1. Uncanny Valley by Anna Wiener: When a book shakes your identity to its foundation, it deserves the best book of the year slot. Uncanny Valley is a memoir of Anna Wiener’s plunge from the NYC literary world into the Silicon Valley tech world. She manages to reveal the deep flaws of tech culture without demonizing the people who participate in it. Anna has a gift for presenting her observations and experiences and letting the reader draw their own conclusions, making the book a powerful experience of discovery (not to mention the fact that the book is a joy to read for the writing style alone). I saw a side of myself in this book that I did not like, and I will be coming to terms with that for years.
2. Swarmwise by Rick Falkvinge: Rick Falkvinge is the founder of the Swedish Pirate Party, a political party in Sweden that won a seat in the EU Parliament on a budget of 50,000 Euros (their competitors spent 6 million). Swarmwise is Rick’s manual for how to make a swarm to accomplish large scale change. The book is lucid, concrete, general, and has almost zero fluff – practically every line is either a concrete step involved in running a swarm or an explanation of the principles behind the steps.
3. All About Love by bell hooks: What captivated me about All About Love is how bell hooks draws on a clear and compelling definition of love, “the will to extend one’s self for the purpose of nurturing one’s own or another spiritual growth… Love is as love does. Love is an act of will – namely, both an intention and an action. Will also implies choice. We do not have to love. We choose to love” as well as at the components of love: “To truly love we must learn to mix various ingredients – care, affection, recognition, respect, commitment, and trust, as well as honest and open communication.” I appreciated how concrete these ideas are and it gives me somewhere clear to start incorporating them into my daily practices. The one thing I didn’t like about the book was that some of the claims bell hooks made felt sweeping and undersupported. But overall, it was a thought-provoking and actionable book.
4. Ultralearning by Scott Young: Scott Young provides an excellent blueprint for how to master difficult skills (he’s used his methodology to do enough MIT undergrad courses to get a degree in a year, and learned four different languages in a separate year). Even if you don’t need to learn a skill in such a concentrated period of time, Ultralearning is still valuable for understanding the framework in which skills develop.
5. Writing Down the Bones by Natalie Goldberg: The key idea I took from Writing Down the Bones is that the practice of writing can be a form of meditation, as a way of getting to the raw truths of our experiences. In contrast with many of the dryer, more vaguely academic books I read, Writing Down the Bones was moving. It made me want to write. Natalie offers practices to smooth the writing process (like writing in a cafe with a friend or having a writer’s group where you can read work aloud) mixed in with her experiences as a writer. If you want a book to help you see writing with fresh eyes, this is the book.
Honorable Mention. The Personal MBA by Josh Kaufman: The Personal MBA is the IKEA-brand version of getting an MBA: Kaufman gives you all the concepts and you put them together yourself. But what a great set of concepts it is: Josh covers everything from the day-to-day running of a business to accounting, marketing to management. I plan on keeping a copy of this book to refer to as I look at different organizations and start to understand how they work.
Other Contenders (in no particular order):
- How to Talk So Teens Will Listen and Listen So Teens Will Talk by Adele Faber and Elaine Mazlish
- Rework by Jason Fried and David Heinemeier Hansson
- At the Existentialist Cafe by Sarah Bakewell
- Multipliers by Liz Wiseman
- Emergent Strategy by adrienne marie brown
The Pragmatic Philosopher 