73 Books Like When Generations Collide

People always ask me what one does at what stage of a child’s development. I always send them to Madeline Levine’s book to understand what their children are experiencing and what they’re capable of at different stages.

She’s candid about how living lives of affluence can negatively impact our children and what we can do to connect, love, and invest in their growth.

I think this is the most important book that one could read about raising kids amid wealth and privilege.

Edwards-Pitt conducted her research based on the experiences of inheritors who have found their paths to personal fulfillment, and it’s very compelling to hear—in their own voices—what they believe led to their successes.

Many years ago, Kristin helped me to name that next gen can be “paralyzed by predecessor, privilege, and possibilities.” First-world problems that most people don’t get to experience. 

However, if you are the child of a successful entrepreneur or have inherited wealth and philanthropic interests to allocate, there can be real challenges with finding your purpose.

She’s now dedicated a whole book to finding your way through growing up with wealth to find a life full of meaning alongside the ability to make an impact.

I found this to be one of the most readable books.

In A Wealth of Possibilities, Ellen shares lessons learned and anecdotes from her twenty-five years of experience advising more than one hundred wealthy families.

While many professionals in the field use lingo that only they can decode, Ellen gives practical advice, commonsense approaches, and helps those of us navigating this complex terrain—meaningful solutions to the challenges confronting this particular group of families.

I highly recommend this book.

I thoroughly enjoyed Jeff Gordinier’s book because I found myself engaged in worlds of reflection and revelation. I have long battled with the disconnect and discomfort between my achievements and self-promotion. I struggle mightily with an innate desire to contribute meaningfully and with powerful anxiety that pulls me back into the shadows of reclusiveness and isolation.

Leadership often requires daring to step into the light, to share one’s voice, and to embrace the potential of vulnerability. It’s easy for me to become jaded and to succumb to despair in a world where I feel increasingly less prepared to tackle. Gordinier offers reflections of hope and compassion in this digital age. I find glimpses of light in small acts of kindness, where empathy shines brightest amid growing chaos. I want to dare not just dream of a better world but take those initial courageous steps toward making Gen X “teen spirit”… show more.

Wells’ novel takes readers to the heart of the pain that an adult daughter experiences at the hands of a troubled mother.

It explores how the pain and trauma of being a woman in a culture that doesn’t value women equally are passed down through generations and how each generation picks it up and carries it, in similar but different ways.

This “wound” shows up in the relationships of mothers who grew up in the 1950s and 60s and their daughters who grew up in the 1970s and 80s. The mothers want so much for their daughters to have more freedom than they themselves did, but instead find themselves experiencing fear, bitterness, and unexpected jealousy.

Inspired by the works of Thomas Wolfe, Conroy’s autobiographical novel begins after his high school years, with flashbacks to earlier days as it leads toward the end of each of his parent’s lives.

Once a brutal alcoholic, his ex-military father remains verbally abusive but allows a viable relationship with Conroy, the eldest son, while the mother fantasizes relentlessly. As adults, Conroy and his six siblings try to make sense of the negative repercussions they endure from their chaotic, unstable childhood.

I appreciated Conroy’s sincerity, especially when he witnesses another one of his novels being made into a movie and realizes he is watching art in its creation. “It was so powerful in its purity and its sheer honesty that it shook me, terrified me. But it changed me. That is what art always does.”

I love this book because it gives adult daughters clarity on the generational trauma mom might be acting out with them when in conflict together. By looking at patterns of behaviors (criticizing, dismissing, avoiding), social expectations of each generation (i.e., stay home, be small, be a caregiver, be polite), and mom’s own trauma, adult daughters can look at mom with more awareness and compassion.

I loved the grandma-mother-daughter genogram exercise in this book, which maps out these patterns in such a powerful, visual way!

I don’t know of anyone else who so captures time, place, and the idiosyncratic language of the moment that we tend to shake our heads at years later but is exactly right at the time. Winslow is a magician with the nuances.

Here’s how the novel opens in Laguna Beach, California. "Is what O is thinking as she sits between Chon and Ben on a bench at Main Beach and picks out potential mates for them. "That one?" she asks, pointing at a classic BB (Basically Baywatch) strolling down the Boardwalk." "Chon shakes his head." And further down, "O was made for sunshine.' "California girl."

I live in California. I grew up here. Winslow captures the moment. Future historians should read him.

I recommend this book because it made me reflect deeply on where my financial success derailed. Since 2017, I have strongly advocated for the rapid expansion of innovative technology like Bitcoin, crypto, and artificial intelligence, through hosting podcasts and writing books. After reading this book, I was shocked that I agreed with the need for a more cautious approach. I thought about the benefits and drawbacks of rapidly advancing technology and why it makes sense to be more careful.

I believe Gen X is not just the bridge between the analog and digital worlds but also the connectors and innovators that will drive our global economy forward. I grew up not feeling special, but this book helped change my perspective. I have shared traits, such as resilience and adaptability, with my fellow Gen Xers. I now wish to use my voice to strengthen relationships in our increasingly digital age. I… show more.