Self-Study Philosophy (A 9-Book Plan for Beginners)

If I could go back and redo the beginning phase of my self-directed studies in philosophy I’d start by taking a more systematic approach to my reading. 

Instead of diving headfirst into the classics and jumping haphazardly from Aurelius to Rousseau to Aristotle, I’d create a reading plan that, on top of a few accessible classics, also included introductory books and technique books to ground me in the basics of philosophy as a practice.  

This would’ve saved me some serious headaches and confusion, and helped me get more out of the classic works. So, to help others avoid my failings, I’ve created this reading plan for beginners self-studying philosophy. 

It contains nine books spanning three categories, each of which serves a unique function: 

  • Introductory Books That Give You a Tour of the Field 
  • Classic Works of Philosophy That Beginners Enjoy
  • Technique Books That Help You Read and Do Philosophy

As for reading order, I’d start with the first book in the first category, and then cycle through the three categories until you’ve finished all nine books. 

So you’d do one from Introductory books, then one of the Classics, then a Technique-Based book, and so on. 

I’ve found this cyclical reading approach satisfying because every few weeks you’re reading a different type of book. Nothing gets stale. 

I’m currently using this method to self-study English Literature so that I don’t have to read 8 weighty Victorian novels in a row. 

After reading these nine books, you’ll be ready to tackle harder classical works of philosophy, debate big ideas, and self-learn philosophy with greater efficiency and success, perhaps with our 7-step self-education roadmap.

Books That Introduce You to the Field of Philosophy 

Introductory books are books that welcome the newcomer to philosophy and give them a tour around this wonderful if often dizzying academic field of study.  

If you read all three introductory philosophy books below you’ll learn some of the major problems of philosophy, understand the development of western thought and its key philosophers, and, lastly, get a firsthand account of what it’s actually like to engage in philosophical inquiry (you might go mad and walk naked through the streets!). 

The Problems of Philosophy 

The Problems of Philosophy is a work by Bertrand Russel, a famous British logician and philosopher, and it’s been essential reading for philosophy students since its print date in 1912. 

In about 100 pages (my copy’s clocks in at 75), Russell introduces you to some of the major questions of philosophy, like “does matter exist?”, and discusses how key philosophers from Bishop Berkeley to David Hume have attempted to answer these deceivingly simple questions. 

Russel is clear and precise in his writing, and takes care to explain things so a true beginner can understand them. That doesn’t mean it’s all easygoing. Some of the ideas about epistemology and metaphysics that he presents are complex and abstract. 

I think that this mild difficulty is actually a good thing for a beginner. It makes the book a good testing ground for your curiosity in the subject. It’s a good preview for some of the more challenging works you’ll come across in your self-directed studies. 

Further, Russell not only introduces you to some of the main theories and issues in the field, but also shows you what reading philosophy is like — slow, careful, at times frustrating, and, ultimately, rewarding. 

On some pages I found myself spending five to ten minutes rereading and mulling it over, especially the ones on epistemological topics, just to make sure that I truly grasped the concepts and their implications. 

Overall, it’s a classic intro philosophy book that keeps ending up on desks of new philosophy students around the world. 

I found that it gave me a deeper appreciation for what philosophers do, and how they explore all the considerations that make a seemingly simple question like “is that table brown?” intriguingly complex. 

The History of Philosophy

The History of Philosophy is a huge and sweeping book at 700 pages, one that I admittedly haven’t actually completed, but that I keep going back to when I want to learn more about a specific philosopher or philosophical movement or era. 

That’s not to say it serves best as a reference book. Far from it, A.C. Grayling does a great job of tracing the development of philosophy 2,500 years from the pre-socratics all the way to the modern day, and he does it in an entertaining and accessible way. 

He shares not only the arguments and ideas of history’s greatest philosophers, but also their foibles and funny anecdotes, like how Thales, a pre-socratic philosopher who believed water was the originating source of all things, died of heat stroke while watching the Olympic games. Talk about irony. 

The book also touches on other philosophical traditions outside of the West, such as the philosophies of Buddha and Confucius, making this a more expansive work than Bertrand Russell’s The History of Western Philosophy. 

Overall, this is an excellent way to learn the major ideas and thinkers of philosophy. Plus, you’ll meet philosophers you want to learn more about, and then you can go buy their works to dive deeper into the interesting ideas this book summarizes. 

