I believe a quiet morning with a cup of coffee and a good book to be one of life’s greatest pleasures. Unfortunately, life is short, such mornings (as a parent) are rare, and there are far too many good books out there. All this inevitably raises the question: What to read with the limited time available?

One obvious solution is to make a list and follow it. Over the years, however, I’ve often found myself making well-intentioned lists of books to read, only to discover that I never end up reading the books I put on those lists. In fact, if I put a book on a list, it often guarantees that I won’t read it at all! Turns out, I’m not alone. In The Pleasures of Reading in an Age of Distraction, Alan Jacobs writes something eerily similar:

I used to try to determine in advance what books I would read over the summer, but eventually realized that to put any book on such a list nearly guaranteed that I would not read it.

Speaking with friends about this, it seems a more common phenomenon than I realized.

What is it about reading lists that causes us to fight and squirm against their linear plodding as if they were straightjackets? Why do they fail us so? I think the answer is simply the joy of serendipity. For me, much of the joy of reading lies in the discovery of the unexpected. Jacobs calls this reading at Whim:

It helps us to make a vital distinction between what I shall call whim and Whim. In its lower-case version, whim is thoughtless, directionless preference that almost invariably leads to boredom or frustration or both. But Whim is something very different: it can guide us because it is based in self-knowledge—it can become for us a gracious Swiss pedagogue of the mind.

Whereas whim feels directionless or aimless, capital-W Whim feels like working with a compass, but perhaps lacking a map. You know the direction you may want to go, but not necessarily the territory.

I believe you should choose what to read in the same way you might want to wander an unfamiliar, foreign city, directed by a strong sense of personal interest, but with a mind open to side-quests and spur-of-the-moment opportunities, any of which you may abandon at a moment’s notice, and without guilt. As Jacobs writes:

Read what gives you delight—at least most of the time—and do so without shame. And even if you are that rare sort of person who is delighted chiefly by what some people call Great Books, don’t make them your steady intellectual diet, any more than you would eat at the most elegant of restaurants every day.

The accumulation of prestige is both a poor motivator for reading, as well as a poor reason to read. Following a reading list of “Great Books” is like using a tourist guide map, guaranteeing that you see all the major landmarks or attractions, but also ensuring you’ll never discover anything new or unusual off the beaten path. Plus, you’re likely to get bored. Not all the Great Books are “great” for everyone.

A recommendation algorithm often offers no better fare, acting like a tour guide who takes you only to those locations they believe will align with your interests — or worse, only align with your interests. On this, the idea of recommendation algorithms, I’m reminded of one of my previous reflections on the value of randomness and something James Bridle wrote in Ways of Being:

We learn, change, develop and grow when we move and entangle ourselves with the world in unexpected ways, and we do so best when we are fully engaged participants in that journey, not passive recipients of algorithmic and corporate diktats.

Reading at Whim is entangling yourself with the world, embracing a bit of randomness. The creators of algorithms often have a vested economic interest to direct us in specific ways, not always to our benefit. Instead, deep self-knowledge, cultivated over years of trial and error, can guide us in exciting but unexpected ways no algorithm can ever approach.

When I pick up new books, they tend to align with some flickering spark of curiosity deep within me I can’t always quite explain. Jacobs refers to this feeling as a kind of “accidental sagacity:”

The cultivation of serendipity is an option for anyone, but for people living in conditions of prosperity and security and informational richness it is something vital. To practice “accidental sagacity” is to recognize that I don’t really know where I am going, even if I like to think I do, or think Google does; that if I know what I am looking for, I do not therefore know what I need; that I am not master of my destiny and captain of my fate; that it is probably a very good thing that I am not master of my destiny and captain of my fate. An accidental sagacity may be the form of wisdom I most need, but am least likely to find without eager pursuit.

Accidental sagacity is a precursor to Whim, and the “sagacity” implies that this is not about pure self-indulgence. There is value in challenging ourselves, in reading difficult works, things outside our comfort zone, or even books we know we won’t 100% agree with. For instance, a common bit of reading advice suggests that one should read deeply in related topic areas or works by the same author to maximize connections and learning. Earlier this year I finally read The Count of Monte Cristo. If I were to follow this advice to the letter, I might have then read other works set during or about the French Revolution to deepen my understanding of the surrounding historical context — a biography of Napoleon, the Three Musketeers, Scaramouche or maybe Tom Reiss’ The Black Count.

I’m sure some of these other works would have been rewarding, but Whim directed me elsewhere at the time. By the time I had finished The Count of Monte Cristo, I had already discovered numerous other books on different topics that struck my fancy and were more in-line with my own personal research interests. In several cases, I had already bought them and they were lying in a stack next to my bookshelf, patiently waiting for me to crack their covers. (While I try to practice minimalism in many areas of my life, reading is not one of them. I admit I’m something of a compulsive used book buyer — a happy practitioner of the art of tsundoku.)

All this brings me back to reading lists. It’s not that reading lists are wrong or useless, it’s that usually we approach their compilation in the wrong way. Rather than treat them as a checklist, I’ve found it’s better to treat them as something of a virtual bookshop or library — a way of remembering things we might want to read, but that we are never obliged to read.

This is where I’ve found technology to be helpful. Visual bookmarking tools like Pinterest or MyMind or the open-source Hoarder make excellent virtual bookshelves. Any time I come across an interesting title — referenced in something I’m currently reading, or mentioned on a podcast, or shared on social media, or discovered while browsing around my local bookstore — I add it to my visual list. The image of the cover makes the book far easier to find and recall. Of course, I might not read it for months or years later, or likely never at all. It doesn’t matter. It’s always there for me to revisit and decide, whenever the Whim strikes.