ASH AMBIRGE

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Where’s Your God Damn Pineapple?

In: Life,

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:

How?

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?

Enter your email address and I'll rummage around in my bag of tricks for JUST the thing.

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40 thoughts on "Where’s Your God Damn Pineapple?"

  1. RebeccaTracey says:

    You are so fucking right. As usual. I am probably the queen of choosing the shoulds over the shouldnts. I’d rather live a life laughing at all the stupid things i’ve done than always wondering ‘what if’…. Except for that that time I sailed around Fiji with a swiss polygamist… that one could have probably been left at what-if. Heh.

    1. TMFproject says:

      HAHA! That happened?!

      1. RebeccaTracey says:

        Oh, that happened. My friend and I were too cheap to pay for any actual tours in Fiji, and we met this man with a ghetto homemade catamaran. Obviously, it seemed like a good idea to accept his offer to take us sailing. Until that first night, playing scrabble by candlelight in the middle of the ocean, when he managed to spell “MOLESTER” using all of this letters, and looked at us in the darkness, cackling the kind of laugh of horror films right before someone gets their head chopped off. Scariest night of my life. But it makes for a good story, which is the very least you can get out of these experiences, right!?

  2. RebeccaTracey says:

    You are so fucking right. As usual. I am probably the queen of choosing the shoulds over the shouldnts. I’d rather live a life laughing at all the stupid things i’ve done than always wondering ‘what if’…. Except for that that time I sailed around Fiji with a swiss polygamist… that one could have probably been left at what-if. Heh.

    1. TMFproject says:

      HAHA! That happened?!

      1. RebeccaTracey says:

        Oh, that happened. My friend and I were too cheap to pay for any actual tours in Fiji, and we met this man with a ghetto homemade catamaran. Obviously, it seemed like a good idea to accept his offer to take us sailing. Until that first night, playing scrabble by candlelight in the middle of the ocean, when he managed to spell “MOLESTER” using all of this letters, and looked at us in the darkness, cackling the kind of laugh of horror films right before someone gets their head chopped off. Scariest night of my life. But it makes for a good story, which is the very least you can get out of these experiences, right!?