100 books like Winning

By Tim S. Grover, Shari Wenk,

Here are 100 books that Winning fans have personally recommended if you like Winning. Shepherd is a community of 11,000+ authors and super readers sharing their favorite books with the world.

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

Book cover of The 10x Rule: The Only Difference Between Success and Failure

Steve Mastroianni Author Of Hobby Boss: Turn Your Passion Into Profits Online

From my list on to kick you into high gear.

Why am I passionate about this?

I have been interested in motivation, productivity, and growth my whole life. I find it fascinating how we all have 24 hours; however, some people can maximize that time to create success while others let it go to waste. It all comes down to mindset. As an entrepreneur, I’ve consumed countless books, courses, and coaching programs to create what I call the “Rockstar Mind.” It has helped me tour the world opening for bands like KISS, write two best-selling books and 3 hit songs, and run two online businesses while supporting my young family during a global pandemic. I’m always looking for the edge to create more impact in my day.

Steve's book list on to kick you into high gear

Steve Mastroianni Why did Steve love this book?

This is my go-to book to feel motivated and get back into taking action (or “massive action” as Grant calls it). I highly recommend getting your hands on the audiobook version and setting the speed to at least 1.5x to get a world-class pep talk from one of the most energetic and best action-takers out there. I guarantee it will inspire you to get more out of your day.

By Grant Cardone,

Why should I read it?

2 authors picked The 10x Rule as one of their favorite books, and they share why you should read it.

What is this book about?

Achieve "Massive Action" results and accomplish your business dreams! While most people operate with only three degrees of action-no action, retreat, or normal action-if you're after big goals, you don't want to settle for the ordinary. To reach the next level, you must understand the coveted 4th degree of action. This 4th degree, also know as the 10 X Rule, is that level of action that guarantees companies and individuals realize their goals and dreams. The 10 X Rule unveils the principle of "Massive Action," allowing you to blast through business clich s and risk-aversion while taking concrete steps to…


Book cover of The Subtle Art of Not Giving a F*ck: A Counterintuitive Approach to Living a Good Life

Dr. CI Author Of DEI-ing: A Guide to Navigating the Gotdamn Mess They’ve Made of Diversity, Equity, and Inclusion

From my list on pushing you into badassery.

Why am I passionate about this?

I’ve been in the DEI trenches for over 20 years, and let me tell you, it's been one hell of a ride. As a Black woman navigating this shit show, I've seen it all—from clueless executives to well-meaning “allies” who can't get out of their own way. My passion? Calling out the bullshit and actually making DEI work. I've gone toe-to-toe with tech giants, founded Inclusology, and now I'm tackling a second PhD because I believe in the work, even at is most discouraging. DEI-ing is my no-holds-barred guide to creating real change. I’m all about busting AI bias and building DEI that sticks, not just some feel-good fluff. 

Dr.'s book list on pushing you into badassery

Dr. CI Why did Dr. love this book?

This book had me saying, “Finally!” It taught me to let go of the nonsense and focus on what really matters. Mark Manson doesn’t hold back, and I appreciate that. This book is a reality check on how limited our time is—death is coming whether we like it or not—so we better start living right.

It’s not just a book; it’s a guide to cutting the crap and enjoying life before it’s too late.

By Mark Manson,

Why should I read it?

8 authors picked The Subtle Art of Not Giving a F*ck as one of their favorite books, and they share why you should read it.

What is this book about?

New York Times Bestseller In this generation-defining self-help guide, a superstar blogger cuts through the crap to show us how to stop trying to be "positive" all the time so that we can truly become better, happier people. For decades, we've been told that positive thinking is the key to a happy, rich life. "F**k positivity," Mark Manson says. "Let's be honest, shit is f**ked and we have to live with it." In his wildly popular Internet blog, Manson doesn't sugarcoat or equivocate. He tells it like it is-a dose of raw, refreshing, honest truth that is sorely lacking today.…


Book cover of Work Less, Make More: The counter-intuitive approach to building a profitable business, and a life you actually love

John Lamerton Author Of Big Ideas... For Small Businesses: Simple, Practical Tools and Tactics to Help Your Small Business Grow

From my list on ambitious, lifestyle business owners.

Why am I passionate about this?

I used to hate lifestyle businesses, looking down my nose at them, saying (as many others do!) that they weren’t real businesses. After a “lightbulb moment,” I now proudly describe myself as an ambitious lifestyle business owner – someone who designs their business around their lifestyle, rather than the other way around. Work to live, not live to work! As well as Big Ideas... for Small Businesses, a bestselling book about how to build a lifestyle business, I also host the Ambitious Lifestyle Business podcast, where I interview other lifestyle business owners, discovering how what an ambitious, lifestyle business looks like for them.

John's book list on ambitious, lifestyle business owners

John Lamerton Why did John love this book?

