The 13 Best Books I Read in 2020

(Reading Time: 6 minutes)

2020 was the year I learned to quit a book.

See, I have a problem.  Maybe you have it too.  Once I start a book, I feel guilty about putting it down.  Even if it’s awful.  Mom & Dad said, “Don’t start something you’re not going to finish,” and I guess I took that to heart.

But then, earlier this year, I was about 10% into a book when I stumbled over this chunk of verse:

“The Kennedy assassination is the Rubik’s Cube of American history: The subject can be held up to the light and viewed in many different configurations.”

I closed that book immediately, and forever.  I felt great about this.  And a new habit was born.

So, in 2020, I abandoned more books, and finished fewer books, than usual.  After averaging 45 books a year over the prior three years, this year I completed 21.  The good news: The ratio of “what I recommend” to “what I read” is better this year than in any year prior.  Of those 21 books, I recommend 13 to you here.

Otherwise, the setup for this list is similar to that of prior years:

As either a warning or a selling point, most of these aren’t business books, and most weren’t released in 2020.

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 the book title).  This is for your convenience – I’m not an Amazon affiliate and I’m not here to make money off your clicks.  If it’s available to you, I do recommend that you support your local independent bookseller.

With that, here are the books that helped me to laugh and learn in 2020. 

Trailblazer: The Power of Business as the Greatest Platform for Change, Marc Benioff.  Though I don’t love the self-congratulatory title, I enjoyed most everything else about Trailblazer.  Benioff, the founder and co-CEO of Salesforce, is in a better position than most to make the case that values can drive value.  And he’s not afraid to acknowledge his mistakes as a leader.  For those that are so inclined, there’s plenty of support here for the notion that businesses can do well by doing good.

The Simple Path to Wealth: Your Road Map to Financial Independence and a Rich, Free Life, JL Collins.  On Twitter or on cable news, personal finance is a shrieking swirl of “hot tips” and “secrets.”  In the hands of JL Collins, it’s a time-tested set of clear principles.  In terms of lifetime value, you couldn’t do much better to gift this to someone in their twenties (or any age, really).

Life Itself: A Memoir, Roger Ebert.  I didn’t want this book to end.  Ebert was such a strong writer: Empathic, observant, wise, self-deprecating.  This story could have only been written by him – growing up in the small college town of Urbana, IL; joining one of the great newspaper rooms in the ‘60s; becoming regionally, then nationally, and then internationally famous; drinking too much and then not at all; finding the love of his life late in life – but Ebert is never self-important or off-putting.  I highlighted huge portions of this book, but one quote, near the end of Life Itself, stands out: “We must try to contribute joy to the world. That is true no matter what our problems, our health, our circumstances. We must try. I didn’t always know this, and am happy I lived long enough to find it out.”

Range: Why Generalists Triumph in a Specialized World, David Epstein.  The thesis here runs counter to the “10,000 hours of practice” camp.  But Epstein makes a compelling and at times counter-intuitive case: That in complex environments (i.e. much of life and leadership), generalists are better equipped than specialists.  If you have any interest in performance or achievement, this is worth your time.

The Great Gatsby, F. Scott Fitzgerald.  I’m not going to waste your time by reviewing a certified masterpiece.  I’ll only say that on this, perhaps my fourth reading of Gatsby, I marveled at Fitzgerald’s painstaking care for the language.  Every word is right where it needs to be.

Catch-22, Joseph Heller.  I revisited this one for the first time in a few decades.  The humor remains almost oppressively absurdist, the plot difficult to parse, the sense of futility overwhelming.  But that’s the point.  The main character, Yossarian, is a US bombardier stationed in Italy in WWII; he very much does not want to die, but he’s surrounded by indifference, bureaucracy and profiteering.  I can’t imagine what a breakthrough this book must have been when it was first published in 1961.

The Biggest Bluff: How I Learned to Pay Attention, Master Myself, and Win, Maria Konnikova.  You needn’t be a poker nerd like myself to enjoy The Biggest Bluff.  The book details the year Konnikova spent learning to play poker, starting as a complete novice.  Without spoiling the ending, it goes pretty well for her.  Konnikova is both a Ph. D. in psychology and a contributing writer to the New Yorker; though the mechanics and culture of poker can be a bit impenetrable to newbies, she has a skill for making them accessible and for drawing out the lessons.

The Splendid and The Vile: A Saga of Churchill, Family and Defiance During the Blitz, Erik Larson.  I will read anything Larson writes, and this 2020 release maintains his high bar.  The Splendid and the Vile focuses on the early days of Britain’s involvement in World War II – Hitler invaded Belgium and Holland on Churchill’s first day as prime minister, and 45,000 Brits were about to die in German bombings.  As always, Larson expertly weaves multiple storylines: Though Churchill’s public leadership was exceptional, his private life was not without its drama, and you’ll learn much about both here.

Churchill: Walking With Destiny, Andrew Roberts.  At over 1100 pages, this one is a commitment.  It’s also been called the best single-volume biography of Churchill and was very well-reviewed on its 2018 release.  I appreciate that Roberts clearly admires Churchill, but doesn’t consider him infallible.  I also appreciate the exhaustive research, which provides necessary context throughout.  Go with The Splendid and the Vile if you want a moment in time; go with Walking With Destiny if you want broad scope.  Even better, go with both.

Excellence Wins: A No-Nonsense Guide to Becoming the Best in a World of Compromise, Horst Schulze.  “There’s always a market for the best” has long been a business truism.  In Excellence Wins, Schulze, the co-founder and former president of Ritz-Carlton, draws back the curtain on one of the best service organizations in the world.  It’s an easy read, filled with timeless principles and wisdom, not jargon or newly-invented “frameworks.”  I’d recommend it to most anyone, but especially to anyone leading a team of service professionals.

A Man Without a Country, Kurt Vonnegut.  Vonnegut has long been my go-to for humanist wisdom.  A Man Without a Country is a kind of brief semi-memoir in the shape of interconnected essays.  As with all Vonnegut, the morals are made more digestible with a spoonful humor and a clear, simple writing style.  This was not the first time I’ve read this and it probably won’t be the last.

Consider the Lobster and Other Essays, David Foster Wallace.  In a year as chaotic as 2020, Wallace was a fine escape.  In part, this is because you can’t read Wallace without complete focus: His essays never arrive exactly where you’d expect them to, and they’re full of tangents (often in lengthy footnotes).  Several of the topics here – Tracy Austin, the Adult Video Network’s annual awards ceremony in Vegas, John McCain’s 2000 presidential run – have a foot in popular culture, so this is a good entry point for those unfamiliar with Wallace’s unique mind.

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 yourself.

What did you read & love in 2020?  I’d love to know.

If you’re in the mood for tumbling down a rabbithole, here are my lists from prior years:

The 26 Best Books I Read in 2019

The 20 Best Books I Read in 2018

The 16 Best Books I Read in 2017

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About Matthew Fenton: Matthew is a former CMO who helps brands to focus, stand out and grow.  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’s based in Chicago.

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