I’ve devoured a massive number of books on how to live a better life, and these are the ones that have towered above the rest.
Daring Greatly: How the Courage to Be Vulnerable Transforms the Way We Live, Love, Parent, and Lead
There aren’t that many books that change your life, demand repeated reading, and linger within you long after you’ve put it down. Daring Greatly (my review) is one of them. Brené Brown writes about something I’ve always grappled with but never identified until reading her book; shame and the deep-seated fear of not being good enough to be loved.
We all wrestle with these demons, and Brown spent more than a decade researching their roots. I kept yelling (inside) at the many times she described exactly what I’d been doing and secretly thinking my whole life, helping me to make sense of it all, and steps to take to overcome my fears.
Joy on Demand: The Art of Discovering the Happiness Within
If you’ve ever wanted to meditate, but either didn’t know how, couldn’t stick with it or found other texts too obtuse, read Chade-Meng Tan’s Joy on Demand.
Written by a Google pioneer, Tan’s book is the most practical guide to meditation that I’ve found. It’s written with good humor, an engineer’s precision, and profound respect for Buddhist psychology.
Mindfulness in Plain English
But if you’re looking for a deeper dive into the hows and whys of meditation, including common problems and how to solve them, you won’t get better than Bhante Gunaratana’s classic book Mindfulness in Plain English.
My favourite biography of the Buddha is one that admits it’s impossible to write a definitive biography of the man who lived more than 2,500 years ago. The myths of the Buddha are intimately intertwined with his history, and one can’t be pried from the other without reducing the whole.
What Karen Armstrong deftly does instead is craft Siddhartha Gautama’s story against the background of his times, and Buddha delivers both an illuminating story of his search for enlightenment, as well as an introduction to what he taught.
When Things Fall Apart: Heart Advice for Difficult Times
In When Things Fall Apart, Chödrön writes about how Buddhism can help you cope with the hard changes of life, akin to what she calls “standing on groundlessness.” I recommend When Things Fall Apart, but I can just as easily recommend The Places That Scare You, and Living Beautifully (my reviews).
The Open Road: The Global Journey of the Fourteenth Dalai Lama
The Open Road is a beautifully written introduction to the Fourteenth Dalai Lama and Tibetan Buddhism. Pico Iyer has known the Dalai Lama for more than three decades, and in The Open Road he reveals layers of the man and his community with uncommon intimacy.
While Iyer remains respectful to his subject, he doesn’t lose his journalistic edge; The Open Road holds as many hard truths about the history of Tibetan Buddhism as it does tender moments about the Dalai Lama. It remains one of my most beloved books, as much for its subject as its transcendent prose.
Tiny Beautiful Things: Advice on Love and Life from Dear Sugar
Cheryl Strayed’s Tiny Beautiful Things is a beautifully written book on facing the worst that life has to offer. Her words are raw, heartfelt, harsh when necessary, but always compassionate. Think of Strayed as a kindly, worldly aunt who’s not afraid to tell you to go fuck yourself when you’re full of shit, but always has your best interests at heart.
When life sucks and you don’t want a platitude, Tiny Beautiful Things offers an incandescent light of authenticity on bookshelves full of banality.
The Way of the Superior Man: A Spiritual Guide to Mastering the Challenges of Women, Work, and Sexual Desire
There’s no way to escape this book’s bombastic title, but David Deida’s The Way of the Superior Man has helped me understand what it means to be a man more than any other text out there. Just the part on the difference between masculine and feminine energies alone is worth the price of the book.
To be clear, the ‘superior’ in the title doesn’t refer to being superior over women, but as a call for men to be better than before. Fair warning: you might hate this one.
So Good They Can’t Ignore You: Why Skills Trump Passion in the Quest for Work You Love
Like almost everyone, I bought into the popular belief that “following your passion” was good advice. It really wasn’t, or at the least, it wasn’t complete advice, and I wish I had Cal Newport’s So Good They Can’t Ignore You earlier in my life to explain why.
Not only does Newport debunk the passion belief, he also takes you on a journey to find out what works instead to build a career that gives you mastery, autonomy and purpose. Far from the commonplace touchy-feely advice, So Good They Can’t Ignore You provides practical, sensible advice on how to end up loving what you do for a living.
Deep Work: Rules for Focused Success in a Distracted World
After So Good They Can’t Ignore You, Cal Newport follows up with another singular, constructive book on how to become so good they can’t ignore you. In today’s hyper-distracted environment, the ability to do deep work is becoming increasingly rare, but great, amazing, world-changing work is always a product of deep work. In Deep Work, Newport gives you the tools to make it happen.
First Things First
Stephen Covey’s First Things First is one of those books that changes the way you live your life. It certainly changed the way I looked at productivity, not as a way to get lots of things done, but as a way to make sure I got the right things done. More than just a tome on time management, First Things First gives you the tools to ask just what it is you want to spend the time of your life on.
Getting Things Done: The Art of Stress-Free Productivity
While First Things First excels at high altitude mission control, Getting Things Done shines at street-level tactics. David Allen’s Getting Things Done (GTD) system can get complicated and unwieldy, but once you get it, GTD gives you a fighting chance to turn vision into action. The plus side is that getting into GTD is easier now than it was before, with a wealth of apps built on the system.
Think of First Things First and Getting Things Done as a complementary pair, I wouldn’t recommend one without the other.
The War of Art: Break Through the Blocks and Win Your Inner Creative Battles
The War of Art is a must-read if you hope to make a living making things. While war sounds like an ill-suited way to describe creativity, Steven Pressfield makes the compelling case that every person who wants to bring something new into the world is fighting a war; a war against doubt, laziness and fear.
If we do not come to this war ready to fight tooth and nail, we’ll succumb to what’s easier than making art: making nothing. The War of Art names your enemy, gives you tools to fight it, and lets you know that you’re not alone when you’re facing the resistance against creativity.
On Writing: A Memoir of the Craft
There are many other writing books that have improved my writing mechanics, but King’s On Writing is one I return to when I want to refocus on the essentials.
Writing to Change the World
Writing to Change the World is less a textbook, and more of a manifesto. If you want specific recipes to improve your writing, there are other books for that. But if you want a case to write for reasons bigger than yourself, you’ll find Mary Pipher’s book invigorating.
Writing to Change the World both inspired and challenged me not to play small, and to continue using my writing to fight a good fight, even if my words only move the world by a single millimetre.