How to Get a Well-Rounded Self-Education Outside of School (My Approach, Strategies, & Mistakes)

“I began my education at a very early age; in fact, right after I left college.” — Winston Churchill

Have you ever heard a public intellectual speak or read the work of an erudite writer and thought to yourself:

“They must have such a well-rounded education; it seems as if they can talk on any subject with eloquence and precision; how can I get an education like that outside of school?” 

Over the past four years I’ve been thinking a lot about that question, and trying to answer it through experimentation with self-study (you can read my story here). 

Some of the books I read over the last 4 years.

After graduating college with an econ degree, I realized I was still insufficiently educated, and severely under-read. 

What I wanted was a broad foundation in the major subjects I was interested in but didn’t study in school — philosophy, history, literature, politics, a few of the sciences, art, psychology, etc — as well as some familiarity with the classic books and the better reading, thinking, and writing skills that flow from serious reading. 

And so I started trying to get this education on my own, autodidact-mode. 

Today I’ll share what I’ve learned after my first four years of self-education and wide reading, including my four-pronged approach to lifelong learning, several strategies for effective self-directed study, and some mistakes I’ve made along the way. 

These are my ideas about self-education, some of them won from the trenches of self-experimentation, others based on my research of autodidacts, thinkers, and creatives I look up to.

They aren’t rules. Everyone’s education will be unique, so keep that in mind as you read. 

I hope in reading such a guide that you’ll find a few tactics to try out for yourself, and gain some food for thought regarding your own well-rounded self-education and how you want to approach it. 

Who is this Guide For?

“Self-education is, I firmly believe, the only kind of education there is.” — Isaac Asimov

I hope this helps anyone give themselves a well-rounded self-education.

Whether you’re forgoing college, or went to college already but feel like you didn’t get a chance to study the subjects you wanted to, then this guide is for you. 

I think this is a lot of people; we go to school too young and without finding our authentic interests. Plus, a lot of us have to specialize in technical subjects to make the degree price worth it. 

Really, this guide will apply to anyone who likes to learn and wants to start moving towards their intellectual potential. 

Before we jump into what I call the 4-pronged approach of self-education, I wanted to call out my free 8-step checklist for self-learning the basics of any new subject systematically:

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Now let’s jump into the meat and potatoes of the guide.

My Favorite 4-Pronged Approach to Self-Education 

“Education is not just about going to school and getting a degree. It’s about widening your knowledge and absorbing the truth about life.” – Shakuntala Devi

After four years of self-study, I’ve landed on a 4-pronged approach to self-education and lifelong learning that is giving me a great balance of breadth and depth. 

I’ll review the prongs and then show you how I’m doing each one: 

  • Gain Mastery in One Subject: You can think of this as your grad degree. I like to also add a concentration to this; a subdiscipline of the subject (e.g., American History could be a concentration for someone wanting to focus on history). Building mastery in a subject not only opens doors, it’s also great for your self-esteem and confidence. 
  • Become Well-Read in 2-4 Subjects: This is where you’ll gain expertise in a few subjects you find fascinating, whether that’s art history, philosophy, physics, or Russian literature. Read how to become well-read to learn more. 
  • Build a Basic Foundation in Each Major Subject: Think of this as your liberal arts portion of your self-education, where you’ll get at least a solid enough understanding of the basics to converse well about the subject with someone who majored in it. 
  • Quickly Learn New Topics As-Needed: This is the part where you quickly learn smaller topics that will help you achieve your goals or that are just super fascinating to you. It could be discipline, a new career skill, plant biology, or any diversion from the base of your education (the first three prongs). 

I like to have this approach in the back of my mind because it gives me the guiding principles that will help me make decisions, short-term and long-term, about my self-education. 

When you know your educational north stars you’re better able to decide which book to read next, what subject to tackle this quarter, or which subdiscipline to build a DIY curriculum around. 

I like to think of the four-pronged approach as a 4-year guide, but you can also extend it over a longer period of time, a lifetime even.

My Current 4 Prongs of Self-Education 

Here are my current four prongs for the next couple years:

  • Mastery: Literature (with a concentration on classic novels). 
  • Well-Read: Western history, philosophy (mostly political phil), and nature (sort of my own combo of environmental sciences, religious studies, and nature writing – I love to hike in the mountains so thought this would enhance the experience). 
  • Foundations: Pretty much all the arts, humanities, social sciences, and a few of the natural sciences. I should probably also learn some basics of STEM fields to balance myself out, but we’ll see. 
  • As-Needed: This prong gives you freedom to take breaks from your long-term education goals. Life tells you what you need or want to learn quickly and you go learn it. For me, I’m learning a lot about online business right now because I’m growing this blog.  

