16 Parenting Books I Swear By For Raising A Confident, Happy Child

In my work with parents both in-person and in my online parenting course, I’m often asked for my advice on raising a confident, happy child. My ability to answer that question comes, in part, from the brilliant parenting, psychology and child development experts I’ve had the privilege of learning from. The parenting books I’ve listed below (in no particular order) have profoundly impacted both my work and motherhood journey, and I’m excited to share them with you.

In lending this virtual library to you, I hope these resources make you feel more confident and supported in your parenting. I do want to remind you, though, that good parenting is not a measure of how many books you’ve read. You’ve got everything you need inside of you to be a good enough parent; it’s in your factory settings. All of that time you spend nurturing, caregiving, and picking the kids up and dropping them off? That is enough, and you are enough just as you are.

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Parenting Books For Raising Confident Children

1. The Gift of Failure by Jessica Lahey

Your kid forgot his homework. Again. You spy it sitting on the table by the front door, where he neglected to slip it into his bookbag. You can easily stash it in your briefcase and drop it off on your way to work. Do you do it?

No way, says middle school teacher and journalist Jessica Lahey. The author of The Gift of Failure, Lahey urges parents to let our kids learn and grow through the mess of their mistakes. Unlike so many books out there that shame parents into compliance, Lahey writes with humor and compassion about the ways we’ve helicoptered our kids into fragile, dependent, risk avoidant creatures. She also bravely counts herself among the people she’s calling out: “I had to stop equating the act of doing things for my children,” she writes, “with good parenting.”

Hard-hitting yet warm and wise, The Gift of Failure is essential reading for parents, educators, and psychologists nationwide who want to help children succeed.

2. Parenting from the Inside Out by Daniel Siegel and Mary Hartzell

In Parenting from the Inside Out, child psychiatrist Daniel J. Siegel, M.D., and early childhood expert Mary Hartzell, M.Ed., explore the extent to which our childhood experiences shape the way we parent. Drawing on stunning new findings in neurobiology and attachment research, they explain how interpersonal relationships directly impact the development of the brain, and offer parents a step-by-step approach to forming a deeper understanding of their own life stories, which will help them raise compassionate and resilient children. 

Parenting from the Inside Out has been essential to my work as a parent and an educator. Its message is a foundational piece of my online parenting course, Enough As We Are. 

3. Mothering While Black by Dawn Marie Dow

In Mothering While Black, sociologist Dawn Marie Dow breaks down how the frameworks typically used to research middle-class families focus on white mothers’ experiences, inadequately capturing the experiences of African American middle- and upper-middle-class mothers. In examining the complex lives of the African American middle class—in particular, Black mothers and the strategies they use to raise their children to maintain class status while simultaneously defining and protecting their children’s “authentically Black” identities—Dow considers how these mothers apply different parenting strategies for Black boys and for Black girls, and how they navigate different expectations about breadwinning and childrearing from the African American community. 

At the intersection of race, ethnicity, gender, work, family, and culture, Mothering While Black sheds an essential light on the exclusion of African American middle-class mothers from the dominant cultural experience of middle-class motherhood. In doing so, it reveals the painful truth of the decisions that Black mothers must make to ensure the safety, well-being, and future prospects of their children.

4. Raising Happiness by Christine Carter

Ask any parent what they want most for their child, and you’re bound to hear “happiness” in at least the top five. Much like failure, happiness is a learned trait—one we can model and help build in our children from their earliest years.

Drawing on what psychology, sociology, and neuroscience have proven about confidence, gratefulness, and optimism, and using her own chaotic and often hilarious real-world adventures as a mom to demonstrate the do's and don’ts in action, Christine Carter, Ph.D boils the parenting process down to 10 simple happiness-inducing steps.

Complete with a series of “try this” tips, secrets, and strategies, Raising Happiness is a one-of-a-kind parenting book that will help you instill joy in your kids—and, in the process, become more joyful yourself.

5. The Optimistic Child by Martin Seligman

In this era of making children feel good, the research continues to show that they have never been more depressed. Why? That’s the question Martin E. P. Seligman, the best-selling author of Learned Optimism, and his colleagues tackle in The Optimistic Child: A Proven Program to Safeguard Children Against Depression and Build Lifelong Resilience. 

Seligman offers parents and educators a program clinically proven to cut the risk of depression in half, teaching children to apply critical optimism skills that can curb depression, boost school performance, and improve physical health. 

6. The Second Family by Ron Taffel

While families of origin certainly hold extraordinary influence over the lives of teens, to consider these are the only “families” they encounter daily is to overlook a massive power force shaping their day-to-day lives. The Second Family, as defined by Dr. Ron Taffel, illuminates the new set of rules by which kids operate by shining a light on the pervasive influence of peer groups and pop culture. 

It is nearly impossible to understand today's teens or preteens without understanding The Second Family. If you’ve ever had the thought, “This is not the child I know,” let this book guide you.

8. Parenting by Heart by Ron Taffel

It’s the question on all of our minds: How do you get your child to open up to you? Where do we find “quality” time? What discipline techniques work for young children, and why? 

An empowering book that emphasizes real-life parenting situations and practical, compassionate solutions, Parenting by Heart is filled with specific advice tried by thousands of families. Taffel shows what actually will work (instead of what “should” work) and does so in a way that makes sense. 

