Chasing Failure: How Falling Short Sets You Up for Success

by Ryan Leak

By blending personal stories, inspirational anecdotes, riveting psychology, get-up-and-go encouragement, and just plain practical step-by-step advice, Ryan Leak shows how chasing failure just may be the quickest way to success.

We all have something we'd love to do, but often our fear of failure outweighs the potential of our destiny. But what if we found out that failure could actually help us succeed? Through Ryan Leak's journey of chasing the girl of his dreams to his NBA fantasy and his encounter with five-time NBA champion Kobe Bryant, Chasing Failure helps us remove every excuse for not pursuing the life we want to live.

In this book Ryan also talks about the science behind why people are afraid to fail, mixing in real-life stories and adding practical steps to help us intentionally chase failure. As he says, "God promises to be with you always, even through the failure." This book is for the dreamers who have been afraid to move--and even those who have been afraid to dream. Ultimately, Chasing Failure will help us build confidence in what God has called us to do. As a motivational speaker, whether addressing people in corporations, churches, or youth events, Ryan has a message of failure is right around the corner, so be brave enough to chase it! The good life is on the other side.

Genres: Nonfiction, Self Help, Audiobook, Business, Professional Development, Personal Growth, Personal Development

220 pages, Kindle Edition

First published June 22, 2021

About the author

Here's what you need to know about Ryan Leak: He's a husband to Amanda and dad to Jaxson. After that, he's an author, filmmaker, and speaker. He's known as an ultimate risk taker from his two documentaries: The Surprise Wedding and Chasing Failure. Ryan proposed to his wife and married her on the same day, having planned their wedding in secret for two years. That documentary went viral in 2013 and the Leaks have been featured on Good Morning America, The Today Show, The Queen Latifah Show, and many other various media outlets. Ryan's most recent film is called Chasing Failure where he went on a journey to conquer his fear of failure by trying out for an NBA team. Ryan travels the country and teaches people how to remove the limitations that keep them from dreaming. And now, he teaches people how to be UnOffendable. You can follow Ryan on Instagram + Twitter: @ryanleak

Reviews

[Leah · Rating 2 out of 5]

I really wanted this to be better because it was written by one of my churches teaching pastors. I feel that it was heavy on "bullet point" thoughts but didn't get into much substance. Some of his stories he sort of alluded to but invited the reader to go check them out on YouTube or Google but I am not going to. Just retell the account in the book, rather than ask me to care enough to search for it, is how I feel about it. I like the concept that failing is perfectly acceptable and we should not give up on our dreams.. But it was a quick read and had some good things to ponder. If you enjoy a self-help book that is easy and fast, go for it.

[* A Reader Obsessed * · Rating 3 out of 5]

3.5 Stars

Inspiring and encouraging. Definitely great pointers to truly consider because you can’t fail, nor learn and grow, unless you’ve actually made an effort to try. It’s for sure scary to put oneself out there but a necessity to take that first step at accomplishing your goals. I’m going to give it a better go of it!!

[E.A. · Rating 5 out of 5]

I wasn’t sure what to expect when I read this book (a book about failing?) but I was blown away by not only the concept, but the practical advice and encouragement I got from audiobooking it.

Here are two quotes out of many that stuck out to me:

"When you tell people about your dream it creates accountability for you to actually do something about it."

"Just because someone is better than you at something don’t mean you have to live intimidated by them.”

Leak’s focus on failure is so refreshing. It’s the idea of taking a chance because the worst that can happen is it doesn’t work out. But, at the same time, you can’t forget the chance that it WILL work out or something better might come from the risk. He also points out that failure can be a good thing – it can help us pivot when our dreams aren’t quite right or it can help us buckle down and get better to reach that success.

You’d better believe I’ll be re-reading this in the future!

I highly recommend this book in hardcover, but if you’re a #audiobook fan I’d recommend that even more because there is bonus content added at the end of each chapter where the author answers early-reader questions. There is SO much good content in this book and I think it would be great for anyone at *any* stage of life.

My rating: 5*

——
Thanks to the publisher for this gifted copy! All opinions are my own!

