The Magic of Rereading Your Favourite Books

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This month, I’m starting to revisit some familiar reads—rereading specific books and oeuvres that I’ve read over the last few years, starting with one of my all time favourite books: Mastery by Robert Greene. While I’m still incorporating a majority of new reads into my monthly book rolodex, my goal for the next several months is to revisit an old book flame every few months.

The criteria for my reread inclusions are:

  • books that have had a big influence on me during a specific point in my life;
  • a ‘paradigm-shifter’; one that has shaken up my long held beliefs. A perspective that, as Rick Rubin so eloquently puts “[allows me] to glimpse at life through a different window. One with the potential for a glorious new view”;
  • a read that I just simply enjoyedwhich could be a novel that gave my spirit a boost and provided me with a more positive and inspiring outlook on life or;
  • A more complex read that was “above my level” at the time of reading—I found it challenging to grasp at the time, either because I needed to go through it a second time with a fine tooth comb or because I didn’t have the foundational knowledge to really benefit from it.

I’ve refrained from rereading books over the last year quite simply because I wanted to explore new philosophies and expand my breadth of knowledge. At the same time, I felt that I already derived the general gist of the books I read in the past. Why reread it then? Isn’t it a waste of time when there’s so much more literature out there to explore and sink my teeth into? There was also the novelty principle; that is, fresh insights and perspectives can be more pleasurable than repetition. As humans, we crave new experiences. Trodding on familiar ground can be monotonous. 

Yet what I’ve found is that by revisiting older reads that fit my aforementioned criteria, I can be awarded many new gifts. It can be highly fruitful and rewarding, sometimes more so than reading something new for the first time.

It would be a beautiful thing if one could know once and for all what one has learned, only things are different; everything learned must be refreshed from time to time by repetition, otherwise it is eventually forgotten.—Arthur Schopenhauer, Parerga and Paralipomena Volume II

Sometimes, our memories aren’t as great as we think. I may beleive that I remember the intricate details of a book, but when I start rereading it, I realize how much of the book I didn’t absorb. When we read, especially for long periods of time, we can lose focus; the mind drifts and we don’t absorb all the content. Perhaps, we’ve mindlessly consumed pages without really absorbing anything. Our mind was wrapped up in a previous idea we were thinking about, what we’re going to snack on next, or that email we forgot to respond to yesterday has resurfaced to cloud your thoughts. A drifting mind is inevitable. 

This obviously depends on the book, but especially with more complex reads and difficult literature, the reread always bears more fruit the second time around. Even if we do slightly remember the gist of the text, rereading will make the content pop and help cement it in your memory. Actively taking notes, highlighting important passages, and marginalia whilst reading can make the content stick more. Transcribing some of our key findings to a commonplace book, notebook, or scribbling some of our key takeaways in the inside of the cover are also fantastic active reading habits to help us remember more, and get the most out of what we read.

Deriving the novel in the same

Our minds are a very powerful thing. If we revisit a book thinking that it’s going to be dry and stale, then guess what? It’s going to be. 

“Since mere repetition bores us, we must always be learning something new in addition, hence aut progedi, aut regredi [either progress or regress].” –Arthur Schopenhauer

So how can we make rereading more interesting? Finding the new in the old is a reframing practice. We must actively seek the new in the old, otherwise, we won’t pay attention. We may already have an opinion on rereading, but like me, I can be convinced to give it a go if I learn some benefits and practical takeaways that make it worth my time. That’s my goal with the postto try and convince you to fall in love with your favourites reads for a second time, but also to discover the benefits for yourself. The mental tools that are the sharpest and most useful, are the ones we craft ourselves. 

The answers we seek may not be in the future, but in the past

One day, the great philosopher Immanuel Kant was casually rereading the work of another great philosopher, David Hume. While reading Hume for the second time, Kant had an epiphany—a ‘eureka’ moment if you will. Hume was an empiricist and said that the only way we can know truth is by experience, yet Hume was deeply skeptical of this method. How can we really be sure of anything? The human intellect and sense experience is deeply flawed. While in the midst of rereading Hume, Kant famously wrote:

I freely admit that it was the remembrance of David Hume which, many years ago, first interrupted my dogmatic slumber and gave my investigations in the field of speculative philosophy a completely different direction.

