The 26 Best Books I Read in 2019

(Reading Time: 9 minutes)

2019 was another good year for reading things.  I completed 48 books, 26 of which I recommend to you here.

As either a warning or a selling point, most of them aren’t business books, and most weren’t released in 2019.

Instead of ranking them, I’ve listed them alphabetically by author, a cop-out if there ever was one.  And I’ve provided links to Amazon for each (just click on the title).  This is for your convenience – I’m not an Amazon affiliate and I’m not here to make money off your clicks.

With that, here are the books that made me laugh, cry, think and act in 2019.  Many of these came to me via personal recommendation, and my hope is that you’ll find a few of them intriguing enough to check out.

Selling the Invisible: A Field Guide to Modern Marketing, Harry Beckwith.  Originally released in the ‘90s, Selling the Invisible was one of the first business books I read that wasn’t dry, academic and dull.  Beckwith makes clear that this is a “how-to-think-about” book, not a “how-to” book, and his principles of services marketing stand up two decades later.  It’s a bit repetitive in spots, but that wouldn’t keep it off my list of the 20 best business books of all time.

Civil War Stories, Ambrose Bierce.  I picked up this collection because it includes “Occurrence at Owl Creek Bridge,” which Kurt Vonnegut once called “the greatest American short story.”  Bierce was a Civil War veteran from Ohio, and he writes with compelling detail about how this war was fought, and how it affected soldiers, their families, and citizens.  It’s said that Bierce influenced Hemingway, and I can see that.            

The Great Beanie Baby Bubble: Mass Delusion and the Dark Side of Cute, Zac Bissonette.  A well-researched but easy-to-read history of the man, the company and the supporting cast that took Beanie Babies from “zero” to “inescapable” to “zero again” in a few short years.  It’s one of the more fascinating stories in business and pop culture, with underlying themes of ego, bubble psychology and good ol’ greed.

The Boys in the Boat: Nine Americans and Their Epic Quest for Gold at the 1936 Olympics, Daniel James Brown.  The Boys in the Boat is the story of the working-class, Depression-era college students who won the gold in rowing in Hitler’s Germany.  The central character, Joe Rantz, had a childhood that most of us wouldn’t trade for, and his personal struggles are a proxy for the long odds this crew faced.  An inspiring read and one that was very difficult to put down.

HR on Purpose: Developing Deliberate People Passion, Steve Browne.  Full disclosure: I know Steve from my days in Cincinnati; we had opportunity to re-connect this year, after which I picked up HR on Purpose and finished it quickly.  You don’t have to be an HR practitioner to get a lot from this book, since it’s informed by an overall philosophy of business (and life).  But if you are in HR, this will help you do better work.

Designing Your Life: How to Build a Well-Lived, Joyful Life, Bill Burnett & Dave Evans.  In the span of two days, this book was recommended by someone in my accountability group (thanks, Jule!) and I learned that my favorite neighbor teaches courses to inmates based on it.  So I thought the universe was trying to tell me something.  Burnett & Evans show you how to apply design thinking to your life, which necessarily requires that you challenge many of the assumptions you may have about what your life & career “should” be.  Designing Your Life will require you to put in more work than most books, but if you’re at a crossroads or just unsure about “what’s next,” it will get you unstuck. 

Where I’m Calling From, Raymond Carver.  Carver’s last collection provides a perfect entry point for those unfamiliar with this master of the short story.  These are tales of common men and women, usually with things changing for the worse, told in a spare and simple style.  Often heartbreaking, always moving.

Atomic Habits: An Easy & Proven Way to Build Good Habits and Break Bad Ones, James Clear.  This has sold about a zillion copies, but with good reason: Clear’s framework is intuitive and simple (though I’d argue that changing habits is rarely “easy”).  The initial draw for me was that, as a soloist, my time is my inventory and my habits determine my outcomes.  The pleasant surprise was the context – the link that Clear draws between our habits and our identities.  Choice quote: “Every action you take is a vote for the type of person you wish to become.”

Ecstatic Cahoots: 50 Short Stories, Stuart Dybek.  These brief stories, many set in Chicago, move from the realistic to the surrealistic and back.  Dybek is a captivating writer, dealing with themes of freedom, desire and trust with imagination and dark humor.

The Win Without Pitching Manifesto, Blair Enns.  The Win Without Pitching Manifesto should be required reading for all creatives and consultants, especially those concerned with winning new business on the right terms.  Sage words: “If we are pomegranates, then we will resist being pushed into a process designed to compare apples to apples.”

Man’s Search for Meaning, Viktor Frankl.  The most significant book I’ve read in my life, period.  This year’s reading was perhaps my 15th since it was recommended to me in my mid-twenties.  “Ultimately, man should not ask what the meaning of his life is,” Frankl writes, “but rather he must recognize that it is he who is asked. Each man is questioned by life; and he can only answer to life by answering for his own life; to life he can only respond by being responsible.”  Frankl survived four concentration camps in WWII, which provides a powerful backdrop to the philosophy contained herein.

