10 Self-Help Books for Turning Failures into Massive Success

by | Apr 30, 2024 | Books & Stories

I’m gonna let you in on a little secret – failure is actually one of the most valuable things that can happen to you in life. Whoa, whoa, I know what you’re thinking – “But failure is the worst! It makes me feel like a total loser.”

Well, let me tell you, that couldn’t be further from the truth. You see, failing simply means that you took a chance and went for something. And even though it didn’t work out this time, it brought you one step closer to figuring out what will work.

Failures are actually hidden opportunities to learn, grow stronger, and get back up swinging until you nail it.

The real losers? Those are the people who never risk failing in the first place because they’re too afraid to put themselves out there and chase their dreams. So if you’ve recently hit a roadblock or taken a tumble, congratulations! You’re way ahead of those stick-in-the-muds.

And hey, you’re definitely not alone in this whole failing thing. Even the most successful people we admire today, from business moguls to super athletes to inspirational leaders, have all tasted their fair share of sour, rotten failure. But instead of letting it stop them, they used it as fuel to come back fiercer than a boxer going into the final round.

10 Inspiring Self-Help Books to Conquer Failure

Bouncing back from failure is a skill you can develop and get better at over time, kind of like building up your other muscles. And luckily, some of those mega-successful “failure graduates” have gifted us with personal playbooks on exactly how they did it.

These top 10 self-help books, written by people who have walked the walk and failed their way to the top, are stuffed with hard-hitting truths, inspiring stories, and surprisingly simple mindset shifts to help you shake off your defeats and blaze a new path to victory.

Whether you’re feeling down after a tough breakup, got let go from your job, or are just kind of stuck in a rut, these reads will reignite your inner fire and show you how failure is actually one of your greatest superpowers when you know how to work it right.

The Obstacle Is the Way by Ryan Holiday

1. The Obstacle Is the Way by Ryan Holiday

Okay, let’s be real – life can totally suck sometimes. One minute you’re coasting along thinking everything’s fine, and the next, BAM! – a devastating problem smacks you right in the face. Whether it’s losing your home, your job, or simply not achieving an important goal you set, obstacles like these can make you feel like just calling it quits.

But according to Ryan Holiday, these roadblocks are actually opportunities in disguise. See, Holiday was a mega-successful guy at a really young age, having renounced college to advise billionaires and work with huge names like the NCAA. But then his career took a crazy nosedive that left him feeling like an epic failure.

That’s when he discovered the timeless wisdom of ancient Stoic philosophers, who believed that the obstacles thrown our way are actually the way to develop resilient mindsets, unstoppable perseverance, and the mental toughness to power through anything.

In this fascinating book, Holiday breaks down smart strategies used by history’s greats to turn failures into fuel for an even bigger comeback.

Remember, some of the most revered figures, from George Washington to Steve Jobs, wouldn’t have achieved their legendary success without first overcoming colossal failures and using them as stepping stools.

You Are a Badass by Jen Sincero

2. You Are a Badass by Jen Sincero

In a world that constantly barrages us with negative messages about how we’re not rich/popular/attractive/successful enough, it’s no wonder so many of us feel like total failures! That incessant stream of criticism, from others but mostly from our own inner bullies, can drain our self-confidence and convince us to abort our dreams before we’ve even started.

Well, Jen Sincero is here to stop that negative self-talk dead in its tracks with her brilliant wake-up call of a book, You Are a Badass. Packed with hilarious stories, no-nonsense truths, and inspired assignment ideas, it’s like an extended pep talk from your wisest, most blunt best friend.

Her core message is simple – you need to stop letting your inner doubts, fears, and crappy misconceptions about success control your life.

Instead, she teaches how to tune into your authentic inner “badass” and tap into its inherent confidence, vibrant courage, and ability to manifest incredible things in life.

Sincero herself went from being a broke, aimless loser sleeping on a cheap mattress to becoming a bestselling author, success coach, and motivational speaker. With her trademark irreverent humor, she’ll respark your unapologetic self-love and belief in your own abilities to persevere through any setback or failure.

