In order of recommendedness, here are some books I have found really useful.
In order of recommendedness…
You are a Badass: How to Stop Doubting Your Greatness and Start Living an Awesome Life, Jen Sincero
Summary: A straightforward manual for building self-esteem and setting your life on the powerful path.
Orbiting the Giant Hairball: A Corporate Fool's Guide to Surviving with Grace, Gordon MacKenzie
Summary: How to be creative and support other creative individuals in the workplace.
Braving the Wilderness: The Quest for True Belonging and the Courage to Stand Alone, Brené Brown
Summary: How to be true to yourself even when you’re very, very, very, very alone, and having to be courageous.
How to Win Friends and Influence People, Dale Carnegie
Summary: A very dated classic, yet there are no modern books its equal. Outlines how to be a good person, at the most basic level.
Do The Work, Steven Pressfield
Summary: A must-read for anyone who struggles with writing or any other project that requires sustained attention over time.
On Writing: A Memoir of the Craft, Stephen King
Summary: An autobiographical account of King’s relationship with writing. Inspiring, heartfelt, and honest.
If at Birth You Don't Succeed: My Adventures with Disaster and Destiny, Zach Anner
Summary: A brilliantly written autobiography from a comedian featured on the Oprah Winfrey Network, and his own YouTube channel, among other things. Tremendously inspiring, and laugh-out-loud funny.
The Success Principles(TM): How to Get from Where You Are to Where You Want to Be, Jack Canfield and Janet Switzer
Summary: Essential factors for a successful life, however you define that.
The Autobiography of Benjamin Franklin, Benjamin Franklin
Summary: It turns out that this old white guy was a pretty amazing dude with some pretty ground-breaking ideas. I tried doing a modern translation of his book a couple years ago and may get around to it yet, but for now, read the original.
Loving What Is: Four Questions that can Change Your Life, by Byron Katie and Stephen Mitchell
Summary: Learn to react logically to any situation, no matter how emotional.
The Four Spiritual Laws of Prosperity: A Simple Guide to Unlimited Abundance, Edwene Gaines
Summary: How to be prosperous through spiritual means and actually make the world a better place. - or - You don’t have to be a soulless a-hole to be rich.
Bird by Bird: Some Instructions on Writing and Life, Anne Lamott
Summary: Essential instruction for writers.
Rising Strong: How the Ability to Reset Transforms the Way We Live, Love, Parent, and Lead, Brené Brown
Summary: Both research-based and heart-based, this book will transform how you see your own ability to recover from failures and trauma.
The Art of Exceptional Living (audio only), Jim Rohn
Summary: A collection of inspiring talks on how to seize control of your life and do better.
Spontaneous Happiness, Andrew Weil
Summary: How to use nutrition and mindfulness to address mental health to create emotional buoyancy.
How to Build Self-Discipline: Resist Temptations and Reach Your Long-Term Goals and Grit: How to Keep Going When You Want to Give Up, Martin Meadows
Summary: Pretty self-explanatory titles.
Gumption: Relighting the Torch of Freedom with America's Gutsiest Troublemakers, Nick Offerman
Summary: Stories from America’s history from a very upstanding American citizen.
Call Me Ted, Ted Turner
Summary: The autobiography of Ted Turner, a surprisingly heart-centered and wonderful human.
The Creative Habit: Learn It and Use It for Life, Twyla Tharp
Summary: How to build a habit of getting your creative work done, even though you have a lot of other stuff to do.
Born Standing Up: A Comic’s Life, Steve Martin
Summary: An autobiographical book about Steve Martin’s ascent to superstardom. Full of anxiety attacks and unexpected foibles.
The Alchemist, Paulo Coehlo
Summary: I had resisted reading this book for a long time because of how intensely woo-woo it was, but I finally broke down on a long road trip. It is a magical tour across many lands, with a fairly obvious message: the treasure is inside you all along. Also, it’s literally where you were just sleeping, like, 10 years ago.
Shoe Dog: A Memoir by the Creator of Nike, Phil Knight
Summary: The unlikely rise from his parent’s basement to the top of the greatest shoe company in the world.
The 15 Invaluable Laws of Growth: Live Them and Reach Your Potential, John C. Maxwell
Summary: Build an attitude of continual growth.
Grit: The Power of Passion and Perseverance, Angela Duckworth
Summary: A research-based approach to the importance of having grit in your approach to life.
The Art of Asking: How I Learned to Stop Worrying and Let People Help, Amanda Palmer
Summary: It’s not easy to ask for help, but people really do want to help you.
Astrophysics for People in a Hurry, Neil deGrasse Tyson
Summary: If you want to be astounded by the infiniteness of the Universe, this is your book.
Think and Grow Rich, Napoleon Hill
Summary: UGH, Napoleon! See, here’s this book… it’s a book from the 1930s, and the content -- the meat of the content -- is good. But he’s sexist and racist. If you can get around it, great. If not, here is your fair warning to steer clear. This may be a good candidate for a modern translation.