My 3 Biggest Challenges Self-Studying Philosophy (& Their Solutions)

Studying philosophy with the help of a teacher is hard enough. 

Doing it alone can sometimes feel silly and hopeless, prompting thoughts like “who the hell do you think you are?” 

But, if you stay the course, the intellectual results will occur — slowly, subtly, like a good philosopher laying out a nuanced argument, but emphatically in the end. 

In the spirit of helping you pursue your study of the heights of human thought, here are three of the biggest challenges I’ve encountered over my 4 years of self-studying and reading philosophy, as well as three tactics that have helped me overcome them. 

I hope it helps you on your journey of self-education in philosophy. 

Challenge #1: Finishing Hard Philosophy Classics 

How many philosophy books have I sacrificed at the altar of my ego? 

How many times have I said, “this is taking too long and I barely understand it and I need to hit my Goodreads reading goal of 52 books this year!” before dropping a book. 

Too many times, especially in my early years of self-education. 

Finishing hard classics, from Leviathan to something as short as The Republic, was a serious challenge for me. 

Now I know the reason why I kept struggling. I was trying to go too fast.

Here’s the one piece of advice I’d give to my past self: slow the hell down and enjoy the ride. 

Solution #1: Take it Slow 

Today will mark my completion of Nietzsche’s Beyond Good and Evil, a 200 page book. 

It took me about a month to get here — much longer than I’d expected and planned for. 

For three weeks in a row I had to leave my weekly planner’s checkbox next to “Finish BGE” unchecked. 

Another week, another failure to finish the book. 

The book was just packed with so many complex ideas, expressed in such poetic prose, that my brain could only handle around 10 pages per day. 

There were so many places to stop and ponder, to set up a tent and excavate. So it took me a while. 

But that’s okay! A duration with that classic is probably a good thing! 

If you’re self-learning philosophy, you have to be okay with taking it slow. You have to shake off the mindset of more books = more knowledge. It doesn’t. 

If you try to speed read something like Nietzcshe, going 30 pages per hour, you might be able to finish it in a week, but you’ll miss a hell of a lot of the beautiful hidden gems of thought. And your comprehension will suffer. 

Plus, you won’t finish the project having spent hours thinking about the text and writing down your reflections when you come across a marvelous passage or line. 

Therefore, you won’t have achieved the same level of insight and intellectual development as you could have had you slowed down. 

Philosophy is meant to be chewed slowly, like a fine steak. 

Chew too fast and you’ll choke, suffocating and failing to breathe in any of the wisdom. 

Being comfortable with spending weeks or months with a book has helped me finish books I would’ve thrown away if I was still under the persuasive idea of “I need to finish this ASAP to hit my reading targets.”

Readers of classics in philosophy, go slow. 

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Challenge #2: Spotting & Understanding Key Concepts in Classics

When I read The Republic, I left with an upsetting and demotivating feeling that I had missed the point. 

I suspected there were a lot of key concepts in the text that I had misunderstood or just missed entirely, passing them by like an unprepared tourist in a new city without a guide or map files past a national landmark in their pursuit to explore the city. 

I hated feeling this way, but for some reason I kept reading classic works without doing what students and scholars do when they’re confused — get help! 

Perhaps I felt like using secondary material was cheating, or doing so would hurt my ego. Whatever the reason, forgoing books, videos, and articles about the book, created by people who know a lot about the book, was a silly mistake, one that wasted me a hell of a lot of time. 

Solution #2: Use Secondary Sources (Learning Material About the Book)

Secondary literature refers to any piece of learning material that is about the classic book. It could be a YouTube video summary of a book or a Sparknotes page analyzing a chapter. 

It might also be an entire book, such as Nietzche’s Moral Philosophy, which I’m reading in tandem with Nietzsche’s Beyond Good and Evil and On the Genealogy of Morals in my DIY Nietzcshe course

In college, many students in philosophy actually read several scholarly articles about the books they study, each article elucidating, interpreting, or arguing with a certain aspect of the great book.  

When I started using secondary literature, I started to feel so much more knowledgeable about the classics I was reading. 

Using secondary sources to supplement your reading will also help with challenge number one, finishing hard books. 

Why’s that? 

Well, the more you understand the book the more satisfied you’ll be with your reading session. And, as a result, the more motivated you’ll be to open the book tomorrow. 

I go more in-depth on the benefits of secondary sources in my article One Piece of Advice Hurting Your Ability to Enjoy the Classics. Check it out. 

Challenge #3: Staying Consistent in my Self-Directed Studies

Studying philosophy without the prospect of earning a degree from your efforts is a noble endeavor. 

You have to truly love the subject and value the wisdom of these authors to stay the course. 

That said, all love affairs have their ups and downs, their moments of intense intimacy and those of drudgery and boredom. 

I’ve had my fair share of both, and when the latter takes the reign, my motivation to push forth has often faltered. 

Without anyone to hold me accountable but myself, I’ve at times given up and postponed my reading until I feel that spark again. 

Solution #3: Have a Project You Work on in Public

When your self-directed studies serve a larger project that’s meaningful to you, you’ll be more motivated to study, especially if it’s public. 

People are counting on you to teach them about what you’re reading. 

My project is this blog, and the book reviews I write on each book I read. In fact, at its inception, this blog was primarily for holding me accountable to do my reading. 

But a philosophy-based project can take many forms:

  • A series of essays about philosophical ideas. 
  • A YouTube channel where you talk about philosophy. 
  • A newsletter where you teach people a concept a week. 

If you don’t want to do it in public, that’s totally okay. You can work your way up to it. Start by just creating something with what you learn in philosophy. 

Over time your confidence in your expertise in the subject will grow, and you may be more willing to put your learnings out there for the world to see. 

As an added benefit, having a project will also make your learning stick more. It’ll force you to really learn the material, like a teacher would, instead of complacently missing key points and walking around with gaps in your understanding of an important concept. 

Bottom Line: Self-Learning Philosophy is Hard, But Rewarding

Teaching yourself philosophy is hard, but totally worth it. 

If you want to take a more systematic approach to learning the subject, check out the 7-Step Roadmap to Self-Learn Philosophy

If you want to be a crazy person and study it like a student in college — an ambitious one who actually does the readings — check out the DIY Philosophy Curriculum, which you get free when your join the autodidact newsletter.

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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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