The Success Principles by Jack Canfield

3. The Success Principles by Jack Canfield

When I was younger, I always wondered what “successful” people did differently to accomplish their big, shiny goals while I kept stumbling around going nowhere fast. Well, lucky for us, human success dispenser Jack Canfield has cracked the code and graciously shared the answers in his iconic book, The Success Principles.

Canfield’s pretty legit in the success wisdom department – after overcoming learning challenges like dyslexia as a kid, he grew up to co-create the motivational Chicken Soup for the Soul book series, which has sold over 500 million copies around the world. Now that’s what I call a comeback!

In The Success Principles, he maps out 64 tried-and-true principles for achieving any goal or dream, based on studying the habits and mindsets of top achievers in all fields. Covering everything from how to break down your vision into actionable steps to developing unwavering self-belief, this book is like an encyclopedia of successful human habits that you can adopt at any age.

And the real magic is, these principles aren’t just for big, audacious dreams – you can apply them to make a comeback from smaller failures too, like getting back on the job hunt after being laid off or finally completing that workout regimen you’ve given up on a million times.

Daring Greatly by Brené Brown

4. Daring Greatly by Brené Brown

Why is it that even smart, talented people with huge potential often get paralyzed by fear and never take the leap to chase their greatest ambitions? According to Brené Brown, a leading researcher on shame and vulnerability, it’s because we’re so terrified of the pain and embarrassment of potential failure.

Her book Daring Greatly explores how too many of us have become afraid of putting ourselves out there and opening up to experiences that really matter because the sting of rejection or defeat is too much to bear. We sacrifice our grandest dreams, our self-worth, and even our closest relationships to avoid that failure feeling.

But Brown argues that by continuing to shut ourselves off and play small to sidestep possible humiliation, we’re missing out on the richest experiences and opportunities life has to offer. Daring to risk failure and live vulnerably is the only path to wholehearted living and unleashing our true potential.

This book is a powerful, compelling call to “show up and be seen” in our lives by adopting self-compassion, killing our shame demons, and embracing the courage to fail spectacularly while going after what we want most. It’s the ultimate pep talk to help get out of your own way and open yourself up to happiness, belonging, and greater success than you imagined possible.

Start With Why by Simon Sinek

5. Start With Why by Simon Sinek

Everyone hits a funk sometimes where it feels like you’ve lost your inner fire or motivation for what you were working so hard to accomplish. After a major failure, it’s especially easy to start questioning whether your original goals and dreams were even worth the struggle.

Enter Simon Sinek to get you unstuck and reconnect with the passion that drove you to pursue those ambitions in the first place. See, Sinek says that the most successful people and organizations in the world are effective because they prioritize their “Why” – their high-level purpose, cause, or belief that inspires everything they do.

Too many failure-fearing folks get bogged down in the “Whats” of superficial achievements and material gains, losing sight of their deeper “Why” reason for doing it all. By shifting your mindset to start with that core sense of meaning and motivation first, you’ll not only reignite your enthusiasm, but also inspire others to get on board with you.

The best part is, Sinek breaks down exactly how to find your own “Why” and use it as a filter for making decisions that feel truly aligned and fulfilling. With it, any failure simply becomes a detour on the path to living your purpose, rather than a catastrophic dead end.

Option B by Sheryl Sandberg & Adam Grant

6. Option B by Sheryl Sandberg & Adam Grant

Dealing with devastating loss is one of the most brutal forms of failure anyone could experience. One minute you’re coasting through life, feeling like you’ve finally “made it”… and the next, that perfect reality comes crashing down in the worst way.

Sheryl Sandberg was living the dream as the insanely successful Chief Operating Officer of Facebook. She had achieved massive career heights, wrote a bestselling book, and seemed to have it all – including a loving husband and family to share it with.