9. No-Drama Discipline: The Whole-Brain Way to Calm the Chaos and Nurture Your Child's Developing Mind by Daniel Siegel and Tina Payne Bryson

From the brilliant authors of The Whole Brain Child, No-Drama Discipline should, in my opinion, be required reading when one becomes a parent. Highlighting the fascinating link between a child’s neurological development and the way a parent reacts to misbehavior, Siegel and Bryson provide an effective, compassionate road map for dealing with tantrums, tensions, and tears—without causing a scene.

The authors break down the impossible: how to reach your child, redirect emotions, and turn a meltdown into an opportunity for growth. 

10. How to Raise an Adult by Julie Lythcott-Haims

Drawing on research, conversations with admissions officers, educators, and employers, and her own insights as a mother and as a student dean, How to Raise an Adult brilliantly highlights the ways overparenting harms children, their stressed-out parents, and society at large. 

Check this parenting book out for practical strategies that underline the importance of allowing children to make their own mistakes and develop the resilience, resourcefulness, and inner determination necessary for success.

11. Best Friends, Worst Enemies by Michael Thompson

I often tell parents that friendships are our very first classroom. Friendships are where we develop skills for connection, conflict and compromise. But intimacy can also be painful. Children can cause suffering, not only for their peers but for parents as well. 

In Best Friends, Worst Enemies, Michael Thompson, Ph.D. and Catherine O’Neill Grace illuminate the crucial and often hidden role that friendship plays in the lives of children from birth through adolescence.

12. How to Talk So Kids Will Listen and Listen So Kids Will Talk by Adele Faber and Elaine Mazlish

Many have called How to Talk So Kids Will Listen and Listen So Kids Will Talk a “parenting Bible,” and for good reason—the groundbreaking parenting book gives us the know-how needed to be more effective with our children and more supportive of ourselves.

I recommend this book to friends and students all the time! It’s an illuminating, down-to-earth read that will almost certainly make you a more confident, compassionate parent. 

13. Social Media Wellness by Ana Homayoun

Parents constantly ask me about social media, and while I’ve spent years studying the evolution of this second social universe children exist in, I am deeply impressed by the work of Ana Homayoun. 

Today’s students face a challenging paradox: the digital tools they need to complete their work are often the source of their biggest distractions. Students can quickly become overwhelmed trying to manage the daily confluence of online interactions with schoolwork, extracurricular activities, and family life. Social Media Wellness was the first book to successfully decode the new language of social media for parents and educators and provide pragmatic solutions to help students.

Parenting Books for Raising Confident Girls 

14. Queen Bees and Wannabes by Rosalind Wiseman

I have been so honored to learn from and work with my friend Rosalind Wiseman over the years. In her groundbreaking book, Queen Bees and Wannabes, Rosalind took us inside the secret world of girls’ friendships, breaking down the power structures that have shaped girls’ lives for so long.

After spending more than a decade listening to thousands of girls talk about the powerful role cliques play in shaping what they wear and say, how they respond to boys, and how they feel about themselves, she dissects each role in the clique: Queen Bees, Wannabes, Messengers, Bankers, Targets, Torn Bystanders, and more. She discusses girls’ power plays, from birthday invitations to cafeteria seating arrangements and illicit parties. She takes readers into “Girl World” to analyze teasing, gossip, and reputations; beauty and fashion; alcohol and drugs; boys and sex; and more, and how cliques play a role in every situation.

It’s one of my most recommended parenting books, and for good reason. Queen Bees and Wannabees is a girl world encyclopedia.

15. Girls and Sex by Peggy Orenstein

While the media has focused—often to sensational effect—on the rise of casual sex and the prevalence of rape on campus, in Girls and Sex Peggy Orenstein brings much more to the table. She examines the ways in which porn and all its sexual myths have seeped into young people’s lives; what it means to be the “the perfect slut” and why many girls scorn virginity; and the complicated terrain of hookup culture and the unfortunate realities surrounding assault. In Orenstein’s hands these issues are never reduced to simplistic “truths;” rather, her powerful reporting opens up a dialogue on a potent, often silent, subtext of American life today—giving readers comprehensive and in-depth information with which to understand, and navigate, this complicated new world.

The candid truths found in Girls and Sex have been instrumental in both my work with girls and my understanding of my own identity and upbringing. If you’re parenting or working with girls in 2019, this parenting book should be at the top of your list. 

16. Untangled: Guiding Teenage Girls Through the Seven Transitions into Adulthood by Lisa Damour

In Untangled: Guiding Teenage Girls Through the Seven Transitions into Adulthood, Dr. Lisa Damour provides an excellent framework for understanding girls by revealing the seven distinct developmental transitions that turn girls into grown-ups, including Parting with Childhood, Contending with Adult Authority, Entering the Romantic World, and Caring for Herself. This book is required reading for parents and teachers of girls!

17. Cinderella Ate My Daughter by Peggy Orenstein

Confession time: I’m raising a princess-aholic. No matter how many bright, feminist manifestos I strategically place in my daughter’s line of vision, #princesslife continues to reign supreme.

Again from Peggy Orenstein, Cinderella Ate My Daughter pulls no punches in its dissection of the effects of girlie-girl culture, from premature sexualization to rising rates of narcissism and depression. Orenstein offers a radical, timely wake-up call for parents, revealing the dark side of a pretty and pink culture confronting girls at every turn as they grow into adults.