5 Things I Wish I Had Done More of In My 20s

The other day while I was driving to work, Alanis Morissette’s “You Oughta Know” song came on and I was transported to my 20s and all the fun and troubling times I had in that decade.


Cindy 20s
Dear 23 year-old me


I’m generally not the type of person that looks back on life with regrets. And to be fair, my 20s were pretty amazing. I’m a firm believer that every struggle, every joy, every experience, and every tear has shaped the person I am today.


Even though I spent a long time getting to where I am now, there are some things I wish I would have focused more in my 20s. If I could travel back in time, here are 5 things I would have done differently:

Made a bigger effort to stay in touch with friends

I wish someone had told me back then that one day in the future, you will want to talk with people who knew what you were like in your glorious youth. They knew the you who was still figuring things out, the you who was giddy with wild plans and adventures, and the you who had so many dreams, insecurities, and doubts. How nice to be able to reminisce about how far you’ve come.

Worried (a whole lot) less about everything.

I mean, really, a lot of the worrying I did back then was totally useless and probably added a few frown lines I sport today. I worried constantly about my relationships, my insecurities, my student loans, my outfits, my accomplishments vs others, people’s opinions of me, and blah, blah, blah. Life would have been easier if I had kept that worrying at bay because all it did was waste precious lifetime hours that I’ll never get back. I know that hindsight is 20/20 but being less self-aware and more life aware would have been wonderful.

Challenged the status quo more

During that decade, I lived life “going with the flow”, doing what everyone else was doing, and while everything was all nice and dandy, it really was like a cop-out. I probably missed out on so many amazing opportunities because I didn’t take charge. Challenging the status quo at work, with friends, in my relationships, or at school would have allowed me to grow and prosper, to stand out. I see that clearly now, and I fight not to go with the flow, but to be a rebel and a leader.

Practiced a stricter skin care routine

When you’re young with perfect skin you think it’s going to be like that for a very long time. I pretty much just used soap and water to clean my face. I wish I had pampered my skin with more TLC, facials, creams, and sunscreen.

Done more to create art of various forms

Or indulged a lot more time in personal hobbies like writing, painting, photography, sports, dancing, and ballet. I didn’t have kids, after all, and I had all the time in the world.

The really great thing about all this is that by examining my personal story I set out to live a more fulfilling life right now and in the future. Lest we forget that the real beauty of being rocking over 40 is that we’re still young enough, and have the energy to do the things we’ve always dreamed about.

Is there anything you wish you would have done in your 20s? Please share in the comments!


Rocking Over 40 Founder





  1. I just turned 20 in may and feel like I’m failing at most of these. Challenging the norm is the only one I’m good at!
    Good read! It really does make me thing about what the future holds.

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