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 ten percent 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, never trust the government, save now, spend later. What I like to call “thinking under the influence.” (Some day they’ll issue citations).

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.


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, and to dismantle any hint of favorability, I decided to raise the bar and ask for a free coffee instead of a discounted one. The following activity is based on real events.

Me: Good morning. I’ll have a macchiato, please.
Worker: Sounds good. Would you like the single origin? (That’s the fancier coffee).
Me: Yeah, let’s do that. And make it a double.

With an aim to be calm and present in my request, I wait patiently for the tallied total before dropping the F-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. (I hear it tastes better too).

Worker: That’ll be $2.93.

Hmm… that’s my usual price. 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, ten percent off – the original task.

For a split second, I consider accepting the discount, chalking up a victory 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 and having my desire understood, 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. 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 sh*t! 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.
Worker: Have a good one!

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.


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

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. Free coffee is a bonus.

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. Rise. Radiate. Release.

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

People want to help. They always have and they always will. @tjolwig (Click to Tweet!)

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 promotion at work, remember:

You’re only asking a question.


Try your own Coffee Challenge. Share your story in the comments below.

In the words of Thomas Edison, “Just when you think you’ve examined all the options: you haven’t.”

If free lunches don’t exist, I’m living proof that coffee does.

Happy asking!

T.J. Olwig is the writer and creator behind the blog Keepin’ It Light, what he calls an “opportunity to live consciously.” When he’s not writing, you can find him in a coffee shop, yoga studio or on the road. Currently, he’s traveling the country with his yellow lab Gus and Betty White (that’s his car). The goal? To play fetch in all 50 states.  He calls it “Fetch in 50.” You can follow him on Twitter, IG or FB.



Image courtesy of Leeroy.