Who wouldn't want to work less and make more?

James Schramko feels like an Australian version of me: he's started, built and sold multiple successful businesses over a couple of decades. He's been there, done that, and sold the T-shirt – but prefers to spend his days surfing rather than working.

This book shows you how he achieves that work/life balance – by working less and making more.

By James Schramko,

Why should I read it?

2 authors picked Work Less, Make More as one of their favorite books, and they share why you should read it.

What is this book about?

Work Less, Make More is a dense delivery of solid systems and sane advice. It's not 80/20, it's 80/20 squared. Every few pages, James punches you in the face with an instantly actionable hack.
~ Perry Marshall, Author of 80/20 Sales & Marketing, Ultimate Guide to Google AdWords, and Evolution 2.0

James gives massive value in a fun and easy-to-read book. Real, actionable ways to cut your hours while increasing your income. Want to know how to do it in your own business? Get this and find out!
~ Jonathan Mizel

In Work Less, Make More, James proves that keeping…


Book cover of How the Best Get Better

Steve Mastroianni Author Of Hobby Boss: Turn Your Passion Into Profits Online

From my list on to kick you into high gear.

Why am I passionate about this?

I have been interested in motivation, productivity, and growth my whole life. I find it fascinating how we all have 24 hours; however, some people can maximize that time to create success while others let it go to waste. It all comes down to mindset. As an entrepreneur, I’ve consumed countless books, courses, and coaching programs to create what I call the “Rockstar Mind.” It has helped me tour the world opening for bands like KISS, write two best-selling books and 3 hit songs, and run two online businesses while supporting my young family during a global pandemic. I’m always looking for the edge to create more impact in my day.

Steve's book list on to kick you into high gear

Steve Mastroianni Why did Steve love this book?

This is a pretty rare recommendation and I only heard of this gem through my first ever business coach Alex Jeffreys who was being coached by Dan Sullivan at the time. When he mentioned the title How the Best Get Better I knew it would be perfect for a high-achiever like me and it was love at first listen. Dan is a master of creating innovative technology for the mind that helps entrepreneurs navigate the inherent challenges of their market and operate their business with 100% clarity and confidence. This is a once-a-year listen for me and I highly recommend you track down a copy and check it out.

By Dan Sullivan,

Why should I read it?

1 author picked How the Best Get Better as one of their favorite books, and they share why you should read it.

What is this book about?

Global forces, unleashed by the application of the microchip, have caused an entrepreneurial revolution in every society on the planet. The most successful entrepreneurs are taking advantage of new capabilities to create greater wealth and autonomy for themselves, while providing new income and employment opportunities for millions of others. The best entrepreneurs are also role models and teachers for countless others. Entrepreneurs have a results-oriented concept of how the world works. By focusing strategically on their most important abilities, relationships, and opportunities with a passionate, long-term commitment, they are able to create value for others, which assures their continued success.…


Book cover of The Zigzag Principle: The Goal Setting Strategy that will Revolutionize Your Business and Your Life

Tissa Richards Author Of No Permission Needed: Unlock Your Leadership Potential and Eliminate Self-Doubt

From my list on leveling up your leadership.

Why am I passionate about this?

I’m a TedX and keynote speaker, leadership expert, and corporate facilitator. I’m also a repeat software founder and CEO. I work extensively with Fortune 1000 and hyperscale organizations to connect leadership and culture directly to organizational outcomes, as well as diversifying C-suites and corporate boardrooms. I’m passionate about guiding leaders to measurable outcomes and helping others learn from failure (yes, it happens to all of us!) Over the years, I’ve learned the key is understanding and embodying your own values so you can build resilience for yourself as an individual, your team, and your organization as a whole. I hope my list of recommended books helps you do just that!

Tissa's book list on leveling up your leadership

Tissa Richards Why did Tissa love this book?

We all need to have our conditioning challenged occasionally, and this book does exactly that.

It takes the idea that success is a straight line and turns it on its head. Rich Christiansen argues that the best goal setting isn’t linear. Instead, he encourages readers to literally zigzag to their goals. His book is important because it teaches leaders how to be nimble, flexible, and resilient.

The zigzag principle is simple, powerful, and offers a totally new way of approaching business (and life). 

By Rich Christiansen,

Why should I read it?

1 author picked The Zigzag Principle as one of their favorite books, and they share why you should read it.

What is this book about?

Zigzag Your Way to Success!

Have you ever set your sights on the top of a mountain and then started your ascent by heading straight through the trees and up the sheer cliffs? Or driven in your car to the other side of town-as the crow flies? Of course not! Because you instinctively know that, just as a river has to wend its way around obstacles, the best route is never actually a straight line!

