Lessons I Learned From My 20’s


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Welcome to Format Free Friday, when I break the format of answering your questions and I dispense that which we rarely welcome in life: Unsolicited Advice.

For most of us, our decision-making skills in our 20’s didn’t evolve much from our decision-making skills when we were teens. The difference, at least for me, is that I had access to money, I had access to more credit, and no one could legally stop me from making bad choices. Below is an incomplete list of the biggest mistakes I made in my 20’s and the lessons learned from each. Human behavior being what it is, my 20-something readers will no doubt repeat many of my mistakes, despite my below-referenced cautionary tale:

“Put that on my Amex.” I got my first Amex card when I was 18. By the time I was 34, I had a black card. In between, I charged every imaginable expense on my American Express card because my annual goal was to rack up enough points to get free flights to Europe each summer. This was all well and good while money was flowing in, but when a certain ex-husband foreclosed me from my money during my separation and subsequent divorce, and I continued to rack up enormous monthly Amex bills which were multiples of my NYC rent, well, I was screwed. And if I told you how many months it took for this to happen before I changed my ways and learned to spend the green stuff in my wallet rather than the titanium card that sat in the front of it, you wouldn’t have much empathy for me. Lesson Learned: Spend Cash. Never Charge. Although I still have an Amex card (platinum, mostly for nostalgia… and my ego) I haven’t used it since 2010. If I haven’t saved the money, I don’t buy the [insert here].

“I have to be married before I’m 30.” And because of this irrational belief, I spent my 20’s husband-hunting instead of living my life. I had a fear that I’d fall off a chronological cliff at age 30, that I’d no longer be attractive and that I’d have reached some marriage expiration date. When I found myself divorced at 35 and dating, I realized just how unfounded my fear was. Moreover, I wondered if maybe I made a mistake by being the goal-oriented nut that I was, and not dating (women), back when he and I both knew that I looked at women more intently than he did. Lesson Learned: Do not hyper-focus on age. 30 Is the new 20.But do freeze your eggs if you want kids and you’re not ready to have them in your 30’s. More on that in a future post.

“We need to talk. NOW.” When I tell you I didn’t have even the weakest emotional muscle built by age 29, I’m not exaggerating. If someone upset me, I let it rip. I thought getting things off my chest made me emotionally healthy. What I didn’t know is that it takes skill to express oneself appropriately. Needless to say, I hurt a lot of feelings in my 20’s and allowed some important people to drift away. Lessoned Learned: Read the book Keeping The Love You Find to learn the communication skills & relationship skills that no one in our broken educational system deems important enough to teach us as kids.