[Rachel Thomas · Rating 1 out of 5]

this dude tried out for the nba to “fail on purpose”, this is the same thing as me trying out for the olympics

i fear this is why self help books get a bad rep (i only read this bc i got it for free from a work book club)

[Juan Genao · Rating 4 out of 5]

Ryan Leak has a down-to-earth style of writing that is refreshing to read. He shares multiple stories on how he has “chased failure” and all the lessons that come with that thinking framework. His advice is clear and concise, making it so palatable for anyone who reads this. Excellent read.

[Howard · Rating 5 out of 5]

I bought this one at random. I was surprised by what Ryan talked about. Talking to Kobe Bryant about trying to get into the NBA just totally floored me! He puts a new meaning to "Just Do It" I like his talking about many of his speaking engagements where he made some doozies of mistakes, but he just owned up to them, and they improved his career. Incredibly sensible advice in this book. The Audio version has bonus content that features questions from his pre-readers - some of them were quite intense, and added more value to this incredible work. So chase failure and beat it up when you catch it :-)

[Suzanne Capitano · Rating 4 out of 5]

I was listening to this audiobook when it was returned and I only had 23% more to go. The book was only 4 hours long but I forgot it was on my shelf and then when I got a notification that it was being returned, I tried to finish it and I failed. You know what? Having listened to most of the book, I knew that was ok and I could pick it up again. Popular book; I had to wait over two months! I’m so glad I did because this is one of the best reads about trying, learning and moving along. If you have the chance to listen to Ryan read the you the book, even better because there are bonus content questions at the end of every chapter.

[Nursebookie · Rating 5 out of 5]

TITLE: Chasing Failure
AUTHOR: Ryan Leak
PUB DATE: June 22, 2021
AUDIO LENGTH: 4 hours 9 minutes
NARRATED BY: Ryan Leak

Review:

The audiobook narration by the author was fantastic! This is an amazing book for leaders and anyone who fears failure unable to live out their full potential.

Leak takes us through a different mindset where failure can actually help you succeed. With real life stories and examples, Leak takes the readers through an inspirational and motivational journey.

Ryan Leak’s book is a must read for all of us. I gleaned a lot just by reading and listening to this amazing book.

[Razvan Rogoz · Rating 5 out of 5]

I was not expecting much from this book - just the same message I’ve heard again and again. Which is not a bad thing by itself, because it is a good message.

However, this book has heart and it feels more like a personal conversation with a good friend than anything else. And its philosophy of “chasing failure’ makes perfect sense - you fail forward.

It is a short book, you can finish it in four hours or less. It is inspiring and it contains some valuable wisdom. Go for it.

[Josh Argo · Rating 5 out of 5]

I’m not a self help book person at all. I feel like they’re normally just repetitive and get old after awhile but I did enjoy this one. It was short, to the point and the narrator/author (same person) had a dynamic voice that kept it interesting.

[James · Rating 4 out of 5]

Down to earth, encouraging book!

[Stacey Shaw · Rating 4 out of 5]

Motivating book! I love the idea of getting a win everyday.

[Jon Marks · Rating 4 out of 5]

I am going to keep beating it into my brain that it’s ok to fail until I believe it

[Jason Frasca · Rating 5 out of 5]

Overall, I think this is executed well and has an excellent concept! This book seems to turn our most common fear, fear of failure, upside down! Such a motivating perspective, how we learn the most from failing, so we should reframe and embrace the lessons failure teaches us.

The author has quite a few anecdotes sprinkled through, most of them personal, which helps demonstrate and embody his teaching. This book has a great balance of motivation, empowering readers, encouraging hard work and being proactive with feedback and criticisms, with an underlying Biblical and Christian perspective.
I highly recommend!

