100 Must-Read Books About Starting Over

This post is sponsored by The Quarter-Life Breakthrough by Adam Smiley Poswolsky

the-quarter-life-breakthroughAfter realizing that his prestigious job with the Peace Corps was actually making him miserable, Adam “Smiley” Poswolsky was forced to tackle a crucial question: How do you find work that provides a sense of purpose, creates impact and pays the rent? Brimming with practical exercises and stories of people discovering how to work with purpose, The Quarter-Life Breakthrough offers fresh, counterintuitive and inspiring career advice for anyone stuck in a quarter (or third)-life crisis


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. A 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 and 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

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