Cassidy Gard’s 10 Best Books to Read at Life’s Crossroads
I have always been drawn to memoirs. Reading one feels like being handed someone’s private journal, with permission to enter the most observant and vulnerable corners of a life. I always knew I would write one. In my early 20s, I started emailing myself fragments I did not want to lose: a sentence I overheard on a downtown sidewalk in New York, a feeling I could not yet explain, a quote that hit me in the chest. Tiny shards of meaning. Years later, I opened my Google Drive and found 15 years of notes waiting for me, little time capsules from former versions of myself, full of things I had completely forgotten and once felt desperate to preserve. Add to that the stacks of journals I have carried across cities, and a pattern becomes obvious. I have always been fascinated by the interior worlds of women, what drives us, what undoes us, what remakes us.
The first memoir I read was Eat, Pray, Love when I was 16. One line has stayed with me ever since: “I crossed the street to walk in the sunshine.” I still do that. If I am walking and the sunnier side is across the road, I cross and think of that sentence. My own memoir, Cosmic Goodness: Surrendering the Shadows to Live in the Light, publishes May 12, 2026 (pre-order here). I began writing it in 2017, after my first major heartbreak and my father’s death landed within six months of each other. The book follows my coming of age in my 20s and at the threshold of 30, when career ambition, grief, dating, identity, and the desire for family all collided. It moves through the high-pressure years of building a life in the media, the private fallout of loss and inherited pain, and the spiritual and emotional reckoning that forced me to rebuild from the inside out. At its core, it is a story about learning to trust yourself after rupture, choosing love without abandoning your ambition and discovering that reinvention is not a single leap but a thousand small acts of courage.
In my book, I write about what I call ‘hurricane women,’ inspired by John Green’s line in Looking for Alaska: “If people were rain, I was drizzle, and she was a hurricane.” I found that quote at a pivotal time, dating while deep in a demanding career and quietly terrified that if I did not make space for love, I would miss my chance to build a family. As the daughter of an alcoholic, I often felt like an emotional orphan. A friend once told me, “Just be easy and breezy. They love that.” I answered, “I am windy and complicated.” Green’s line helped me make peace with an interior world that never aligned with bite-sized clichés. So I turned to books. I found women writers who transformed their messiest truths into art. I am obsessed with quotes, those 10- to 20-word lines that can rewire a mindset and redirect a life. I even opened every chapter of my memoir with one, pulled from the thousands saved in my phone notes.
The books below (and the quotes I’ve pulled from them) didn’t just inspire me—they gave me permission. Permission to be complicated, to be a hurricane, to take up space. They reminded me that the sharp, messy parts of ourselves aren’t flaws to be fixed but truths to be honored. And when I finally gave myself that permission, my own story came pouring out.
- The Happiness Project by Gretchen Rubin
- Women Who Run With the Wolves by Clarissa Pinkola Estés
- A Return to Love by Marianne Williamson
- Tiny Beautiful Things by Cheryl Strayed
- Big Magic by Elizabeth Gilbert
- Untamed by Glennon Doyle
- All About Love: New Visions by bell hooks
- The Life-Changing Magic of Tidying Up by Marie Kondo
- Daring Greatly by Brené Brown
- The Let Them Theory by Mel Robbins
The Happiness Project by Gretchen Rubin
- “When you can’t decide between two courses of action, choose the bigger life.”
Making decisions from a place of fear leads us to live smaller lives. This quote stopped me in my tracks because it gave me a compass for navigating which paths to follow. It became an immediate exercise in choosing the direction most aligned with my dreams. Fear always offered me the smaller life, the safer life, the quieter life. This line challenged me to make choices that expanded me rather than diminished me.
Women Who Run With the Wolves by Clarissa Pinkola Estés
- “There is a time in our lives, usually in mid-life, when a woman has to make a decision—possibly the most important psychic decision of her future life—and that is, whether to be bitter or not. Women often come to this in their late thirties or early forties. They are at the point where they are full up to their ears with everything and they’ve ‘had it’ and ‘the last straw has broken the camel’s back’ and they’re ‘pissed off and pooped out.’ Their dreams of their twenties may be lying in a crumple. There may be broken hearts, broken marriages, broken promises.”
