7 Books That Give You the Courage to Finally Start Over

Life doesn’t come with a reset button—but it does offer second chances. Whether you're emerging from a divorce, changing careers, moving cities, or simply feeling lost in the noise of everyday life, starting over can feel terrifying. But here’s the truth: it’s also one of the most empowering decisions you can make.

At some point, we all reach a crossroads where we ask: “Is this it?” And in that vulnerable space, the right words can light the path forward.

Below is a list of 7 books that give you the courage to finally start over. These aren't just self-help platitudes; they’re written by people who’ve walked through fire, questioned everything, and emerged stronger—and they’ll guide you to do the same.

1. Untamed by Glennon Doyle

Untamed is a fierce, liberating memoir about breaking free from societal expectations to live a life rooted in truth. Glennon Doyle recounts her journey of leaving behind a picture-perfect life to follow her heart—and her intuition. The book speaks directly to anyone who’s been told to stay small, polite, or quiet. With raw storytelling and empowering insights, Doyle challenges us to stop asking for permission and start trusting ourselves. It’s a manifesto for women—and anyone—ready to stop performing and start living authentically. Reading Untamed feels like sitting down with a wise, wild friend who believes in your deepest potential.

2. The Midnight Library by Matt Haig

In The Midnight Library, Matt Haig explores the power of choice and the weight of regret through the imaginative story of Nora Seed, a woman given the chance to explore infinite versions of her life. Each book in the library represents a different path she could have taken, asking the powerful question: What if you had done it differently? This novel blends philosophy with fiction in a way that’s deeply reflective and surprisingly hopeful. It’s perfect for those at a crossroads, reminding us that every life has value—and that sometimes, starting over means simply choosing to see things differently.

3. Tiny Beautiful Things by Cheryl Strayed

Tiny Beautiful Things is a collection of profoundly moving advice columns written by Cheryl Strayed under the pseudonym “Sugar.” Through these letters, Strayed responds with compassion, wisdom, and brutal honesty to readers facing heartbreak, addiction, fear, and loss. What makes this book so powerful is its deep emotional resonance—Strayed never offers cliché solutions but instead mirrors back strength and love. For anyone navigating uncertainty or grief, it’s a comforting reminder that you’re not alone.

4. Year of Yes by Shonda Rhimes

In Year of Yes, acclaimed TV producer Shonda Rhimes recounts a transformative year where she challenged herself to say “yes” to everything that scared her. From public speaking to self-care, she pushes beyond her comfort zone and discovers joy, confidence, and personal power. Rhimes’ candid storytelling, humor, and vulnerability make this memoir incredibly relatable and inspiring. It’s a reminder that growth often hides behind the word no, and that our lives can radically shift when we embrace the unknown. For anyone ready to reclaim their voice and face life head-on, this book is a bold, empowering invitation to begin.

5. You Are a Badass by Jen Sincero

In You Are a Badass, Jen Sincero blends bold humor, tough love, and practical wisdom to help readers kick fear to the curb and start living intentionally. Through short, energetic chapters, she tackles self-doubt, procrastination, and limiting beliefs with straight talk and real-world advice. What makes this book stand out is its unapologetic confidence—it’s like having a personal cheerleader who also tells it like it is. Sincero’s message is clear: you already have what it takes, you just need to believe it. It’s the perfect read for anyone on the brink of transformation who needs a push (or a shove) forward.

6. Broken Open by Elizabeth Lesser

Broken Open is a gentle but powerful exploration of how life’s greatest challenges can become the gateways to personal transformation. Elizabeth Lesser draws from her own life, spiritual teachings, and the stories of others to illuminate the path through grief, change, and loss. Rather than avoiding pain, Lesser invites us to embrace it, understanding that being “broken open” allows our true self to emerge. The book offers profound spiritual insight and emotional honesty without being preachy. It’s a deeply compassionate companion for those navigating life transitions, showing that even in the messiness of change, we can find meaning and beauty.

7. When Things Fall Apart by Pema Chödrön

Pema Chödrön’s When Things Fall Apart is a spiritual guide for navigating life’s most difficult moments. Rooted in Buddhist philosophy but accessible to all, it offers profound insight into how we can use pain, fear, and uncertainty as paths to wisdom and peace. Chödrön encourages us not to run from discomfort, but to lean into it with curiosity and compassion. Her writing is both poetic and practical, filled with stories, teachings, and meditations that speak to the heart. If you’re in the midst of a personal upheaval, this book offers solace—not by fixing your pain, but by transforming your relationship to it.

Conclusion

Starting over isn't about failure—it’s about finally choosing yourself. Each of these books offers a lens through which to see your transition not as an end, but as a beginning.

If you’ve been waiting for a sign, let this be it: You are allowed to rewrite your story.

The next chapter starts when you pick up the pen.