100 Must-Read Books About Starting Over

My mom was 53 when she enrolled in college.  Though she’d always wanted to be a teacher, she instead got married, had kids (thanks for that, by the way!), and worked for decades in title insurance. She was well respected and made a good living. She seemed to be a pretty settled person and I don’t think anyone saw the dramatic changes coming.

The first catalyst was an article in the Tampa Tribune detailing the career of a woman in her late 70s who was retiring from a lifetime of teaching. It dawned on my mom that she not only still had time to get her degree, but she had time to go on and teach for 25 years. “I could really do this,” she thought. And then she did. She started over.

I love my mom, and I love this story. I knew I wanted to highlight books that tell similar tales of people starting over, but as I started researching books to add to the list, I had to ask myself: What exactly does it mean to “start over?”

In my mom’s case, it meant turning her back on one career to get the education she needed for another. In many of the books on this list, starting over meant moving to another country, whether by choice, because they’d been displaced, or fleeing atrocities so awful I have trouble really wrapping my brain around them. Some stories deal with divorce or breakup, others with teenagers terrified of starting a new school, some are about tackling a new hobby that ends up changing the way they define themselves or doing something they’ve always been afraid of. Some of the books on this list are memoirs, and some are fiction. Some are uplifting, some are humorous, and some are soul-crushing. Some are all of the above.

Sometimes a person gets to make the choice to start over. They get to step off the paved road they’ve been traveling on comfortably and they get to make a decision to create a new path all their own. And others are forced to start over, often in a place they don’t want to be with people they don’t want to claim.

Everyone in these stories came out the other side. Sometimes much better off, sometimes much worse for wear. Some gained life-long relationships and some lost everyone they’d ever loved. These are stories of people starting over in ways both big and small.

1. A Good American by Alex George
2. How to Be Both by Ali Smith
3. The Good House by Ann Leary
4. Ladder of Years: A Novel by Anne Tyler
5. Extra Virgin by Annie Hawes
6. Dry by Augusten Burroughs
7. Running the Books: The Adventures of an Accidental Prison Librarian by Avi Steinberg
8. An American Brat by Bapsi Sidhwa
9. Jasmine by Bharati Mukherjee
10. Openly Straight by Bill Konigsberg
11. The Year of Magical Thinking by Joan Didion
12. Cruel Beautiful World by Caroline Leavitt
13. Native Speaker by Chang-Rae Lee
14. Wild by Cheryl Strand
15. Her by Christa Parravani
16. The Underground Railroad by Colson Whitehead
17. The Book of Unknown Americans by Cristina Henríquez
18. A Piece of Cake: A Memoir by Cupcake Brown
19. Eat the Document: A Novel by Dana Spiotta
20. What is the What by Dave Eggers
21. Spanish Lessons: Beginning a New Life in Spain by Derek Lambert
22. The Beautiful Things that Heaven Bears by Dinaw Mengetsu
23. A Saloonkeeper’s Daughter by Drude Krog Janson
24. Breath, Eyes, Memory by Edwidge Danticat
25. The Chalet School in Exile by Elinor M. Brent-Dyer
26. Island Sojourn by Elizabeth Arthur
27. Eat, Pray, Love by Elizabeth Gilbert
28. Starting Over by Elizabeth Spencer
29. When I Was Puerto Rican by Esmeralda Santiago
30. The Storied Life of A.J. Fikry by Gabrielle Zevin
31. A Life in Men by Gina Frangello
32. Mona in the Promised Land by Gish Jen
33. Mistress of My Fate by Hallie Rubenhold
34. Teeth by Hannah Moskowitz
35. What I Talk About When I Talk About Running by Haruki Murakami
36. Maya’s Notebook by Isabel Allende
37. The Warmth of Other Suns: The Epic Story of America’s Great Migration by Isabel Wilkerson
38. Lost & Found by Jacqueline Sheehan
39. Lucy by Jamaica Kincaid
40. Beyond the Sky and the Earth: A Journey into Bhutan by Jamie Zeppa
41. The Exact Same Moon: Fifty Acres and a Family by Jeanne Marie Laskas
42. The Grapes of Wrath by John Steinbeck
43. Missing Mom by Joyce Carol Oates
44. How the Garcia Girls Lost Their Accent by Julia Alvarez
45. Tell Me Three Things by Julie Buxbaum
46. The Buddha in the Attic by Julie Otsuka
47. For My Next Act . . . Women Scripting Life After 50 by Karen Baar
48. The Age of Reinvention by Karine Tuil
49. The Readers of Broken Wheel Recommend by Katarina Bivald
50. The Awakening by Kate Chopin
51. The Lost Husband by Katherine Center
52. How to Party with an Infant by Kaui Hart Hemmings
53. Beautiful Music for Ugly Children by Kirstin Cronn-Mills
54. King of the Screwups by KL Going
55. When I Lived in Modern Times by Linda Grant
56. Anne of Green Gables by LM Montgomery
57. Lady Oracle by Margaret Atwood
58. The Heart Goes Last by Margaret Atwood
59. And I Shall Have Some Peace There: Trading in the Fast Lane for My Own Dirt Road by Margaret Roach
60. Rachel’s Holiday by Marian Keyes
61. Summer at Tiffany by Marjorie Hart
62. A Thousand Days in Venice: An Unexpected Romance by Marlena de Blasi
63. Lit by Mary Karr
64. Dear Mr. You by Mary-Louise Parker
65. How I Live Now by Meg Rosoff
66. Belzhar by Meg Wolitzer
67. Blame by Michelle Huneven
68. The First Bad Man by Miranda July
69. Sideways on a Scooter: Life and Love in India by Miranda Kennedy
70. How to Get Filthy Rich in Rising Asia by Mohsin Hamid
71. America the Beautiful by Moon Unit Zappa
72. Under the Wide and Starry Sky by Nancy Horan
73. Nicotine by Nell Zink
74. Before the Fall by Noah Hawley
75. Giants in the Earth by Ole Edvart Rolvaag
76. Esperanza Rising by Pam Munoz Ryan
77. Fallen Land by Patrick Flanery
78. The Alchemist by Paulo Coelho
79. French By Heart: An American Family’s Adventures in La Belle France by Rebecca S. Ramsey
80. Dear Fang, With Love by Rufi Thorpe
81. On the Outside Looking Indian by Rupnder Gill
82. Rule of the Bone by Russell Banks
83. Between Shades of Grey by Ruta Sepetys
84. The Mouse-Proof Kitchen by Saira Shah
85. Second Draft of My Life by Sara Lewis
86. The Truth About Forever by Sarah Dessen
87. The Opposite of Me by Sarah Pekkanen
88. The Arrival by Shaun Tan
89. Queen of the Mosquitoes by Snakes
90. The Ice Cream Queen of Orchard Street by Susan Jane Gilman
91. An African in Greenland by Tété-Michel Kpomassie
92. How to Sleep Alone in a King-Size Bed by Theo Pauline Nestor
93. The Leftovers by Tom Perrotta
94. On Mexican Time: A New Life In San Miguel by Tony Cohan
95. A Bend in the River by V.S. Naipaul
96. When Wanderers Cease to Roam: A Traveler’s Journal of Staying Put by Vivian Swift
97. Homegoing by Yaa Gyasi
98. Across Many Mountains: A Tibetan Family’s Epic Journey from Oppression to Freedom by Yangzom Brauen
99. Panic in a Suitcase by Yelena Akhtiorskaya
100. Their Eyes Were Watching God by Zora Neale Hurston