I’ve never met a person who’s gone broke buying books.

☝That’s something I’ll stand by forever. A good book can change your outlook, your mood and open you up to a new way of thinking. It can change the course of your day, week and even your life.

Books are invaluable.

Which is why reading is fundamental to how we learn at Drift. It’s fundamental to how I approach problems and search for inspiration. And that’s why I’m always looking for that next great read. And why I reached out to this amazing community at the end of last year to hear must-reads for 2020.

So here it is, 50 books on my must-read list this year.

– DC

P.S. What books did I miss? Which on my list have you already read? Which are you most looking forward to reading? Reply to this email to let me know.

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The Must-Read Books On Leadership

Some of the world’s most successful companies encourage employees to ship and share every day. This has become a common mantra here at Drift, and I owe this type of thinking to authors like James Clear. Here are the other leadership-related titles recommended to me:

  1. Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones by James Clear
  2. Lost & Founder: A Painfully Honest Field Guide to the Startup World by Rand Fishkin
  3. Leaders Eat Last: Why Some Teams Pull Together and Others Don’t by Simon Sinek
  4. Herding Tigers: Be The Leader That Creative People Need by Todd Henry
  5. The Making of a Manager: What To Do When Everyone Looks To You by Julie Zhuo
  6. It Doesn’t Have To Be Crazy At Work by Jason Fried & David Heinemeier Hansson
  7. Trillion Dollar Coach: The Leadership Playbook of Silicon Valley’s Bill Campbell by Eric Schmidt, Jonathan Rosenberg, and Alan Eagle
  8. What You Do is Who You Are: How to Create Your Business Culture by Ben Horowitz
  9. Multipliers: How the Best Leaders Make Everyone Smarter by Liz Wiseman
  10. Turn The Ship Around by L. David Marquet
  11. An Elegant Puzzle: Systems of Engineering Management by Will Larsen
  12. “Who Says Elephants Can’t Dance?: Leading a Great Enterprise Through Dramatic Change” by Louis V. Gerstner Jr.

The Must-Read Books On Business

How you position your business and the trust customers have in your brand is everything. The titles in this section touch on how and how NOT to approach business in 2020. In particular, The Cluetrain Manifesto is one I’d recommend to almost anyone. Because it looks at how the dawn of the modern internet has changed every facet of our culture, how we do business and how people interact with companies.

  1. The Cluetrain Manifesto: The End of Business as Usual by Rick Levine, Christopher Locke, Doc Searls, and David Weinberger
  2. Obviously Awesome by April Dunford
  3. Get Together: A Book on Building Community by Bailey Richardson, Kevin Huynh, and Kai Elmer Sotto
  4. The Challenge Culture: Why the Most Successful Organizations Run on Pushback by Nigel Travis
  5. How Brands Grow: What Marketers Don’t Know by Byron Sharp
  6. Bad Blood: Secrets and Lies in a Silicon Valley Startup by John Carreyrou

The Must-Read Books On Empowerment

If you read my newsletter last week, you know we’re working hard to make Drift, tech, and frankly, corporate America, a friendlier place for women, people of color and other minority groups. That’s why I was especially drawn to these books on empowerment. And why I’ll be making my way through this list this year:

  1. The Memo: What Women of Color Need to Know to Secure a Seat at the Table by Minda Harts
  2. How Women Rise: Break the 12 Habits Holding You Back from Your Next Raise, Promotion, or Job by Sally Helgesen and Marshall Goldsmith
  3. Like a Mother: A Feminist Journey Through the Science and Culture of Pregnancy by Angela Garbes
  4. Just the Funny Parts: …And a Few Hard Truths About Sneaking into the Hollywood Boys’ Club by Nell Scovell
  5. Dignity: The Essential Role It Plays in Resolving Conflict by Donna Hicks
  6. The War of Art by Steven Pressfield

The Must-Read Books On Personal Development

Thinking In Bets was one of my favorite books in 2019. Written by professional poker player Annie Duke, the book is perfect for not just leaders like myself who make big decisions everyday, but those who struggle to “think on their feet.The books in this section are must-reads for anyone looking to get better every day.

  1. Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts by Annie Duke
  2. The Copywriter’s Handbook: A Step-By-Step Guide To Writing Copy That Sells by Robert W. Bly.
  3. What Do You Do With An Idea by Kobi Yamada (Author) and Mae Besom (Illustrator)
  4. The Third Door: The Wild Quest to Uncover How the World’s Most Successful People Launched Their Careers by Alex Banayan
  5. Thinking, Fast and Slow by Daniel Kahneman
  6. Never Split the Difference: Negotiating As If Your Life Depended On It by Chris Voss and Tahl Raz
  7. How to Change Your Mind: What the New Science of Psychedelics Teaches Us About Consciousness, Dying, Addiction, Depression, and Transcendence by Michael Pollan
  8. Marketing Rebellion: The Most Human Company Wins by Mark Schaefer
  9. Bullshit Jobs: A Theory by David Graeber
  10. The Power of Habit: Why We Do What We Do in Life and Business by Charles Duhigg
  11. The Algebra of Happiness: Notes on the Pursuit of Success, Love, and Meaning by Scott Galloway
  12. Stillness Is The Key by Ryan Holiday
  13. Super Thinking: The Big Book of Mental Models by Gabriel Weinberg and Lauren McCann
  14. Getting To Yes: Negotiating Agreement Without Giving In by Roger Fisher, William L. Ury, and Bruce Patton
  15. Influence: The Psychology of Persuasion by Robert Cialdini
  16. Range: Why Generalists Triumph in a Specialized World by David Epstein

The Must-Read Books For Fantastic Storytelling

Malcolm Gladwell has always been a go-to for me. His approach to non-fiction is masterful. Talking To Strangers offers some of the best insight into his writing process and how others can become more mindful listeners – and learners. Here, other top picks on storytelling:

  1. Talking to Strangers: What We Should Know about the People We Don’t Know Malcolm Gladwell
  2. Energy and Civilization by Vaclav Smil
  3. Educated by Tara Westover
  4. Sapiens: A Brief History of Humankind by Yuval Noah Harari
  5. Recursion by Blake Crouch
  6. The Ride of a Lifetime: Lessons Learned from 15 Years as CEO of the Walt Disney Company by Robert Iger
  7. The Nickle Boys by Colson Whitehead
  8. The Outsider by Stephen King
  9. Maybe You Should Talk to Someone: A Therapist, HER Therapist, and Our Lives Revealed by Lori Gottlieb
  10. The Surrender Experiment: My Journey into Life’s Perfection by Michael Singer

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