7 Books That Teach You How to Handle Failure Like a Pro
These books don’t glorify success and get honest about failure, falling apart, and finding your way back
Look, failure is the first punch we all take early on—usually when that test score tanks and the world feels like it’s closing in. For some, it’s the sinking guilt of not having put in the hours. For others, it’s just plain confusion: “What went wrong?”
Then there’s the parental disappointment that is a special kind of pressure which can make failure feel like the end of the road. We grow up in this ultra-competitive world that glorifies winning and sidelines failure like it’s a dirty secret.
But we all fail. Yet, most of us don’t really know how to deal with it. We either spiral into the pity party or bury the whole thing deep down, missing what failure can actually teach us.
Obviously, failure isn't a selective process for some to grow in life or be redirected to their true callings. Even the most successful have seen many falls. Before Harry Potter became a global phenomenon, author J.K Rowling faced a brutal string of rejections and personal setbacks.
A single mother on welfare, battling poverty and depression, she sent her manuscript out to 12 publishers—12 no’s. Most people would’ve quit. But she didn’t. Eventually, a small publisher took a chance. And the rest? Well, that’s history. Though Rowling’s story is about magic in books, it’s also about the kind of resilience that turns failure and rejection into fuel to keep going.
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So, what's stopping you from risking it and preparing for failure if it comes your way? A lot of the times, if not real conversations with someone who's been through it, books become the perfect helping hands. Here are some fantastic books that will teach you a little bit about life and failure, the kind of mindset that you need to develop to face dejections that can arrive any hour of the day or your lifetime.
Born a Crime by Trevor Noah
A memoir packed with humor, failure, and survival, growing up in apartheid South Africa. Trevor’s early life is filled with setbacks, but his voice is pure gold.
Educated by Tara Westover
Tara grew up in a survivalist household with no formal schooling. Her journey to education and the pain of breaking away from her family is full of failure, both personal and systemic. It hits hard.
I Have a Dream by Rashmi Bansal
A collection of stories about 20 idealists who think and act like entrepreneurs in India and who failed, pivoted, and tried again. The people described are real people, driven by purpose, who risked everything. If you want the desi version of grit, this is it.
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I’m Glad My Mom Died by Jennette McCurdy
A darkly funny, brutally honest memoir of a child star's toxic relationship with her mother and the failures of the entertainment industry. This one hit hard with millennials and Gen Z for its vulnerability and clarity.
Maybe You Should Talk to Someone by Lori Gottlieb
A therapist goes to therapy. Gottlieb’s memoir is packed with stories of people failing at life, love, and identity including herself. It's honest, compassionate, and deeply relatable.
Everything I Know About Love by Dolly Alderton
A coming-of-age memoir filled with dating disasters, job failures, and emotional chaos. Alderton writes like your sharpest, funniest friend who’s been through some real stuff and lived to tell it.
The Difficulty of Being Good” by Gurcharan Das
Less personal memoir, more philosophical — but deeply relevant. Das explores the Mahabharata through the lens of modern life and failure: moral failures, social struggles, internal contradictions. It’s heavy, but resonates.
