A Letter To My 30-Year-Old Self : Kaitlin Olivero

two women in the art institute of chicago Photo : Alanna Bagladi

Dear 30-year-old Kaitlin,

Based on how the first three years of my twenties have gone, I cannot even imagine what life is like at the end of them. 30.  Wowza (I hope you still say cool words like that). I’m sure the last seven years have been exciting and ever-changing. At 23, life was moving really super fast… I do hope that by 30 the world has turned a little more slowly and life has settled down just a bit.

Where the heck are you? Back in Chicago? Finally out in NYC? Or have you already explored and chosen a place to settle down? I know you must be in a larger city, working in a museum (right?) that you are in awe of every day. What track did you decide on in your coveted museum career? Perhaps you’ve been curating shows or maybe you are no where near a museum. I hope you are still in nonprofits though, if so, then you are super close to that student loan forgiveness threshold! About those… I hope you are in a good place financially, as well as professionally (I am not so worried about career, I know you are still super ambitious).

I wonder if you have started that family you’ve been dreaming of all your life. The plan was always to be starting that family of curly-haired monsters right about now, I think you have stuck to your guns on that matter. Maybe you are already a mama! Speaking of mamas, I hope you are never too far from your mom – I know she is still your best friend. I hope you still see your extended families for every holiday and that you have even started hosting a holiday or two! Oh my goodness, do you have a house? Maybe you still rent, which is a-ok, but it would be pretty swell if you’ve bought something! I think that would also mean your shopping addiction went on the back burner, I hope that happened shortly after you turned 24 at least.

I hope you’ve been traveling, seeing new things, meeting all sorts of people (and keeping friends close)… just enjoying life. I hope you are still visiting Disney World regularly and that you never lose that Disney love. You better have gone to Tokyo Disneyland and Hong Kong Disneyland by now! Hopefully the Frozen craze has long since ended, but that you still love to sing “Love is an Open Door” with Nick. Hold on to that magic, no matter what anyone says!

I hope you grew out your hair, despite wanting to chop it all off because it is a curly, thick mess (by the way, what color is it?). I hope you have a big Christmas tree to decorate. I hope you still watch The Office, as Michael Scott can always cheer you up. I hope you have kept in shape, toning those arms so your Picasso dove tattoo on your arm doesn’t flap away. Hey, maybe you got another tattoo! I hope you figured out that the iPhone is better than that one time you tried an Android. I hope you are full of love, happiness, and success. And I hope you still take selfies.


Your 23-year-old self. If you forgot what you were doing at that age, check Timehop.


Kaitlin Olivero : Curly haired, art lovin’, loud talkin’, gal who’s twenty-something and ruthless. Most likely to become a Museum Director and to shop literally til she drops.