If you take a look at my self-education plan for 2024, you’ll see that most of the DIY curriculum courses I’m taking fall into one of the subjects I’ve listed in the “mastery” and “well-read” prongs. 

By the way, you can also apply this 4-pronged self-education approach to skills as well, mastering one skill, becoming great at 3, etc., 

It’s just a great way to think about becoming well-rounded while also gaining specialization. You get the benefits of both — expertise and cross-pollination. 

You become a master and a polymath (wondering if you have polymath personality traits?)

What if You Don’t Know Which Subjects to Focus On?

It’s likely that if you’re just starting out in self-education you won’t know which subjects are most interesting to you. If you do, that’s great! 

If not, start with the Foundations prong (third one down) and then identify in your reading and studies which subjects you’re enjoying the most. Move those into the well-read prong. 

After you’ve spent some time really studying a few, taken enough online courses and read enough books, I can guarantee one will call out to you as your favorite subject. That’s at least what happened to me with literature. 

You can always move them around as your curiosities change. Maybe over the next four years your focus is political science. And then the next 3 your focus is botany. 

You’re not locking yourself in forever. 

However you choose to use it, I’ve found this 4-pronged approach to be an extremely helpful tool for planning out your self-education.

Wondering why self-education matters so much? Read the 10 reasons to engage in it regularly.

Strategies for Getting a Foundational, Broad Self-Education

I usually like to write step-by-step guides, but I think getting a well-rounded education is far too personal an endeavor to prescribe something so specific. 

Everyone’s journey in self-education will differ dramatically.

It’s also something I’m still learning how to do myself — 4 years is still beginner territory I think. 

Therefore, I believe the best way for me to help you is to share some of the principles and strategies that have worked well for me over the past four years of educating myself. 

I hope that by seeing how I approach self-education you’ll be better able to craft a self-learning plan that works for you. 

Focus on Reading Books, Especially Classic Ones

Whenever I read biographies about the great men and women I look up to — Teddy Roosevelt, Jack London, John Adams, Virginia Woolf — I’m always astounded and inspired by how much they read and how seriously they took it

And when I peruse their libraries (check out this series by AoM), I can’t help but notice that a large portion of their education came from reading classics. 

I find that many of the public intellectuals, thinkers, and writers from the 20th century and today also spent plenty of time wrestling with the Great Books — those most influential to the intellectual tradition and culture.  

I suspect that it was these facts about the educations of the people I looked up to that inspired 23-yr old me to start reading the classics. 

And I know it was the benefits I got from reading them — to my thinking, my knowledge, my spirit, my communication, my understanding of human nature and myself — that made me keep them front and center of my self-directed studies, even when they were a challenge (after all, it’s that challenge that sharpens our intellect). 

So, although courses, modern books, podcasts, YouTube, and textbooks are all useful tools for self-learning, I am persuaded that the great books, across all the subjects, should play a key role in any self-education plan.  

For more reasons to consult the great thinkers of the past, check out my article on why you should read more old books

Study Topically Across Your Well-Read & Mastery Subjects

At first, I studied haphazardly, jumping from topic to topic and not really gaining much more than a surface-level understanding of each topic. 

I think that was okay to start, as a way to just test the waters of different subjects and see what I liked. 

But now I’m doing more topical studying. This way I can at least become somewhat well-read and conversant in a topic before moving on. 

Reading topically is picking a topic and reading 3-5 books on that topic before moving onto the next topic. 

When I say across subjects, I mean the ones in your Mastery or Well-Read slots of the four-pronged self-education approach I discussed above. 

Though feel free to read outside of them too! This is just how I’m doing things. 

Here are the topics I’m self-studying this year and how I’m doing it:

  • The American Civil War (5 books) 
  • Modern Poetry (a hefty haul of poems and the Yale Online Course)
  • Nietzsche (3 books and 1 lecture series)
  • Classic Novels (9 books)
  • Nature/Solitude (6 books and a few essays)

As you can see, they fall into my focus disciplines of history, literature, philosophy, and nature.

I really like doing this topical studying format because it allows you to build a strong foundation in whatever it is you’re learning, say existentialism or artificial intelligence.  

