The best books on discipline, writing, and disciplined writing

Why am I passionate about this?

The reason I’m so fascinated by stand-up and books on writing is because I have done both. For a brief time I was a comedian, and the lessons in creativity and writing I learned along the way helped me find the career of copywriting. I’m passionate about learning how great writers write, and more importantly, keep writing, even when they don’t feel like it. I like to be inspired with lessons I can bring with me to every Word doc I open up.


I wrote...

You are not that funny: Stories from Cleveland Stand-Up

By Joshua Womack, Rebecca Ferlotti (editor),

Book cover of You are not that funny: Stories from Cleveland Stand-Up

What is my book about?

Josh Womack had a short run in stand-up comedy, but along the way he met some interesting people who left a profound impact on him. In his second book, Josh talks about falling in and out of love with comedy. You'll recognize some of the names, but you'll also hear the backstories of why certain venues hold a special place in the hearts of former and current Cleveland comedians. If you're a fan of stand-up and the stories behind the stage, You are not that funny is worth the two-drink minimum.

Shepherd is reader supported. When you buy books, we may earn an affiliate commission.

The books I picked & why

Book cover of The War of Art: Break Through the Blocks and Win Your Inner Creative Battles

Joshua Womack Why did I love this book?

The War of Art is one of those ‘If you were on a desert island and could only bring one book with you’ kind of books.

I have read it 5-6 times and the words in it inspired me and kept me on the path to finish both of the books I’ve written. Straight-forward, short chapters… probably my favorite book of all-time. Even if you’re not a writer, there’s a good chance Pressfield’s words will resonate with you.

By Steven Pressfield,

Why should I read it?

22 authors picked The War of Art as one of their favorite books, and they share why you should read it.

What is this book about?

A succinct, engaging, and practical guide forsucceeding in any creative sphere, The War ofArt is nothing less than Sun-Tzu for the soul.

What keeps so many of us from doing what we long to do?

Why is there a naysayer within? How can we avoid theroadblocks of any creative endeavor—be it starting up a dreambusiness venture, writing a novel, or painting a masterpiece?

Bestselling novelist Steven Pressfield identifies the enemy thatevery one of us must face, outlines a battle plan to conquer thisinternal foe, then pinpoints just how to achieve the greatest success.

The War of Art emphasizes the resolve…


Book cover of The Obstacle Is the Way

Joshua Womack Why did I love this book?

Ryan Holiday, like Steven Pressfield, is a no-nonsense writer whose words inspire you to start that project you’ve been putting off.

Already started it but running into some, well, obstacles? Holiday describes in his book how obstacles are a good thing and inspires us to look for creative solutions. This book made me reframe how I look at challenges, both personally and professionally.

By Ryan Holiday,

Why should I read it?

5 authors picked The Obstacle Is the Way as one of their favorite books, and they share why you should read it.

What is this book about?

We give up too easily. With a simple change of attitude, what seem like insurmountable obstacles become once-in-a-lifetime opportunities. Ryan Holiday, who dropped out of college at nineteen to serve as an apprentice to bestselling 'modern Machiavelli' Robert Greene and is now a media consultant for billion-dollar brands, draws on the philosophy of the Stoics to guide you in every situation, showing that what blocks our path actually opens one that is new and better.

If the competition threatens you, it's time to be fearless, to display your courage. An impossible deadline becomes a chance to show how dedicated you…


Book cover of Steal Like an Artist: 10 Things Nobody Told You about Being Creative

Joshua Womack Why did I love this book?

To create anything, you have to fight, scratch, and claw your way there.

Austin Kleon shows you how to take ideas and inspiration from just about anywhere and make something uniquely your own. He also exposes you to the idea that people do care about what you are passionate about. “The more open you are about sharing your passions, the closer people will feel to your work.”

By Austin Kleon,

Why should I read it?

8 authors picked Steal Like an Artist as one of their favorite books, and they share why you should read it.

What is this book about?

When asked to talk to students at Broome Community College in upstate New York in the spring of 2011, Austin Kleon wrote a simple list often things he wished he'd heard when he was their age: 'Steal like an artist; Don't wait until you know who you are to start making things; Write the book you want to read; Use your hands; Side projects are important; Do good work and put it where people can see it; Geography is no longer our master; Be nice (the world is a small town.); Be boring (it's the only way to get work…


Book cover of Disrupt Yourself: Putting the Power of Disruptive Innovation to Work

Joshua Womack Why did I love this book?

