What I Wish I Knew in High School (and what I hope my daughters know when they get there)

I was not cool in high school.

At all.

I wasn’t unpopular by any means.

I knew just about everyone in school (it was a small high school) and I’d say I was well-liked enough.

I had an awesome group of close friends, most of whom were on the swim team.

But even in my little group of close friends, I still often felt like the ugly one or the fat one or the stupid one or the whatever-negative-thing-you-can-think-of one.

I had super short hair that was really curly in the front. I was a major tomboy for most of my childhood. I didn’t really know how to wear make up. The boys weren’t exactly beating my door down. And we didn’t have much money when I was in high school, but I lived in a super rich town. So I wasn’t exactly fashionable like the majority of girls I went to school with.

I spent most of high school thinking all the other girls were prettier, smarter, thinner, and way cooler than I was.

And I was sure that if I could just be more like them, then I’d be truly happy.

I was voted the class clown my senior year.  I did feel like I at least had my sense of humor going for me.

So I wasn’t exactly shy.

I was probably overcompensating for all my insecurities.

I bet from the outside, people thought I was totally confident and happy and unphased or unaffected by what anyone else thought or said.

Through all of high school and college, and to be honest, most of my twenties I compared myself to other people. I was always sure that they were strong and happy and well adjusted and I was envious of their lives that I was sure were pretty much completely perfect. Or at least very very close to it.

After high school and college, things changed for me a little. On the outside, anyway. I was thin and my hair was longer. I had great skin. It turned out that I had a pretty decent sense of style. I was a size two or four. I had an amazing wardrobe and a seriously kick ass shoe collection. I had a good job, and I had a nice car.

I wasn’t going home from work and rolling around in piles of money, but I was doing fine.

And I was finally getting the boys’ attention.

I was also still painfully insecure and still constantly comparing myself to everyone else who I knew had their shit together in every single way.

And those high school thoughts kept going through my head.

If I was a little prettier, I’d be happier.

If I was ten pounds lighter, I’d be happier.

If I own that pair of shoes, I will definitely be happier.

If I can get that guy to be my boyfriend… 

All my problems will be solved!

Even as I turned the corner to my thirties, I was still trying to get access into that elite group of cool chicks.

I don’t even know what the elite group of cool chicks even was.

I just felt like I still wasn’t in it.

Now I aspire to be like a different kind of woman.

And don’t get me wrong.

I don’t want to be someone else. Not anymore!

It’s taken me 47 years, but I am finally pretty happy with myself.

I realize now that it’s okay to be flawed.

Some flaws I accept as things that may never change.

Others I am working on.

But now I don’t think to myself, “If I was more like her, if I had her house or her car or her face or her ass or her husband (I don’t want anyone else’s husband but you know what I mean) or her bank account I’d be so much happier.”

Because none of those things matter.

Those girls that some of us aspire to be like, the ones who appear to have their shit together, the ones who are pretty or smart or rich or tall or thin or whatever…

I just want you to know that whatever you have going on in your head,


they’ve got it going on theirs, too.

In fact, there’s a pretty good chance they’ve got it going on even more in their head than you do in yours!

However perfect things seem for those perfect girls with their perfect exteriors and their perfect boyfriends and their perfect cars and their perfect hair, I guarantee you 150% that they are no happier than you are.


Let’s look at Angelina Jolie, for example.

She is arguably the most beautiful woman on the face of the planet.

She’s fucking loaded.

She’s definitely not stupid.

She’s thin.

She’s married to Brad Fucking Pitt.

For the moment, anyway.

She’s talented. She’s won an Oscar for crying out loud!

She’s got her pilot’s license and she’s all tatted up and she flies all over the place to the mansions she’s got in different parts of the world.

So she’s gorgeous and she’s smart and she doesn’t give a flying fuck about what anyone else thinks and she’s a bad ass and she’s got more money than any person could ever possibly need.

Even a person with six kids.

And her life is a fucking shit show.

Being beautiful and talented and rich and seemingly perfect on the outside is not a guarantee of anything.

And so what do I wish I knew then that I know now?

Well, I wish I had put as much effort into trying to spend time with people I felt a genuine connection with rather than people who were really nothing like me.

I wish I realized that what was really important wasn’t being popular. That the cool kids weren’t more confident than I was.

In fact, I think in many ways, the cool kids are less confident than everyone else in high school.

I wish I had realized that every kid in high school had some serious issues to deal with.  Whether it was a messed up home life or family members with addiction issues or anxiety or depression or eating disorders or whatever the hell it was, we all have issues.

And I wish I spent more time trying to surround myself with people who were focused or driven or intelligent or hilarious than I did with people who I believed would make me happier because they had somehow managed to gain access into an elite group of people where you didn’t necessarily even possess any elite qualities.

Because the people I  feel most connected to now?

The ones who make me laugh and who make me think and who inspire me to do and be a better person?

They are some of my fellow uncool kids.

In fact, there is one person who I find so incredibly intriguing now, a person who is so smart that most of the time he posts stuff on Facebook I literally have no fucking idea what the hell he is talking about, that I can’t even believe he would find anything I said even remotely interesting.

Same with another guy I went to high school with.

He is so smart and so funny.

I bet he was just as funny back in high school.

I wouldn’t know because I never attempted to spend any time getting to know him back then.

Same thing with a friend of mine who is now a college professor.

And another one who is the chief of surgery.

And another guy who went completely blind when he was 13 and is the only blind person to reach the summit of Mount Everest.

What the hell!

Why wasn’t I trying to spend more time with these people when I was in high school?

Because they are some of the coolest people I know! They are people who help me aspire to bigger and better things, people who make me laugh on a daily basis, and people who have also been very encouraging and supportive of not only the blog, but of my family when we were recently going through some really rough times!

I’m sure they all have their fucked up issues too. But they also possess so many qualities that I’d like to strengthen in myself. So many qualities that actually do affect a person’s overall level of happiness. So many qualities that I find attractive in a human being. And they have nothing to do with a bank account or the number on the tag in their jeans.

So the point I’m hoping to make, especially for young girls in high school and college and their twenties, is that the girls (and guys) who so often appear to have it all, well…  they don’t.

This isn’t to say they don’t have anything to offer as human beings. This isn’t to say that they aren’t good people. This isn’t to say that you shouldn’t be friends with them.

But we are all struggling. We are all trying to find our way. We are all messed up.

Even Brangelina.

What makes us happy isn’t having a connection with certain group of people of a particular status. And it’s not being classically beautiful. And it’s not having the best looking boyfriend in school.

It’s having a connection to other people who you already feel comfortable with. It’s having a connection with people who build you up. It’s having a connection with people who support you. It’s having a connection with people who make you laugh. It’s having a connection with people who do their own thing and let you do your own thing.

Because that’s what helps you discover the things about yourself that are really awesome.

And when you do that, that’s when you find confidence and strength and happiness.

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