The 11 Best Books about Failure (and How to Overcome It)

P.J McNulty
January 30, 2024 | 10 mins

For many of us, failure is often seen as a dreaded outcome. So, it's no surprise that books about failure – or rather, overcoming and rising above said failure – often reach best-seller status. After all, learning from our past failures and those of others provides a huge opportunity for immense learning and growth.

These books are not just stories of setbacks. They are blueprints for success, resilience, adaptation, and eventual triumph. And whether you're just interested in finding some of the best books about failure for your own reading, or you'd like to write your own nonfiction book on the topic, we've rounded up a list of some of the best.

The best books about failure

While this isn't an all-inclusive list of all the books on failure (would that even be possible to create or read?!?), this is a great mix of some of the top authors in this genre.

Each one offers unique perspectives and actionable insights, giving you a rich understanding of how failure can catalyze success. Plus, along with a short synopsis of each book about failure, we've provided a tip for how to use it as inspiration for writing your own book!

1. Failing Forward: Turning Mistakes into Stepping Stones for Success by John C. Maxwell

Books About Failure — Failing Forward: Turning Mistakes Into Stepping Stones For Success By John C. Maxwell

John C. Maxwell, a renowned leadership expert, challenges us to look at the positive side of failure. In Failing Forward, he dissects the anatomy of mistakes and how they can become stepping stones to success.

Maxwell doesn't just offer platitudes but provides practical strategies to transform failure from a regret into a resource. Through engaging stories and real-life examples, he illustrates how changing our perspective on failure can lead to significant personal and professional growth.

Tip: Learn from Maxwell's approach to transform your personal and professional setbacks into compelling narratives. His methodology for identifying the lessons in each failure can also be a how-to guide for anyone interested in writing their own self-help book.

2. The Other ‘F' Word: How Smart Leaders, Teams, and Entrepreneurs Put Failure to Work by John Danner and Mark Coopersmith

Best Books About Failure — The Other 'F' Word: How Smart Leaders, Teams, And Entrepreneurs Put Failure To Work By John Danner And Mark Coopersmith

Danner and Coopersmith offer a practical guide on harnessing failure. They explore real-world examples where failure led to success in business and leadership.

This book delves deep into the concept that failure, when approached correctly, can be a powerful tool for innovation and growth. By exploring the experiences of various leaders and companies, it provides actionable insights for turning the tables on failure to foster a culture of resilience and adaptability.

Tip: They take an analytical approach to finding groundbreaking ideas and solutions. Regardless of your subject matter or topic, you can do the same to inspire other entrepreneurs and business owners.

Related: The Best Business Analysis Books

3. Adapt: Why Success Always Starts with Failure by Tim Harford

Best Books About Failure — Adapt: Why Success Always Starts With Failure By Tim Harford

Economist Tim Harford emphasizes adaptability in the face of failure. This book is a testament to the power of trial and error in achieving success.

Harford compellingly argues that the key to overcoming obstacles and achieving success is not in avoiding failure but in learning how to adapt to it effectively. Through a series of captivating case studies from various fields, he demonstrates how innovative approaches to failure can lead to breakthroughs and unexpected solutions.

Tip: Embracing change and learning from missteps can be a powerful theme in any book. Don't be afraid to add personal anecdotes about failure in your book. This will humanize you and help your readers connect more deeply.

4. Black Box Thinking: Why Most People Never Learn from Their Mistakes—But Some Do by Matthew Syed

Best Books About Failure — Black Box Thinking: Why Most People Never Learn From Their Mistakes—But Some Do By Matthew Syed

Matthew Syed didn't write a psychology book exactly, but he does explore the psychological link and relationship between failure and success. He uses examples from various fields to illustrate how learning from mistakes is a key indicator of someone's future progress.

Syed's analysis goes beyond the surface, showing how the willingness to engage with and learn from failures can drive innovation and efficiency. Drawing on compelling case studies from healthcare, aviation, and sports, he reveals how adopting a ‘black box' methodology from the aviation industry can help us to transform our approach to mistakes.

Tip: Syed takes the approach of dissecting failures and, in doing so, really helps you understand the concepts. You can do the same by presenting detailed case studies in your book.