Zen and the Art of Motorcycle Maintenance 

Robert Pirsig’s Zen and the Art of Motorcycle Maintenance is two things at once — 1) a fictionalized autobiography about a philosophy teacher and his motorcycle journey with his son, and 2) a philosophical inquiry into how to live a quality life. 

It’s a good book for beginners to read because it shows you a philosopher reasoning and thinking, at times even going mad in an effort to answer the questions that intrigue him.  

I read this book early in my self-directed studies, during a backpacking trip through Europe after graduating college, and it completely transformed my outlook on my relationship with work. I found myself more open to losing myself in work I beforehand considered nothing but frustrating. 

“When you want to hurry something, that means you no longer care about it and want to get on to other things.” — Robert Pirsig 

For example, after I returned from a 2-month voyage, my father and I assembled a squat rack and bench together to put in our garage. 

The old me would’ve avoided the task or groaned my way through it, but having read Pirsig speak so lovingly about the zen of working as a mechanic, I decided to treat it like an opportunity to create something, as well as bond with my father.   

Instead of being boring or tedious, the work became satisfying. Sure, we encountered problems and felt frustration, but we solved them, and the thrill of success much outweighed any annoyance caused by having to redo a step or drop down on our knees to search for a missing screw. 

Now, having read it a few years ago, I don’t remember all of the specific scenes or the philosophical arguments he elucidated, but I do take his zen mindset with me whenever I encounter an issue that requires patience and problem-solving to fix. 

Bonus Book: If you like politics and want to get a survey of political philosophy and its major debates and thinkers, check out An Introduction to Political Philosophy by Jonathan Wolff. 

I’m currently reading it and its helping me see how different thinkers like Hobbes and Locke are related to one another, either attacking or developing on each other’s arguments. Philosophy really is a great, ongoing conversation. 

Philosophy Classics That are Accessible to Beginners

Next are some of the more accessible classics — books that scholars and philosophers have been interpreting, reflecting on, arguing with, and referencing for centuries. I’ve listed one from Ancient Greece, one from the Stoics, and one from the Renaissance.  

Don’t mistake accessible with fast. These books still reward slow and careful reading. They’re just not as complex as something like Hegel. Plus, their writing style is clear, and to understand their major points you don’t need any knowledge of the others works they’re responding to. 

Plato’s Five Dialogues

I read these dialogues during the pandemic when I was taking an online course from Yale called Introduction to Political Philosophy, which I highly recommend.

I remember being struck many of Socrates’ arguments, especially the one behind his decision to stay in prison and face the death penalty even when he had a way out. 

The collection, Plato’s Five Dialogues, translated by G.M.A Grube, shares five conversations between Socrates and his contemporaries on such topics as political obligation, citizenship, the immortality of the soul, impiety, and morality. 

These dialogues are a great starting point for someone self-learning philosophy because they introduce you to Socrates, the man who many call the originator of the Western philosophical tradition. 

It also helps that these dialogues are pretty short, about 20 or so pages each, and written in dialogue-style like you’d see in a novel — a few people debating and going back and forth. 

To see what the socratic method in action, and to see how those involved in a debate can remain respectful, open, and searching throughout the process, read this book. 

Seneca’s Letters From a Stoic

The Stoics have experienced a bit of a heyday in the recent decade thanks to writers like Ryan Holiday who are devoted to bringing the remarkably practical philosophy to the lives of modern people.  

One of the most popular Stoics in Ancient Rome was Seneca, and one of his most famous works was, and still remains, Letters From a Stoic.

The book weighs in at 250 pages, and is filled with thoughtful advice on various aspects of life, from how to deal with loss to the correct way to approach making friends. It will give you a great introduction to the Stoic school of thought. 

One piece of advice that sticks with me is that you should be incredibly skeptical and careful when deciding if someone deserves to be your friend, but once you do, you should treat them like a partner in life and share everything in your soul and mind, the good and the ugly, with them without fear or embarrassment. 

The impressive intentionality Seneca brought to his days certainly inspired me to do the same, and I think it’s an important book for anyone to read, not just those looking to learn philosophy on their own. 

We’re all in need of more mentors in our lives, and Seneca certainly serves the role with thoughtfulness and grace, if at times a bit of cold pragmatism. 

Rousseau’s Political Writings 

This collection of essays and political treatises was another book I read while taking the online course Introduction to Political Philosophy. Rousseau’s Basic Political Writings is accessible to beginners because most of the ideas are easy to understand, and so is his writing. 

I recommend it also because of its fresh and often controversial ideas, its beautiful prose, and its influence on not just the field of political philosophy but also on the trajectory of European history, as his theories were alive and active in the minds of many French Revolutionaries.  