Some key concepts I learned and wanted to share (spoiler alert):
-the technical term for the fear of failure is atychiphobia
-"Failure awareness"- the concept that awareness of possible failure, tends to discourage us from trying. Young children are often not aware of failure, which is seen time and time again as they learn to walk, to speak, etc. without fear.
-The distance between our dreams and realities is intimidating. We often talk ourselves out of dreaming!
-failure is an event, not an identity!
-we need to refocus on what we dream for, not what others tell us to dream
-we need to be comfortable failing by trying, rather than failing by not trying
-the author writes quite a bit about pro-basketball and what we can learn from these athletes. To quote Kobe Bryant:
“Everything negative - pressure,
challenges - is all an opportunity for me
to rise."
-to quote Thomas Edison-
How did it feel to fail 1,000times?” Edison
replied,“ I didn’t fail 1,000 times. The light
bulb was an invention with 1,000steps.”
-consider having a partner to keep you accountable through life's challenges - an "accountability partner"
-we should refocus on "chasing failure" over "chasing success". We will find our successes faster! Early failures help us find our true passions and allow us to "find our sweet spot"
-"phantom discouragement"- a ten encompassing how shame is triggered when we see other people getting complimented
-empathy is the antidote to shame!
-criticisms are helpful but we should evaluate them. Are they accurate?
-"rejection therapy"-getting more comfortable with rejection

I highly recommend this book! This will be one that I buy, re-read and share many times!

[Garyu.Ide · Rating 5 out of 5]

This book was written by Ryan, who once dreamed of becoming an NBA player, and the lessons he learned in that journey. This book clarifies that failure is not a negative curse that everyone says it is, but instead it is a gift that is only given to whom take action to live their dream instead of keep on dreaming them. Failure is something to be achieved and, matter fact, shows a higher value than success itself. He indicates that failure should never be feared but should be there to be achieved. Through his story of his idols, he teaches readers the value of being courageous and running into failure to surpass whom you were yesterday.

[Living My Best Book Life · Rating 5 out of 5]

Chasing Failure is a new and fresh approach self-help book. Ryan Leak shares personal experiences to show that he was willing to fail so that we can all learn to succeed.

The book is an interesting take on following your dreams. Ryan introduces his theory on 'chasing failure'. He points out that you really have nothing to lose if you chase your dreams. For example, he always wanted to be in the NBA. He was 28 and wrote a few emails to multiple NBA teams. When some responded and said no, he still took it as a win because that meant that they actually read his email. One day, he got a response from Phoenix Suns and would get a tryout. That is not something that you hear of... like ever. During his tryout, he realized that maybe it wasn't the right calling because although he was good at basketball there were others who were just plain outstanding. But he didn't let this deter him to finding out exactly what his purpose in the world is.

He also describes a moment where he met the GOAT, Kobe Bryant. Kobe influenced so many including Ryan and so he was more than excited to meet Kobe. He wanted to make an impression so he told him about his idea about 'Chasing Failure'. Kobe told him he wanted to see the final product. What stuck out to me the most was how one person can make an impact on you. I think that is the beauty about Ryan's journey. Yes, he took risks and failed at some but he learned so much about himself. Like how motivating and personable he is. I feel like this is exactly why he will change lives and make an impact because he did the work himself. He didn't just give people a list of how to change their lives, he made a list that came from hard work and failure that ultimately led to his success.

I give Chasing Failure 5 stars. This is a fresh and personable self-help book that will resonate with so many people. His outlook on life will make people want to join him on the journey of chasing failure. What do you have to lose? Go out there and make something happen!

[TJ Totland · Rating 3 out of 5]

In Chasing Failure: How Falling Short Sets You Up for Success, author Ryan Leak flips the traditional narrative around success and failure, offering a bold and refreshing perspective. Rather than avoiding failure, Leak encourages readers to pursue it—intentionally and strategically—as a pathway to growth. Drawing from personal experiences, including his audacious attempt to try out for an NBA team without professional credentials, Leak illustrates how embracing the possibility of failure can unlock courage, creativity, and resilience.
The book blends motivational storytelling with practical advice, making it accessible to readers from all walks of life. Leak’s tone is conversational and authentic, which helps demystify the fear of falling short. He challenges readers to redefine success not as perfection or achievement, but as the willingness to take risks and learn from setbacks. Each chapter builds on this theme, offering actionable steps to reframe failure as a necessary ingredient for progress—whether in career, relationships, or personal development.
What makes Chasing Failure stand out is its empowering message: that failure is not the enemy, but the evidence of effort. Leak’s insights are especially relevant in a culture that often celebrates flawless outcomes while ignoring the messy process behind them. By encouraging readers to chase failure rather than run from it, the book becomes a catalyst for transformation. It’s a compelling read for anyone looking to break free from fear and pursue a life of bold, purpose-driven action.

[Robert Davidson · Rating 5 out of 5]

one of the best!