This passage hit me profoundly when I became a mother and found myself negotiating the resentments of the mental load. I was not yet in my late 30s, but I could already feel the weight of accumulating disappointments, especially when everything seemed to fall on me, and I had to learn the language to rebalance domestic responsibilities. Estés gave language to something I was terrified of becoming: bitter. This book helped me understand that anger can be information, grief can be initiation, and pain does not have to harden into bitterness. Her work taught me that acknowledging this crossroads was the first step toward choosing differently—choosing wildness, choosing to reclaim the parts of myself I had abandoned to be more palatable. It can become wisdom if you are willing to face it.
A Return to Love by Marianne Williamson
- “It takes courage…to endure the sharp pains of self-discovery rather than choose to take the dull pain of unconsciousness that would last the rest of our lives.”
My memoir explores generational trauma with extremely candid and revealing stories about being the daughter of an alcoholic—stories that once brought me great shame about the way I grew up. For years, I carried shame and numbness. Through attending Al-Anon, I met hundreds of other people, and a type of healing began. Marianne’s words cracked me open. I had delayed grief and had been numb to what I grew up with for so long. This book opened something in me, and if it had not, the pain would have remained buried beneath the surface far longer. Avoiding pain does not erase it. It only buries it deeper.
I write extensively about self-esteem in my book. Self-trust is a major thread in my memoir. It can be difficult to access the innermost parts of ourselves, but I sometimes imagine my adult self advocating for my childhood self, saying, “This pitch is REALLY good. It’s meaningful, it matters, and it would be beneficial to take a look at it.” I spent a year working on my book proposal, and when it was finally time to send it out into the world in the hope of securing a traditional book deal, I had to remember that playing small would mean not believing it was possible. When I did receive a book deal, I did not feel diminished. I felt bursting with aliveness and self-confidence that my stories mattered. Yours do too. Your ideas deserve to take up space, whether you are a writer, an entrepreneur or simply a woman building something that matters to you.
Tiny Beautiful Things by Cheryl Strayed
- “Wanting to leave is enough.”
I read Wild shortly after my dad was diagnosed with terminal cancer. We were estranged at the time, and in a twist of fate, I went on to take care of him for two years. I write about the grief and devastation of becoming a caregiver to someone who never took care of you as a child. Her work met me in the exact place where love, grief, anger and duty collided. Many times, I returned to Cheryl’s two books, Wild and Tiny Beautiful Things. During the pandemic, when I was single, alone, and desperately lonely, I started hiking portions of the Pacific Crest Trail. I would think to myself, “Cheryl hiked this exact trail.” I hoped whatever magic of nature that lived in her would rub off on me.
Big Magic by Elizabeth Gilbert
- “A good-enough novel violently written now is better than a perfect novel meticulously written never.”
I am a self-proclaimed perfectionist, and perfectionism can look productive while quietly killing momentum. It can also lead me to stall, pause and never actually finish the work because I fear it is not good enough. Gilbert’s book taught me to make friends with fear. She has a note where she tells fear: “Dearest Fear: Creativity and I are about to go on a road trip together. I understand you’ll be joining us, because you always do. I acknowledge that you believe you have an important role in my life and that you take it seriously. But I will also be doing my job on this road trip, which is to work hard and stay focused.” Elizabeth’s framing of fear as a passenger, not the driver, changed how I create. Completing something is more important than never doing it out of fear that it is not perfect. That lesson helped me stop sitting on projects for years. Finishing imperfect work is what builds a life. Waiting for perfection is what stalls it.
Untamed by Glennon Doyle
- “This life is mine alone. So I have stopped asking people for directions to places they’ve never been.”