It wasn’t Kant’s first read of Hume that helped him gain the flash of inspiration and insight that would literally change the history of philosophy forever; it was the second time ‘round. Rereading Hume paved the way for his revolutionary work, The Critique of Pure Reason. The answer was not to be sought in future knowledge that was yet to be obtained, but instead, it was from revisiting the past.

When we’re dealing with a particular problem in life or feeling stuck, sometime the answers we seek are not to be found in the new; new works, new knowledge, new insights, new experiences, but rather, in the old; the solution may lie behind us. Stephen West, host of the Philosophize This! podcast says:

Sometimes you may want to reread things that you’ve already read in the past because, who knows, for whatever reason, when you read it the first time, you weren’t in the right frame of mind to receive it. Maybe you weren’t feeling well that day. Maybe you were just too young and naïve to realize the wisdom of it back then.

I’m not saying that rereading a book is going to give us the epiphany to create our greatest work or birth our best ideas, but it could. Perhaps rereading can help us too, wake from our “dogmatic slumber”. ” Some of my best ideas have come when I’m out for a run and relistening to an old book, course, or to one of my favourite albums on repeat. Go into the experience with an open mind and see what comes.

New perspectives

If you don’t look at yourself and think, ‘Wow how stupid I was a year ago,’ then you must not have learned much in the last year. – Ray Dalio

Each year is packed with new life experiences and hopefully many of us grow from these year-over-year. If you’re someone who’s focused on self-development, reads books, wants to keep growing—placing amelioration as a top priority in your list of yearly goals, you’ll likely realize that your perspectives change. If we exhibit a sense of humility, we realize that we contradict ourselves, that what we thought even a year or two ago may be completely wrong or obsolete.

When we approach an old book, we show up differently. We view it from a different lens. We are different people today than we were two years ago, a year ago, last monthwe are even different than we were yesterday. Epicharmus, the Greek dramatist and philosopher said, A man who borrowed money in the past does not owe it now, and that a man invited to breakfast yesterday evening turns up this morning uninvited. Both are different people.” (Montaigne, Essays)

We are constantly changing and maturity, brings a new frame of reference. I remember reading Big Magic by Elizabeth Gilbert in 2015 when it was first published. I reread it again in 2020—3 years after I began a writing practice. I really liked the book the first time I read it, but the second time, I read it through the lens of the writer and artist; I experienced the book’s contents in a completely different way.

The river
where you set
your foot just now
is gone–
those waters
giving way to this.
now this.

Fragments, Heraclitus

Michel De Montaigne said that, “[each] subsequent age to which birth is given is forever undergoing and destroying the previous one.We are always reinventing ourselves.

If you really pay attention while rereading and are on the lookout for the new, you will find it. I can guarantee that. 

What I end up finding or discovering from my reread depends on the book: the complexity, the enjoyment principle, and how present I was while reading the first time. When I started reading philosophy I gave myself the grace of being okay with not fully understanding the workit helped break down the barriers to get started. I told myself I would reread it again down the road. And that’s what I did. To appreciate some books they need to be read slowly and analytically; some require supplementary material to truly grasp the concepts and get the most out of what the author has to offer.

The writer in me has become more analytical as I read. I’m hypervigilant of style, prose, and how various authors structure their content. I read actively and analytically—both skills which have exponentially improved my writing. 

But we don’t always need to gain some intellectual or academic benefit. Sometimes, rereading is just plain ol’ fun. You get to relive the nostalgia when you read the first time—especially with fiction. I shared my criteria for how I select books I want to reread, but it may not be yours. What books you decide to circle back to is up to you, but I suggest that if you’re only reading the new, try dipping back into familiar ground, and see what happens—see if some magic appears. Because it just might.

Just at the river where I step
is not the same, and is,
So I am as I am not.
Fragments, Heraclitus



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