The Coffee Challenge.  Heard of it?  Here’s how it works:

Go to a coffee shop and order a coffee — a water, a pastry, a venti mocha frappa thingy — it doesn’t matter.  Then, ask for 10% off.

That’s it.

Simple enough, right?

I was listening to the Tim Ferriss podcast recently when this so-called “comfort exercise” was brought to my attention.  A terrific idea, I thought.

The point being that many of the limitations (I’d say the majority) we experience in life are completely self-inflicted.  Get a degree, don’t turn right on red, save now, spend later. What I like to call “thinking under the influence.”  (Some day they’ll issue tickets).

On the one hand, the Coffee Challenge is a direct shot at “the system.” In actuality, however, it’s less about rebellion than it is yoga for your comfort zone.  The idea is to stretch it by doing one of the most basic, yet daunting of human activities…

Asking for what you want.

MY COFFEE CHALLENGE EXPERIENCE

Full disclosure: The coffee establishment in this experiment, I have frequented more than once. I’m familiar with the people. That said, I’ve never received a discount on anything… EVER.  It’s not one of those places.  In light of my familiarity, I decided to raise the bar and ask for a free coffee instead of a discounted one.  Here’s how it went down.

Me:  Hi.  I’ll have a double macchiato, please.
Worker: Sounds good. Would you like the single origin? (That’s the fancier stuff).
Me:  Yeah, let’s do that.

With an aim to be calm and present in my request, I wait patiently for the tallied total before dropping the bomb…

Me:  Can I have it for free?
Worker:  Uhhh… yeah, sure.

Wow, that was easy. Almost too easy. I was kind of expecting a little bit of a struggle, but hey, I believe in a benevolent Youniverse.  Free coffee here I come.

Worker:  That’ll be $2.93.

Hmm… we must have different definitions of “free.”  Ah, I get it.  We’re playing it cool because there are other customers around.  Gonna pull the old “fake credit card” swipe.  I dig.  Wink wink.

And then, as I reach for my wallet, I realize that this isn’t the case at all, but a simple lapse in communication.  He didn’t charge me for the fancy espresso — that’s what he thinks I want for free, which perfectly arrives at, of course, 10% off – the original task.

For a split second, I consider accepting the discount and calling it a day.  You know, one of those can’t-say-I-didn’t-give-it-a-try copouts.  But let’s face it, I wouldn’t be able to walk away fulfilled with my attempt. Why?  Because that’s NOT what I asked for.  Whether I get the free coffee or not, I don’t care.  But clearly delivering my desire, that’s a must.  Carry on now, T.J.

Me:  Oh no, sorry.  I’d like the whole thing for free.
Worker:  The whole thing?!?  (Said with a cryptic laugh).
Me:  Yes, can I have a free coffee?

He’s not so much laughing at me as he is impressed by my request (of course he is).  Steadily, I smile right back at him, a gesture confirming my sincerity. Now, he seeks to understand.

Worker:  Are you strapped for cash or something?
Me:  No.
Worker:  Waiting on a check?
Me:  Nope. (I could lie and play the pity card, but that would sully the intent of the Challenge).

Now he’s really thinking.  It’s written all over his face.  So this guy doesn’t want the drink upgrade and he’s not down on his luck. And then, like a child grasping its first word, I watch it all register.

Holy shit! I think this guy might just be asking for what he wants. That’s it.

Worker:  Alright, just tell the barista what you’d like.
Me:  Thank you.

As I walk away, he’s grinning from ear to ear. No ire or even a hint of discourtesy. Just a big ole I-have-no-idea-what-just-happened-but-I-respect-the-hell-out-of-you type of smile.

And that’s how you drink free coffee.

THE TEN COMMANDMENTS OF ASKING

1. Clarity is king.
You can never be too specific. That’s right, even the word “free” can get misinterpreted.

2. Ask as if.
Imagine, visualize, and bless the intent with Victory. This is your request. Everything is better when it’s qualified with Love.

3. If it’s a No…
Be gracious and appreciative. Humility goes a long way. Plus, you’re a badass just for asking.  And that’s the whole point.

4. If you’re uncomfortable asking…
…that’s because it’s important to your soul’s purpose. Nerves get a bad rap. Work with them by following through.

5. Brevity is your ally.
Short and sweet always does the trick.

6. Buy this book.
Read this book.

7. Stay detached.
Showing up is your only job.

8. People want to help.
They always have and they always will.

9. Sometimes you have to ask twice.
And that’s OK.

10. You don’t ask, you don’t get.
Gandhi said this.

Bonus commandment:

Keep things in perspective.
Whether it’s a napkin or a coffee or a raise in salary, remember:

You’re only asking a question.

AN OPPORTUNITY FOR YOU

Try your own Coffee Challenge.

In the comments below, feel free to share your experience.

Happy asking!