You become a mini-expert. And you really find out if it’s something you want to perhaps study over the long-term. 

It also kind of feels like you’re taking a college course in it, especially if you actually do take an online course or create a DIY course around the topic. 

Integrate Projects / Essays into Your Studies

It’s taken me a while to come to terms with the fact that the act of turning your readings and studying into something is a much better way to internalize what you’ve learned than just consuming with no output. 

In school we are assigned tests and essays, as they help us remember what we’ve learned. (Ultralearning makes the power of testing yourself abundantly clear). 

But when you’re an autodidact, it can be hard to get yourself to do these things without someone forcing you to, since it’s hard work. 

So, it’s only recently that I’ve begun to integrate testing into my self-directed learning. The payoff to retention and depth of understanding has been incredible.  

Write a Book Review for Everything You Read

I’ve started writing reviews for every book I read. (check out 10 reasons to review your books). 

The review process is a forcing function for deeper reflection and more attentive reviewing of my notes and marginalia. 

I’ve found that the act of writing the review clarifies my understanding of the content and helps me formulate an informed opinion on the subject of the book, and on the book itself.

Your projects don’t have to be book reviews, though I have seen tremendous benefits to retention and comprehension from doing them. 

Other Self-Testing Methods

Self-tests can also be essays where you answer some question. This works well when you’re studying a subject topically. 

For example, if you were studying the civil war, you organize your five books around helping you answer some big question about the civil war that will be your essay topic. 

You could also create a YouTube channel or Twitter account or something around your top subjects and share your findings with the world. 

Or, you could actually find an exam or essay online at MIT OpenCourseware or on some college syllabus and do those. 

Anyway, testing is probably a bit advanced, so if you just can’t get yourself to do it at first don’t worry so much! 

Later you may naturally start to feel the urge to write about what you learn. I know I sure did. 

Use Online Courses or DIY Courses

There are so many great free and paid online courses these days, especially for beginner-level intros to major academic fields.

My favorite website is Open Yale Courses, where you can watch lectures and see the readings and assignments from real Yale courses. 

Right now I’m taking one on Cervantes’ Don Quixote.  

Some other great online course sites are:

  • Coursera: They have a lot of free courses but also some paid ones with certificates. 
  • YouTube: If you type “{subject} lectures” you can usually find some recordings of college courses. 
  • The Great Courses: These courses cost money, but they’re usually high-quality, and they have a ton of interesting lectures by professors on humanities subjects. 

If you can’t find an online course that covers your topic, then create your own course for it. Sometimes I’ll do this even if there is an online course covering it, simply because I don’t like how the course is structured (a lot of courses online are more edutainment than education). 

To create a DIY course, find 5-7 books on the topic, including one textbook or introductory book, and get reading. 

If you need help figuring out what books to read, or how to structure your course, I highly recommend using MIT OpenCourseWare as a resource. There you can find syllabi for hundreds of MIT University courses. 

You can also integrate videos or podcasts into the course as well to give you an audio element, and even create assignments for yourself. 

Example DIY Course

For example, next month I’m taking a DIY course on Nietzsche, where I’ll be reading 3 of his major works — Beyond Good and Evil, On the Genealogy of Morals, and Thus Spoke Zarathustra. 

I’ll also be listening to 7 lectures on Nietzsche that I found on YouTube. As for assignments, I plan to write an essay on his works (I don’t know what question I’ll try to answer yet since I don’t know enough about his writings). 

And for accountability, I’ve recruited a classmate, my friend Ted, who will be reading and discussing these works with me over Zoom every 2 weeks. 

Use Self-Education Roadmaps to Gain Footing in New Subjects

A self-education roadmap is a step-by-step guide that helps you gain an intellectual foundation in a new subject. 

In other words, it’ll make you conversant in the most important concepts, and you’ll walk away with a mental map of the discipline as a whole, since you’ll have been exposed to its major subdisciplines. 

As you get further into any roadmap, the content gets more difficult and the subject matter more narrow, just like you might find in a university degree. 

I’ve created a lot of self-education roadmaps over the last year, for various subjects. It’s quite addicting.

It takes a fair amount of time and research to build one out. 

You have to get an understanding of the outline of the subject, see how colleges are teaching it and how people have learned it, and figure out the best free resources and books out there to build the ramp towards foundational understanding. 

But it’s so worth it. 