Then in an instant, Sandberg’s charmed life shattered when her husband Dave unexpectedly passed away. Just like that, all her hard-earned accomplishments felt empty in the face of such profound personal failure and loss.

This crushing experience shook Sandberg to her core and forced her to rebuild herself from the ground up. Through deep pain and struggle, she discovered her own capacity for unimaginable resilience, strength, and perseverance in the darkest of times.

In Option B, Sandberg shares raw insights from her journey of grief and recovery, as well as stories from others who have risen from life’s biggest gut punches – job losses, illnesses, abuse, and more.

Her message is simple yet powerful – even in our most epic failures and tragedies, we are never stuck with just one option.

We all have the ability to make a different choice, an Option B, to create a fresh start and rebuild our lives in unexpectedly beautiful ways.

This book is a candid, inspiring pep talk about finding the courage, support systems, and space for feeling all the difficult emotions that come with failure, while still cultivating hope to move forward, one brave step at a time. Anyone who’s felt hopelessly stuck in one of life’s deepest chasms will find solace, wisdom and the motivation to choose Option B.

Rising Strong by Brené Brown

7. Rising Strong by Brené Brown

And speaking of rising from the ashes of failure, no one quite arms you with the tools for that life reformation like Brené Brown. This wise, wonderful lady is back on our reading list with her book Rising Strong, based on over a decade of research on vulnerability, shame, courage and worthiness.

As she unpacks in Daring Greatly, we’re all terrified of putting our authentic selves out there and risking the failure and emotional pain that comes with it. So we develop all these unhealthy coping mechanisms like blame, lashing out, making cheesy bumper sticker affirmations, or just burying our vulnerability in endless numbing distractions.

But with Rising Strong, Brown lays out her revolutionary process called “The Physics of Vulnerability” to short-circuit those nasty tendencies after a fall. Based on thousands of stories from folks of all ages and backgrounds, she breaks the steps down into:

The Reckoning, where we overcome our dread of admitting failure and get radically honest with our emotions about the tough event.

The Rumble, where we actively decide how we want to live and story-edit the failure for meaning and learning opportunities. This is the meat of the work where we shed decaying beliefs and armor up new reserves of courage.

The Revolution, where we emerge with powerful new integrity to live by and a mindset shift that lets us show up in the world with deeper authenticity.

It’s a gritty, wholehearted path for owning our stories, learning from our mistakes, and ultimately developing a “hustle for worthiness” that future failures can’t shake. We’re talking life-changing tools for being brave enough to show up and risk falling, while knowing you can always find the strength to get back up again.

Mindset by Carol Dweck

8. Mindset by Carol Dweck

Here’s a sneaky source of failure that often flies under the radar – those deep-rooted thoughts and beliefs we carry about our own abilities and potential. If you catch yourself thinking things like, “I’m just not good at this,” or “Screw it, I’ll never make it, so why try?” then you’ve likely fallen victim to a fixed mindset.

Stanford psychologist Carol Dweck blew the lid off this phenomenon after years of research tracking students’ attitudes about failure and struggle.

Her game-changing book Mindset revealed that we all tend to operate out of one of two mindsets – fixed ones, where we see traits like intelligence and talent as unchanging and failures as permanent roadblocks, OR growth mindsets, where we understand that abilities can be developed through commitment and a willingness to fail forward.

Crazy, right? Those simple mindset differences influence everything from our confidence when facing challenges, resilience for bouncing back from setbacks, and overall levels of achievement in any pursuit. The growth mindset approach allows us to see failures as simply temporary steps in a learning process, kind of like the software updates your brain needs to level up.

Mindset is jam-packed with real life examples and rock-solid techniques to help identify and re-wire your own thinking, both for kids learning new skills for the first time and adults trying to make a career comeback. It’s a profound, yet surprisingly simple, mindset shift that will knock your fear of failure on its butt and open up new windows of possibility for the life you truly want to create.

