On taking risks and making progress

Work, risk, and progress.

America’s Team: The Gambler and His Cowboys is a documentary about Jerry Jones and the Dallas Cowboys. In the opening sequence, as he talks about the years leading up to the day he bought the team, we get a glimpse into how Jones approaches work and business.

After a string of failed business ventures, Jones was in massive debt. “In the 80s, I was really good at drilling wells, and I was really good at borrowing money,” he says. In debt to the tune of $50 million, and with a long list of creditors circling, he decides to put it all on the line by investing $800,000 into another oil well.

It’s the most money he’s ever put on a well.

When they turned the well on for the first time, it screamed, spat, coughed, and then “it roared like Niagara Falls.” It was a gusher. Jerry Jones’ gamble had paid off—That single well netted him $100 million, and put him in the position to fulfill his ultimate dream of buying the Dallas Cowboys.

These are circumstances and financial stakes that few of us can relate to, or even fathom. But numbers aside, this is a story about the value of taking risks.

“In the roughly 4.5 million years since our ancestors came down from trees and started walking on two feet, progress has always been made as a result of two things: Work and risk,” writes copywriter George Tannenbaum in his blog AdAged.

Very few people are willing (or able) to gamble $800,000 on an oil well like Jerry Jones. But that doesn’t mean we’re not capable of taking risks, because risk is relative.

Maybe it’s sharing your art with the world.

Or cold calling a prospect.

Or moving interstate for a new job.

Or launching a business before you feel ready.

Or saying no, when everyone expects you to say yes.

Or speaking up in a meeting with a contradictory perspective.

Or hitting publish on a blog post you weren’t sure you should share.

How much or how little you risk isn’t the point. The point is you have something to lose, and you choose to do the thing anyway. Because when there’s something to lose, there’s something to work for.

And that’s how you make progress.

“Work and risk. They’re hard. They’re what I believe in,” writes George.

So do I.