I’m reorganizing my bookshelf at 61, and I realize these ten books are more worn than my favorite jeans. Coffee stains, tear marks, angry underlining, and notes in the margins that say things like “THIS!” and “Call therapist immediately.”
These aren’t just books I read. These are books that grabbed me by the shoulders, shook me awake, and said, “You’re not crazy, you’re not alone, and you’re not too old to change everything.” They found me at exactly the right moments, usually the worst moments, and became my guides through midlife chaos.
If you’re over 50 and feeling lost, stuck, or just tired of self-help books written by 30-year-olds who think wrinkles are a tragedy, these books are for you. Written by women who’ve actually lived, failed, survived, and thrived. No toxic positivity. No “just manifest it” BS. Just real wisdom from real women who get it.
1. “Year of Yes” by Shonda Rhimes
I’ve already written a whole review of this book, but it deserves to be number one. This book made me say yes to starting Enlightenzz at 61. Yes to public speaking despite wanting to vomit. Yes to boundaries. Yes to joy.
Shonda’s an introvert who created Grey’s Anatomy and runs an empire. If she can say yes to her fears, I can say yes to mine. The book isn’t about saying yes to everything. It’s about saying yes to what scares you and what feeds you. At 50+, we need both.
Read this when: You’re stuck in “no” mode and life feels small.
2. “Untamed” by Glennon Doyle
I threw this book across the room three times. Not because it was bad, but because it was too true. Glennon writes about being a “good woman” (following all the rules) versus being a free woman (following your truth).
At 58, I read the chapter about her divorce and sobbed. Not because I wanted a divorce, but because I realized how many cages I’d built for myself. Good CFO. Good wife. Good mother. Good woman. Where was the real me in all that good?
This book gave me permission to be disappointing. To set boundaries. To stop being everyone’s emotional support animal. Building confidence after 50 started with untaming myself.
Read this when: You’re tired of being good and want to be free.
3. “The Gifts of Imperfection” by Brené Brown
Brené Brown ruined my life in the best way. This book about vulnerability and shame hit me like a truck. I’d spent 50+ years perfecting my armor, and she’s telling me to take it off? In this economy?
But she was right. The armor was killing me. Perfectionism was exhaustion in disguise. The chapter on “letting go of what people think” should be required reading for every woman over 50. We’ve spent decades managing everyone’s opinions. It’s exhausting and pointless.
Read this when: You’re exhausted from trying to be perfect.
4. “Women Rowing North” by Mary Pipher
Finally, a book about aging written by someone who’s actually aging! Mary Pipher is in her 70s and writes about navigating later life with honesty and grace. No “60 is the new 40” nonsense. 60 is 60, and that’s not a tragedy.
She talks about everything: caregiving for aging parents (while you’re aging yourself), body changes, loss, purpose, joy. The chapter on resilience made me cry. The chapter on gratitude made me laugh. This book feels like having coffee with a wise friend who’s a few steps ahead on the path.
Read this when: You need someone who understands that aging is complex, not catastrophic.
5. “Big Magic” by Elizabeth Gilbert
This book about creativity found me when I thought I had no creativity left. Gilbert argues that creativity isn’t just for artists. It’s for anyone brave enough to live curiously. At 59, I thought it was too late to be creative. This book said, “Too late? You’re just getting started.”
Six months after reading this, I started Dutch pour painting. I was terrible. I kept going. Now I sell paintings. Gilbert was right: The point isn’t to be good. The point is to be creative. At 50+, we need creation, not just consumption.
Read this when: You think you’re not creative or it’s too late to start.
6. “Rising Strong” by Brené Brown
Yes, another Brené book. This one’s about getting back up after falling. At 50+, we’ve all fallen. Divorce, death, job loss, health scares, dreams that died. This book is about the reckoning, the rumble, and the revolution that happens when you choose to rise.
The section on “the story I’m telling myself” changed how I process everything. When Curtis was sick, the story I told myself was “I’m going to be a widow.” That story was killing me faster than his illness. This book taught me to question my stories, especially the scary ones.
