100 books like The Obstacle Is the Way

By Ryan Holiday,

Here are 100 books that The Obstacle Is the Way fans have personally recommended if you like The Obstacle Is the Way. Shepherd is a community of 10,000+ authors and super readers sharing their favorite books with the world.

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Book cover of The Power of Now: A Guide to Spiritual Enlightenment

Margarette Allyn Author Of Running from Yesterday: A True Story of Hope, Courage and Love

From my list on making it fun to be a better person.

Why am I passionate about this?

One of the most important lessons I learned from my grandma is that children have no fear or self-doubt unless they are taught to have these feelings, and then it's a choice to continue to believe in self-doubt. However, I was paralyzed by it after her death. I stopped being a carefree kid and started living through emotional survival. I lived a life of physical, mental, and emotional turmoil, and by a miracle, I was spared and given a chance to change it all. I am a dancer, writer, performer, and speaker, following every dream I've had. 

Margarette's book list on making it fun to be a better person

Margarette Allyn Why did Margarette love this book?

I heard of this book before I got sober. I felt it was too “Western trying to be Eastern Healers” and for people who had personal dysfunctions that I couldn't relate to. 

I came across it again after sobriety and realized that I was running from my past and making up a future based on my fears of the past, never really being present, which was a wack in the gut for the better. The road to healing was way more understandable when I accepted the present, knowing that I also had the power to change anything I wanted. 

By Eckhart Tolle,

Why should I read it?

23 authors picked The Power of Now as one of their favorite books, and they share why you should read it.

What is this book about?

**CHOSEN BY OPRAH AS ONE OF HER 'BOOKS THAT HELP ME THROUGH'**

The international bestselling spiritual book, now with a new look for its 20th anniversary. Eckhart Tolle demonstrates how to live a healthier, happier, mindful life by living in the present moment.

************

'I keep Eckhart's book at my bedside. I think it's essential spiritual teaching. It's one of the most valuable books I've ever read.' Oprah Winfrey

To make the journey into The Power of Now we will need to leave our analytical mind and its false created self, the ego, behind. Although the journey is challenging, Eckhart…


Book cover of Letters from a Stoic

Chuck Chakrapani Author Of Unshakable Freedom: Ancient Stoic Secrets Applied to Modern Life

From my list on Stoicism for beginners.

Why am I passionate about this?

I am the Editor of the free online magazine The Stoic and the author of some twenty books on Stoicism. My day job is President, Leger Analytics, and I am also a Distinguished Visiting Professor at Ryerson University. I am not a professional philosopher. I study and write about Stoicism because it helps us to live better, free of fear, anxiety, worry, or anger.

Chuck's book list on Stoicism for beginners

Chuck Chakrapani Why did Chuck love this book?

Seneca was one of the last of the ancient Stoics who lived during the time of Nero. Towards the end of his life, he wrote several letters to a young prefect, Lucilius. These letters were not just meant to be read by Lucilius but the generations to come as well. Seneca’s letters are well written and cover a wide range of topics as they relate to the art of living. These essays are a ‘how to’ guide to living.

Why this translation? Although there are 124 letters in all, modern translators tend to translate just a selection. Robin Campbell is no exception. I chose this translation because it is as good as any and it is not pricey.

By Lucius Seneca, Robin Campbell (translator),

Why should I read it?

5 authors picked Letters from a Stoic as one of their favorite books, and they share why you should read it.

What is this book about?

'It is philosophy that has the duty of protecting us ... without it no one can lead a life free of fear or worry'

For several years of his turbulent life, in which he was dogged by ill health, exile and danger, Seneca was the guiding hand of the Roman Empire. This selection of Seneca's letters shows him upholding the ideals of Stoicism - the wisdom of the self-possessed person immune to life's setbacks - while valuing friendship and courage, and criticizing the harsh treatment of slaves and the cruelties in the gladiatorial arena. The humanity and wit revealed in…


Book cover of Enchiridion

Eve Poole Author Of Leadersmithing: Revealing the Trade Secrets of Leadership

From my list on what you really need to know about leadership.

Why am I passionate about this?

It is shocking how many leaders suffer from imposter syndrome, and how little practical advice is out there about how to help. It’s been my mission to identify not only precisely what leaders need to be able to do well, but also how can they learn these things in the most efficient and durable way. Leadersmithing sets out a practical path to mastery and provides the toolkit leaders will really need. After I wrote it, I took on some senior leadership roles of my own. Even before Covid I had stress-tested the wisdom of this book, and post-covid I am even more confident that this leadership book really helps.

