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The best of the Weekly Contrarian: 2020 Edition

Posted in the following categories: Motivation

Before I share with you the best of the Weekly Contrarian from this year, I want to take a moment to thank you for inviting me to your inbox every week. I’m deeply grateful for your support.

I have one ask from you as we wrap up 2020.

I write these emails to inspire each of us to reimagine the way we see the world, and the way we see ourselves within the world. Please take a moment to think of the people in your circle, and consider who would benefit from seeing the world (and themselves) differently. Forward this email to them and ask them to sign up at Tell them why you think they would enjoy these emails, and that you’d love to hear any ideas that are sparked as they read them each week. If 2020 has taught us one thing, it’s the importance of finding new ways to connect. So let this weekly email be a spark for connection and new conversations.

Now, onto the best of 2020… (drum roll please…)

The five most popular articles I wrote this year

  1. Why I’m leaving academia
  2. How to think for yourself
  3. How to lose friends and alienate people
  4. Why empathy can backfire
  5. This is toxic

The best five books I read this year

  1. The Biggest Bluff by Maria Konnikova. I read this book during a beach vacation. It was so captivating that I might have developed a tan line (tan rectangle?) in the shape of the book. It chronicles Konnikova’s journey from not knowing the number of cards in a deck to competing in the World Series of Poker. As she writes, “This book isn’t about how to play poker. It’s about how to play the world.” I loved it.
  2. The Infinite Game by Simon Sinek. This book takes home the prize for “The book I’ve highlighted the most in 2020.” Here’s the basic idea: There are finite games, like chess, with clear rules and a clear endpoint. And then there are infinite games where there are no fixed rules and no winners or losers. The goal is not to win, but to keep playing. People who approach life as an infinite game innovate and inspire more (and have more fun along the way).
  3. City of Thieves by David Benioff. I bought a copy of this book at Broadway Books, my favorite indie bookstore in Portland (which is currently open by appointment). The co-owner, Kim, told me that this is “the perfect novel.” She wasn’t kidding. The story takes place during the Nazi siege of Leningrad. The book veers from funny to terrifying and back to funny in a matter of pages. It also serves as a great reminder that, as tough as things have been in 2020, they could be much worse.
  4. Free Play: Improvisation in Life and Art by Stephen Nachmanovitch. This is a must read for anyone doing creative work. It shares how we can create more of those beautiful moments when, as the author writes, “the work flows and work is play and the process and the product are one.” I also loved this line: “Out of tune? With what? Out of tune with my preconceived benchmark of ‘in tune.’”
  5. How to Change Your Mind: What the New Science of Psychedelics Teaches Us About Consciousness, Dying, Addiction, Depression, and Transcendence by Michael Pollan. Quake books, as Tyler Cowen describes them, are books that shake you to your core and jolt you of your current perspective. This was a quake book for me. Pollan does a brilliant job of dissecting the latest research on psychedelic therapy and debunking the myths that have been surrounding psychedelics since the 1960s when they became associated with the counterculture. The book is part scientific investigation and part captivating memoir about Pollan’s own life-changing experiences with psychedelics.

The best five movies and shows I watched this year

  1. Giant Little Ones (Hulu). Coming-of-age movies usually miss the mark. This one knocks it out of the park. I loved it.
  2. Ozark (Netflix). Fantastic acting and brilliant screenplay.
  3. The Marvelous Mrs. Maisel (Amazon Prime). One of the best shows I’ve seen in recent memory. Rachel Brosnahan is brilliant.
  4. Fleabag (Amazon Prime). I try not to binge anything (slowly savoring is more my thing), but I came close to binging this show (which, for me, means watching two episodes back-to-back). The writing is incredibly witty, and I love the running audience commentary.
  5. The Queen’s Gambit (Netflix). Lives up to the hype. Beautifully written and filmed.

Happy holidays to you and yours,


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