12 Things I Know Now, I Wish I Knew Then

When we were in our twenties, my best friend and I pledged to take a Greek island cruise together when we turned 40. We fantasized about lounging on exotic beaches, drinking full-bodied wines and sampling rich foods without a care in the world. But while we were waiting for that milestone birthday to roll around, marriages, children and careers made it harder to find the time and the money for an international trip. My 40-year-old self would warn me not to wait too long for the things I want and tell 20-year-old me that when planning my travel itinerary, not even the sky should be the limit.

I spent most of my twenties complaining about my thighs, hips, and midsection. Little did I know, I would never look better. So rather than hiding in dark, baggy clothes that did nothing for my figure, my 40-year-old self would definitely tell the me of my twenties not to pass up an opportunity to wear a short skirt, a crop top, or a bikini. And when it comes to color, the brighter, the better.

Maybe it was all of the Disney princess movies we watched as kids or the incessant ticking of our biological clocks as we got older, but my fortysomething friends and I were definitely out here trying to lock it down something serious in our twenties. Some of us were successful, and some of us weren’t. But we all agree that if we had to do it all over again, we wouldn’t be in such a rush for anyone to put a ring on it. These days, we realize that we had a lot to learn about ourselves as young women before we could be good partners to anyone else or know if we even wanted to be anyone’s partner at all. And at least in my case, good things come to those who wait.

Since I feel like this is a safe space, I’ll admit that I spent a lot of time in my twenties trying to be as close to perfect as possible. I held my tongue when I should have raised my voice. And more often than not, I opted to stay in peaceful waters rather than rock the boat. So I couldn’t agree more with my friend who said she’d tell her twentysomething self to be herself rather than someone she thought others wanted her to be. Because as the saying goes, “Those who mind don’t matter and those who matter don’t mind.”

We all agreed that if we had to do it all over again, we’d practice good financial habits. That means everything from treading lightly with credit cards to investing for the future. Now that we can (hopefully) see retirement on the other side of the rainbow, we’re looking forward to living like The Golden Girls. 

One of my girls told me that fear of failure often got in the way of things she wanted to do. And she admitted that she wished she given her younger self more freedom to make mistakes. Whether it was going after a new job or moving to a new city, she’d encourage herself not to be afraid to try new things.

The fact that I could call on my girls at a moment’s notice for their help with this piece is a testament to the strength of our friendship and just another reason why I rock with them. Twenty years ago, I had no idea I’d be talking about kids’ soccer games and dance recitals with the same girls who helped me get over breakups and were down to roll on every crazy road trip. But damn, I’m glad I am.

We all went through high school French or Spanish, but none of us really used the language we learned to its full potential. Whether it was studying abroad or even just taking a solo trip to immerse ourselves in a foreign culture. Now that my middle schooler is taking French classes, I’m hoping to be able to pick up where I left off. Besides, it sounds a lot cooler when you can cuss somebody out in another language.

I’m sure they won’t mind if I brag on them a bit, but my girls are doing the damn thing in their respective careers. So I was surprised when one of my most educated and successful friends said that if she had to do it all over again, she would have chosen a career that allowed her to hone her creativity over a more traditional career path. Our parents told us that after college, you find a good corporate job and work until you retire. But in her 30s and 40s, my friend has discovered a love of things like woodworking and landscape design that leave her feeling a lot more fulfilled. You know what they say, when you do what you love, it definitely doesn’t feel like work (that is, unless you’re doing what you love at 8:00 in the morning.)

Being a strong Black woman is great and all, but sometimes you gotta take your cape off and let others be there for you. Our fourtysomething selves want the twentysomething versions to know that when the going gets tough, that’s the time to call on your crew.