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Where’s Your God Damn Pineapple?

In: Feeling Dead and Uninspired

There's always a reason why you shouldn't.

Shouldn't spend the money.

Shouldn't be so frivolous.

Shouldn't miss work.

Shouldn't be irresponsible.

Shouldn't act so hastily.

And a million other reasons why you shouldn't do what you've been wanting to do.

The real question, of course, isn't whether you should or you shouldn't.

Because when it comes to something you deeply, ferociously want–shouldn't doesn't exist.

The real question is:


This past weekend, one of my dearest, bestest, I'll-distract-the-waiter-while-you-shove-the-bread-in-your-purse friends decided to toss all of her shouldn'ts aside and follow me to my seasonal home in Costa Rica.

She probably shouldn't have spent the money.

She probably shouldn't have been so frivolous.

And she probably shouldn't have missed work, among other reasons.

But she did.

And do you know why?

Because she didn't let her shouldn'ts become her should.

She didn't let the reasons why not overpower the reasons why.

And instead of wasting her energy convincing herself why she shouldn't…

She figured out how she could.

…And then she strolled off the plane eating a god damn pineapple.

It's never about the reasons why you shouldn't.

It's always about the reasons why you should.

So what's the next plane you're strolling off, and where's your god damn pineapple?

Feb 8


I Hate Mantras, And YET—I Love This One for When You’re Kinda Sorta Shitting Your Pants

I have a mantra (despite wanting to slit my throat upon hearing the word “mantra.”) Are you ready? My mantra is this: WHO CARES HOW YOU FEEL ABOUT IT? GO ANYWAY. Which sounds really kinda wrong, right? We’re a culture based on f-e-e-e-e-e-e-l-i-n-g-s. But sometimes, you have to override the ones that I call false […]

In: Feeling Dead and Uninspired, Feeling Disillusioned With Life


Jul 20


Stay Foolish. Stay Wise. Have CONFIDENCE.

Rules–particularly the dogmatic variety–are most useful for those who aren’t confident enough to make their own damn decisions.   For the rest of us, there’s vodka–so we can cope with the decisions we were foolishly wise enough to make.   So help us, Grey Goose.   Amen. -Excerpt from my forthcoming book, The Middle Finger […]

In: Feeling Dead and Uninspired


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