8 Lessons From the Other Side Prolonged Singledom…



When I hear women talk dating today …the lack of mature guys, available time when you are building a career or business or simply living independent life… it makes me think some things don’t change (all that much). This could have been my friends and I talking 20 years ago. We wanted a serious career and serious fun…in whichever order but even better together. We met and socialized with the people we worked with …a lot. Perhaps not living together like some people in Silicon Valley but often sharing summer homes, apartments and almost 24/7 social / work lives.

Of course there were those that got right down to the business of getting serious about getting married but most of us were happy to focus on that later. We were kicking ass and didn’t need a “better half.” Just an amazing partner …when we were ready. For some it happened later than sooner and for some along the way they found out they didn’t need it or want it. Others are happy they waited. Some wish they knew a few things then. There are different expectations and motivations today but the pressure and worry of when and if and to date or mate is still there.

So what did we learn from all this that we can impart? A view from the other side:

1. Dreams change

 “Usually what you think you want at 20 is different than what you find you want in your 30s and 40s. Sometimes the choices you make add up to a different path than you dreamed about at 20. It’s not that your dream didn’t come true…you simply became another dream.” – 40-something, financial advisor / investor

2. Being alone does not mean lonely

“I love people. I love myself. I love the time with myself and that’s my biggest gift. I’m not one of those people who needed to get married.  I’ve dated and I’ve had fun but I just like being by myself.”  – Doctor, athlete and dog rescuer 

3. Getting married is a choice not a rite of passage

 “I know I will die a fulfilled woman. I have filled my life with people and trips and opportunities that I would never have had If I was married — not in the way I’m having them now. That doesn’t mean I will never get married but I have led the life that excites me.  – 40-something, runs own strategic marketing and events firm

4. You can change your paradigm

“Honestly, I love living alone. I do. I absolutely love it! I love my solitude. I love solace. Even in my twenties I was brazenly independent. I more recently got into a relationship and I really love him. We’ve been talking about moving in together but I’m not sure. He really likes his alone time too. So maybe we’ll just create a new paradigm. Together but apart.” – 40-something, producer, writer, designer, Los Angeles, CA

5. There are tradeoffs…but they often payoff 

“Part of me wishes I was married and had kids but I’m very happy that I have a career for myself and for all the experiences I have had. I’m into culture and seeing the world and I would want my kids to do that.  I can give those experiences back to my children one day.  If I had gotten married at 25 and never experienced any of that my children would never be able to get that from me”.  – 40-something, design firm executive/ entrepreneur (since this interview, got engaged and baby plans on the way)


“What I thought I wanted from life in my 20s and where I ended up in my 40s are completely at odds. The image of what I wanted then never aligned with the reality of what it meant and what it cost to have it. I couldn’t have imagined my current circumstances back then…but I also can’t imagine and wouldn’t want a different life than what I have today.  – 40-something, financial advisory / investor, single, childless by choice

6.  Don’t be all work and no play

“I would say that If you’re going through that phase where you’re really focused on your career, it’s so easy to get sidetracked. The years just go by. Just don’t spend a lot of time staying in relationships that you know aren’t right just to have something to do”.  – 40-something, design firm executive/ entrepreneur

7. Partner priorities change

“I never would have dated my husband in my twenties. I would not have recognized his qualities . He is Type B and I am Type A. He is into kite surfing and going to Bali. I wouldn’t have looked at him twice. I was looking for drive and ambition. I associated that with a suit. All I knew  was work. But in my 40s I was able to see that he had drive and ambition… but also an incredible sense of balance. It works. I can relax a little because I see he does have drive and he pushes himself a little more because of me. – 40-something, San Diego California, fashion, married mom

8. If you really really know you want kids….adjust your priorities

 “I wanted a career and to travel and to live in a big city. If I had really wanted kids I would have needed to make an adjustment earlier to create a path that would make it possible. It’s not fair but for women there is an expiration date on fertility. We all thought we had plenty of time. That is something 20-somethings today can learn from us. Don’t “opt out before you opt out” …but you can make adjustments. You can have children and a career but you have to give up some things. You will have a family but you can’t spend a month in Europe. You have to decide what is important. It doesn’t matter if you choose something that is different that the status quo.  Who knows maybe you will meet someone later on who has kids and be a great step mom or be a great aunt.”  – 40-something, survived and thrived a 20-something divorce, travel industry executive, recently married

Point is you …you don’t always end up where you thought you would be but it is all good. I will follow up sometime soon with lessons from the other side of getting mated in your 20s. 40-somethings…send me your stories!

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