5. The Up Side of Down: Why Failing Well Is the Key to Success by Megan McArdle

Best Books About Failure — The Up Side Of Down: Why Failing Well Is The Key To Success By Megan Mcardle

McArdle introduces the concept of failing well – a new idea to many of us. Failing is a part of life, but as she shows us, you can learn how to do it more gracefully.

Through engaging narratives and insightful analysis, McArdle argues that the ability to fail well is a crucial skill for achieving success. She explores how individuals and organizations can bounce back from setbacks by adopting a mindset that views failure as an opportunity for growth and innovation.

Tip: Use McArdle's “find the silver lining” approach to share your own stories about resilience. Use a mix of empathy and motivation to help readers understand that even the darkest days and moments can – and likely will – pass.

Related: How to Write a Motivational Book

6. Fail Fast, Fail Often: How Losing Can Help You Win by Ryan Babineaux and John Krumboltz

Best Books About Failure — Fail Fast, Fail Often: How Losing Can Help You Win By Ryan Babineaux And John Krumboltz

Babineaux and Krumboltz have one of the more proactive books about failure. In a way, they even encourage you to fail. Why? They argue that rapid iteration and learning from small failures can lead to significant achievements.

“Fail Fast, Fail Often” encourages embracing failure to overcome perfectionism, innovate, and grow personally. The authors offer strategies for learning from failures to achieve greater success, making it a key resource for those eager to enhance their learning and reach their objectives faster.

Tip: Apply their philosophy to the structure of your book, illustrating how each minor setback can be a learning point and encouraging your readers to embrace and learn from their failures.

7. Mindset: The New Psychology of Success by Carol S. Dweck

Best Books About Failure — Mindset: The New Psychology Of Success By Carol S. Dweck

Carol S. Dweck didn't necessarily write one of the books about failure. Instead, she wrote the opposite and shared how a growth mindset can be pivotal in learning from setbacks.

She argues that embracing a growth mindset—the belief that abilities can be developed through dedication and hard work—enables us to thrive during challenges and learn from failures.

Tip: Follow Dweck's lead and equip your readers with the knowledge and mindset they need to succeed. After all, simply knowing something is seldom enough to create lasting change. This is why we encourage all our aspiring authors to explore their own self-talk and improve their mindset as they start writing a book!

8. Bounce: Mozart, Federer, Picasso, Beckham, and the Science of Success by Matthew Syed

Best Books About Failure — Bounce: Mozart, Federer, Picasso, Beckham, And The Science Of Success By Matthew Syed

Syed examines how high achievers use failure as a learning tool. He blends stories from sports, art, and business to demonstrate this.

By analyzing the practice habits, mindset, and determination of figures like Mozart and Federer, Syed offers readers a new perspective on success — one that values persistence, learning, and adaptability above all. This book is compelling for anyone interested in the secrets behind world-class performance across various domains.

Tip: Many books about failure are anecdotal based on the author's lived experience. If you want to stand out, use Syed's approach and highlight commonalities of thought leaders in your space, celebrities, or other well-known figures to drive home your point. This could be an especially good approach if you struggle with imposter syndrome as an author (spoiler: we all do) and want to bring in the experiences and stories of more well-known people.

9. How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life by Scott Adams

Best Books About Failure — How To Fail At Almost Everything And Still Win Big: Kind Of The Story Of My Life By Scott Adams

If you're someone who uses humor as a coping mechanism, this is one of the better books on failure. In it, Scott Adams shares his personal journey in this memoir-turned-self-help-book, highlighting how numerous failures led to his success as the creator of Dilbert.

Adams's candid recounting of his many setbacks and his witty insights offer a refreshing perspective on failure. Through his story, Adams illustrates the power of perseverance, strategic risk-taking, and the importance of maintaining a sense of humor throughout life's challenges.

Tip: Adams’ personal narrative style can inspire your own writing tone. Business, failure, money – all these topics don't have to be approached seriously. If you like to take a light-hearted approach to life and business, this will also be more authentic to who you are as an author.