Eve's book list on what you really need to know about leadership

Eve Poole Why did Eve love this book?

Epictetus is the Stoic who inspired the Roman Emperor Marcus Aurelius. Stoicism is the intellectual origin of cognitive behavioral therapy and a way for leaders to train themselves to focus on the things they can change, rather than breaking their hearts over things over which they have no control. The Enchiridion has the virtue of being much shorter than Aurelius’ Meditations, and contains pithy observations and advice like ‘it is not events that disturb people, it is their judgment concerning them,’ and ‘don’t hope that events will turn out the way you want, welcome events in whichever way they happen: this is the path to peace.’ Leaders need to be good at detachment, and Stoicism can provide valuable tools to help.

By Epictetus, George Long,

Why should I read it?

2 authors picked Enchiridion as one of their favorite books, and they share why you should read it.

What is this book about?

Although he was born into slavery and endured a permanent physical disability, Epictetus (ca. 50–ca. 130 CE) maintained that all people are free to control their lives and live in harmony with nature. We will always be happy, he argued, if we learn to desire that things should be exactly as they are. After attaining his freedom, Epictetus spent his career teaching philosophy and advising a daily regimen of self-examination. His pupil Arrian later collected and published the master's lecture notes; the Enchiridion, or Manual, is a distillation of Epictetus's teachings and an instruction manual for a tranquil life. Full…


Book cover of A Guide to the Good Life: The Ancient Art of Stoic Joy

Vitaliy Katsenelson Author Of Soul in the Game: The Art of a Meaningful Life

From my list on that bring meaning to your life.

Why am I passionate about this?

I am an investor who happens to love writing, music, and simply life in general. I was born in Murmansk, Russia, where I spent my first 18 years. My family moved to Denver in 1991, and I have lived there since. I’m CEO of IMA, a value investing firm where I have creative freedom to focus on things I love. I was so fortunate to stumble into writing; it has completely rewired my mind by providing a daily two-hour refuge for focused thinking. I am constantly on the lookout for new stories and fresh insights. Writing is what keeps me in student-of-life mode, and there is so much to learn!

Vitaliy's book list on that bring meaning to your life

Vitaliy Katsenelson Why did Vitaliy love this book?

This book is solely responsible for hooking me on Stoic philosophy, prompting my deep exploration of practical aspects of life in my own book and, most importantly, the application of them to my daily life. William’s writing is easy to follow, and his advice is very practical. I’d advise you to start reading the book from chapter four; and then when you are done with the book, come back to the first three chapters.

By William B. Irvine,

Why should I read it?

6 authors picked A Guide to the Good Life as one of their favorite books, and they share why you should read it.

What is this book about?

One of the great fears many of us face is that despite all our effort and striving, we will discover at the end that we have wasted our life. In A Guide to the Good Life, William B. Irvine plumbs the wisdom of Stoic philosophy, one of the most popular and successful schools of thought in ancient Rome, and shows how its insight and advice are still remarkably applicable to modern lives.

In A Guide to the Good Life, Irvine offers a refreshing presentation of Stoicism, showing how this ancient philosophy can still direct us toward a better life. Using…


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

Peggy Dean Author Of Mindful Sketching: How to Develop a Drawing Practice and Embrace the Art of Imperfection

From my list on creative books for the wildly imperfect artist.

Why am I passionate about this?

My journey into art began as a serendipitous discovery that unfolded through curiosity. As a “can’t-be-tamed” creative, I understand the tug-of-war artists feel – craving to learn skills and create “quality” pieces, while also thumbing the snooze-fest of sticking to one thing. Been there, done that, got the paint-splattered t-shirt. This has ignited a passion for encouraging others to find their own creative voice, as I've navigated the same path while building a multifaceted career in watercolor, gouache, line drawing, urban sketching, brush lettering, and calligraphy…need I go on? The thing is, I will because there is still so much to be explored.

Peggy's book list on creative books for the wildly imperfect artist

Peggy Dean Why did Peggy love this book?

I can't recommend this book highly enough, and here's why: it completely shattered my misconceptions about originality in the creative process. Kleon's candid and approachable narrative made me realize that all art is, in some form, a reinterpretation or recombination of what already exists.

