All Woman
  • Home
  • Relationships
  • Features
  • Fashion & Beauty
  • Health & Fitness
  • Your Rights
  • Parenting
  • Advice
    • Home
    • Relationships
    • Features
    • Fashion & Beauty
    • Health & Fitness
    • Your Rights
    • Parenting
    • Advice
6 major regrets a woman usually has after age 40
All Woman, Features, Relationships
 on May 19, 2025

6 major regrets a woman usually has after age 40

Marie BERBICK-BAILEY 

SOMETHING shifts in a woman when she crosses 40. It’s not just the hormones or the physical changes—it’s the reflection in the mirror that suddenly holds questions we didn’t ask in our 20s or 30s.

As a mother of three boys, who wanted to have a girl child by age 40 — a dream that didn’t happen, I can tell you this: hitting 40 is not a crisis — it’s a clarifier. Things become clearer. What matters and what never did, becomes painfully obvious.

In my work coaching and counselling women I’ve found that most of us have a few common regrets that show up in our 40s. The good news? It’s still possible to course-correct, and create the life you really want.

Here are six of the most common regrets women face after 40, and how you can avoid or recover from them.

 

1) Not loving herself enough sooner

So many of us spent our younger years putting everyone else first — our children, partners, jobs, even church responsibilities — until we ran dry.

By the time we hit 40, we realise we’ve poured out for everyone else but haven’t poured into ourselves. We regret not setting boundaries, not choosing ourselves, not saying no when we should have, not travelling to see the world, not buying some things we wanted for ourselves.

My sis, it’s not selfish to prioritise yourself — it’s survival. You can’t pour from an empty cup.

 

2) Staying too long in the wrong relationship

Whether it was a marriage or a situationship, many women regret the years they spent trying to fix what was never meant to last. We tell ourselves, “I stayed for the kids”, or “I didn’t want to start over”.

But deep down, we mourn the version of ourselves we lost while begging someone to love us right. But I also know the power of leaving when staying is killing your peace. You deserve joy — not just endurance.

I’ve talked to so many women who are dealing with this deep regret. Don’t become a statistic.

 

3) Not pursuing her dreams

By 40, many women realise that while they were busy building others, their dreams sat on the back burner. That business idea, that book, that degree —they kept putting it off for “someday”.

Now “someday” feels closer than ever, and the regret of not starting earlier can hit hard. But here’s the truth: It’s never too late. Your purpose doesn’t expire with age — it gets sharper. Go sign up for that course. Check your bucket list. Live.

 

4) Caring too much about what people thought

We wasted so much energy trying to look perfect, act right, and please people who still found something to criticise. The regret? Not living authentically.

By 40, we begin to ask, “Why did I give them so much power?” The older you get, the more you realise that peace is better than popularity.

Start choosing yourself, even if it means disappointing others. You were never meant to shrink to fit into their expectations.

 

5) Neglecting her health

Let’s be real: fried chicken tastes good, but high blood pressure doesn’t. Many women regret ignoring their physical and mental health in their younger years. Skipping check-ups, not exercising, stress eating, and putting self-care last now comes with consequences.

Your 40s are a wake-up call to prioritise your wellness — not just for looks, but for life. Don’t wait until the diagnosis to start caring about your health. Prevention is better than cure.

 

6) Not releasing toxic friendships sooner

Some friendships needed to end ten years ago. But we held on out of loyalty, history, or guilt. Now, we regret not protecting our peace.

By 40, your circle should bring you strength, not stress. If someone constantly drains you, disrespects you, or competes with you — they’re not your friend.

Letting go doesn’t make you mean. It makes you mature.

 

If you’re over 40 and feeling any of these regrets, don’t stay stuck. Use them as lessons, not life sentences. You still have time to love yourself deeply, pursue your calling boldly, and protect your peace fiercely. Your next chapter can be your best one — but only if you decide that regret is not where your story ends.

Marie Berbick Bailey

Marie Berbick-Bailey is a certified master life coach, resilience coach, ordained minister, author, motivational speaker, wife, mother and big sister dedicated to empowering women to heal, thrive, and walk in purpose. Connect with her at www.marieberbick.com, www.marieberbickcoach.com . E-mail marieberbick@gmail.com.

 

{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
0 Comments · Make a comment