I own lots of different motivational books. Most fall into what I call The January Class. By that I mean they are great reads in January while you are making your New Years Resolutions. But the information and motivation won’t stick around past January. Within a month or two, it’s back to business as usual. This book is radically different.

I freely admit I bought this book and let it sit in my Kindle library for months. When I finally got around to reading it, the reason was perfectly clear. I bought this book to help me with a dream; a dream that I was very consistently talking myself out of. It was destined for failure, and I didn’t want to fail. So if I never get started, I can’t fail, right?

Not only did this book motivate me to chase that dream, it has given me extremely practical advice on how to do it. And this is advice that I have already put into action with my day job, to spectacular results.

Buy the book and read it eventually. You’ll be glad you did.

Full disclosure: Ryan is on the staff at my church, and I already held him in very high esteem and regard. It’s very possible that I’m biased, but I still think you will benefit from this book.

[Debbie Rozier · Rating 5 out of 5]

This book is wonderfully narrated by the author and one of the better personal growth books I’ve ever read!

I love this audio because it mixes Ryan’s own stories, and gives both micro and macro steps, advice, and examples on how we can deliberately chase failure to achieve a dream.

The audio also has bonus content after every chapter that Ryan answers that have been asked by advanced readers.

I think what really made me think was when Ryan asks at the beginning of the book, “What would you do if you knew you couldnt’t fail?”

This statement really made me think as my chapter in life will change in a year from now as I will be an empty nester and will live most of the year in Illinois instead of Florida where I’ve lived for over 20 years. I will be 54 years old, starting over trying to find a new tribe of people, and I’ll have to get a different job or figure out what to do with my time.

I’ve already listened to this book twice. The first to listen and absorb, the second time to take notes. I feel confident that I will be listening to this book many more times over the course of the next year or two. I’ve also purchased the book for my husband.

[Ashley · Rating 5 out of 5]

Chasing Failure is by far one of the best books I have read in the personal and professional development space (and I have read more than I care to count!) Ryan's take on how instead we should be running unabashedly towards failure instead of success is such a profound mindset shift. So many authors write messages around failure and how "if we fail, we actually learn" which is true, but it’s not the whole picture. The either “we win or we learn” Maxwellian principle, although true, misses the motivational and relevant piece of how we actually should instead AIM for failure, not just believe in the by-product of the knowledge gained. Chasing failure is a way to break free of perfection-seeking, which paralyzes so many to take any action to build towards the life they want. The relatable stories Ryan tells, his intentional communication strategies, and his obvious love of people is palpable in the pages of his book. Do yourself a favor and stop reading this review and go buy the book! You won’t regret it!

[Mollie Vick · Rating 3 out of 5]

I thought this book was good- chasing failures is something I struggle with and it was a good way to look at failure as a way to grow and by failing you are reaching your full potential instead of just not even trying things to begin with. He gives lots of examples of very successful peoples failures which is inspiring. It shows you how to rely on other people and share you goals so it makes you more motivated to accomplish them. It tells you that sometimes your goals aren’t meant for you and you learn that through failures and it leads you to another path. I really enjoyed the section that talked about how to fight shame, how to have little wins every day, how to start today and not tomorrow, and how to use failures as a positive and even how to give grace to yourself and others! I did feel like at times I was like okay I’ve heard this before but maybe I should actually apply it. Lots of sports talk which I’m fine with just not for everyone

[Karen_RunwrightReads · Rating 4 out of 5]

The message of this book is to embrace failure because missteps teach us how to overcome fear. It’s a simple theme but feels elevated in this book as Leak’s writing is really engaging and he has some great personal stories that make this a fun but also very inspiring read. I loved reading about how he tried out for a NBA team at a time when it’s pretty much if you haven’t been scouted and recruited, you have no shot. But I also love that he gives these practical take-aways at the end of each chapter so you can not just be entertained by his failures but be inspired to go try and fail until you try and succeed for yourself. I get a lot of these “types of books” from publishers but this is one of the few that I want to keep and reread when I need a dose of inspiration.
Note: I received a free copy from Thomas Nelson Publishers via TLC Book Tours.

[Isabel · Rating 1 out of 5]

Dnf.