This book came into my life at a pivotal moment, just when I was grappling with the dreaded "impostor syndrome" and the paralyzing belief that everything I created needed to be unprecedented. Kleon's perspective is liberating. He argues that embracing influences and integrating them into your work is not only acceptable but essential for creativity. 

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 Meditations

Brian E. Johnson Author Of The Role Ethics of Epictetus: Stoicism in Ordinary Life

From my list on Stoicism through the eyes of a philosophy professor.

Why am I passionate about this?

I am an associate professor of philosophy at Fordham University. I earned my Ph.D. at the University of Chicago (the same institution where the fictional Indiana Jones is said to have earned his doctorate!). I specialize in Greek and Roman ethics with a particular emphasis on Stoicism.

Brian's book list on Stoicism through the eyes of a philosophy professor

Brian E. Johnson Why did Brian love this book?

While riding on the New York subway one day, the young woman sitting next to me was reading from the so-called “Little Black Book” (a collection of daily thoughts often read by members of Alcoholics Anonymous). After closing the book, she pulled out this very edition of Marcus Aurelius and I could not help but comment to her that she had made a great choice. Not only does the theme of the “Serenity Prayer” go back to Stoics, but Marcus Aurelius’ Meditations (literally titled “To Himself”) show the thoughtful and meditative side of Stoicism. In addition, Marcus Aurelius seems to be practicing what we now call spiritual exercises. Last, what is especially striking is that the Emperor Marcus Aurelius wrote many of these entries while he was stuck on military campaigns; thus, we see up close a man utilizing Stoicism to grapple with the messiness of life.

By Marcus Aurelius, Martin Hammond (translator),

Why should I read it?

2 authors picked Meditations as one of their favorite books, and they share why you should read it.

What is this book about?

'Their icy blasts are refreshing and restorative. They tell you the worst. And having heard the worst, you feel less bad' Blake Morrison

Written in Greek by the only Roman emperor who was also a philosopher, without any intention of publication, the Meditations of Marcus Aurelius offer a remarkable series of challenging spiritual reflections and exercises developed as the emperor struggled to understand himself and make sense of the universe. While the Meditations were composed to provide personal consolation and encouragement, Marcus Aurelius also created one of the greatest of all works of philosophy: a timeless collection that has been…


Book cover of Big Magic: Creative Living Beyond Fear

Dr. Caroline Brookfield Author Of The Reluctant Creative: 5 Effortless Habits to Expand Your Comfort Zone

From my list on trying new things even if you are scared.

Why am I passionate about this?

I was driven to become a veterinarian for as long as I could remember. Then, in high school, I developed a love of performance. I felt stuck. Should I choose art or science? I chose science, and despite a great career, I felt like something was missing. When I reconnected with my creativity through stand-up comedy, entrepreneurship and other non-artistic creative outlets, I found out what I had been missing. Why do we drop creativity for science? It was a common story. I dove into the research on creativity, and was blown away by how a bit of creativity can make us happier, more resilient, and make workplaces more effective.

Dr.'s book list on trying new things even if you are scared

Dr. Caroline Brookfield Why did Dr. love this book?

In this book, I loved the way the author explains the creative process and what it takes to engage your muse and catch ideas. In a different way from The War Of Art, I learned what holds us back from expressing ourselves creatively and how we can overcome this fear of being seen.

Elizabeth Gilbert shares stories and philosophies about how to be more creative every day in a funny and optimistic way.

By Elizabeth Gilbert,

Why should I read it?

18 authors picked Big Magic as one of their favorite books, and they share why you should read it.

What is this book about?

Readers of all ages and walks of life have drawn inspiration from Elizabeth Gilbert's books for years. Now, this beloved author shares her wisdom and unique understanding of creativity, shattering the perceptions of mystery and suffering that surround the process - and showing us all just how easy it can be. By sharing stories from her own life, as well as those from her friends and the people that have inspired her, Elizabeth Gilbert challenges us to embrace our curiosity, tackle what we most love and face down what we most fear. Whether you long to write a book, create…


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

Dr. Caroline Brookfield Author Of The Reluctant Creative: 5 Effortless Habits to Expand Your Comfort Zone

From my list on trying new things even if you are scared.

Why am I passionate about this?