To learn how to create your own self-education roadmap and break into any new subject, check out my free 8-part checklist, which you’ll receive when you join the autodidact newsletter:

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If you don’t want to create your own, check out the ones I’ve created. For example, here’s one for political science, and another for philosophy, and a third on botany.

You don’t have to follow them verbatim. 

They’re more so informed suggestions. Feel free to tweak them to fit your educational aspirations and learning style. 

Make Flexible Reading Plans

Every year I like to create an annual reading plan. Usually I create 4-7 categories I want to explore and then pick books for them. 

So you might say this year I’m gonna read mainly within these categories: 

  • The US Presidents
  • Political philosophy 
  • Classic satire novels
  • Contemporary fiction
  • Evolutionary psychology 

Then you can choose which books you want to read for each.

Lately, many of the books on my plans have overlapped with the courses I’m taking on my own. That’s just because I really like reading topically and becoming a slight expert in something. 

For instance, this year I’m taking 5 online or self-made courses and so about 30 of the 50 books I plan to read are for those courses. 

This gives me 20 books to play with. It makes it so I don’t feel suffocated by structure. It allows me to go read that book that a friend recommended to me or that I saw during one of my romps through the bookstore.  

Reading plans help you set your reading intentions for the year. 

I like to make them have synergy with my four-pronged self-education goals as well as the DIY courses I’m taking, but that’s just what has worked well for me. 

I find it motivating to know that all my self-education plans work together to achieve my learning goals. 

Either way, it’s a thrilling process to get to see all the books you’re going to read the coming year. 

Further reading: How to create an annual reading plan.

Create Entire DIY Curriculums 

After you’ve been engaging in self-education for a while, you might discover that you are drawn to one specific subject — your mastery subject perhaps. 

Maybe you want to gain the equivalent of an undergraduate education in that field of study? 

To do so, create a DIY curriculum, a self-made, self-directed curriculum that approximates what you’d find at a top university (albeit without any sort of political aims corrupting the free pursuit of knowledge). 

I did this recently. 

I created a DIY curriculum for philosophy that’s based on Yale’s requirements for its students majoring in philosophy. 

It consists of 12 courses —some self-made, some online college courses — and, since I love the classics, it requires plenty of those as reading. 

This is a longer commitment than any of the other self-education strategies we’ve discussed, so I’d recommend doing it only once you’ve truly identified that subject that drives you wild with curiosity time and time again. 

Although, you could also create a curriculum consisting of classes from multiple subjects. This is after all a great way to develop intellectual range. 

I’ve played around with the idea of creating one for American Studies to learn more about my home country, where I’d take 4 classes on American Lit, 4 on American History, and 4 on American Politics. We’ll see if I ever get around to making and pursuing it. 

By the way, check out my article on why solitude is essential for autodidacts, polymaths, and aspiring thinkers and creatives of all sorts. 

Use “Crash Coursing” to Learn A Single Topic Fast

Lying in bed the other morning, I was too lazy to get up, and so started to scroll on YouTube, letting the algorithm control my experience. 

Then, I remembered something a friend had told me that reminded me of a better way to use my time. 

He said he learned the basics of rental law really quickly through a learning method he called “crash coursing”. 

Basically, it’s just going down a wormhole on the internet. 

He reads an ultimate guide article and then whenever he comes across a term he doesn’t know he opens a new tab to an article about that term. 

By the end of the two hours he’s got a pretty solid understanding of the topic.

That morning, I wanted to learn about Literary Criticism, because it’s something I’ve read a lot of but didn’t really know how to define. 

My website of choice was Wikipedia, and pretty soon I was on a page reading about hermeneutics and other esoteric topics related to lit crit that just fascinated me. 

I find this method, crash coursing, to be the most satisfying and quickest way to get the barebones of a small topic. 

Try it out when you need to beef up on some term that’s been holding back your studies, or when you just need to learn something for practical sake.

Tips for Getting a Well-Rounded Self-Education

Here are just some helpful truths about self-education that I’ve stumbled upon over the course of four years of doing this practice almost every day. 

Let Your Curiosity Take the Wheel

The best part about self-education is that you’re free to study what interests you and, unless it’s totally necessary for your development, ignore what bores you. 

Curiosity is the best source of motivation to learn. As long as you’re studying stuff that thrills you, you’re going to hit the books and take those online courses.

