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40 Women Over 40 Reveal What They Wish They'd Known At 20

Shoulda, woulda, coulda.

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Graphic of different women over 40
Adriana Bellet
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While I’m not one to focus on “shoulda, coulda, woulda” as a life philosophy, I do look back at certain moments and wished I’d chosen differently. For example, I took 10 years off from freelance writing to raise and homeschool my two boys. While I would do it all over again in a heartbeat, I do wish that, during that time, I’d continued to write, stay abreast of technology and keep in touch with my professional network. Rebooting a writing career at 50 was one of the toughest things I’ve ever done.

The Girlfriend decided to ask 40 women over age 40 what they’d do differently, knowing what they know now. Here’s what they had to say:

  1. Leslie Blanchard (55, author, Oklahoma): My husband of 33 years and father to our five children was killed eight months ago in a tragic accident. If I could hit the rewind button, I’d cherish every single minute with him. I would've let “the little things” go so much quicker and just loved what we had together. It was one of a kind.
  2. Fran Shively (48, executive assistant, New Jersey): I would have read more books — lots of all different kinds. I’d have done this for myself, but also, if I was an avid reader when I was younger, my son would probably also have developed a love of reading.
  3. Lisa Leshaw (50-plus, mental health professional and writer, New York): I wish I'd taken a gap year to explore the world prior to college and marriage.
  4. Billie Ruth Lomonaco (40-plus, childcare worker, Florida): I would have stayed in college, found a career that brought me joy, and not married just to piss off my mother. I would have waited for the right man.
  5. Jen Cullins (53, travel support rep, Pennsylvania): Don't waste your time and life working in a job or industry that is just a paycheck — think bigger!
  6. Jennifer Reece (43, office manager, Colorado): Travel to experience different places. I wish I had figured out how to do more family trips (nothing extravagant) to show my kids how to experience the world without needing tons of money.
  7. Cindy Neuhaus (45, medical coder, Kentucky): Live on my own. I went straight from my parents’ house to an apartment with my now-husband. I never really got the chance to go out and explore things on my own.
  8. Amy Hartl Sherman (63, retired flight attendant and stay-at-home mom, Illinois): I wish I had recognized I was clinically depressed earlier and sought help sooner. That was when I was home with young kids.
  9. Nicole Cain Cutrell (47, stay-at-home mom, Florida): I wish I had developed good eating and exercise habits. It’s such a hard thing to do when you’re older.
  10. Jennifer Heinly (58, PR consultant and adjunct professor, California): I would have “lived in the moment” more and not stressed over the small stuff. Life is too short!
  11. Anne Bardsley (45-plus, author, Florida): I wish I knew I had power. I didn’t find out until I was 45. My husband told me women have all the power ... whaattt???
  12. Mary Craig (56, church sacrament coordinator, Connecticut): I regret waiting to get married and having kids so late.
  13. Deborah Goldstein (53, trade show marketer, Kansas): I wish I had continued taking more schooling, especially in technology.
  14. Leslie Stolasz (52, federal government attorney, Maryland): Being successful in life has nothing to do with how much money you make or how “high” your position is, but rather your ability to give unconditional love and bring happiness to others.
  15. Kathryn Streeter (49, writer, Washington, D.C.): I regret not having the wisdom and foresight to invest in a better stroller. Pushing two kids around the city in a subpar stroller left me physically exhausted.
  16. Shirley Kaminski (60-plus, retired, Florida): I’d be more assertive and not let people take advantage of my kindness. Plus, I’d make more time for myself.
  17. Lisa Conway (54, salon owner, Pennsylvania): I wish I hadn't jumped into long relationships at a young age and enjoyed the freedom of my youth more.
  18. Alexandria McHale (53, NICU RN, Texas): What I know now is that we are all unique and should enjoy living life our own way. Stress less and enjoy more!
  19. Linda Wiseman (53, chief marketing officer, Connecticut): I wish I had maintained fitness after competitive sports. Stress reduction is key with career and family pursuits. Comebacks are hard-earned, but essential for self-care.