You can consult every single love coach, career guide and mentor possible, but no one is going to know the path to your highest good as well as your inner being does. In my book, I write, “You cannot outsource your becoming.” I truly believe in listening to your angel guides. Mine speak to me in the middle of the night. When I was aching to become a mother, I had a dream so vivid that I saw two children playing at my feet. In the dream, I felt it completely, and when I woke up, I missed my unborn children, but somehow it also gave me certainty that I would become a mother one day. That dream made me exhale. This quote reminded me to trust my inner knowing over outside influence. It made me stop seeking input from others to figure out where to go. No one knows. Only you. You do not need to take courses or hire coaches. Everything is up for monetization now, and much of it pulls us farther from our interior world, making us feel like we have to rely on someone else. These books teach you how to access that wisdom on your own.
All About Love: New Visions by bell hooks
- “Knowing how to be solitary is central to the art of loving. When we can be alone, we can be with others without using them as a means of escape.”
I write in my book about the importance of taking yourself on dates—doing nice things for yourself so that it becomes ingrained deep within you before you expect someone else to do it for you. One of the biggest hurdles of motherhood was losing my alone time. I was so consumed with my children that I rarely left time to do anything for myself, and I did not want to miss a thing. But I believe alone time is vital for women, especially. It is when I daydream. For me, alone time is not a luxury. It is where I can hear myself think, imagine and reset.
The Life-Changing Magic of Tidying Up by Marie Kondo
- “To truly cherish the things that are important to you, you must first discard those that have outlived their purpose.”
This book matters to me because our environments are deeply important to our well-being. As a mom, you accumulate a lot of stuff—piles, clutter and excess that quietly builds over time. It is a daily practice to find things to recycle or donate. I no longer keep anything solely because it is sentimental or was a gift. My head is much clearer when my countertops are not overflowing. I feel overwhelmed when there are stacks of things everywhere. This book teaches you how to discern what to keep and what to release, so excess does not accumulate in your home. I learned that physical clutter creates emotional static. Letting go is not harsh. It is choosing clarity.
Daring Greatly by Brené Brown
- “Unused creativity is not benign. It does not dissipate. It metastasizes. And unused creativity turns into rage, grief, shame, judgment.”
I got my book deal when I was seven months pregnant with my second son. My first son had just turned two, and I knew what newborn life would look like. It felt like now or never. If I did not get the book deal before I gave birth, it would be another 18 months before I could focus again. After my first son was born, I worked on my book proposal in stolen moments—30 minutes here, 45 there. It was challenging for my ADHD brain to start and stop. I felt an urgency to submit my proposal before my second child arrived, and when it happened, it invigorated me to have a place to pour all my creative energy. I did not feel regret or sadness that my manuscript had stayed on the shelf, because I had taken the thoughts floating in my head and turned them into something real. Creativity does not have to mean art, entertainment or music—it can be anything you bring into existence from nothing. To see your ideas manifest is, to me, an integral part of identity for women. This book sharpened that understanding and transformed the parts of myself I once felt shame about into fuel. This quote captures what I now believe: creativity is not optional for many women. It is survival.
The Let Them Theory by Mel Robbins
- “Nobody owes you anything. But you owe yourself everything.”
Before I discovered this book, I truly struggled with round two of adolescence—something called matrescence, coined by author Lucy Jones, which describes a second wave of adolescence after becoming a mother. For me, it felt like returning to high school: mothers forming cliques around playgroups, subtle social hierarchies emerging overnight. Everyone talks about how important mom friends are, and I agree, but it took me time to find a group rooted in kindness. There were mean-girl dynamics in the mix, too. Until I discovered Mel Robbins’s book, The Let Them Theory, it hurt to feel like I could not break into those circles. I feared my son was not socializing enough, so I spent time with people I did not genuinely feel aligned with. This idea helped me stop internalizing those exclusions. “Let them” gave me distance. “Let me” gave me power. When I turned my focus inward, it helped me conserve emotional energy for what truly mattered. I stopped trying to be chosen and started choosing my own life, and everything else began to fall into place.