I’m often reminded of this line from Martin Eden, a novel by Jack London about a self-made intellectual and writer:

“The more he studied, the more vistas he caught of fields of knowledge yet unexplored, and the regret that days were only twenty-four hours long became a chronic complaint with him.”

Jack London, Martin Eden

The struggle is that sometimes we forget self-learning is supposed to be enjoyable. (I often do and have written about it in this article).

Sometimes we fall back into thinking there are certain things we must read or know about in order for society to respect us. Don’t do that. 

Always give your curiosity veto power over any reading list or syllabus, or else you might suffer the demotativing effects of doing something your heart isn’t truly invested in. 

This is why at the start of every roadmap I say to feel free to make it your own and skip around. I want people to use them as templates, ideas, not rulebooks. 

We need to learn to guide our own educations, shake off the mindset of the student at the foot of the teacher. 

Guides help but not when they become prisons. 

Find Role Models to Fuel Motivation

Autodidactism is at times a lonely endeavor. You can feel like you’re working in the dark, with very little certainty of your progress. You can feel doubt. You can worry you’re spinning your wheels.

The best way to overcome these feelings, other than monitoring and testing yourself in writing and conversation (where I’m sure you’ll see gains), is to have role models. 

These are people who did great things with the knowledge and mental skills they obtained primarily through self-directed study. 

Here are some pieces of motivation:

  • Jack London and Louis A’mour were both self-taught novelists.
  • Abraham Lincoln’s formal education amounted to about 1 year; the rest he gained by reading and experience. 
  • Churchill said his true education really began after college.
  • There are countless authors, even history writers, who did not study their subject in school but instead studied it madly outside of school and wrote a book on it. 
  • Look at the tech entrepreneurs Elon Musk, Bill Gates, and Steve Jobs.

Go find someone who used their time wisely, read lots of books, experimented, and made something great out of their education. 

Put a picture of them on your wall, or keep some quotes nearby. Whenever you’re feeling uninspired to learn, or doubtful of the purpose of reading, go meet with your models. They’ll set you back on the path to wisdom and knowledge in no time. 

Here’s a cool tidbit about Emerson’s autodidactism, from a The CuriousWorthy article:

“One could argue that the heart of Emerson’s true education occurred outside of the classroom. Although he attended Harvard University, he was an unexceptional student who graduated without distinction. He felt at odds with his peers and kept mostly to himself. He however read extensively and throughout his life was exposed to and influenced by the ideas of those such as Thomas Carlyle, Montaigne, Goethe, and Swedenborg. His true education, he conducted himself.”

My biggest inspiration is probably Jack London, a self-taught writer and intellectual, who recounts his self-education years in thrilling detail in his semi-autobiographical novel Martin Eden (check out three reasons all autodidacts should read this book).

Have a Notetaking System 

My note taking system has been in flux ever since I began my self-education. 

It’s honestly been the hardest thing for me to nail down, especially since I’m studying multiple subjects and reading different types of books for different purposes. 

This keeps me from having a set system because the genre of the book and the purpose of reading determines the ideal note taking method. Therefore, I need multiple systems, and I’ve slowly been figuring out how to optimize each one. 

My note system for a classic literature book review is totally different from the system I use when reading history. 

And then there are lecture notes too. 

And then there is review of notes, categorizing them, and using them. 

I’m not going to get too into the weeds here. I’ll probably write an article on it later. 

Don’t worry about this as much as I am. I’m neurotic about notes for some reason. 

I think it’s because they have to do with a sense of “losing” something. By failing to take a note, I may lose it, but by taking too many notes, I lose the will to review them. The balance is what I’m calibrating for. 

Anyway, you might already have note-taking systems that work for you. 

If not, and if you’re a beginner, focus on capturing the main takeaways from each book you read, perhaps one from each section. And then be able to summarize the book and express its key arguments or themes. 

Your system should develop as you grow as a self-learner and identify what you need out of a notetaking system. 

For online lectures of 45 minutes in length, I try to write out 10 notes for each one. 

Here’s the current note doc for the course I’m taking on American Literature. 

I also like the idea from ParkNotes to use one journal for each DIY course you take, and fill it up with notes so it’s like your expert guide to the topic. 

Pro Tip for Organizing Notes: I like to use Evernote to categorize my most important notes by theme, and build out a sort of second brain. I also use a physical commonplace book to capture the snippets of wisdom that are most helpful to me. 

Read Some Current Events

Reading about current events that are closely related to the subject you’re studying will allow you to draw connections between theory and practice, concept and real-world impact. 