  20. Kelly Steiner (54, relationship manager, Arizona): I would have not sweat the small stuff. What I thought was big, wasn’t.
  21. Karen Dellinger (62, business owner, New Jersey): I wish I hadn’t started my own business 29 years ago. I never realized that when you own a business, you never completely have a day off. The responsibilities and the stress are always there.
  22. Sue Pinky Benson (40-plus, Realtor, Florida): I would have stopped worrying so much about what others thought and embraced who I was earlier. I would tell myself to own my story. Do you!
  23. Betsy Hornick (53, writer/editor, Illinois): I wish I had worked less and made more memories with my three kids.
  24. Kim Whitaker (54, paralegal, Virginia): I wouldn’t sweat the small stuff. I would take time to enjoy every second of life and not worry about what I can’t control.
  25. Cheryl Kaufman-Bennett (53, national advertising manager, Massachusetts): I wouldn’t change anything — trials, tribulations, struggles all make me the person I am, and this evolving never ends.
  26. Adrienne D. (40-plus, vegan short-order chef, Ohio): I would not have settled for the meds I was taking to treat my depression. They only partially worked, and I didn’t know it! I could have had a much better quality of life.
  27. Pattie Delevan (53, certified holistic health coach, Pennsylvania): I wish I hadn't worried so much about what other people think and just followed my heart.
  28. Tracey Noonan (56, CEO and cofounder of Wicked Good Cupcakes, South Carolina): I wish I had learned early on that I didn’t need to be such a control freak. Other people are as competent as me (if not more so!). Allowing someone to help when I needed it would have made my life so much easier.
  29. Angela Taylor (47, technical writer, Connecticut): Confidence in myself, trust in myself, my judgment, my gut. I was a smart, independent, brave girl; I just didn't know it.
  30. Mary Ellen Lemieux (56, therapist, California): I would have married later — I was 25; gone back to grad school sooner — I was 50; but mostly, I would have ignored all the parenting advice about how to get an inquisitive, happy boy with ADHD to sit still and “behave.” Instead, I should have homeschooled him and let him be him.
  31. Kim Reall (54, partnership and certification manager, Rhode Island): I wish I kept in better touch with my friends from my home state and took time to visit them more often. I also wish I had gone for my graduate degree while I was home raising my young children instead of waiting until my late 40s.
  32. Lourdes Pelaez-Kingery (46, stay-at-home mom, Texas): I wish I could have gone for a medical degree. After being a stay-at-home mom for more than 20 years, I went back to school and got my Certified Nurse Assistant certification. I’m hoping to go back to school next year to pursue a nursing degree.
  33. Tina Ley (49, senior category manager, Maryland): I would have pursued a career that was more people and less business. Teaching, social work, foster care are areas I wish I had gone into.
  34. Catherine Donohue (56, early intervention special educator, Pennsylvania): My biggest regret is not finishing my master’s degree.
  35. Mary Ellen Mitchell (54, president of a prescription benefit management company, Ohio): I would have listened to advice from my mentors not as criticism but as an opportunity to learn from others’ experience and mistakes.
  36. Theresa Knapp (51, administrative assistant, Massachusetts): I wish I had gotten my BA and MA right away and NOT gotten the AA and worked. Once life gets rolling, it's tough to get it done in a timely manner after having kids.
  37. Susan Howard (56, stay-at-home mom, Ohio): I’m an attorney and gave up my career. I can honestly say that I wouldn’t have done anything differently. I had one shot at raising three humans and thought that infinitely more important than any career.
  38. Trisha Ventker (51, publisher, Colorado): I wish I would’ve cared more for my health in the past and gotten more sleep, ate better, and stayed closer to positive people.
  39. Laura Coffey (48, senior writer/editor for and book author, Washington): I wish I had made time to exercise consistently (instead of in fits and starts from time to time)!
  40. Julie Burton (51, founder and owner of ModernWell — a cooperative workspace and wellness center for women, Minnesota): I would be kinder and more accepting of myself and others. I would lead my life with more passion and less fear.

Lisa Beach is a freelance journalist and copywriter. Her work has been published in the New York Times, Good Housekeeping, Parents, Eating Well, USA Today Best Years, and dozens more. Check out her writer’s website at