HOUSE RULES

  1. We welcome reader comments on the top stories of the day. Some comments may be republished on the website or in the newspaper; email addresses will not be published.
  2. Please understand that comments are moderated and it is not always possible to publish all that have been submitted. We will, however, try to publish comments that are representative of all received.
  3. We ask that comments are civil and free of libellous or hateful material. Also please stick to the topic under discussion.
  4. Please do not write in block capitals since this makes your comment hard to read.
  5. Please don't use the comments to advertise. However, our advertising department can be more than accommodating if emailed: advertising@jamaicaobserver.com.
  6. If readers wish to report offensive comments, suggest a correction or share a story then please email: community@jamaicaobserver.com.
  7. Lastly, read our Terms and Conditions and Privacy Policy
ALSO ON ALL WOMAN
FATHERHOOD: Honouring the unseen backbone of the family
All Woman, Features
FATHERHOOD: Honouring the unseen backbone of the family
JEROME MORGAN 
June 9, 2025
FATHER’S Day comes every year, neatly marked on the calendar, sandwiched between summer plans and graduation parties. The cards flood store shelves, f...
{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Aunt wants guardianship over orphaned kin
All Woman, Your Rights
Aunt wants guardianship over orphaned kin
Margarette MACAULAY 
June 9, 2025
Dear Mrs Macaulay, I’m seeking advice regarding obtaining legal guardianship for my deceased sister’s child. There is no father in the picture or on t...
{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
The thrill has gone
Advice, All Woman
The thrill has gone
Christopher Brodber 
June 9, 2025
Counsellor, I’m reaching out because I’m struggling with something I can’t deal with on my own. My partner and I have been together for five years, an...
{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Styled with intention: The bold vision of Kwela Cole
All Woman, Features
Styled with intention: The bold vision of Kwela Cole
June 2, 2025
THE world of fashion is constantly evolving, and 24-year-old stylist and creative director Kwela Cole is not merely curating daring looks — she is des...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Hot bots and smart toys: Women reboot romance with AI and roses
All Woman, Relationships
Hot bots and smart toys: Women reboot romance with AI and roses
Lichelle Palmer 
June 2, 2025
“SO babe, what’s on your mind? You can talk to me, no filter necessary.” Thirty-four-year-old musician Soyini W says that was the start of her long ta...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
6 strategies to rebrand yourself after divorce
All Woman, Relationships
6 strategies to rebrand yourself after divorce
Marie BERBICKBAILEY 
June 2, 2025
DIVORCE is not the end of your story — it’s the closing of one chapter and the beginning of another. I know this not just as a coach, but as a woman w...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
My wife is leaving me
Advice, All Woman
My wife is leaving me
Christopher Brodber 
June 2, 2025
Counsellor, I think my wife is planning to leave, and is taking steps to protect herself before she does this. Nothing has happened in the marriage, t...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
From bump to breakdown
All Woman, Health, News
From bump to breakdown
Breaking the silence around motherhood and mental health
June 1, 2025
“STOP the foolishness, you just tired.” It’s a phrase that too many Jamaican mothers hear when they try to speak up about the emotional toll of mother...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
❮ ❯
Scroll
Polls
FATHERHOOD: Honouring the unseen backbone of the family
All Woman, ...
FATHERHOOD: Honouring the unseen backbone of the family
JEROME MORGAN 
June 9, 2025
FATHER’S Day comes every year, neatly marked on the calendar, sandwiched between summer plans and graduation parties. The cards flood store shelves, f...
{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Aunt wants guardianship over orphaned kin
All Woman, ...
Aunt wants guardianship over orphaned kin
Margarette MACAULAY 
June 9, 2025
Dear Mrs Macaulay, I’m seeking advice regarding obtaining legal guardianship for my deceased sister’s child. There is no father in the picture or on t...
{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
The thrill has gone
Advice, ...
The thrill has gone
Christopher Brodber 
June 9, 2025
Counsellor, I’m reaching out because I’m struggling with something I can’t deal with on my own. My partner and I have been together for five years, an...
{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Styled with intention: The bold vision of Kwela Cole
All Woman, ...
Styled with intention: The bold vision of Kwela Cole
June 2, 2025
THE world of fashion is constantly evolving, and 24-year-old stylist and creative director Kwela Cole is not merely curating daring looks — she is des...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Hot bots and smart toys: Women reboot romance with AI and roses
All Woman, ...
Hot bots and smart toys: Women reboot romance with AI and roses
Lichelle Palmer 
June 2, 2025
“SO babe, what’s on your mind? You can talk to me, no filter necessary.” Thirty-four-year-old musician Soyini W says that was the start of her long ta...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Archives
Polls
Recent Posts
FATHERHOOD: Honouring the unseen backbone of the family
All Woman, ...
FATHERHOOD: Honouring the unseen backbone of the family
JEROME MORGAN 
June 9, 2025
FATHER’S Day comes every year, neatly marked on the calendar, sandwiched between summer plans and graduation parties. The cards flood store shelves, f...
{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Aunt wants guardianship over orphaned kin
All Woman, ...
Aunt wants guardianship over orphaned kin
Margarette MACAULAY 
June 9, 2025
Dear Mrs Macaulay, I’m seeking advice regarding obtaining legal guardianship for my deceased sister’s child. There is no father in the picture or on t...
{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
The thrill has gone
Advice, ...
The thrill has gone
Christopher Brodber 
June 9, 2025
Counsellor, I’m reaching out because I’m struggling with something I can’t deal with on my own. My partner and I have been together for five years, an...
{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Styled with intention: The bold vision of Kwela Cole
All Woman, ...
Styled with intention: The bold vision of Kwela Cole
June 2, 2025
THE world of fashion is constantly evolving, and 24-year-old stylist and creative director Kwela Cole is not merely curating daring looks — she is des...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Hot bots and smart toys: Women reboot romance with AI and roses
All Woman, ...
Hot bots and smart toys: Women reboot romance with AI and roses
Lichelle Palmer 
June 2, 2025
“SO babe, what’s on your mind? You can talk to me, no filter necessary.” Thirty-four-year-old musician Soyini W says that was the start of her long ta...
{"xml":"xml"}{"allwoman":"All Woman", "jamaica-observer":"Jamaica Observer"}
Archives
All Woman
Jamaica Health, Beauty, Weddings &` Motherhood Stories for the Jamaican Woman.
Sections
  • Relationships
  • Features
  • Fashion
  • Health & Fitness
  • Your Rights
  • Parenting
  • Advice
  • Relationships
  • Features
  • Fashion
  • Health & Fitness
  • Your Rights
  • Parenting
  • Advice
Jamaica Observer, © All Rights Reserved