If I Could Go Back 20 Years and Tell Myself What I Know Now…

You are now in your thirties. You’ve had time to reflect on your past. The good, the bad, and the oh so ugly. Your questionable choices in men(boys really), friends, fashion and festivities. The way you viewed the world before the ginormous responsibilities of real life ensued.

For the 20 years of “what was I thinking?” these are the things that I would go back and tell myself.

  • Trying to be pretty is overrated!
  • Wear your retainers! Mom and dad paid good money for that metal mouth and dropping 3 grand out of your own pocket for them in your 30’s because you neglected your nightly routine for the last 15 years is a pain…literally and kinda makes you look like an idiot.
  • Be yourself. The people who matter will love you for being just that.
  • Contrary to popular belief, the Wet N’ Wild “666” lipliner (your soul mate circa 1998) will not always be the most popular lipstick. If you need a moment, I completely understand.
  • You are young and impressionable. Be aware of controlling douchebags.
  • Don’t rush marriage. Yes, he is gorgeous and you want to have his babies, but trust me, He will wait. Finish school and travel like a mother effer.
  • Enjoy your breast size now because although this may seem impossible, they will become smaller.
  • Time flies! But seriously, time is a sneaky little bitch that will creep up on you like a leopard in the Serengeti. Make the most of it!
  • Your bunion has become an asshole. Please don’t continue to torture it with those God awful shoes just because you think they are cute. Payback is a bitch in your 30’s…thank you very much.
  • Accept your body. It will make beautiful babies. Give it a break.
  • You wont believe this, but those blue jean overalls that you retired 18 years ago and swore to never wear again are back in style so leave them in attic for me.
  • Beware of manipulators…and on July 8th 2000…the delicious and incredibly dangerous “Long Island Ice Tea.”
  • The Running Man is still your signature move.
  • You know that big chunky sour glob of puke called “pride?” swallow it. Love and accept because friends and family can and do leave us all too quickly.
  • Be thankful for your lack of chin hair.
  • Go fishing with your dad.
  • High waisted pants are back in style. I still refuse to wear them, so our taste hasn’t changed on that one.
  • Pick good friends. If you still have them in 20 years, you did well.
  • Don’t talk shit about the minivan…you will drive one!
  • Notorious B.I.G, Ice Cube, Bell Biv Devoe and the like will become “old school” jams, but it’s all good.  You will still bump em’ with pride.
  • When you find “the one,” there will come a time when farting in each other’s presence is not only acceptable, but encouraged.
  • For God sakes get out of the tanning booth! I know you think bronze is better, but it’s not worth the health scares, surgery and scars in your future. Trust me…I talk a lot of shit about you for this one.
  • You will have more confidence in your 30’s then you ever thought possible. It’s beyond awesome and absolutely worth the wait.
  • When the time comes, know that the pain in your stomach is not from eating the bad chorizo, it is in fact an appendicitis.
  • Keep writing. You never know where it can take you.

As another birthday passes, I can’t help but to reflect on the me 20 years ago. What I thought life was supposed to be like in the future and how incredibly different the truth is. No, I am not rich in terms of money. No fancy car, no high-profile career, no vacation home in Paris…sigh. But I have a husband who adores me, three healthy children, and the best friends anyone could ask for. There is no dollar sign for that kind of wealth. More wrinkles, and grays…and jet black chin hairs means more laughs, more time and more memories being made. What would you go back and tell yourself?

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About the author

Sara Pittman

Sara is from sunny San Diego CA. She is a wife, busy mother of 3 and amateur chef stumbling through organized chaos on a daily basis using sarcasm and humor to soften the blow...that's what she said. She will take any opportunity to demonstrate the running man in public and enjoys being a sarcastic smart ass.


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  • LOL – I held out on the minivan as long as I could, with 3 kids now I couldn’t stay away any longer. I am surprised that I actually like it 🙂

  • This is fantastic! I’m finding out the hard way about the whole wearing the retainer thing. And the boobs getting smaller bit. And pretty much all of it lol. Great post!

  • I read your post in the morning and I’ve been walking around ever since trying to think of something to tell my younger self. I keep rejecting what I come up with. For example, I thought to tell my younger self to give more thought to a career and not to get stuck in a field I hated – Business. But if I didn’t go into that field, I wouldn’t have met my husband and he is the love of my life. I could have told my younger self not to worry about the weight, but I would be lying. I’m close to 40 and I still work out every day because I want to look good. I really came up with nothing.

  • Love the list. Another one would be “Trying to be popular at school is overrated”. I just hated how everyone tried to be in the cool group – hey, it doesn’t matter!

  • I am now in my 50’s and must agree with just about everything you said. Time does fly. Oh and here is one to add (I have shared this one with my girls as they grew up): You never feel any older than you were in your early 20’s. I still identify with that “me” and don’t really understand why the current 20-somethings look at me like I’m old and uncool. (Maybe because I use terms like “uncool” LOL)

  • I LOVE this post Sara! It really does capture 20 years. There have been times I catch myself in public and think “My younger self would not approve”. Then I remember who my younger self was (riddled with insecurity) and think of how happy I am in the moment and I don’t care. People can judge all they want. The one person’s opinion I truly care about, he doesn’t care if the clothes match perfectly or I torture myself with stilettos.

    I too am not where I thought I would be from a finance or career standpoint but I am SO HAPPY with life. A great guy, family and friends and it totally makes the 20 years of wandering through whatever you want to call it, worth it.

    I am one year into my 30’s and love it. I thought I would hate it. That confidence you mention is amazing. Something that needed to build in its own time.

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