For example, if you’re self-studying psychology, it makes sense to start reading the Psychology section of Scientific American

This way you’ll see real-world psychologists and researchers providing their findings, and the concepts and theories you’re learning about will take on a whole new level of importance. 

As a sucker for political and social issues and the views on them, I watch a lot of political commentary and debate.

I’ve found that my knowledge of political philosophy and history greatly enhances my ability to think about these events and contemporary arguments in an informed, balanced way

I’ve also noticed that watching the news helps me better understand the ideas and events I’m reading about in my history and political philosophy books. It’s a reciprocal relationship. 

Further, the news helps me remember what I’ve read by promoting retrieval practice. 

For instance, if you hear about an economic policy to make more affordable housing, it might remind you of something you read in Adam Smith or Max Weber or any other social thinkers or lectures on the topic. 

That act of going back to remember what you learned, and using it to give you perspective on the news story, hammers it deeper into your memory. 

Oh, and knowing something about current events is often good conversation ammunition as well, if that matters to you. 

For smaller self-education tactics, check out my article on 14 ways to educate yourself every day.

Mistakes I’ve Made in my Self-Education 

I could write an entire book about the ways I’ve delayed and complicated my self-education. BUt here are some of the biggest mistakes I’ve made in self-directed learning. 

Focusing on Too Many Subjects at Once

I like to study no more than three, but ideally two, subjects at any given time. For example, this quarter I’m studying literature and philosophy via 2 online courses. 

I’ve made the mistake in the past of studying too many disciplines at once, and thus making very little progress on each, which can be quite demotivating to the new student. 

Trying to Remember Every Single Thing I Read

My early notetaking system had me basically underlining and writing down everything somewhat interesting, which resulted in me remembering almost nothing from the books I read. 

Now I try to be more selective. I sometimes go through two rounds of notetaking, where the second round is just reviewing my notes and filtering the wheat from the chaff. 

If you’re reading non-fiction, I’ve found a good rule of thumb is to find one takeaway from each section. That adds up over time, and adheres well to Atomic Habits’ principle of getting 1% better every day. 

Forgetting That Learning is Primarily a Fun Thing to Do

My fiance sometimes has to remind me that my studying routine is self-imposed, and that there’s no reason to make myself unhappy from it. 

If you’re doing some study technique you dislike, or that requires massive amounts of discipline to do regularly, then maybe you need a new approach. 

Most books and approaches will become enjoyable after you stick to them for a bit and get the hang of things, but some just won’t click with your temperament. If that’s the case, ditch them. 

The last thing you want is to burn out from your self-education. It’s supposed to be a time of exploration and excitement, not tedium and agony. 

Remember to follow your curiosity, a tenet of self-education I sometimes struggle to follow

Creating Inflexible Reading Plans

This mistake goes hand in hand with the one above. At first I would make or find insane reading lists that I told myself I had to stick with. 

For instance, at 25, I tried to read all of The Well Educated Mind’s reading list of great works of Western history/politics, chronologically. 

Halfway through Herodotus — the first books — I found myself putting off my studies. Why? Because the book wasn’t that interesting to me anymore. After learning about Cyrus, I just didn’t really care enough to read the next 500 pages. 

Day after day I clocked in 0 pages because that was the book I HAD to read. This strict adherence to the list was doing a disservice to my studies. 

Eventually I gave up, and then felt super bad about myself. But there was no way to react. I should’ve told myself it’s okay, you can come back to it, which I plan to in a few months.  

Also, you can pursue reading plans over the long term, and take breaks from them. That’s what I’m doing with the history/politics classics list, dipping in every couple of months. 

To sum it up, leave some room in your reading plans to explore what interests you in the moment, and give yourself grace when you fail to stick to one.

Neglecting Personal Development / Professional Books

The one type of book I did read a lot in college was the personal development book in the likes of How to Win Friends and Influence People. 

These books are actually super helpful for mindset and practical tips for succeeding in your goals. 

I think I got a bit snobby for a bit during my first few years of self-directed study in the classics. But lately I’ve made a return to them and am finding it beneficial. 

I try to read one a quarter if only for the inspiration they provide. Also, cool thing, you’ll find that you can read and digest them so much faster than you used to be able to if you spend some time training your brain on harder prose and more complicated books.  

Anyway, neglecting these types of books for the sake of feeling like a scholar is silly, and something I don’t recommend. 