This specific collection includes the following works: 

  • On the Sciences and Arts
  • On the Origin of Inequality 
  • Political Economy
  • The Social Contract
  • The State of War 

I especially liked the first essay, Discourses on the Sciences and Arts, where he argues against common sentiment and states that the development of the arts and sciences is a net negative for society, not a net positive. 

Overall, this book a great collection for any beginner in philosophy looking to learn about enlightenment politics, economics, and philosophy all from one book. 

Books That Help You Read & Think Like a Philosopher

When I first read The Republic I got almost nothing out of the exercise because I approached it more like a novel than a work of philosophy, reading it too quickly and rarely stopping to investigate the arguments or to think over how an idea relates to what I already know. 

The below three books will help you avoid this pitfall and approach philosophy books as a philosopher would. They’ll help you improve at understanding, analyzing, and critiquing complex arguments, as well as think about philosophical questions and ideas. 

How to Read a Book

Before I read How to Read a Book by Mortimer Adler I was under the impression that I was pretty damn good at reading dense non-ficiton books. 

He showed me that, although I had the basics down, reading is a skill, like writing or soccer, that I could seriously improve at through practice and study. 

In the instructive guide, Adler covers the different types of reading — elementary, inspectional, analytical, and synoptical reading — their purposes, and how to do them effectively.

He also introduces you to the different types of books and genres and shares the best ways to approach each one. 

After studying this book and applying its tactics to your philosophy readings you’ll comprehend more and be better able to form a critical opinion about the books and the arguments they advance, an opinion that you can communicate with other people in conversations and in writing. 

The Philosopher’s Toolkit

Philosophy books consist primarily of arguments. It’s therefore a good idea to become comfortable with identifying, analyzing, and judging arguments, as well as creating your own. 

The Philosopher’s Toolkit helps you do just that, providing you with the concepts and thinking strategies to more effectively verify and critique the arguments in the books you read. It helps you do philosophy. 

The book begins by teaching you the fundamentals of logic and how arguments work — their various parts, different types of arguments, what makes one valid or invalid, etc., 

Next you’ll learn about common fallacies, important philosophical concepts, tools that great philosopher have employed to critique the works of others. 

Weaved in throughout the book are references to great arguments and philosophers, so you’ll also get some history of philosophy while you read it. 

Not only will this book help you come up with more informed opinions about the philosophy books you read, but it will also help you create airtight arguments that convince people and win them to your side of thinking, a skill that’s applicable to almost any field or profession. 

The Socratic Method: A Practitioner’s Guide 

Eminent philosophers, and scholars in general, reach greatness not just because they can figure out sound answers to tough questions, but because they know which questions to ask in the first place. 

Effective inquiry begins with a smart question, and Socrates was the grand master in this regard. He was so good at asking questions and showing smart people how little they really knew about their subjects of expertise, that he was actually thrown in prison and sentenced to death. 

The Socratic Method, A Practitioner’s Guide, will teach you the various ways Socrates formed his questions, and his reasons for doing so. The result of learning his method is that you’ll become better at asking questions yourself. 

You’ll also become better at identifying gaps in your knowledge around a certain topic, which will lead to both humility and an opportunity to fill those gaps and become wiser in the process. 

What Books to Read Next? 

If you conquer this reading list and still have a thirst for more self-directed study in philosophy, you should focus now on reading the classics. 

Consider picking one major topic or idea — democracy, happiness, war, etc., —  and reading what different philosophers had to say about it. In doing so you’ll become a relative expert on that issue and of course better at philosophy as well. 

Or you could:

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Alternatively, you could start from the beginning of philosophy (Plato) and work your way through the great works of philosophy chronologically, thereby cultivating a strong sense of the development of the field and its ideas. It’s an insanely structured way to read but if you like that sort of thing and adore Western philosophy go for it. 

Keep in mind that although reading plans like these are helpful, the best thing you can do when deciding what to read next is to follow your curiosity. 

Nothing will keep you more motivated than that, and, for the most part, reading philosophy consistently and closely is more important for your development as a thinker than what you read. 


After graduating college with an econ degree I realized I was still anything but well-educated. Over the last 4 years, I've been trying to fix that, autodidact-mode — by reading books and engaging in self-directed study across multiple subjects. On this blog, my goal is to share my learnings and help others get a well-rounded education outside of school. Education, after all, is a lifelong process, one well worth the investment.

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