It Doesn’t Have to Be Crazy at Work, Jason Fried & David Heinemeier Hansson.  Much like Selling the Invisible, this book traffics in short, focused chapters that pack a lot of wisdom per ounce.  Fried & Hansson describe the approach to culture – “the calm company” – that they’ve put in place with their company, Basecamp.  A sample of their thinking: “The best companies aren’t families. They’re supporters of families. They’re there to provide healthy, fulfilling work environments so that when workers shut their laptops at a reasonable hour, they’re the best husbands, wives, parents, siblings, and children they can be.”  Entirely reasonable, but rarely practiced.

Imagine Me Gone, Adam Haslett.  This 2016 novel was a finalist for the Pulitzer, for, in their words, “the quiet and compassionate saga of a family whose world is shaped by mental illness and the challenges and joys of caring for each other.”  Haslett brings his characters fully to life; their struggles with depression never seem shallow or contrived.  It’s a compassionate and at times brutal read that will stick with you long after you’ve completed it.

Big Deal: A Year as a Professional Poker Player, Anthony Holden.  This is one of the recognized poker classics, originally published in 1990, when the game was very different than it is today.  Holden, a journalist, traveled the world playing poker for a year, and this account captures all the highs and lows.  It’s not necessary to be a poker nerd such as myself (though it may help) to enjoy this entertaining read.

High Fidelity, Nick Hornby.  Another of my comfort-food titles, which spawned one of my comfort-food movies.  Unlike the film, it’s set in London, and Rob Gordon is a little less charming (though every bit as lost) than John Cusack’s portrayal.  Like the film, it’s ultimately about rejection, obsession and getting in one’s own way.

Thinking, Fast and Slow, Daniel Kahneman.  A classic that I’m a little ashamed to admit I just read for the first time.  Kahneman lays out two modes of thinking: System 1, which is emotional, instinctive & rapid, and System 2, which is more logical and deliberative.  The two don’t always play well together.  This book is dense with supporting evidence and a-ha moments, and is perhaps the definitive word on “thinking about thinking.” 

We Learn Nothing and I Wrote This Book Because I Love You, Tim Kreider.  Kreider was a new discovery for me this year.  In these self-reflective essays, Kreider is empathic toward others, often tough on himself and always funny as hell, which makes his lessons easy to absorb.  If in doubt, start with We Learn Nothing.

Dead Wake: The Last Crossing of the Lusitania and Isaac’s Storm: A Man, a Time and the Deadliest Hurricane in History, Erik Larson.  Though neither of these quite rise to the level of The Devil in the White City, they both reflect Larson’s gift for marrying exhaustive research to a compelling narrative.  Dead Wake is about the sinking of the Lusitania by a German U-boat in 1915; a series of decisions, and a few minutes of time, made all the difference between safe passage and tragedy.  Isaac’s Storm moves less swiftly, but the description the Galveston hurricane of 1900 – still the deadliest natural disaster in US history, taking an estimated 8,000 lives – is horrifying in its graphic detail.   

Digital Minimalism: Choosing a Focused Life in a Noisy World, Cal Newport.  After reading this book, I cut my iPhone screen time by 75% in a single week, and it’s remained at those low levels for as long as I’ve followed the principles in this book.  Far more than the trite list of tips often offered on this topic (e.g., “Turn off those notifications!”), Digital Minimalism will help you identify which tools to use, for what reasons, and in what ways.

One More Thing: Stories and More Stories, B.J. Novak.  If you only know Novak as “Ryan the temp” from The Office, you’re missing out.  Novak’s humor is always erudite and at times absurdist; if you’re a fan of Steve Martin’s essays, you’ll enjoy One More Thing.  My wife & I read this poolside on our honeymoon in 2016 and frequently nudged each other to share the particularly funny parts; on my second reading, I found the premises just as imaginative and the twists just as surprising.

Good Strategy Bad Strategy: The Difference and Why It Matters, Richard Rumelt.  This is one of the few business books I’d recommend to nearly anyone.  Rumelt nails what strategy isn’t – such as goals, visions, and values, all of which are necessary, but none of which mean that strategic thinking has actually happened.  He also addresses the power of focus, the importance of defining obstacles and the application of strengths, among other topics.  Importantly, he emphasizes diagnosis, which is often overlooked in practice, as we rush to “get the plan done.”  “A great deal of strategy work is trying to figure out what is going on,” Rumelt writes.  “Not just deciding what to do, but the more fundamental problem of comprehending the situation.”

Calypso, Me Talk Pretty One Day, and When You Are Engulfed in Flames, David Sedaris.  I go back to certain authors like some people go back to favorite musicians, and Sedaris is one of those.  If I’m feeling rotten about the world, or some aspect of it, Sedaris always makes me feel better.  These three titles are probably my favorites in his catalog.

What did you read and love in 2019?  Please let me know in a comment or via email.  And here’s to expanding horizons further in 2020!

If you’re super-curious, here are my “best books” lists from 2018 and 2017.

About Matthew Fenton: Matthew helps challenger brands to focus, grow and win.  Since founding his consultancy, Three Deuce Branding, in 1997, he’s helped hundreds of brands to achieve “brand clarity.”  His consulting services and speaking engagements help brands to focus on what matters through positioning, strategy and ideation.  Contact Matthew here.  He calls Chicago home.

Copyright 2019 – Matthew Fenton. All Rights Reserved. You may reprint this article with the original, unedited text intact, including the About Matthew Fenton section.