In The Zigzag Principle, Rich Christiansen applies a foundational law of nature to business management, entrepreneurship, goal-setting, and life in general as he explores why…


Book cover of Obliquity: Why Our Goals Are Best Achieved Indirectly

Chris Buckingham Author Of Business Planning for Games

From my list on translating your great ideas into a winning games business.

Why am I passionate about this?

Games and playing have always played a part of my life. I have created games and businesses and been fortunate enough to have worked with both at various levels as a mentor and guide. For me, this is the gift that keeps giving. The tee-shirt wearing creatives and the suit folk with their business acumen we seek to help scale our ideas. I have worked for years at the nexus of these tribes, and still find it a thrill to learn about the visions people have for the wonderful world of games and play and the oblique outcomes we couldn’t have predicted.

Chris' book list on translating your great ideas into a winning games business

Chris Buckingham Why did Chris love this book?

When we put our ideas out there in the real world, we take a risk.

It is an element of being entrepreneurial. But sometimes we can do something in service to others that creates value way beyond what we imagined. Something that has a good impact for those we serve. But this something may have been unpredicted, unseen in the planning stages.

Obliquity teaches us we can focus on the features or the benefits of what we do. This may not result in wealth for the founder, it may not mean a mega exit for the company in a few years. But equally, it may mean a bigger impact for the communities we serve and greater cohesion among those people than we had predicted when writing our business plans.

By John Kay,

Why should I read it?

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

What is this book about?

"John Kay tells a fast-paced detective story as he searches for the surprising secret to success...Brilliant."
-Tim Harford, author of The Logic of Life

In this revolutionary book, economist John Kay proves a notion that feels at once paradoxical and deeply commonsensical: the best way to achieve any complex or broadly defined goal, from happiness to preventing forest fires, is the indirect way. We can learn how to achieve our objectives only through a gradual process of risk taking and discovery-what Kay calls obliquity. The author traces this seemingly counterintuitive path to success as it manifests itself in nearly every…


Book cover of Goals! How to Get Everything You Want - Faster Than You Ever Thought Possible

Andreas Creutzmann Author Of Soft Skills for the Professional Services Industry : Principles, Tasks, and Tools for Success

From my list on soft skills for professionals and entrepreneurs.

Why am I passionate about this?

At the very beginning of my studies, I asked myself a question that still accompanies me today: “Why are some people successful and others not?” I've always been interested in people who are successful through their own efforts instead of building on the success of previous generations through their heritage. In my search for what distinguishes successful from less successful people, I began to read a variety of relevant books and attend seminars. These books and seminars dealt with the topics of success, personality development, marketing and sales, rhetoric, psychology, and management as well as self-management and personal productivity. To date, I've read several hundred books on these topics and attended a number of seminars.

Andreas' book list on soft skills for professionals and entrepreneurs

Andreas Creutzmann Why did Andreas love this book?

Brian Tracy stands for professional and personal success.

I have read many of his books and listened to his lectures. In his book Goals, he shows you how to set goals and achieve them. Goal clarity is a prerequisite for all success.

In this book you will learn everything about goal setting and how to achieve goals.

By Brian Tracy,

Why should I read it?

1 author picked Goals! How to Get Everything You Want - Faster Than You Ever Thought Possible as one of their favorite books, and they share why you should read it.

What is this book about?

Based on more than 20 years of experience and 40 years of research, this book presents a practical, proven strategy for creating and meeting goals that has been used by more than 1 million people to achieve extraordinary things in life. Author Brian Tracy explains the seven key elements of goal setting and the 12 steps necessary to set and accomplish goals of any size. Using simple language and real-life examples, Tracy shows how to do the crucial work of determining one's strengths, values, and true goals. He explains how to build the self-esteem and confidence necessary for achievement; how…


Book cover of The 4 Disciplines of Execution: Achieving Your Wildly Important Goals

Donald Summers Author Of Scaling Altruism: A Proven Pathway for Accelerating Nonprofit Growth and Impact

From my list on essential reading for nonprofit leaders.

Why am I passionate about this?

I have spent most of my adult life using entrepreneurial business practices and principles to redesign and transform nonprofits. From my very first nonprofit organizational acceleration, I was hooked. The wealth one receives from helping other people is so much richer and more satisfying than money–altruism is truly life's greatest pleasure. You know the movie The Sixth Sense where the little kid sees dead people everywhere? I am the same way, except everywhere I look, I see uncaptured opportunities for social impact. I live and breathe social impact strategy, governance, financing, evaluation, and change management. Because by fixing problems in those areas, organizations are able to do more to make the world a better place.  

Donald's book list on essential reading for nonprofit leaders

Donald Summers Why did Donald love this book?

Planning is easy, but execution is hard. Nonprofit leaders can gain a clear, practical understanding of how to measure and execute an organization's progress toward social impact goals with the clear, simple, and compelling four disciplines of execution.