I was driven to become a veterinarian for as long as I could remember. Then, in high school, I developed a love of performance. I felt stuck. Should I choose art or science? I chose science, and despite a great career, I felt like something was missing. When I reconnected with my creativity through stand-up comedy, entrepreneurship and other non-artistic creative outlets, I found out what I had been missing. Why do we drop creativity for science? It was a common story. I dove into the research on creativity, and was blown away by how a bit of creativity can make us happier, more resilient, and make workplaces more effective.

Dr.'s book list on trying new things even if you are scared

Dr. Caroline Brookfield Why did Dr. love this book?

As I read this book, I felt like the author was looking into my soul. I loved the short, punchy observations and challenges to anyone seeking to share their creativity. The Resistance is a force universal to everyone who is trying to share a little piece of themselves, and I love the way that it is broken down in this book.

I realized that when I could see what was holding me back from expressing myself, I was able to find strategies to mitigate that fear. This book was instrumental in my ability to express myself as an author and speaker. 

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 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich

Why am I passionate about this?

I have always tried to be "the best that I can be'' at anything. These books helped me be the best that I could be at commercial investment real estate sales...without hype...just good solid advice.

Adam's book list on books for anyone looking to begin a career in commercial investment real estate by authors who "have been there and done that"

Adam Von Romer Why did Adam love this book?

Tim Ferris is a genius. In his book, he describes how he crafted a lifestyle while building a very successful business. This book demonstrates how to make the most of your extremely busy day in commercial real estate and creates a "maximum value/productive capacity" that is crucial when getting started in a commercial investment career.

He discusses how he went from micro-managing everything to virtually managing nothing, all while traveling the globe and having some life-changing adventures. He is the undisputed king of outsourcing and taking back control of your life.

I read this book and started to implement some of his concepts immediately, and while I am not working 4 hours a week, I am not working 60-70 hours either; I am getting down there!


By Timothy Ferriss,

Why should I read it?

11 authors picked The 4-Hour Workweek as one of their favorite books, and they share why you should read it.

What is this book about?

A new, updated and expanded edition of this New York Times bestseller on how to reconstruct your life so it's not all about work

Forget the old concept of retirement and the rest of the deferred-life plan - there is no need to wait and every reason not to, especially in unpredictable economic times. Whether your dream is escaping the rat race, experiencing high-end world travel, earning a monthly five-figure income with zero management, or just living more and working less, this book is the blueprint.

This step-by step guide to luxury lifestyle design teaches:

* How Tim went from…


Book cover of Magic of Thinking Big

Stephen Key Author Of One Simple Idea: Turn Your Dreams Into a Licensing Goldmine While Letting Others Do the Work

From my list on for inventors with big ideas.

Why am I passionate about this?

The traditional way of commercializing an invention — patenting, prototyping, then marketing it — doesn’t work very well and never has. When I found an easier way to share my creativity with the world, it changed my life, because the feeling you get when you hold something in your hand that you first imagined in your head is second to none. My 10-step process breaks down barriers so that everyone who has an idea — young or old, rich or poor — can get in the game of bringing it to market. I’ve published 5 books, 1,000 articles, and more than 700 videos to help others take advantage of the power of open innovation.

Stephen's book list on for inventors with big ideas

Stephen Key Why did Stephen love this book?

Being a creative person is a journey, that’s for sure, and not an easy one. It’s tough and it takes courage, but you can get there. Along the way, how do you prevent yourself from getting discouraged, especially when you’re focused on bringing a big idea to life? Reading this timeless book on the importance of mindset never fails to motivate me. Follow its advice, and you will be able to climb the highest of mountains and pick yourself back up when you get knocked down. A must-read for inventors, entrepreneurs, and anyone with an idea.

By David M. Schwartz,

Why should I read it?

1 author picked Magic of Thinking Big as one of their favorite books, and they share why you should read it.

What is this book about?

More than 6 million readers around the world have improved their lives by reading The Magic of Thinking Big.

First published in 1959, David J Schwartz's classic teachings are as powerful today as they were then. Practical, empowering and hugely engaging, this book will not only inspire you, it will give you the tools to change your life for the better - starting from now. His step-by-step approach will show you how to:

- Defeat disbelief and the negative power it creates
- Make your mind produce positive thoughts
- Plan a concrete success-building programme
- Do more and do…


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