Read this when: You’re face-down in the arena and need help getting up.
7. “When Things Fall Apart” by Pema Chödrön
A Buddhist nun writing about suffering shouldn’t be funny, but Pema has this dry humor that gets me. This book saved me during Curtis’s health crisis. When everything was falling apart, Pema said, “Good. Now you can see what’s real.”
She teaches that uncertainty is life’s only certainty. That groundlessness is actually ground. That falling apart is how we grow. It sounds like BS until you’re actually falling apart, then it’s the only thing that makes sense. My visualization practice started after reading her thoughts on meditation.
Read this when: Your life is in pieces and positive thinking feels like lying.
8. “The Second Half of Life” by Angeles Arrien
This book reframes aging as a spiritual journey, not a decline. Arrien talks about the “eight gates of initiation” in the second half of life. Sounds woo-woo, but it’s practical. The gate of “generativity” inspired me to start mentoring. The gate of “authenticity” made me stop dyeing my hair.
She argues that 50+ is when we’re supposed to become elders, not older. Elders have wisdom to share. Older people just have complaints. This book made me choose elder. Starting new things in midlife is part of becoming an elder, not trying to stay young.
Read this when: You want to age with purpose, not just panic.
9. “You Are a Badass” by Jen Sincero
Yes, the title is ridiculous. Yes, it’s a bit much. But this book’s energy is contagious. Sincero writes about money, success, and self-sabotage with humor and zero BS. The chapter on money blocks could have been written about me. My money mindset makeover started with this book.
At 57, I thought I was too old to be a badass. This book said age is irrelevant. Badassery is about deciding you deserve good things and going after them. Even with hot flashes. Especially with hot flashes.
Read this when: You need a kick in the pants and a pep talk.
10. “The Artist’s Way” by Julia Cameron
This book about creative recovery has been on my shelf for 20 years. I’ve done the 12-week program four times. Morning pages (three pages of stream-of-consciousness writing) saved my sanity more than once. Artist dates (solo adventures to feed your creativity) got me out of my rut.
Cameron argues everyone is creative. Creativity isn’t just art; it’s any original thought or action. At 50+, when society tells us we’re done creating, this book says we’re just beginning. My morning affirmations practice evolved from morning pages.
Read this when: You feel creatively dead and need resurrection.
The Books That Didn’t Make the List (But Almost Did)
- “Atomic Habits” by James Clear (great for building new routines)
- “The Body Keeps the Score” (essential for trauma healing)
- “Burnout” by the Nagoski sisters (explains why we’re so tired)
- “The Subtle Art of Not Giving a F*ck” (for when you need permission to care less)
- “Everything Happens for a Reason (And Other Lies I’ve Loved)” by Kate Bowler (for when toxic positivity makes you homicidal)
How These Books Changed Me
Before these books: Perfectionist. People-pleaser. Exhausted. Living everyone else’s life but mine.
After these books: Still imperfect. Boundaries established. Energy returning. Living my actual life.
These books didn’t fix me. They gave me permission to stop trying to be fixed. At 50+, we don’t need fixing. We need freedom. Freedom from others’ expectations. Freedom from our own harsh judgments. Freedom to be exactly who we are, wrinkles and all.
Your Reading Plan
Don’t try to read all ten at once. Start with one that speaks to where you are right now. Read it slowly. Underline things. Write in the margins. Throw it across the room if necessary. Let it change you.
Then share it. Pass it on. Tell someone else over 50 that they’re not alone. That’s what these authors did for me. That’s what I’m doing for you. Start your morning with a few pages. End your day with wisdom instead of worry.
P.S. – Curtis asked why I have three copies of “Year of Yes.” One for lending, one for reading, and one backup in case the other two disappear. He thinks I’m crazy. I think I’m prepared. Some books are too important to risk being without. These ten books? They’re not just on my shelf. They’re in my DNA now. And yes, I judge people by their bookshelves. Sorry not sorry.
