3 Things I've Learned About Reading In the Midst of My Quest to Read Every Pulitzer Winner

I’ve been knee-deep in my Pulitzer Project since I announced it two years ago. In that time, I’ve averaged 1.5 Pulitzer-winning reads per month. I should probably pick up the pace a little bit, but as I’ve said before, I consider it to be more of a lifetime project than something I’ll speed through.

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Introducing the Pulitzer Project: A Quest to Read All Prize-Winning Books (Including Non-Fiction)

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Even though I’m just a fraction of the way through (you can track my progress here), I’ve already read some amazing books and learned some truly eye-opening things about the world and about human nature.

I’ve also uncovered a few interesting ideas about the act and art of reading itself.

There are Unheralded Treasures Waiting to be Found in the Stacks

Most of what is read these days has been chosen by algorithms. Whether on Amazon, Goodreads, TikTok, Substack, or elsewhere, odds are pretty high that whatever you’re reading was first spotted online. When’s the last time you browsed a library and bookstore and chose something that you hadn’t heard of or didn’t gravitate towards because of an online recommendation?

All this algorithmic reading is not inherently bad, but it does mean that there are books that get lost — that aren’t sucked into that vast whirlpool of feeds and likes and clicks. Unsurprisingly, plenty of those books are fantastic.

Because of my Pulitzer Project, I’ve encountered dozens of titles that would never have crossed my path if not for my big spreadsheet. There are books that I’ve finished and immediately thought, “Why isn’t this more well-known?!” Titles like The Beak of the Finch (1994), Years of Grace (1930), and Eleanor and Franklin (1971) come to mind.

Much of it is simply recency bias. The book marketing machine is all about new and shiny books by big names; if it doesn’t make a splash right away, it gets left behind. On the other end, books that are already defined as “classics” continue to get good press and great sales numbers. Think Steinbeck, Dickens, and Austen. Books in the middle zone — not new and not necessarily a “classic” — remain on shelves but hardly ever get discovered or, sadly, read.

Reading from a list or well-defined project will help you discover books that the crowds aren’t reading. It’s intellectually fulfilling, for sure, but it’s also just fun and kinda cool to be reading great books that are mostly un-read in our modern era.

A Sustained Reading Project Satisfies Your Longing to Learn

Ever since graduating college I’ve had an itch to keep learning. For many years, my job at a men’s lifestyle magazine satisfied that longing. When I moved into the tech and business world, my gig wasn’t quite as mentally stimulating, so I had to look elsewhere. As an adult, that path can be hard to find. Rather than embarking on learning new skills or specific projects, what we often do — myself included — is jump through Wikipedia pages and too-quickly scroll through too many “interesting” articles.

I’ve tried Coursera classes and Great Courses lectures, but have always had a hard time sticking with them, even when self-paced. I don’t entirely know why; perhaps my personality just isn’t suited to that type of learning experience.

The best way to satisfy your desire for lifelong learning is to embark on a challenging reading project. Period. It may require some endurance and even discipline, but it’s always enjoyable to check another book off your list. And most of all, it’s just a delight to learn new things and to go deeply into unexplored intellectual waters.

If you’re reading this, I can almost guarantee you’re someone who has a desire to learn new things. Find yourself a reading project and start in:

• Read a biography of every ________. My four-year project of reading a biography of every POTUS was incredibly rewarding and enlightening. I highly recommend it if you’re in the mood for a long-haul history/biography challenge.

• Read through a prize list. Pulitzers, National Book Awards, Edgar Awards, etc. Find an award and a category and get to it.

• Read through an author’s entire canon. Even the duds. You get unmatched insight into their storytelling and growth (or lack thereof). Plus, it’s wildly satisfying to be able to say you’ve read all of ________’s books. There are only a couple folks I can say that for, but I’m pretty close on a handful of others.

• Go deep on a subject. Embrace your WWII-obsessed middle-age dad status. Or whatever other subject you’re into. Do some research and make a list of the 50 best books on that topic — new, old, fiction, non-fiction, make sure you get it all.

Awards May Not Determine a Book’s Value, But They Always Say Something Interesting

The Pulitzer Prize-winning books get a lot of flak every year. “What were they thinking?” “They picked wrong, again!” “Why didn’t ______ win?” It’s like clockwork, really. The problem, I think, is in how we frame these prizes. If we tend to think of them as coronating the great book in that category for that year, we’re bound to be disappointed. Reading is just too subjective for that. Even this year’s fiction winner, James, was met with plenty of disapproval, despite it being among the most consistently well-reviewed books I’ve ever encountered. (I thought it was a fantastic book, for what it’s worth.)

Instead, we need to look at prize-winning books for what they say about our culture in that particular moment. Books are always reflective of what’s happening in broader society, in one way or another. A title that won the Pulitzer Prize for Fiction in the 1920s may not be a “great” book by my standards, but it sure as heck says something interesting about culture in that decade — what was valued in terms of themes, character traits, commentary, prose, etc.

A literary prize does not determine a book’s lasting value, but with the right approach, it will always have something bigger to tell us.