10. Antifragile: Things That Gain from Disorder by Nassim Nicholas Taleb

Best Books About Failure — Antifragile: Things That Gain From Disorder By Nassim Nicholas Taleb

Taleb introduces the concept of ‘antifragility', where systems benefit from shocks and failures. He expands on the idea that in contrast to fragile things that break under stress, some entities grow stronger when exposed to volatility, randomness, and disorder. This groundbreaking concept applies to economic and financial systems, individual resilience, and personal growth.

Taleb's insights encourage embracing uncertainty and making the most of unpredictable events. By learning to love and exploit our own vulnerabilities, we can move beyond mere survival and into a realm where we thrive by becoming antifragile.

Tip: Use Taleb’s concept to explore themes of resilience and growth in the face of chaos, showing how entrepreneurs can thrive in unpredictable environments.

11. Fail Better: Design Smart Mistakes and Succeed Sooner by Anjali Sastry and Kara Penn

Best Books About Failure — Fail Better: Design Smart Mistakes And Succeed Sooner By Anjali Sastry And Kara Penn

Sastry and Penn offer a framework for making the most of failures using innovation and design thinking. This is a must for any creative or business owner.

“Fail Better” provides readers with actionable strategies to intentionally use failure as a tool for innovation. The authors argue that by designing experiments and projects in ways that make failures informative and productive, individuals and organizations can accelerate their learning and subsequent success. This approach not only demystifies the process of failure but also empowers readers to embrace setbacks as a necessary step toward achievement.

Tip: Their structured approach to writing a book about failure should inspire your own book outline. First, develop a framework for your readers about the topic you want to write about. Then, break each piece into chapters with action steps at the end.

Need another example of this in action? Chandler Bolt does this in his book Published. as well!

Should you write the next book about failure?

Each of these books about failure offers a unique lens through which to view life's inevitable setbacks. As you consider writing your own book, these insights may offer some much-needed motivation and highlight the importance of including and unpacking failure in different ways.

If you're seriously thinking, “Wait, should I write a book about failure?!?” Then we've successfully accomplished our mission to inspire you!

The truth is, all of us have a story inside of us. Chances are you've overcome some impressive challenges in your personal or professional life. And sharing those stories could help others on their own journey. Remember that books about failure are not just about wallowing in setbacks. They are actually about illuminating the path to success, often while highlighting a unique methodology the author has discovered or created.

And what could be more impactful for your personal brand?

To really drive home the point, here are some of the top reasons we see people just like you write books about failure, business, and/or entrepreneurship:

  • Establish authority: Put simply, a published book solidifies your position as a thought leader and business owner in your space.
  • Become a public speaker: With your newfound authority, you can become a public speaker, booking paid stages, podcast interviews, and more.
  • Create change in your industry: Your personal experiences with failure provide unique insights that can offer fresh perspectives to readers that are different from generic success stories.
  • Grow your income: Self-publishing via Amazon gives you a new revenue stream and ensures you keep all your book royalties for yourself.
  • Launch or grow a business: Many of our authors have seen firsthand how a book can grow your business. Using it as a free or low-cost lead magnet is just one of the many ways.
  • Leave a legacy: A book is a great way to reach thousands of people around the world, inspiring their own transformation.


You don’t have to write a book about failure alone

Armed with these insights and the profound lessons from the books discussed, you are now equipped to write your own book about failure. Embrace this opportunity to share your journey, impart wisdom, and inspire others.

Remember, your story of failure could be the beacon that guides aspiring entrepreneurs through their darkest hours. Start writing today; your experiences are not just stories. They are valuable lessons waiting to be shared with the world.

But don't be afraid to ask for even more support. Your book should be about failure – not a failure in and of itself.

We offer training, best-selling book coaches, small group coaching, and a proven process to help aspiring authors reach best-seller status and see success in their publishing endeavors. Our authors have written books about failure, growing businesses, launching new businesses, investing, quitting their jobs – just about any topic you can think of. And we'd be happy to help you write and publish yours.

If you're curious about how we could help, schedule a free call. Our book strategists can show you how a book could be the best thing to happen to your business and personal brand this year.

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