The Magic of Thinking Big by David J. Schwartz

9. The Magic of Thinking Big by David J. Schwartz

Raise your hand if you were that bright-eyed kid who dreamed wildly of becoming a famous athlete, artist or superhero when you grew up…only to now find yourself, years later, trapped in a soul-sucking routine that’s a far cry from those lofty childhood ambitions? Yeah, me too.

As adults, it’s easy to let the cynicism and fear of failure gradually shrink our visions until we’re settling for tiny, disappointing slices of life instead of going for the whole dang cake. But according to the late motivational legend David J. Schwartz, author of The Magic of Thinking Big, learning to embrace big, audacious goals is the secret to living a rich, fulfilling life beyond your wildest dreams.

This classic from the 1950s was one of the first hugely influential books on cultivating the mindset and habits of successful people who constantly think bigger than their failures and chase what Schwartz calls “Blue Sky” dreams.

Through hilarious real-life case studies and practical exercises, it teaches timeless principles like:

  • Banishing fear of failure and self-limiting beliefs
  • Learning to out-crazy any rejection or defeat life throws at you
  • Developing the focus and confidence to persevere through obstacles
  • Nurturing big, contagious goals that magnetize opportunity and abundance

While it’s written with entrepreneurs and career dreamers in mind, the wisdom to “think bigger about yourself” is highly effective for anyone who’s felt like a failure in any area of life. Even kids can apply Schwartz’s commonsense strategies for dreaming bolder, expanding out of their comfort zones, and demolishing the bogeymen of criticism and defeat.

If you’re feeling defeated from a recent setback and that little voice is whispering “time to just settle and be realistic,” grab this fun read to shake off those limiting fears and regain the childlike mindset of limitless possibility, no matter your failures.

Grit by Angela Duckworth

10. Grit by Angela Duckworth

We all know that uber-talented person who somehow manages to squander their natural gifts and potential, while someone else with seemingly average abilities goes on to achieve massive success through sheer perseverance. What gives?

According to Angela Duckworth, psychologist and bestselling author of Grit, the difference comes down to one crucial factor – the ability to sustain passion and perseverance in pursuit of long-term goals. In other words, an abundance of stick-with-it-ness, or grit.

Through her pioneering research on grit, spanning from Ivy League undergrads to professional artists to cadets at West Point, Duckworth blows the lid off the myth that success is a product of purely talent or intelligence. Instead, she reveals that having the stamina to rebound from failures, toil relentlessly, and chase lofty ambitions for years in the face of adversity is what truly separates high achievers from the pack.

In Grit, she takes readers on a riveting journey to understand where grit comes from and how to develop and amplify this renewable inner resource, no matter your age or background. Filled with insights from her studies plus conversations with ultra-gritty high performers, the book distills the mindsets, behaviors, and habits of truly gritty people.

You’ll walk away with actionable ways to cultivate your own capacity for sustained effort and resilience over time, harnessing the power of interests, practice, purpose, and hope to propel you past failures and obstacles on the path to your biggest goals. Even kids will get inspired by the authentic grit exemplars and strategies for bouncing back stronger.

Whether your Everest is building a successful business, becoming an elite athlete, or simply persisting at a New Year’s resolution, Grit offers the psychological playbook for developing the fortitude and passion to reach the summit. It’s an essential read to stop failure from deterring you and finally go the distance on what matters most.


No matter if your trail of failures is a mile long or you’re at the start of a huge new undertaking, these 10 brilliant books will transform your perspective on what it really means to fail. They’ll teach you that your setbacks and shortcomings aren’t flaws to be ashamed of, but proof that you’ve dared to live boldly and are now wiser for the experience.

Packed with profound mindset shifts, side-splitting stories, and relatable pep talks from people who pushed past the brink of failure to achieve mind-blowing heights of success, these are the ultimate guidebooks for turning your biggest stumbling blocks into stepping stones.

So go pick up a copy of one or binge them all! Then reignite that fiery inner belief in yourself, use these strategies to get scrappy and fail forward, and get ready to slay bigger and better dreams than ever before. The comeback story of your life is just getting started.