This book reinforces the notion to be brave enough to suck at something new.

We’re all experts in something, but chances are we can learn even more… even if we struggle at first. A really good message for those looking to shake things up in their career. “When we take a step down to gain momentum for the upward surge, for a time we will know less than those around us. This can deal a blow to the ego.”

The message? Don’t let your ego get in the way of learning!

By Whitney Johnson,

Why should I read it?

1 author picked Disrupt Yourself as one of their favorite books, and they share why you should read it.

What is this book about?

Thinkers50 Management Thinker of 2015 Whitney Johnson wants you to consider this simple, yet powerful, idea: disruptive companies and ideas upend markets by doing something truly different--they see a need, an empty space waiting to be filled, and they dare to create something for which a market may not yet exist. As president and cofounder of Rose Park Advisors' Disruptive Innovation Fund with Clayton Christensen, Johnson used the theory of disruptive innovation to invest in publicly traded stocks and private early-stage companies. In Disrupt Yourself, she helps you understand how the frameworks of disruptive innovation can apply to your particular…


Book cover of Born Standing Up: A Comic's Life

Joshua Womack Why did I love this book?

One of the best books ever about stand-up.

Steve Martin talks about perfecting his craft and really gives comedians and fans of stand-up a front row seat to what goes into being a comedian. The grind on the way up, and performing in near-empty places, will make you empathize with Martin and all the comics who started just like him.

By Steve Martin,

Why should I read it?

1 author picked Born Standing Up as one of their favorite books, and they share why you should read it.

What is this book about?

In the mid-seventies, Steve Martin exploded on to the comedy scene. By 1978, he was the biggest concert draw in the history of stand-up. In 1981 he quit forever. This book is, in his own words, the story of "why I did stand-up and why I walked away." Emmy and Grammy Award winner, author of the acclaimed New York Times bestsellers Shopgirl and The Pleasure of My Company, and a regular contributor to The New Yorker, Martin has always been a writer. His memoir of his years in stand-up is candid, spectacularly amusing, and beautifully written. At age ten, Martin…


You might also like...

Rewriting Illness

By Elizabeth Benedict,

Book cover of Rewriting Illness

Elizabeth Benedict

New book alert!

What is my book about?

What happens when a novelist with a “razor-sharp wit” (Newsday), a “singular sensibility” (Huff Post), and a lifetime of fear about getting sick finds a lump where no lump should be? Months of medical mishaps, coded language, and Doctors who don't get it.

With wisdom, self-effacing wit, and the story-telling artistry of an acclaimed novelist, Elizabeth Benedict recollects her cancer diagnosis after discovering multiplying lumps in her armpit. In compact, explosive chapters, interspersed with moments of self-mocking levity, she chronicles her illness from muddled diagnosis to “natural remedies,” to debilitating treatments, as she gathers sustenance from family, an assortment of urbane friends, and a fearless “cancer guru.”

Rewriting Illness is suffused with suspense, secrets, and the unexpected solace of silence.

Rewriting Illness

By Elizabeth Benedict,

What is this book about?

By turns somber and funny but above all provocative, Elizabeth Benedict's Rewriting Illness: A View of My Own is a most unconventional memoir. With wisdom, self-effacing wit, and the story-telling skills of a seasoned novelist, she brings to life her cancer diagnosis and committed hypochondria. As she discovers multiplying lumps in her armpit, she describes her initial terror, interspersed with moments of self-mocking levity as she indulges in "natural remedies," among them chanting Tibetan mantras, drinking shots of wheat grass, and finding medicinal properties in chocolate babka. She tracks the progression of her illness from muddled diagnosis to debilitating treatment…


5 book lists we think you will like!

Interested in creativity, procrastination, and presidential biography?

10,000+ authors have recommended their favorite books and what they love about them. Browse their picks for the best books about creativity, procrastination, and presidential biography.

Creativity Explore 139 books about creativity
Procrastination Explore 15 books about procrastination
Presidential Biography Explore 19 books about presidential biography