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I was a shy kid growing up, so I spent a lot of time reading books. I devoured sci-fi, non-fiction, and every programming book I could find. When the library didn’t have the C++ book I wanted, I taught myself to code by buying book after book from our local Borders (RIP). I was tearing through so many coding books that my dad started returning the ones I’d finished to the bookstore so that we could afford to buy more.

I’ve always thought it’s so cool that the smartest person in the world on a topic I care about spends 2+ years of their life distilling their best ideas into an enjoyable read, and I can get this for just $20. Amazing.

There’s endless free content flying at us hourly now—newsletters, podcasts, tweets, oh my—but how many blog posts or tweets have had anywhere near the lasting impact on your life as a great book?

To continue my essential-reads series (don’t miss part 1 and part 2 of my favorite online essays), I’ve put together a collection of my all-time favorite books, organized by their jobs-to-be-done. When your manager tells you to work on a particular development area—or if you’re just feeling the itch for self-improvement—these are the books I recommend you read.

To keep this list extremely high signal-to-noise, I forced myself to pick only three books per category (so hard!), and only books I’ve completed. I included both classics and under-the-radar gems. And I very much agree with Marc Andreessen’s take that you should mostly read books that are over 10 years old (because those are the books that have stood the test of time), so you’ll notice very few new books.

There are so many great books that I didn’t include here, either because I haven’t had a chance to read them or they just didn’t make the cut. I’m sorry if I didn’t include your book, or a book you love. I probably forgot some important titles, too. That’s why we’ll have a part 2!

P.S. If you’re feeling like you have no time to read, I was in the same boat. Bryan Johnson’s suggestion of reading a book for 10 minutes before bed changed my life. I started reading more books, and I got better sleep! Try it out.

I want to improve my communication skills

I had never written anything online before starting this newsletter, so once I realized this was going to be a thing, I decided I needed to learn something about writing. Friends recommended many different books, and I read them all. But these three had the most practical, impactful, and lasting advice, which is still lodged in my head even now.

1. Nobody Wants to Read Your Sh*t by Steven Pressfield

2. On Writing Well by William Zinsser

3. Storyworthy by Matthew Dicks

Check out my conversation with Matthew Dicks.

I want to get better at executing

If you love this newsletter, you crave actionable, tactical advice and frameworks that you can put into practice immediately. The first two books will give you exactly that, and the third will give you a meta-framework that’ll level up how you approach everything at work.

1. The Great CEO Within by Matt Mochary

2. Scaling People by Claire Hughes Johnson

3. The Goal by Eliyahu Goldratt

Check out my conversations with Matt Mochary and Claire Hughes Johnson.

I want to get better at strategy

I remember reading these books and feeling like, okay, I finally understand what “strategy” is.

1. Good Strategy/Bad Strategy by Richard Rumelt

2. Playing to Win by Roger L. Martin

3. Working Backwards by Colin Bryar and Bill Carr

Check out my conversations with Richard Rumelt, Roger Martin, and Bill Carr.

I want to be inspired to build something great

This bucket of books might be my favorite of the bunch. They showed me how much a singular (relentless) mind can accomplish. Read them, and you’ll be ready to run through walls.

1. The Making of Prince of Persia by Jordan Mechner

2. Build by Tony Fadell

3. Shoe Dog by Phil Knight

I want to become a better manager

These books are among the most mentioned on my podcast. I remember reading High Output Management when I was a baby manager, and it finally taught me what my job actually was. The Making of a Manager is the modern version of that book. And Radical Candor forever shifted how I think about hard feedback.

1. High Output Management by Andy Grove

2. The Making of a Manager by Julie Zhuo

3. Radical Candor by Kim Scott

Check out my conversations with Kim Scott and Julie Zhuo.

I want to become a better leader

I love how the combination of these three books sums up great leadership: push people to do the best work of their lives, but be human about it, and, in the end, the score will take care of itself.

1. Amp It Up by Frank Slootman

2. The 15 Commitments of Conscious Leadership by Jim Dethmer, Diana Chapman, and Kaley Klemp

3. The Score Takes Care of Itself by Bill Walsh

I want to increase my product success rate

These classics taught me the fundamentals of product management: talking to customers, prioritizing roadmaps, and what it takes to build something valuable and impactful.

1. The Mom Test by Rob Fitzpatrick

2. Escaping the Build Trap by Melissa Perri

3. Continuous Discovery Habits by Teresa Torres

Check out my conversations with Melissa Perri and Teresa Torres.

I want to level up my product org

These books are also some of the most mentioned on my podcast, because they’ll shift how you think about the role of product within your organization, and how to make decisions in uncertain environments.

1. Empowered by Marty Cagan

2. Inspired by Marty Cagan

3. Thinking in Bets by Annie Duke

Check out my conversations with Marty Cagan (and, again, Marty Cagan) and Annie Duke.

I want to get better at sales and marketing

With AI making it easier to build, distribution is becoming the bigger bottleneck. This is not a natural strength for most builders, which is why you need to develop your marketing and sales muscle. I learned more about marketing and sales from these three books than from anywhere else.

1. Purple Cow by Seth Godin

2. Obviously Awesome by April Dunford

3. Founding Sales by Peter Kazanjy

Check out my conversations with Seth Godin, April Dunford, and Peter Kazanjy.

I want to be more productive...