After failing to reach NBA and failing to become and architect, the author managed to fail more than failing to catch my attention in the first chapter. Where the stated objective of the book is to give readers the courage to jump from a plane, it gave me enough despair to wish to do it with no parachute. Why did I pay 2€ for this?? The bonus material in the audio version seem to have been added to have some more time in this very short and empty audiobook. I endured up to teve third chapter of the audiobook because I was jogging and this was the only audiobook available.
If you are considering reading this book, don’t. The right message is not failure but perseverance. The title is misleading and shows that this is just another self-help book written because the genre sells well.

[Mike Wright · Rating 5 out of 5]

I was able to listen to the audiobook (from audible) that is read by Ryan himself. Not only did I absolutely find the concept of chasing failure to spark interest, it really captured, for me, the core of what it is that is holding me back. It isn't that I feel that my career has not been successful, but rather I know that I am not experiencing everything that I can because I am letting the fear of failure keeping me from attempting new things. I really enjoyed the stories and the different areas that were called out, and especially loved the section around being compassionate with others. I know that the rest of the world would be more likely to chase failure if we all were more willing to be compassionate to others when they do fail, especially when that failure directly impacts us.

[Kelsey Philippe · Rating 3 out of 5]

Audiobook Edition. 3.5 stars rounded down. This has become another book on my ever growing list of books targeting "self-help". I dont think its the full of bad advice - its actually an amazing concept - youll never really know unless you try. I loved the bonus content the audiobook provided from the authors perspective and answering readers questions but I sometimes found the writing to be a stream of thoughts in a listed format rather than a narrative thar aligns in the way it needs to be continually impactful. Overall I took the ideas I needed to hear, jotted them down, and quickly transitioned into something new.

[Audrey · Rating 4 out of 5]

This book highlights Ryan, the author's, story. It begins with him setting up his plan to chase failure. His goal was to get to the NBA at 6'3 and 28 years old. While he was good at basketball, he was not outstanding and had not been scouted by NBA teams since middle school, like most players. However, with the motivation of chasing failure behind him, he emailed an NBA team to try out for the team. And within thirty minutes, got rejected. But he kept trying, emailing more teams, and eventually he was able to go workout with a team. Though he was the shortest on the court, he was not intimidated and instead embraced the challenge. By the end of the workout, the whole team and coach were cheering him on. While he did not make the team, he got further through chasing failure than he would have by chasing success. The overall theme of this book shows us how chasing failure can take us far, and he offers advice on how to turn a dream into reality, learn from the past, and ultimately be successful. "What would you do if you knew you couldn't fail?" - Ryan Leak

[Dave Weiss · Rating 5 out of 5]

I bought this book in hopes of using it for my doctoral dissertation. It didn't really fit that, instead it dealt with stuff that has been broken in me for a long time. This is one of the most helpful books I have ever read. I also learned all kinds of ways to get myself organized and reaching my goals. It challenged me to take some risks and dare to fail on. my way to success. I would recommend this book to literally anyone, but especially anyone who has a dream they must see become reality. I only wish I could give this more than five stars. I loved this book.

[Elizabeth Welch · Rating 4 out of 5]

I heard Ryan speak and was super excited to read his book. Much of the book was a repeat of what I heard him say- which was fantastic, I just wanted more. Ryan is an amazing speaker with a phenomenal story. I wanted to read more of what I didn’t know. I wanted him to give me more in the book that I heard in that amazing 60 minute talk. If I had read the book before I heard him speak this would be a 5 start review .

[Ian Dawson · Rating 5 out of 5]

An insightful and entertaining read, Chasing Failure delivers excellent points and concepts that show that failure isn't the end, it's the beginning of growth toward success. Author Ryan Leak shares his personal failures and how those led to him becoming successful in his career and in his personal life.

I found this book to be inspiring, and I'm sure many of you will, too. I highly recommend Chasing Failure by Ryan Leak.

[Charla K · Rating 5 out of 5]

Mindset

This book placed a mirror in front of me! The way I look at, embrace, and bounce back from failures has shifted my mindset….my perspective….my thought process. The pointers given in this book is a game changer! This will be the first book I share with my new book club that’s created to encourage, educate, and motivate others. Thank you Ryan for your transparency and vulnerability in writing this book!