Book Review: How to Dream by Deedee Cummings

By Christine MacIntyre

Dreaming is an act of courage. It asks us to look beyond the practical and predictable—to listen for that small, persistent whisper that says, “There’s more.” In How to Dream: A Motivational Guide to a Life of Hope, Success, and Freedom, author, therapist, and entrepreneur Deedee Cummings reminds readers that dreaming isn’t childish or indulgent—it’s essential. It’s how we return to ourselves.

Cummings writes from experience, having worn many hats: attorney, mother, therapist, and founder of Make a Way Media. Her voice carries the authority of someone who hasn’t just studied transformation but lived it. She invites us to imagine a life where hope is not a detour from reality but the most honest reflection of it. The result is a guide that blends reflection, encouragement, and gentle direction—a book that feels like sitting down with a friend who believes in you, even when you’ve forgotten how to believe in yourself.

Early in the book, Cummings poses a question that feels both intimate and urgent: “How do you dream in a world that actively crushes dreams?” For anyone who’s ever set aside their passion in the name of practicality, her words feel like sunlight breaking through a darkened room. She speaks to those of us who once dreamed boldly but grew quiet over time, buried beneath responsibilities, doubt, or the slow erosion of confidence.

Through personal stories, affirmations, and accessible exercises, Cummings gently guides readers back to their inner voice. She doesn’t promise grand outcomes, instead, she emphasizes small, intentional steps. The dream, she insists, doesn’t begin with grandeur—it begins with clarity. With courage. With a quiet “yes” whispered in the stillness of an ordinary morning.

What sets this book apart is Cummings’ ability to marry emotional depth with practical tools. Her background as a therapist infuses each page with compassion and insight. She understands the tangled roots of fear and the lingering wounds that silence ambition. But she doesn’t dwell in pain—she uses it as compost for growth.

Her writing has a rhythm that feels like a heartbeat—steady, human, and hopeful. Each chapter ends with reflective questions that help readers uncover not only what they want, but why they want it. She challenges us to stop waiting for the “right” moment and instead take action now. Dreams aren’t distant destinations, she reminds us: they’re cultivated in our daily choices.

Cummings doesn’t just inspire—she equips. The book is full of actionable advice for readers at every stage of their journey. For those unsure where to start, she offers clear steps: if you can’t fill in the blanks about your dreams, begin by expanding your support circle: consider adding a therapist, mentor, or coach.

She addresses how to manage negativity, to filter out the noise of the world—“The world is loud. Your dreams have to be louder”—and how to rediscover purpose and passion. She explores how to deal with failure and how to stay committed to dreams that may seem out of reach—like her own ambition to produce a Broadway show. “This dream is not easy or quick, but it is something I’m dedicated to. It absolutely can happen. I hang on to that. This dream can happen. And every day I do something to take a step toward that dream.”

Her formula for progress: One Step + The Next Step x The Power of Positivity = Way Made is both motivational and practical. She calls it the Make A Way Mindset, and she doesn’t leave it at theory. She offers dozens of ways to bring it to life—even when resources are scarce. No money? No connections? She encourages readers to read books, attend local events, document your learning, become an expert, and map out your dream.

She also introduces the concept of “inhaling words.…Inhaling affirmations means that you breathe the words in and let them travel throughout your body. You invite the words to live in your mind. You let the words take root. You welcome them and give them room to grow.”

Cummings also shares real-life stories of people who’ve reached various forms of success—not to encourage comparison, but to affirm what’s possible. “We need to be reminded that it is real. It is possible. But... don’t measure your journey by the journey of anyone else.”

Cummings’ book echoes the belief that transformation starts from within—that lasting change isn’t forced but grown through awareness, presence, and intention.

Whether you’re a young dreamer unsure where to begin, a parent modeling courage for your children, or someone quietly rebuilding after life’s detours, How to Dream offers a lantern for your journey. It doesn’t claim to hold all the answers—it reminds you the answers are already within you, waiting to be remembered.

Perhaps the most powerful takeaway from How to Dream is its gentle insistence that dreaming is a form of self-care. It’s not about escaping reality. It’s about reshaping it. When we give ourselves permission to dream, we grant others that same freedom.

As I read, I kept thinking about my own daughter—her boldness, her curiosity, her unshaken belief that anything is possible. Somewhere along the way, many of us lose that. Cummings’ book is a call to remember. To pick up the thread. To begin again.

In a culture that rewards busyness over meaning, her words feel like an exhale. They invite us to slow down, to listen inward, and to ask, “What if I tried again? What if I believed I could?”

How to Dream is more than a motivational book—it’s an act of compassion disguised as a guide. It belongs on the nightstand of anyone longing for a softer, truer life. Deedee Cummings doesn’t hand you a roadmap—she hands you a mirror. And in it, if you look closely, you might just recognize the dreamer you’ve always been.

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