A few months ago, I came across Cassie Boorn and her Letter to My 20-Something Self idea. I loved it — I love the idea of looking back on who I was and seeing what I would have changed. And I love the idea that maybe, possibly, the advice I would give myself could help someone who’s currently that age.

Teal jeans with a color coordinated t-shirt from Northern Reflections, if I'm not mistaken. Probably safe to assume this is smack dab in the middle of the awkward phase.

But then it hit me — at 20, I had a lot of stuff figured out. I mean, sure, I overused my credit cards, which is something I’m still dealing with 11 years later, and I could have been more diligent about using sunscreen. But overall, I’m okay with 20-year-old Kristen. 20-year-old Kristen packed up her mom’s Grand Cherokee and drove from Michigan to Florida to start a new life. She made mistakes, but she’s okay in my book.

No, I didn’t need Future Kristen’s help at 20. I needed Future Kristen to step in years before that. God, did I need her to step in. (Not that I would’ve listened to her, because did I, as a teenager, think anybody knew better than I did? Oh hell no.)

I’ve become incredibly interested in this idea of figuring out when people would go back to their younger selves to offer advice. After asking around, I’ve gotten answers ranging from early childhood, 8 or 9, anywhere within the teen years, and into the 20s. And the reasons are equally varied — some wish they’d worn more sunscreen to avoid damage or cancer, some wish they could go back and spend more time with family or friends who are no longer with us, and many people wish they had realized that they should’ve had more confidence, stayed out of the drama, or just handled circumstances differently.

For me, I think the ideal time would’ve been at the start of my freshman year of high school. I’d had a number of really awkward years prior to that, but I love the idea of a fresh start (see: packing up and moving to Florida), and high school should’ve been that for me. So, below is my letter to 14-year-old Kristen. I’d love to hear from you in the comments, though, on at what age you’d like to give yourself advice and why!


First day of high school. That is one snazzy vest.

Dear Kristen,

It’s the morning of your first day of high school, and your nervous smile is winning the battle over the sparkle of excitement in your eyes. Yes, you’re going to be surrounded by hundreds of kids who are older than you are and who already know where their classes are. Yes, there are going to be cute boys (boys who are taller than you, even!) and there are going to be mean girls. But you don’t need to worry so much about them. Just focus on you for right now.

On Blending In and Fitting In

I know that, despite your carefully planned outfit of a knit vest over a tee and khaki shorts (very stylish in 1994), you’re hoping to blend in. Don’t. You’re not very good at blending in. You’ve got a big smile and a bigger personality. Do not waste your first two years of high school looking down and frowning, even though grunge is in and it seems like being pissed off at life is cool. Smile at people. Make eye contact. And when you walk down Junior Hall with all those boys who make your heart jump into your throat, don’t you dare try to avoid being noticed. Trust me when I say that confidence is pretty much the coolest trait you can possess right now.

Sure, not everyone gets all of your jokes, but you’re actually really, really funny, and if you’re making yourself laugh, someone else is going to join in. And you know what? If they find you funny, chances are great you’re going to enjoy their sense of humor as well. It really doesn’t matter if they’re on your basketball or volleyball team, or if they’re in drama or newspaper or band. When you let down your guard (and you will, believe me), you’ll find that you’re so much happier when you surround yourself with all kinds of people rather than limiting your friendships to people you have almost everything in common with. Even though those people you have loads in common with can be pretty amazing, too.

On Friends

Speaking of friends — don’t take them for granted. Some of these girls are going to be your best friends well into adulthood, so when you get a boyfriend (yes, I promise, you end up with a boyfriend or two), don’t stop making time for them. You’re not going to keep in touch with your exes (no matter how much you think you love them right now, they’re going to be exes, I guarantee it), but some of these girls will be in your wedding.

On Boys

And, speaking of those boyfriends — don’t settle. And don’t sit around and wait to be noticed. If you like a boy, muster up some nerve and say hello or flash him a smile. I promise it isn’t as horrific as it seems. Worst case scenario, he figures out you’re interested and doesn’t reciprocate. Best case, he figures out you’re interested and asks you on a date. And seriously, do you want to look back on your high school years and think about all the cute boys you never talked to? Trust me, the answer is no.

On Gossip

There are going to be times when you’re tempted to say nasty things about people, even about people you like. Don’t do it. Gossip sucks. It hurts people and it leaves you wondering, first, whether somebody knows what you said about them, and second, what everyone else is saying about you. It’s a waste of energy, and even if it makes you feel like you fit in for a moment, you’ll carry an icky feeling in your stomach for far longer than you carried that little spark of elation. When people start spewing lies and meanness, step away and chat with someone else.

When in doubt, be kind. Even if not in doubt, you know what? Be kind. I’m not saying you have to kiss anyone’s ass; far from it. If someone gives you a hard time, stand up for yourself, your friends, and what you believe in. Don’t waste your time trying to become best buddies with someone who you clearly do not get along with. But smile and say hello to the weird guy in the back of the class who looks like he’s having a really bad day,. If you see someone getting pushed around, step in to help. Lend an ear, a shoulder, or a hand when you can.

On Self Confidence

A couple of other things to keep in mind: You’re smart. This is an important part of your personality and is going to be sort of important as you get older with that whole “working for a living” thing. You don’t need to hide it in order to seem cooler or more interesting.

Seek out opportunities to excel in the things you love — this is the time to attend writing conferences and enter contests, because now, it’s free (or at least Mom and Dad will pay for it). Things get more complicated when you’re on your own for those things, believe me.

Other Important Stuff

Run, don’t walk from the tanning bed. I know your friends might do it, but it’s bad for you. You would never smoke (and good for you!), but this is equally dangerous, especially since it turns out that you’re at high risk for skin cancer. If you keep it up, you’re going to end up with some big, ugly scars, and let’s hope that’s as bad as it gets. Stick to the sunless tanning lotion, please.

Hug your your dog Lacey. She’s already old, and she’s a bigger part of your life than you realize. You don’t understand how much it’s going to hurt to lose her.

Sit and talk to Grandma. I know, I know, she’s repeating herself and tells the same stories over and over, but there will be a time when she can’t even remember those stories. Go through pictures and ask her questions about the people in them. Tell her about what’s going on in your life. It doesn’t have to be interesting; she just wants to be involved. And be sure to thank her for picking you up from school so you don’t have to ride the stupid bus. She doesn’t have to do that, you know.

Be a little nicer to Mom and Dad. Here’s a newsflash — everybody has parents. And everybody your age feels a little embarrassed about the fact that their folks have to drive them around. But you know what’s stupid? Being embarrassed that Dad’s dropping you off with the boat on the trailer behind the truck. Why would you be embarrassed that your family has a boat? Because it makes you different? Honey, you are different. In a lot of good ways. The sooner you embrace that, the sooner you’ll start having fun. And you really don’t need to worry about everyone knowing you as Earl’s Daughter. For one thing, it could be way worse. And besides, you’ll make a name for yourself in that small town soon enough. And then you’ll leave, and when you look back, you’ll feel only pride at how many people recognized and admired your folks.

I don’t think I need to tell you this, because, from where I’m sitting (here in the fuuuutuuuuurrrrre), you figured this out on your own, but it bears repeating — take advantage of opportunities as they arise. Follow signs — they’re real and they take you places. Good places.

Oh, and also? When the idea strikes you to become a brunette after years and years of highlights, get thee to a salon.


Future Kristen