Top ten.

One highlighted passage from my 20 favorite books in 2019, a ranked list

(And an unranked list of everything else.)

Michael Sippey
6 min readJan 7, 2020

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A great year for reading. Tolentino, Odell, Rooney and Brodesser-Akner were revelations. I’m blessed to work alongside a bunch of insightful readers: thanks to Siobhan O'Connor for pointing me to Fleishman, Kawandeep Virdee for Nothing, to Samantha Zabell for Rooney and French, and Ev Williams for Kishimi.

  1. Trick Mirror: Reflections on Self-Delusion, by Jia Tolentino. “For hours I watched the blinding swirl of light and cloud move west and I repented. At sunset, the sky billowed into mile-wide peonies, hardly an arm’s length above me, and it felt like a visitation, like God was replacing the breath in my lungs. I sobbed — battered by a love I knew would fall away from me, ashamed for all the ways I had tried to bring myself to this, humiliated by the grace of encountering it now.”
  2. How To Do Nothing: Resisting the Attention Economy, by Jenny Odell. “Resisting definition like headwaters resist pinpointing, we emerge from moment to moment, just as our relationships do, our communities do, our politics do. Reality is blobby. It refuses to be systematized. Things like the American obsession with individualism, customized filter bubbles, and personal branding — anything that insists on atomized, competing individuals striving in parallel, never touching — does the same violence to human society as a dam does to a watershed.”
  3. Normal People, by Sally Rooney. “Outside her breath rises in a fine mist and the snow keeps falling, like a ceaseless repetition of the same infinitesimally small mistake.”
  4. Fleishman is in Trouble, by Taffy Brodesser-Akner. “Toby sat, stunned, and realizing that his entire problem in life was that he could still be stunned by information that revealed what seemed to be true most of the time, which was that things weren’t what they seemed.”
  5. Conversations With Friends, by Sally Rooney. “I loved when he was available to me like this, when our relationship was like a Word document that we were writing and editing together, or a long private joke that nobody else could understand. I liked to feel that he was my collaborator.”
  6. Exhalation, by Ted Chiang. “The conservation of energy means that it is neither created nor destroyed; we are radiating energy constantly, at pretty much the same rate that we absorb it. The difference is that the heat energy we radiate is a high-entropy form of energy, meaning it’s disordered. The chemical energy we absorb is a low-entropy form of energy, meaning it’s ordered. In effect, we are consuming order and generating disorder; we live by increasing the disorder of the universe.”
  7. Nickel Boys, by Colson Whitehead. “Violence is the only lever big enough to move the world.”
  8. Machines Like Me, by Ian McEwan. “Factory settings — a contemporary synonym for fate.”
  9. Trust Exercise, by Susan Choi. “Karen had no room for other people’s unresolved emotions because she had no room for her own lack of generousness.”
  10. My Year of Rest and Relaxation, by Otessa Moshfegh. “Irritation was what I knew best — a heaviness on my chest, a vibration in my neck like my head was revving up before it would rocket off my body. But that seemed directly tied to my nervous system — a physiological response. Was sadness the same kind of thing? Was joy? Was longing? Was love?”
  11. Salvage the Bones, by Jesmyn Ward. “He is a creek becoming a river.”
  12. Circe, by Madeline Miller. “I know how lucky I am, stupid with luck, crammed with it, stumbling drunk.”
  13. Make it Scream, Make it Burn, by Leslie Jamison. “The whole world was making promises it couldn’t keep. The whole world was out to scam you. Vegas was just upfront about it. It put marquee lights around it.”
  14. The Courage to be Disliked: How to Free Yourself, Change Your Life and Achieve Real Happiness, by Ichiro Kishimi. “The fact that you think you can see the past, or predict the future, is proof that rather than living earnestly here and now, you are living in a dim twilight.”
  15. Horror Stories, a Memoir, by Liz Phair. “Everybody thinks my song ‘Fuck and Run’ is about sex, and on one level it is. But it’s also about these moments when real connection and feeling is abandoned in favor of self-preservation. We come together and fly apart like colliding billiard balls because, for whatever reason, we sense annihilation.”
  16. There There, by Tommy Orange. “This world is a mean curveball thrown by an overly excited, steroid-fueled kid pitcher, who no more cares about the integrity of the game than he does about the Costa Ricans who painstakingly stitch the balls together by hand.”
  17. What Art Is, by Arthur C. Danto. “For me, Duchamp’s philosophical discovery was that art could exist, and that its importance was that it had no aesthetic distinction to speak of, at a time when it was widely believed that aesthetic delectation was what art was all about.”
  18. How to Think: A Survival Guide for a World at Odds, by Alan Jacobs. “It is easy to become captive to words, to treat them as though they truly and fully convey genuine knowledge — as though they are real cash money, legal tender, accepted everywhere at their face value, rather than mere counters.”
  19. In the Woods, by Tana French. “It was only much later, in the stale cold light of hindsight, that the little things rose up and rearranged themselves and clicked neatly into place to form the pattern we should have seen all along.”
  20. The Likeness, by Tana French. “We all cut off our own limbs to burn on some altar. The crucial thing is to choose an altar that’s worth it and a limb you can accept losing. To go consenting to the sacrifice.”

The rest of what I read this year…

I read 40+ books this year; probably would have made it through more but I wasted too much time on Stephen King’s The Stand. (Pro tip: if you want to read King, don’t read The Stand, you’ll never get that time back.) Here are the rest beyond the top 20, unordered (other than alphabetically by author) because while some of them are better than others, it’s not worth arguing about.

  • The Valedictorian of Being Dead: The True Story of Dying Ten Times to Live, by Heather Armstrong
  • Dare to Lead: Brave Work, Tough Conversations, Whole Hearts, by Brene Brown
  • Reboot: The Art of Leadership and Growing Up, by Jerry Colonna
  • Pines, by Blake Crouch
  • Recursion, by Blake Crouch
  • White Fragility: Why It’s So Hard for White People to Talk About Racism, by Robin DiAngelo
  • Play it As it Lays, by Joan Didion
  • Stillness is the Key, by Ryan Holiday
  • What You Do Is Who You Are: How to Create Your Business Culture, by Ben Horowitz
  • Super Pumped: The Battle for Uber, by Mike Isaac
  • Farsighted: How we Make the Decisions that Matter Most, by Steven Johnson
  • On Writing: A Memoir of the Craft, by Stephen King
  • The Stand, by Stephen King
  • Building a StoryBrand: Clarify Your Message So Customers Will Listen, by Donald Miller
  • Ruined by Design: How Designers Destroyed the World and What We Can Do to Fix It, by Mike Monteiro
  • Digital Minimalism: Choosing a Focused Life in a Noisy World, by Cal Newport
  • Who is Michael Ovitz? by Michael Ovitz
  • Cumulus, by Eliot Peper
  • How to Change Your Mind: What the New Science of Psychedelics Teaches Us About Consciousness, Dying, Addiction, Depression and Transcendence, by Michael Pollan
  • The Mastermind: Drugs, Empire, Murder, Betrayal, by Evan Ratliff
  • Come With Me, by Helen Schulman
  • Lake Success, by Gary Shteyngart
  • Why Greatness Cannot Be Planned: The Myth of the Objective, by Kenneth O. Stanley and Joel Lehman
  • Let’s Go (So We Can Get Back), by Jeff Tweedy
  • The Making of a Manager: What to do When Everyone Looks at You, by Julie Zhou

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