair our competence in our proper field—or at least for some of the most important tasks we have to perform. The physicist who is only a physicist can still be a first class physicist and a most valuable member of society. But nobody can be a great economist who is only an economist—and I am even tempted to add that the economist who is only an economist is likely to become a nuisance if not a positive danger.Studies in Philosophy, Politics, and Economics
Once again, these are general guidelines that I believe will make your reading in a new area more enjoyable and effectual.
 Note, just because someone is a political philosopher does not mean that’s all they are. Augustine, for instance, was also a theologian.