Where’s Your God Damn Pineapple?

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?


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Quit your job. Work remotely. Travel the world. Find your f*cking self.

Every weekday morning at 8am Eastern you’ll get 3 ideas to help you make big moves and big money. Written by Penguin Random House author, entrepreneur & digital nomad, Ash Ambirge, who likes to believe she still has standards.

The Middle Finger Project has helped over 500,000+ unconventional subscribers ditch the crock pot & go on an adventure. Established 2009 from Santiago, Chile.

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