Many of the authors are kind of like the moral philosophers of Ancient Greece, trying to define terms like good life, happiness, discipline, communication, and productivity; and to give advice on how to do them well. 

Read my top 7 self-education mistakes for a closer look at the things you should avoid.

Best Books on Self-Education (an Autodidact’s Bookshelf)

Below are the books that have been most helpful to me as an autodidact, and that together form the basis of my philosophy of self-education. 

Inside you’ll find inspiring stories, practical tactics and strategies, and the best thinking there is about how to teach yourself new things and become well-educated. 

The Well Educated Mind 

Want to become well-read in the classics of Western thought and literature? This one’s for you. 

Susan Bauer makes a case for giving yourself a classical education and shows you how to do it. 

Along with providing reading lists, she also teaches you how to read and apply the trivium (a classical study method) to 6 major genres: novel, politics/history, autobiography, poetry, theatre, and science. 

Get the book here


You might know this author from the MIT challenge, where he did the MIT computer science curriculum, tests and all, on his own. 

Really an inspiration for me when I started out in self-learning. 

In his book, Scott Young teaches you the 9 principles of Ultra Learning, a form of self-directed learning that is deliberate and intense. He draws from a lot of literature on learning science. 

I apply many of these principles to my own learning projects, and loved his anecdotes of fellow autodidacts. 

Get the book here

Range: Why Generalists Triumph in a Specialized World

This book validated my conviction that it was okay to have wide-ranging interests and pursue them. 

David Stein shows that top performers across many fields don’t usually “pick and stick” from a young age. 

They actually develop range across several skills and/or subjects, and that this range helps them achieve mastery in their chosen discipline. 

Grab the book here

Also, if you consider yourself someone with a lot of interests, read my article Dear Generalist, Don’t be Ashamed of Your Knowledge Lust; it’s a Superpower


Want to learn how to become the best at what you do?

Robert Greene, author of 48 Laws of Power lays out the path to mastering a skill or craft, drawing from his research of the lives of various masters, including Da Vinci, Proust, Darwin, and Henry Ford. 

A concise little book that packs a punch. 

Grab the book here

Deep Work

Cal Newport changed my life with this book. 

By making a case for the fulfilling experience of cognitively-demanding, focused work, it convinced me to quit my sales job and pursue writing. 

Not that there’s anything wrong with sales; many sales convos are deep, but I was cold calling, and sales in general goes against my nature. 

Grab the book here

The Intellectual Life 

If you want a nice meditation on the intellectual life of reading and study, why it matters, and what it means, as well as some tips from a scholar about how to organize your day and take notes, then this book will be a delight. 

The Catholic undertones are there. The writer is a theologian/philosopher, after all.

But it’s a great book regardless of your religious beliefs. It’s not preachy or anything. 

Grab the book here

Don’t have time to read all these books? Try Audible’s 30-day free trial and get a free audiobook (two if you’re a Prime member). 

I love being able to listen to books on walks, while driving, and while doing chores around the house. 

Notice Anything Interesting About These Books?

You may have noticed that four of these books correspond in a way to a prong of my 4-pronged approach to self-education that I introduced in the beginning of this article. 

Mastery for Master Subject, The Well Educated Mind for Expertise Subjects, Range for Intellectual Range, and Ultraleaning for Quick As-Needed Acquisition. 

These books have really influenced how I think about, plan, and execute my self-education. 

Further Reading: I have an article, the autodidact reading list, that goes deeper into the value of the books listed above. Check it out if you want to see how they’ll help you become a better self-learner. 

Bottom Line: Getting a Well-Rounded DIY Education 

If I had to sum up this article, I’d say to pick a few key subjects to gain a foundation in and then move onto others that interest you. 

As you learn more about your tastes and interests, start selecting a few subjects that you want to study for the long-term, and put more of your time into studying those, while still reading across other subjects that make up a traditional liberal arts education.   

And use that chip on your shoulder. Higher education is not the only path to a well-rounded education

Books, online courses, and other learning materials have democratized the intellectual life. 

Go forge your own path, pursue it with diligence, and you’ll be amazed at how much you can learn in just a few years. 

By the way, If you want to get free tips on self-education, please join our newsletter (in doing so you’ll also gain the 8-step checklist to self-learn the basics of any new subject): 

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I sincerely hope this guide has helped. Good luck in your studies. An interesting life awaits!


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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