My Re-Reading List

Why Returning to Books Makes You Wiser, Not Slower

My phone can hold more books than Harvard's entire library.

Just think about that for a second. I'm just a regular knowledge worker with a smartphone, I've got access to more information than every emperor and queen in history combined. And that's not counting the endless stream of articles, podcasts, newsletters, and whatever new medium dropped this week. It's like drinking from a firehose while someone keeps adding more hoses.

It's mind-blowing. And honestly, it's kind of terrifying.

The Productivity Trap

Our obsession with "optimizing" reading to get through our lists is killing our ability to actually learn from books. It’s killing our joy of reading, too.

You know what I mean - those "100 books a year" humble brags, the Goodreads challenges, treating books like some kind of productivity metric. (Read my Slow Reading Manifesto here). No shade to anyone who can plow through them and enjoys it. Reading is a joy. But I’m talking about speed dating through non-fiction or meaningful pieces and not getting anything out of it, simply finishing it for finishing’s sake.

I used to feel low-key shamed for spending two weeks with one book while my friends were crushing through three.

The irony? This approach is actually less productive for me. When we sprint through books, we retain less, understand less, and grow less.

This is why I've started treating reading less like a performance metric and more like a practice. Instead of measuring success by books completed, I measure it by insights gained. Good, worthwhile ones become signals in the noise - classic, evergreen, and worth revisiting.

Sometimes that means spending a month with one book. Sometimes it means returning to a book I've read before instead of starting the hot new release everyone's talking about. It feels counterintuitive, but it's the most effective approach I've found.

These are the books I re-read every year:

I'm gonna make it a little weird and say that I have a relationship with these books. They've become like my home bases - the ones I return to when I need to recenter, reflect, and remember what matters. It's like having a conversation with an old friend who always knows exactly what you need to hear. Each reading reveals new layers, proving that wisdom isn't just about finding new information - it's about letting familiar truths sink in more deeply.

1. The Lessons of History by Will and Ariel Durant

After spending decades writing their massive 11-volume "Story of Civilization," the Durants distilled what they learned into this slim volume that covers the sweep of human history in under 200 pages. It's like having a long conversation with two brilliant historians who help you see the patterns in human behavior across centuries.

Every time I read this book, I find myself spotting patterns that explain today's headlines. The Durants show how these same dynamics have played out countless times before, whether it's wealth inequality, the tension between tradition and innovation, or how economic realities shape cultural values. It's like having a cheat sheet for understanding human nature.

2. Meditations by Marcus Aurelius

Stoicism lately has become popular with the tech bros and the toxic masculine set, but they’ve got it all wrong.

What you have is the world's most powerful man writing reminders to himself about staying humble and kind. It's the original self-help book, with zero marketing and total honesty.

It’s a direct and honest portrayal of someone trying to be a better person amid plague, political intrigue, betrayal, and war. He’s running an empire and reminding himself to not be a jerk.

Here's what makes this book hit different: Marcus never meant for anyone to read it. It's just him, journaling, trying to get his head straight. The most powerful dude in the world, writing notes to himself about staying humble and not being a jerk when things get rough. No filter, no brand-building, just raw thoughts about controlling what you can and letting go of what you can't.

Key ideas that keep resonating with me:

• The only thing we control is our response to events.

• Most of what we worry about is our judgment about things, not the things themselves.

• Everything we observe today has happened countless times before and will happen again.

• Your position in life doesn't matter as much as how you conduct yourself.

Whenever I'm feeling overwhelmed or caught up in things that don't really matter, I return to this book. There's something deeply comforting about reading the private thoughts of someone who, despite having immense power and responsibility, struggled with the same human challenges we all face.

3. Phosphorescence by Julia Baird

The most recent addition to my re-reading list. Baird - a talented biographer and writer - explores how we can cultivate inner light that sustains us through dark times - something that feels particularly relevant these days. What sets this book apart is how it weaves together personal experience of loss and recovery, scientific research, and philosophical insight without feeling either too academic or too self-helpy.

What I keep returning to:

• The importance of awe and wonder in maintaining mental health

• How to find meaning in small moments rather than grand gestures

• The value of maintaining connections to both nature and community

• Ways to cultivate resilience without becoming hard or cynical.

I pick this up during challenging times, not because it offers easy answers, but because it reminds me of the quiet strength we can develop through attention to what truly matters.

The Paradox of Reading Less to Learn More

Here's the real productivity tip: These re-read books become mental models for everything else.

"The Lessons of History" helps me understand current events.

"Meditations" gives me tools for daily challenges.

"Phosphorescence" reminds me how to find light in dark times. Each re-reading compounds its value, like interest on an intellectual investment.

So the next time you feel the pressure to keep up with the latest bestseller or hit your Goodreads goal, consider this: The book you need most is already on your shelf, waiting to reveal something new. After all, the best books aren't the ones you finish quickly—they're the ones that finish you.

A Different Kind of Reading Goal

Want to try this approach? Start small. Pick one book that's stayed with you and commit to re-reading it this month. Don't rush. Let it be a conversation rather than a conquest. You might be surprised at what you discover.

I’ll provide a more detailed walk through of how to curate your own Re-Read List later on.