The best novels exploring the transitions through life

Anna Caltabiano Author Of The Seventh Miss Hatfield
By Anna Caltabiano

Who am I?

I have always been interested in people—specifically exploring what makes us human from different angles and often different disciplines. Overtime, this has taken the shape of writing novels, studying biological anthropology, psychology, and medicine, and sometimes even just people watching. My novels have explored topics such as nonsuicidal self-injury, the pains of growing up, and growing up multicultural. I am currently pursuing a PhD in Psychology.

I wrote...

The Seventh Miss Hatfield

By Anna Caltabiano,

Book cover of The Seventh Miss Hatfield

What is my book about?

11-year-old Cynthia knows she shouldn't talk to strangers. So when her mysterious neighbor Miss Hatfield asked her in for a chat, Cynthia wasn't entirely sure why she said yes. It was a decision that was to change everything. Miss Hatfield is immortal. Thanks to a drop of water from the Fountain of Youth, Cynthia is as well. Cynthia is beginning to suddenly grow up and take on the aspects of her neighbor. She's becoming the next Miss Hatfield. Cynthia must travel back in time to turn-of-the-century New York and steal a painting, a picture that might provide a clue to the whereabouts of the source of immortality. The Seventh Miss Hatfield is a story of the sudden loss of one’s childhood and the painful creation of a new adult identity.

The books I picked & why

Shepherd is reader supported. We may earn an affiliate commission when you buy through links on our website. This is how we fund this project for readers and authors (learn more).

The Unbearable Lightness of Being

By Milan Kundera,

Book cover of The Unbearable Lightness of Being

Why this book?

Most people would probably not think of The Unbearable Lightness of Being as being a coming-of-age novel. Coming-of-age novels often center around younger characters dealing with first crushes, forming an identity, finding a self, separate from family—The Unbearable Lightness of Being is none of that. Instead, I think of it as about a second “coming of age.” This “coming of age” deals with recreating an identity after you do not recognize what your life has become. I find it’s one of those books with something for everyone, though I find myself recommending it the most to college students or those feeling a little lost post-college. Love, the struggle with modernity, the meaning of life—you name it, chances are, Kundera has covered it. For this reason, this is probably my all-time most recommended book.

The Schopenhauer Cure

By Irvin D. Yalom,

Book cover of The Schopenhauer Cure

Why this book?

Dr. Irvin Yalom is a writer and clinical practitioner who is beloved by many in the field of mental health and therapy. I, like many, admire the way in which he tackles the most difficult human dilemmas through intimate stories highlighting the universality of many of these topics. It was difficult for me to pick which of Dr. Yalom’s books to recommend, as I have thoroughly enjoyed each one I’ve read. However, The Schopenhauer Cure is particularly about confronting mortality—the realization of the ephemerality of life and the limitations and acceptance of what we can achieve. Through Dr. Yalom’s adroit depictions of Philip Slate and Julius Hertzfeld, we see the blurred edges of philosophy and psychology, where some of our most basic questions may best be addressed by the melding of the two.


By Laurie Halse Anderson,

Book cover of Speak

Why this book?

High school tends to be a difficult time for a lot of people. There are growing pains, hormones, and heightened emotions, all while trying to establish who you are independently and in relation to other people. For some, this time is made even more difficult when the unimaginable happens. Speak explores healing in the aftermath of violence and rebuilding a part of oneself.

CW: Sexual assault

Wide Sargasso Sea

By Jean Rhys,

Book cover of Wide Sargasso Sea

Why this book?

Many people are familiar with Charlotte Bronte’s Jane Eyre and her mad woman in the attic. Wide Sargasso Sea, written as a prequel to Jane Eyre, turns this on its head and lends another perspective to the Victorian mad woman trope. Throughout this novel, I couldn’t help but ask myself what constitutes madness. How much of what we think of mental illness is societally determined? As we grow up and conform to society's expectations, are those that refuse to completely conform considered “mad?”

The Hours

By Michael Cunningham,

Book cover of The Hours

Why this book?

The Hours tells a story of three women throughout time and their connection to Mrs. Dalloway as they deal with death, sickness, and growing old. In this snapshot of these three women’s lives, we see their meditations on their various life transitions, including their contemplations of death.

CW: suicide

5 book lists we think you will like!

Interested in terminal illnesses, romantic love, and teenagers?

5,887 authors have recommended their favorite books and what they love about them. Browse their picks for the best books about terminal illnesses, romantic love, and teenagers.

Terminal Illnesses Explore 22 books about terminal illnesses
Romantic Love Explore 414 books about romantic love
Teenagers Explore 62 books about teenagers

And, 3 books we think you will enjoy!

We think you will like The Spy Who Came in from the Cold, The Gift of Therapy, and Momma and the Meaning of Life if you like this list.