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Reading Projects: What They Are and How to Set One

Tommy Collison announced that he's reading through 150 Western classics over the next four years. What are reading projects and how can they help you achieve your goals?

Zachary Fleischmann
Zachary Fleischmann
. 5 min read
Reading Projects: What They Are and How to Set One

In November 2020, Tommy Collison, of the Collison brothers, announced that he was going to start a massive reading project. Over the next four years, he is going to read through a list of 150 classic works. Each year will be dedicated to a different theme, including antiquity, the Middle Ages, the Enlightenment, and modernity.

His announcement received a pretty warm reception on Twitter and a lot of people wanted to participate. Reading through a list of 150 classics in Western thought is certainly a noble goal. But a more interesting question is how you can craft a goal of your own.

A thesis that I’m operating with is: your life experience isn’t enough to carry you through the challenges you’ll face. Without extensive reading, you’ll reach a local maxima beyond which you can’t progress because your life experience doesn’t give you enough data to make sound decisions. Reading gives you data from the lives and accomplishments of others. So a reading project is an effort in targeted data collection and the accumulation of patterns. Because the goal is to improve your life, your reading projects should be unique to you.

Types of Reading Projects

There are four different ways you can think about creating a reading project for yourself. You can go for breadth, like Tommy Collison is. Or you can go for depth in a single topic or by an individual author. You can also set a progressive reading goal, where you take on more and more complexity.

Breadth

Tommy Collison’s reading project is a perfect example of a breadth-based one: reading widely across a large domain or field. For every author, his goal is to read their best work. For most authors, that means just one or two books.

The key to a breadth-based reading project is just that: to achieve a wide understanding across a large domain. Tommy won’t become an expert on Shakespeare, but he’ll be able to identify themes and influences from all the works that came before. He’ll also be able to see how patterns from Shakespeare transform and reappear across the rest of Western thought.

A couple of ideas for other great breadth-based reading projects are:

  • Read a biography of the 100 best leaders in history.
  • Pick 10-15 different programming languages and read an introductory book on each.
  • Read one book on each of the major fields of science or mathematics.

A CEO who has read 100 books by and about different leaders would have an incredible library of mental models and patterns to pull from. A software engineer who has learned the fundamentals of multiple different types of programming languages would have an incredible library of idioms and constructs to use in their work. Any of these projects would be really ambitious, but they would give you a wide understanding across the given domain.

Depth of Topic

Another approach you could take to creating a reading project is to read deeply on a single, narrow topic.

When I taught at a coding bootcamp, I read 10 books and worked through multiple different courses all on basic JavaScript. I never lost interest in the topic. Actually, I found it really exciting to approach the same topic from multiple different angles. Different authors had different ways of explaining things. They also emphasized the importance of different aspects of the language. The Secrets of a JavaScript Ninja spent a lot of time on functions and objects. None of the resources I found spent much time on arrays, which was the inspiration for the series of articles I’ve been doing on them.

If you’ve read How to Read a Book, then you’ll recognize this approach as Syntopic reading. It’s a great way of achieving a depth of understanding and the three dimensional exploration of a topic that comes with it.

Creating a depth of topic reading project isn’t as simple as picking a topic and reading everything you can find on it. That’s a good start, but you want to stretch yourself by finding different angles and approaches to the topic.

For instance, there have been hundreds of books published about Winston Churchill, making him a great potential reading goal topic. But if you only read books about Churchill that were published by British authors, you’d get an overly rosy image of the man. A good depth-based reading project picks multiple books on Churchill, published by lots of different authors, approaching his life and achievements from multiple different angles (his childhood, his leadership style, his artwork, etc).

So to craft a topical reading project of your own, pick a subject matter and select a series of books that approach it from different perspectives.

Depth of Author

Instead of reading deeply on a single topic, you could read deeply across a single author: every book by Shakespeare, Kurt Vonnegut, or the Brontë sisters. A depth-based reading project simply means picking a single author and reading everything they’ve published.

In 2018, I read almost every one of Jim Collins’ books: Good to Great, Built to Last, Great By Choice, and How the Mighty Fall. These books perfectly encapsulate the value prop of a good book: for $10-15 dollars, you get the distilled wisdom of a research team that has taken years to systematically study a topic and encapsulate their findings in 350 pages. By reading all of them systematically and in succession, I got that distilled wisdom looking at every angle of a topic for about $50: how great companies are started, how they survive, how and why they fail, how and why they don’t. No MBA class could give me that.

Therein lies the keys to a good candidate for an author based project: their work has to focus on a narrow topic from multiple angles. Josh Kaufman is a great author, but his three books are on three different topics. Each one is helpful in it’s own right, but reading them all together doesn’t provided added benefit because there isn’t a thread that ties them all together.

So when picking an author, pick one who’s work has a consistent set of themes or subjects.

Progressive

A progressive reading goal is when you select a topic and read progressively more complicated or detailed books on the subject.

It’s similar to a topic-based reading project, in that you are focused on a single topic. The difference is that a topic-based project works well for subjects where you have some foundational knowledge that you want to deepen and enrich. A progressive reading project is best when you want to bootstrap that foundation and achieve a high level of competence.

For example, if you want to develop a really sound foundation of the Python programming language, you should go read Learning Python, Fluent Python, and High Performance Python.

Crucially, you should go read them in that order. Learning Python gives you a really good, broad overview of the Python programming language. Fluent Python teaches you how to write Python well. High Performance Python teaches you how to write Python that is fast. It follows the coding idiom: make it work, make it good, make it fast.

Conclusion

A good reading project should be personalized to you and your goals, both in terms of subject matter and length. Tommy’s project will take him about four years to complete 150 books, all of various lengths. The Python reading list I recommended is just shy of 3,000 pages and would take you about 6 months if you committed to reading 25 pages each workday.

That all goes back to my original thesis: your life experience isn’t enough to carry you through the challenges you’ll face in life. A reading project tailored to a specific life goals is perhaps the best way to find new patterns by learning from others.

Reading

Zachary Fleischmann

Zakk Fleischmann is a software engineer and writer. In 2019, he founded Hawthorne Interactive, an agency specialized in building enterprise software for companies, startups, and government agencies