Six Things 40-Something Women Wish They Did More of In Their 20s

Q: What do you wish you did more of in your 20s now that you are in your 40s? – 20-something

A: I get asked this question a lot. By far most women wish they had traveled more …and saved more. May seem a juxtaposition as travel means dipping into your savings. But as one woman said, “Invest in a closetful of experiences.” The bags and purses and clothes are long forgotten but the memories of travel last a lifetime. Learning to travel on your own and seeing how others live helps you gain perspective on yourself and make better decisions. Plus, when you’re young you can deal with traveling on less money.  There are a few other things…for some, dating or having more fun rather than taking life so seriously…but the universal theme is doing things that help you get to know yourself a little better.

1. Traveled More.

I wished that I had spent more time traveling in my 20’s. I don’t mean going to Vegas for a weekend with the girls, but more enriching vacations where you are exposed to different people, different cultures and different experiences rather than working incessantly and waiting for Mr. right to sweep me off my feet.” – 40-something, NY, NY

I wish I traveled more. Even if you don’t have money, it doesn’t have to be a huge ship. It doesn’t have to be Italy. Just this weekend go somewhere, sleep in a bed that’s not your bed, that’s not in this town and see what it feels like. What do you feel like from that experience? Even if it’s still a money issue, give yourself a trade-off. Try to figure out “How much money would I spend if I were in town this weekend?” Take that money and just go somewhere else then and use that as your budget.” –– 40-something, Cleveland, OH

2. Spent more time alone…near or afar.

“I wish I’d spent more time by myself. Don’t be afraid of that. There was a sense that if you weren’t out you were missing out on something. If I was home in the evening by myself, I was an outcast. I was socially ill- adjusted. So I should  find something to do. Call a friend and go out or always needing to schedule activities with people. I would rather have dropped to the floor than go to see a movie by myself or go to a play by myself or go out to eat. I think a lot of people still in their forties have some trouble living on their own.” – 40-something, Los Angeles

“I wish I’d done more things by myself.  I was adventurous in my twenties.  I traveled to far flung places– and went out a lot.  I was always up for a party.  But I didn’t do enough of it on my own.  I always had an entourage.  I think you experience more when you put yourself out there.” – 40-something, NY

3. Saved more. Even if it’s a dollar a day. Do it.

4. Explored more career options.

“Instead of building  a single – focused career, I wish I had tried different industries and skills to assess what I really was good at and what I really wanted to do.” – 40-something, Washington, DC

5. Had more conversations.

“I really do think seeing other cultures has shaped me and educated me beyond anything I’ve ever read in a book at school. The perspectives of people who were different from me, whether it be people from another country or people near my business in the inner city, gave me conversations that aren’t conversations you would ever have if you never left your own neighborhood. Someone once told me, ‘The more people that touch your life, the better your life will be.’ I swear I believe that.  It’s a good thing to be receptive to interacting with people. I think that is something that would be valuable to cultivate in your twenties. I wish I had done more of that.  You obviously want to be cautious when caution is needed and required. But any opportunity that you get to meet somebody and connect can be worthwhile. You know that in 5 minutes. Then you say “Hey nice talking to you.” – 40-something, Cleveland, OH

“Every opportunity is an opportunity. Talk to different people about what they do no matter what the setting. At work or at play. You never know what you will learn or who they will know. You may find out about a career you never even knew existed or you just may find a job.” – 40-something, Rochester, NY

6. Dated more…and different types of men.

“That’s what I wish I had done more. Date around more, get to know different men, different personalities.  Even though I got married later, I dated one man for a long time and I didn’t really get to know myself. I think that’s why my marriage failed because in my twenties, I didn’t explore other men as far as just dating to get to know myself and different types of men and relationships. I had such limited experience.  I would have learned what I like, what I don’t like, or if I’m giving too much emotionally to a relationship which I did in my twenties.” – 40-something, San Francisco, CA

I wish I had dated a bit more frankly.  I was in my first relationship from 17 to 24 years.   It took me a long time to accept that didn’t want to get married straight away and have kids and by that time my 20s were almost half over. Coming from a very traditional background I just thought that was what you did.”– 40-something, New York

The distinction is that these women wish they had dated more for fun rather than to find Mr. Right…at least until their later 20s. As for sex, some women wish they had more, some women wish they had less. And many are happy with the way they did it. For those that wish they had more or had more, they valued that when they were ready to settle down emotionally they knew what they liked physically. For those who wish they had less, they realized they needed more emotional maturity …that they weren’t able to separate the two.

It’s an interesting question and one that we’ll continue to ask:)

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