why you tryin so hard to be cool?

I was sitting on a restaurant patio, waiting for my cheeseburger, and this most excellent question wafted over from a neighboring table.

“Why you tryin so hard to be cool?”

I couldn’t help it - I had to turn and see the people having this conversation. They were two young men, one of them with an effortlessly quirky-chic look going, sitting back in his chair, hands folded, looking at his friend with kind eyes.

Of course he was the one who asked the question: why you tryin so hard to be cool?

Because if you want to get that effortlessly quirky-chic, comfortable in your skin & threads, kind-and-true thing going? There’s only one person you need to impress:




"you know I wrote this while I was lookin in the mirror, right?"

You're so good

Baby there ain't nobody better (Ain't nobody better)

So you should

Never, ever go by the letter (Never ever)

Here: go watch Prince play Cream and then come on back.

I clasped my hands like a delighted toddler, threw back my head, and shrieked in delight the first time I saw this performance.

WELL OF COURSE this song is To Prince From Prince With Love.

I don’t dare presume to know what guided Prince’s revolutionary choices - where to live, what to wear, how and what to play, whom to partner with - but I bet one priceless, assless yellow pantsuit that none of them came from Tryin To Look Cool.

thank heavens for the Interwebs that put this image at the touch of my typing fingers. and thank the photographer, whose name I couldn't find.

thank heavens for the Interwebs that put this image at the touch of my typing fingers. and thank the photographer, whose name I couldn't find.

Prince exemplifies (yes, present tense - still. always.) how Cool comes from deep confidence, unbound creativity, and a generous daring to be wholly oneself - one’s evolving, capricious, learning and growing self.

You're so cool

Everything you do is success

Make the rules

Then break them all 'cause you are the best

the narcissism of needing approval

Think about it: how does it feel to be around a person who desperately needs your approvals and affirmations?

Who constantly interrupts the point they're making to ask questions like “Does this make sense?” and “Do you know what I mean?”

Who feels slighted when you haven’t complimented their new haircut. So upset when you disagree with them that you tend to keep your thoughts to yourself.

I find it draining. And unsettling.

And hey, how does it feel to have an approval-ravenous person as our PRESIDENT?

Trump clearly illustrates the deepest end of the strange paradoxes of the Please-Like-Me needy narcissist:

1.  The more approval-hungry we are, the less likely we’ll be open to real feedback. We seek compliments and affirmations and can’t bear anything else. We want to you to SAY you’re pleased, but we can’t handle hearing how you REALLY feel.

2.  The less self-secure we feel, the more we tend to stoke fear among others. Misery loves company. When I hear someone mocking another person’s taste in music, for example, I immediately suspect they’re worried about the Coolness Rating of their own record collection. So it makes total sense to me that Trump, an indebted, inept businessman, must tell an entire country, “We never win anymore.”

3.  At the extreme, the more we need other people to approve of our doings, the more we tend to control and/or belittle those who don’t. Instead of saying, “I understand I’ve made a controversial decision,” we say, “Everybody agrees with me, and whoever doesn’t is an idiot.” In the weirdest way, our lack of self-assurance makes us over-compensate with an inherently unstable, because insecure, self-aggrandizement.

Probably you’ve witnessed this very thing - especially if you’ve watched the news lately. And probably - because humanness - you have done it a little yourself.

I know I have.

loving yourself is GENEROUS. really.

When I teach about self-love and self-kindness, the most common concern I hear is this:

“But if I love myself that much, won’t I be a selfish, arrogant asshole?”


If you love yourself into self-security, you won’t need to control other people’s reactions to you. You will be strong enough to allow them to disagree with you, and even - maybe - to consider and learn from their criticisms.

If you love yourself, you will be increasingly comfortable in your individuality. You won’t, as Glennon Doyle Melton writes, need to  “send your representative” - your carefully-cultivated-for-status-quo-maintenance self.

If you love yourself, you will Be Real with other people. You’ll let yourself be vulnerable. You’ll be open to authentic connection.

And you’ll be strong: in your sense of self, in your willingness to grow, in your openness to evolving how you show up in the world.

If you stop tryin so hard to be cool, and love yourself so much that you can show up TRUE, in all your mess and quirkiness and beauty, you will inspire with your example.

You will shine like a beacon.

Your people will find you, and it will be such fun, because you won’t feel desperate to make them love you.

You and your people will delight one another by being resonant, but not homogenous. By celebrating - and embracing the challenges of, and growing wiser because of - your differences.

What could be more generous?

In the name of Prince, for the delight of peoples everywhere, and especially for YOU:

Do your dance

Why should you wait any longer?

Take your chance

It could only make you stronger.

all the world's a stage and you should get up on it.

all the world's a stage and you should get up on it.

natalie millerComment