How to Dream by Deedee Cummings

How to Dream: A Motivational Guide to a Life of Hope Success and Freedom is an empowering motivational guide that challenges readers to reclaim their dreams in a world that often stifles ambition. Authored by Deedee Cummings, a best-selling author and therapist, this adult non-fiction book spans 150 pages and serves as a beacon of hope for anyone feeling lost or discouraged in their pursuit of success.

Cummings addresses a fundamental question: How do you dream in a world that actively crushes dreams? In How to Dream, she combines her personal journey with professional insights, drawing from her extensive career as a therapist, attorney, author, and CEO of Make A Way Media. This inspiring guide is designed to help readers turn their dreams into reality by providing practical strategies to overcome self-doubt, fostering a growth mindset, and taking actionable steps toward achieving their goals.

Cummings shares her vision: “My hope for How to Dream is that it will spark conversations in the community about why we have been actively dissuaded from our dreams since childhood. The saddest thing I see in therapy is a person with no dreams because that means they have no hope. What kind of life do you want to have, and why don’t you go get it?” This sentiment resonates throughout the book, offering powerful affirmations and mindset shifts that encourage readers to push past negativity and embrace their true potential.

One of the most striking aspects of How to Dream is Cummings’ emphasis on treating our dreams with reverence and care. She writes, “Your dream is your most cherished aspiration. Protect it, care for it, nurture it, talk to it, feed it, and love it like you would your favorite human being.” This powerful statement transforms dreams from abstract concepts into living entities worthy of our dedication and attention. For those who have lost touch with their aspirations amid life’s demands (looks at myself in the mirror), this perspective offers a gentle reminder to reconnect with our deepest desires and give them the nurturing they deserve.

Cummings also acknowledges the challenges inherent in pursuing our dreams, drawing wisdom from her family legacy: “Dreaming is not for the faint of heart. It takes a belief in something bigger than you and something my mother, Andrea Pecchioni, used to call sticktoitiveness.” This blend of personal heritage and practical wisdom underscores a crucial truth: realizing our dreams requires not just inspiration, but persistent dedication and unwavering belief in possibilities beyond our current circumstances.

Packed with practical advice, How to Dream serves as an essential toolkit for anyone ready to take their life to the next level. Whether you’re struggling to find direction, seeking to reignite your ambition, or needing encouragement to stay the course, this book inspires you to dream bigger, push harder, find freedom, and create the life you’ve always imagined.

Meet Deedee Cummings

Deedee Cummings is not only a professional dreamer but also a prolific author with eighteen published works. She founded Make A Way Media to address the lack of diverse literature and stories that resonate with underrepresented communities. Deedee is deeply committed to literacy and social justice, believing it is never too late to begin anew. Her work has garnered attention from notable media outlets, and she has been recognized for her significant contributions to early childhood education in Kentucky.

A Quick Chat with the Author

What advice would you give to budding writers?

Write. Write now. Just start writing. You wouldn’t believe how many people want to write a book and just never do it. Stop thinking about it and get words on paper. If you are still struggling with that join a group that pours confidence into you like my Make A Way Mindset group. You need encouragement and accountability to make it happen if you are unable to get moving on your own. Stop thinking. Start writing. Get words on paper!

How long have you been writing?

I have been writing for ten years solidly. I wanted to write for years, which is why I gave the advice I did to just get a story down on paper. I did not publish my first book until I was 44 years old.

Where do you write?

This might seem like a silly or frivolous question, but it is not. IT is very important to have a space where your mind can be free. You can’t write at a desk crowded with bills. You can’t write where people will continually interrupt you. You need an area where your mind can be free. I write on my back deck. I am the most productive as a writer in the Summer.

How to Dream is a must-read for anyone seeking to reignite their ambitions and take control of their life’s direction. With its blend of personal anecdotes, practical guidance, and inspiring affirmations, this book encourages readers to dream big and create the life they’ve always envisioned.


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