It is simply terrific for putting strategy into practice. You will learn the key concepts from 4DX. We found reading it like getting a new set of glasses that brings the world of management into focus and allows us to see a pathway to success.

By Chris McChesney, Sean Covey, Jim Huling

Why should I read it?

3 authors picked The 4 Disciplines of Execution as one of their favorite books, and they share why you should read it.

What is this book about?

Fully revised and updated, the definitive guide for leaders on how to create lasting organisational change.

Do you remember the last major initiative you watched die in your organisation? Did it go down with a loud crash? Or was it slowly and quietly suffocated by other competing priorities? By the time it finally disappeared, it's quite likely noone even noticed.

Almost every company struggles with making change happen. The 4 Disciplines of Execution: Revised and Updated is meant to help you reach the goals you've always dreamed of with a simple, repeatable, and proven formula. In this updated edition of…


Book cover of Refuse to Choose! Use All of Your Interests, Passions, and Hobbies to Create the Life and Career of Your Dreams

Erica Sosna Author Of The Career Equation: Coaching a Culture of Career Conversations

From my list on transforming your career or others area of life.

Why am I passionate about this?

Do you know you will spend 80,000 hours at work in your lifetime? And yet we get so little guidance on how to make choices about the work we do. I am fascinated by the world of work and how we navigate it, and thrive in it. I’ve always wondered how people made decisions about how to live and how to approach finding the right kind of livelihood that fits their skills and interests. I’ve made it my job to design a method to help people get specific and clear and help them not only find the work that best utilises their skills and passions but also identifies the environment that works best for us.

Erica's book list on transforming your career or others area of life

Erica Sosna Why did Erica love this book?

If you are anything like me and struggle to decide on one career or one path then this is the book for you. If by working through your passions, skills, etc. you find that there isn’t just one area you want to work in but in fact, you are interested in loads of stuff, then this book will help you manage this challenge and create the life that you want not the one everyone else says you should have.

By Barbara Sher,

Why should I read it?

2 authors picked Refuse to Choose! Use All of Your Interests, Passions, and Hobbies to Create the Life and Career of Your Dreams as one of their favorite books, and they share why you should read it.

What is this book about?

Don't know what to do with your life? Drawn to so many things that you can't choose just one? New York Times best-selling author Barbara Sher has the answer-do EVERYTHING!

"Designed to help you enjoy your many interests without feeling overwhelmed and unfocused"
- Metro New York

Author of Wishcraft and I Could Do Anything If Only I Knew What It Was..., Barbara Sher has become famous for her extraordinary ability to help people define and achieve their goals. What Sher has discovered is that some individuals simply cannot, and should not, decide on a single path; they are genetically…


Book cover of Start With Why: How Great Leaders Inspire Everyone to Take Action

Trudy Worth Author Of Heartful Business: Leading with the World in Mind

From my list on leadership to change the world of work for good.

Why am I passionate about this?

I’ve experienced good organisations and less so in my working life. Likewise, I've experienced the good and less so of leadership. In leading teams and organisations during my career, I, too, have been an example of both, so I’m passionate about helping leaders grow their capability to ‘avoid the less so’ and lead well, with humanity and greater consciousness, to create workplaces where people flourish and organisations that contribute positively to the future of our world.

Trudy's book list on leadership to change the world of work for good

Trudy Worth Why did Trudy love this book?

In my view, this book is a game-changer. Sinek probably agrees, given that it became a bestseller and has seen him become one of the most influential thinkers on leadership of our time. The Golden Circle—Why, How, What—at the heart of the book flips conventional leadership thinking on its head, getting clear on purpose (the why) rather than starting with the what. 

I love the way Sinek brings his thinking and the power of purpose to life with real-world examples, from the Wright brothers, the ‘founders of powered flight,’ through Martin Luther King Jr. to Jobs and Apple.

By Simon Sinek,

Why should I read it?

10 authors picked Start With Why as one of their favorite books, and they share why you should read it.

What is this book about?

THE MILLION-COPY GLOBAL BESTSELLER - BASED ON THE LIFE-CHANGING TED TALK!

WHAT READERS ARE SAYING ABOUT START WITH WHY:

'It's amazing how a book can change the course of your life, and this book did that' Reader Review

'Imagine the Ted Talk expanded to 2 hours long, with more depth, intrigue and examples' Reader Review

'What he does brilliantly is demonstrate his own why - to inspire others - throughout' Reader Review

'Wow. Wow. Wow. I cannot rate this book highly enough to take a different, positive approach to life and work' Reader Review

Discover your purpose with one simple…


5 book lists we think you will like!

Interested in success in life, entrepreneurs, and self-actualization?

Success In Life 262 books
Entrepreneurs 308 books
Self-Actualization 227 books