I’ll second that I wish I had made better effort to stay in touch with a couple high school/college friends. Even some far away family.
Though I like my career, I wonder/wish I might have taken a little different slant to it.
Also - this is a biggie - I wish that H and I had started saving for our kids college education earlier - right from the start - with more consistency.
I strongly believe in using any mistakes as learning experiences. This attitude makes every mistake a positive experience, so I would change no decisions in my life, everyone added some positive aspect to my life.
What @FallGirl said. I also would have changed my major in college as soon as I realized it wasn’t for me, instead of taking the path of least resistance and trying to please everybody, most of whom couldn’t have cared less. Overall, I just wish I’d trusted my gut more and done what I knew in my heart was right for me.
I never would have dated a specific person when I was 19. He brought nothing good to my life and since he was a family friend I’ve never been able to get away from him.
I would’ve made every effort possible to pursue my dream job of being a psychologist instead of ending up with a job I really dislike but need to keep for financial reasons.
Would’ve probably had another child - the first and only was not an easy baby and we got scared.
Would’ve loved not having to go back to work when my son was 11 weeks old - not really a decision, more a necessity but feel guilty about it to this day and I know I would’ve truly enjoyed my time at home with him.
I went to the “wrong” high school for me. I had been admitted to Hunter, an excellent public school in NYC for “gifted” females (since co-ed). But I was also offered a partial scholarship to a very small “convent” day school. My parents saw that as a “sign from God” as well as assumed that private is better than public, and sent me to the private school. While very good academically, that school was not the right “fit” for me socially, and I got in and out without feeling “at home.” I wish I had had the confidence and self-knowledge to advocate for the other choice, as they would probably have gone along with me if I had made a case.
Other regrets:
Not having developed and maintained better health habits decades ago – not too bad, as I never smoked, etc., but diet and exercise should have been stronger priorities.
Wish I had never allowed ANY paperwork/extra stuff clutter to accumulate – again, not so bad, but not fun to be making decluttering a significant agenda now; wish I had kept things in better control from the start. Too much “perhaps useful someday” stuff in my house.
Wish I had kept my mouth shut more at times – again, not a major problem, but being more careful to not say so much is an improvement opportunity for me.
Wow, some really good and interesting replies. I would have stopped and smelled the roses a little more. I was too goal oriented and sometimes I didn’t stop along the way just to relax and have fun. I have a hard time chilling out. I can be too intense sometimes.
I’ll echo and steal the “I should have” keep my mouth closed a few times when I was either too loud or too honest or said things that were 100% true but shouldn’t have been said out loud. That happened with co-workers not so much family members. But, even then, I can’t say I am completely remorseful. I meant what I said and I am glad someone said it although I might have should have said it in a nicer way.
I regret allowing a doctor to have my wife’s tubes tied after our second child was born. We didn’t have time to think about it as much as we should have. We have two healthy, growing, complex kids but we probably would have tried for one more. That is a regret for sure.
Given that my life is a happy one, I would not change the past for fear of mucking up the present, but I would not have gone to RPI. At the time it was 85% male, liberal arts were mostly blown off, and a dog-eat-dog academic environment was no fun at all. I hear it is better now on all counts but was a poor fit for me at the time.
I have always chosen work-life balance over career advancement. I sometimes wonder what life would be like now if I had accepted the offer to become a VP when I was 29 (I was already a Chief Engineer). Instead I stayed a 9-5 design engineer and my choices are gone.
I would have learned to dance while I was young. Learning now that I am comparatively old, slow, and inflexible seems like a waste of time.
I would have had a second child. I was only thinking about my needs and fears back then, when I should have considered the future of my only child.
Where do I begin? You know they say everything happens for a reason. Sometimes people come into our lives as a lesson and others a blessing.
I wish early on I spoke up for myself more. I had an arranged marriage that didn’t work out.
But then I wouldn’t have had an amazing daughter that I have now. I wish I had taken the time to pursue further education before settling down and having a child. I found myself young and single trying to raise a child.
Very difficult. I worked and studied and took care of a little girl by myself. I had to leave my job to take care of her and my health. Now I feel I have a lot on my plate trying to manage everything on my own. I wish I was better organized and a superwoman who was good in balancing everything. My goal now is to take better care of my health and get back to working fulltime so that I can provide a good life for myself and dd. Despite everything I found out how strong of a person I am and having gone through a lot of tough times I survived. I only look forward now and want to take good care of my health and do things to get back into my career that I stepped away from to take care of others.
I need to learn how to say no to others and take control of my own life and not be influenced by family who think they know what I should do with my life. I really need to focus on myself more and do what is good for me. I need to make myself a priority. I hope I am able to share my lessons with my dd so that she can have a happy and successful life. Despite everything she has been my strength and a true blessing.
I should have stayed at my job with the federal government . . .
ETA: On 2nd thought, I don’t really mean that. ^^ Then I couldn’t have homeschooled for the last 9.5 years, and I wouldn’t change that.
^I agree with the fear of mucking around and what would be changed if a change happened. If I had restarted my PhD after my D was born, chances are the second child I had would not have been my S.
And that would be a tragic thing for the universe, as he is a pretty wonderful young man. 
We’ve moved many times. Almost every time, we bought the “wrong” house. And we bought a couple other undeveloped properties. About 2/3 of our real estate experiences were not good. I’d change those. ( OTOH, if we lived in different houses, we would’ve had different neighbors, different experiences…)
H changed jobs during the real estate crash. He moved to another state and I stayed with the kids almost a year to try to sell the house (which took 13 mo. to sell, and we lost a lot on it). If I had to do it over, we would all have moved together, and I would not have bought that house in the first place.
A few more regrets:
I would not have quit piano lessons when I was 12.
I would have picked a different college major (biology instead of English).
I would have had fewer drinks at that New Year’s Eve party back in '82
I would have made my oldest S take that full-ride scholarship.
I would not have taken a particular job that I had a couple years ago–too stressful.
I would have decided not to procrastinate on a million and one different things.
I would have kept my mouth shut many, many times.
I would relax more/worry less about all those things that turned out just fine
I would have spoken up more with praise/compliments for others.
In general, I don’t wonder, “what if. . .?” The past can’t be changed. It’s over. Live and learn from your mistakes.
I am touched by everyone who says they wished they had more children. What a nice testament to the job of parenting. <3
I wouldn’t have let my mother bully me into graduating from college at 19. A student loan for one or two more years would have let me grow up a bit more–and not graduate into a recession. And maybe I wouldn’t have married what’s-his-name (and believe me, that’s a decision I really regret).
Edited to add: and I would have gone out to dinner less and put that money into a stock account. Ha!
I wish I would’ve never started to drink pop.
Ah well.
I wouldn’t have gotten married at 25. Not sure why I felt the rush.
I am really enjoying reading everyone’s responses.
I’ll add from an only child perspective, I’m so happy my parents chose to stop with me. Yes growing up I wanted a sibling (I have a half sibling but we barely talk… it’s complicated) but it definitely worked out for the best that I was an only.
I have a lot of things I’d go back and change! It’s hard to find the one master key that would undo some of the stuff that came later.
I made decisions based on seeking parental approval for far too long.
I should have focused more on building a life of my own, including financial self sufficiency, rather than on finding a husband.
I did, however, have a strange upbringing, and might have acted differently, had I not.