The Most Common Midlife Regrets Among Women—And How to Turn Them Into Wisdom
Midlife is often painted as a crisis and a time for remorse and regrets —but for many women, it’s actually a calling. A call to slow down, take stock, and finally start living for you.
As a health and wellbeing coach who supports women through emotional and life emotional and life transitions, I hear these regrets often. They’re not failures—they're signposts, guiding us back to ourselves.
At 59 I have had a few resets in my life that included changing careers, downsizing, ending non-nourishing relationships and most recently, in 2020, I had a huge reset and left Europe to make a life in the Caribbean.
Nature and the climate had a lot to do with my decision. I also wanted to give myself more time for studying, artistic persuits and charity.
There were many sacrifices, but there was a yearning and calling to be my truest self, my authentic self and so for the first time in life I decided to put myself first and follow my heart’s desires.
There are many studies conducted with elders close to the end of their life questioning their regrets, and I was clear that I didn’t want to live a life of regret and remorse and so I charted a new course.
Here are the most common midlife regrets women share—and how they can become powerful catalysts for change.
1. “I Took Care of Everyone But Myself”
For decades, many women play caretaker—partner, mother, employee, daughter—leaving their own needs at the bottom of the list. This has been a personal realization which I have also had to deal with face on. Midlife brings the realization: No one is coming to save me—I have to prioritize myself.
🔁 Shift it: Start putting yourself on your own calendar. Whether it’s 10 minutes of silence or a solo trip you’ve been craving, your needs matter. Reframe self-care as non-negotiable. Create daily rituals that center you—even simple ones like walking in nature or journaling. When you choose yourself, you teach others how to treat you.
2. “I Didn’t Say No Enough”
People-pleasing and perfectionism can take root early. Many women regret saying "yes" to things they didn't want to do—jobs, favors, even relationships—out of guilt or fear.
🔁 Shift it: Saying “no” is an act of self-respect. You don't owe anyone overexertion or emotional labor that drains you. Practice saying no without over-explaining. Try, "That doesn't work for me right now" and leave it at that. The more you honor your boundaries, the stronger your sense of self becomes.
3. “I Lost Myself in the Roles I Played”
Many women reach midlife unsure of who they are outside of “mom,” “wife,” “employee,” or “caregiver.” They regret never exploring their own identity beyond what others needed from them.
🔁 Shift it: Ask, Who am I when I’m not being useful to others? Let curiosity—not guilt—guide your rediscovery. Reconnect with the passions or interests you abandoned. Rebuild your identity through play, hobbies, or new learning. You’re not starting from scratch—you’re returning to your essence.
4. “I Didn’t Follow My Dreams”
Whether it was a business idea, travel adventure, or creative project, many women regret not taking chances on their passions. Life got busy… and they got used to putting their dreams on hold.
🔁 Shift it: It’s never too late to start. Begin small. That book, course, or calling is still waiting for you. Break the dream down into doable steps. Set one tiny goal this week. Dreams don’t expire—they evolve. Midlife is actually the perfect time to create with more freedom and fewer apologies.
5. “I Stayed Too Long in a Relationship That Didn’t Nourish Me”
Fear of being alone or starting over can keep women in unfulfilling partnerships. Many realize too late that they sacrificed too much for love that didn’t love them back. This again was a painful realization for me: I waited nearly 2 decades for a family member to “see” and respect me. Reseting my expectations has meant releasing from the waiting and wasted energy!
🔁 Shift it: You don’t have to blow up your life. But you do have permission to seek joy, connection, and mutual respect—wherever that leads. Begin by reconnecting with yourself. What does healthy love feel like to you? Set emotional boundaries and speak your needs. Change begins with clarity—then courage.
6. “I Ignored My Body for Too Long”
Burnout, weight changes, hormone shifts, anxiety—our bodies speak loudly in midlife. Many women regret ignoring the signs and not treating their health like a priority.
🔁 Shift it: Your body is not betraying you—it’s beckoning you back. Rest. Move. Nourish. Listen. Schedule those checkups. Work with a holistic practitioner or wellness coach. Tune into your cycle, your cravings, your energy rhythms. Your body is a wise ally, not a burden to manage.
7. “I Let Friendships Fade”
In the hustle of life, friendships can quietly fall away. But in midlife, the lack of sisterhood feels palpable—and many women regret not making time for connection.
🔁 Shift it: Reconnect. Reach out. Join that circle. Women need women—it’s not just nice, it’s necessary. Host a potluck. Text that old friend. Join a book club or retreat. Emotional support from women boosts longevity, confidence, and joy. Your next soulmate friend might be one brave "hello" away.
8. “I Played Small to Be Accepted”
Many women dim their light to avoid judgment—fearing being “too loud,” “too opinionated,” “too ambitious.” Midlife brings clarity: shrinking helps no one.
🔁 Shift it: This is your season to expand. Show up boldly. Take up space. Your voice matters. Speak up in rooms where you once stayed quiet. Share your story—someone needs it. Confidence isn’t about being fearless—it’s about acting from your truth, even with shaky hands.
From Regret to Rebirth
Regret is not the end of the story. It’s a mirror. A wake-up call. A quiet nudge toward the life your younger self wanted—and your older self will thank you for.
So if you’re standing at that midlife crossroad, know this:
It’s not too late. You’re not too old. And you are not behind.
You are exactly where your transformation begins.
Need Support?
If you're ready to reclaim your energy, identity, or joy in midlife, I’m here to support you. Reach out for coaching, workshops, or our upcoming Midlife Reset Retreat in Negril, Jamaica designed especially for women like you.