Beginning way back in 1995, the year I started the 6th grade and entered middle school, I began a tradition with of writing a letter to myself the night before the first day of school. I would then save it and open it the night before school started the next year. I kept up the ritual all the way through college. I usually included things like a bucket list of things I wanted to do that year, my favorite song, favorite band, who my friends were, who I had a crush on. (That name was usually the same name like every year. Sigh… teenage-hood really was a miserable, cruel joke!)

Luckily once I got into highschool, the letters started to become a little less boy crazy, which meant no more “I ❤ So-and-So” scribbled down the side. The letters started becoming kind of motivational. I always had serious anxiety about going back to school (because I sucked at school). So I started writing things like:

Dear Future Self,
Remember, you always shit your pants the night before school and then the whole year goes by and nothing different ever happens! It’s going to be the same thing this year. So suck it up and force yourself to get up on time for once because you promised you wouldn’t spend another Saturday morning in detention for being late every day of the week.

This is NOT The Breakfast Club.

I know, I know, a little over-enthusiastic for the first day. So… enjoy your first detention of the year on Saturday!

(Insert number here) years until FREEDOM!
❤ Past Self

Luckily I survived high school, went on to college where I learned that school isn’t really all that scary. I got a job in my field two months out of college and the rest is history. And today I decided to turn my little tradition around and write to my 16 year old self!

Here it goes…

Dear 16 year old self (1999),

Look, being late is kind of a thing that you do… we both know you try, and people will hate on you for it, but just smile and tell them you had to poop. Because you probably did.

I’m going to let you in on a little secret. “Love” at 16 is like a tornado in a trailer park. Don’t take things so seriously and learn to be real and realize that your judgement of the opposite sex at this stage in your life is extremely clouded (and will be for many years to come)… Like for instance that kid that you’re dating now is a douchebag and will eventually impregnate one of your family members. True story. So while you’re practicing being real, also practice patience, because like a non-curable STD, he will always be around… FOREVER!

Your pink Geo Storm will be the stuff of dreams. Literally. Even when you’re 30, every dream you have where a car is involved, it will be that car. It is the car that all subsequent cars will be measured against. Yes, we know it really isn’t that cool, but you will have some amazing memories in that car. That car will give you your first taste of adulthood and freedom to go wherever the mood takes you. When you’re older, gas will be almost $5.00 a gallon and you will sit in traffic for nearly two hours a day and miss the days that you enjoyed driving around just for the sake of going somewhere. Try to always remember, adventures really aren’t about the destination, but about the journey in getting there.

It’s fuschia, bitches! Everyone who took a ride in this fine piece of machinery was immediately cooler for it.

Speaking of dreams, you will eventually meet the man of yours. He won’t come in the form of a knight in shining armor high upon on a white horse, but rather a 20 year old boy in a white 1983 Chevy Celebrity wearing Harley Davidson boots. He won’t want to meet you at first because he’ll claim he’s “too tired to hang out” but you’ll eventually convince him you’re the coolest shit since sliced bread and then he’ll cave like a 14 year old at a N’Sync concert (in your day) and then he will never go home. I’m not going to lie, shit’s going to get rough. But I promise, eventually one day a man who looks like Kenny Rogers will officiate your marriage. Again, true story.

16 Year Old Self, I know you think you know everything, but you don’t. I’m 30 now and still don’t know everything. But in the future, you will be able to end every debate in mere moments just by simply Googling things on the internet with your cell phone. Your phone will become like an external organ that you will practically be required to have to function normally on a daily basis. But rest easy, cell phones now are nothing like the one step up from Zack Morris things you folks have now.

You’ll also be happy to know, dial-up internet will eventually be replaced by wireless technology. No more tiny velociraptor sounds coming from your modem!

Maybe you could use these phones in the future as paper weights? They’ll be nostalgic one day.

Also, be glad you were young and dumb before the invention of Social Media. Now, safely planted in 1999, you can pull off some shit without feeling compelled to post pictures of it online! You will learn that social media is an public online diary that allows you to look back and see how stupid you were, but with pictures! Unfortunately, so can friends, future romantic interests, employers, in-laws, etcSo BEWARE! A thing called MySpace will take off in 5 years or so, and then it all goes downhill from there.

I wish I could tell you when the time is right to invest in Google, Apple or something worthwhile to prepare for the even farther future, but you still will not have any money. You won’t be hookin’ it on the corner to make ends meet by any means, but we’re definitely not “making it rain.”

Oh, that’s a future saying! You could use it now and trademark it… that might work out for you!

But even though those clouds of Benjamins haven’t rolled in quite yet, you should be proud to know that you’ve made it this far without borrowing a dime from anyone and you haven’t completely destroyed your credit! Except for that outstanding medical bill when you almost chopped your pinky finger off!
(Note within a Note to self: As tempting as it may seem, for the love of God, don’t use a broken mirror to do your hair trying to save time while sitting on the porcelain throne! Yet another instance where you were in a hurry to get somewhere… See what I’m saying here! Being on time is a hazard to your health!)

Some tips to prepare you…

  • Stop buying VHS tapes. When you’re 30 you won’t even own a VCR, so all of those music videos you spent 4 years taping off MTV will be useless.
  • For that matter, stop buying DVDs, too!
  • MTV, VH1 and CMT will no longer play music videos… wtf!
  • Video rental stores will all go out of business!
  • You will have to start scanning and bagging your own groceries but grocery prices will always go up!
  • You will never get lost again, everyone now has a thing called a GPS system! But just to let you know, you will spend most of 2003 lost somewhere in Columbus.
  • Everyone can reach you at any time via your cell phone by calling or texting… which can be a good or bad thing depending on how you look at it.
  • You still have the same cell phone number in 2014 that you had in 1999! Read previous bullet point…

I could go on for days about how much the world is going to change in the next 15 years of your life, but I want there to be some surprises… The main point I’m getting at is that you should just be you. Always do what makes you happy, no matter if it’s “cool” or not.

❤ Always,
30 Year Old Self

P.S. The world does not end at the stroke of midnight on New Years!
So don’t spend 12 hours backing everything up on your computer preparing for the “impending doom” that is foreseen for the year 2000.


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