Look at the fighter jet pictured below—specifically, the cockpit. Then look a little closer. 

The paint job is designed to cause confusion in a dogfight. We’re seeing the bottom of the plane. But the paint job depicts a fake cockpit, making us think we’re seeing the top of the plane. Mimicking the cockpit causes momentary confusion, which might buy the pilot a moment of hesitation to save themselves in the middle of a dogfight. 

It costs almost nothing in terms of time and energy to paint the fake cockpit. Labor time and paint cost are a rounding error. Losing a plane in a dogfight is hundreds of millions of dollars.

Given how easy and simple it is to do, it’s almost stupid not to do it. So I’m coining a term: free upside.

Most of us don’t fly fighter planes, however, so here’s a more relatable example.

The $40 Luxury Hotel

I had always had a thing for Texas skies, open spaces, and cowboy mythology. When I was 24 years old, my friend Nicole and I took a road trip through west Texas, ground zero for all of that. I was loving it; the natural beauty and the gorgeous views bowled me over every time I looked up.

On a Tuesday, we pulled into Marfa, a quirky Texas town famous for its art scene. Marfa was a cool place and becoming cooler: Beyonce had filmed a music video there recently. 

We pulled into “downtown” and started figuring out where we would stay for the night. As broke 24 year olds, we pretty quickly settled on Travelodge, a bargain basement chain hotel outside of town. The nicest hotel in Marfa, El Paisano, was smack dab in the middle. Moviestar James Dean had filmed a movie there in the 50s. Beautiful decor, vintage western art on the walls. Tons of character. My spirit dropped as I typed Travelodge’s address into Google maps. 

I’m not sure if it was the magic of west Texas or what, but I was feeling a little feisty. I called up El Paisano and, in the warmest tone possible, explained that we were passing through town and would love to stay there. But the hotel was outside of our budget. Given it was a slow Tuesday, would they be up for taking us at a discount? 

What’s your budget, the guy asked.

$40 bucks, I said. I felt embarrassed to lowball him. My voice didn’t crack but it was shakier than I would have liked. There was a long pause…and then he gave us parking instructions.

Our eyes went wide. We started yelling and pumping our firsts as soon as the call ended. The rest of the evening was a delight; we strolled through Marfa’s beautiful downtown and rested our heads in a beautiful hotel full of ambiance and character.

It cost nothing to make this ask. Would have been stupid not to try it.

Free Upside is Everywhere

“Free upside” describes a situation where benefits and advantages are conferred at zero—or marginal—costs. Opportunities like this are everywhere. 

Examples:

• If you create a proposal for a company that decides not to work with you, you make minor edits (“find and replace” the company name) and send it to another company in the space
• Asking for the seat with the view at the restaurant you were going to anyway
• If a piece of software is out of your budget, emailing the developer if they’ll give you a discount code

The first step to finding free upside is being aware that there is upside to be had in the first place.

To help illustrate just how accessible free upside can be, I want to introduce you to an exercise that brings this concept to life in a simple, practical way.

The Coffee Shop Rejection Exercise

I build entrepreneurship and innovation education programs for a living. One exercise that changes how the founders I work with see the world is something I call the Coffee Shop Rejection Exercise. Here’s how it works: go to a coffee shop, order a cup of coffee, and ask for a 50% discount.

At first glance, this might feel absurd. You’re about to ask for a discount that isn’t on the menu, and there’s no logical reason they should grant it. It’s not a sale day, there’s no coupon, and you don’t have any special reason for the request. But that’s the beauty of it. 

The goal here isn’t necessarily to get the discount—it’s to push you into a situation that challenges your assumptions about what you’re “allowed” to ask for. The point is to recognize that the cost of asking is nothing.

For first timers, this exercise can be agonizing. They feel intimidated, palms sweaty, heart racing, words stuttering. But what’s the worst that can happen? The barista says no. And in that case, you’re left in exactly the same position you were before—holding a coffee at full price. Nothing lost. But if they say yes, you just scored a win at zero cost. Either way, you gain something valuable: you realize that this small moment, this tiny risk, was available to you all along. All you had to do was ask. And the second time you ask, you barely notice.

This Is Bigger Than Cheap Coffee

Saving a buck on coffee or getting a hotel discount is one thing. But let’s extend this logic to bigger wins. If your boss offers you a raise, it’s worth considering if you should ask for more. If your relationship is on a firm foundation and you ask gracefully, what do you have to lose? Making this ask is trivial but the impact on your bank account is anything but. 

Or what about that good-looking person you always see at the dog park? If you’re considerate and not a creep, is there really that much to lose by striking up a conversation? 

I’ve attended conferences where I bumped into Tim Ferriss, AOL Founder Steve Case, and San Antonio Spurs owner Red McCombs. I pitched myself to each one of them right then and there.

There are circumstances where the upside of asking gets bigger but the downside remains negligible.

You can go bigger. 

I invented this term and wrote this essay to rewire your brain to start noticing free upside. If this term can grab a foothold in your experience of the world, you’ll be more predisposed to recognize it when you see it in the wild. And if you can recognize it in the wild, you can take your shot and reap the benefits. And it costs nothing. 

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Thanks to early readers: Zeyad Mahran, Celeste, Justin Lai, Coco Liu, Jeshua Glanzmann, Becky Isjwara