Dallas Cowboys Legend Turned Entrepreneur Darren Woodson Has Four Cs He Lives By

Darren Woodson starts every day by putting his shoes on.

As a self-proclaimed “workout guy,” Woodson has to start every morning with some sort of physical activity. Even on Sundays. But every morning, he finds himself struggling through an internal battle to become motivated. So he forced himself to overcome.

Woodson rolls out of bed around 5:13 a.m. with no alarm—like clockwork, he says—and goes to the sink to wash his face and look in the mirror. Then he has to put his shoes on.

“No underwear, no shorts. Just shoes,” he said. “I have to pull the power to not get back in the bed. Period.”

And then he goes about his day, considering each small victory along the way a “win.”

That strict discipline isn’t that surprising considering Woodson’s background. Most people know Darren Woodson as the safety that spent his entire 12-year NFL career playing for the Dallas Cowboys.

Wearing No. 28, Woodson was part of three Super Bowl championship wins, five Pro Bowl selections, and 194 career games. At the time of his retirement, he was the Cowboys’ all-time leading tackler.

Woodson grew up in Phoenix, Arizona with a single mother who worked two jobs and raised four kids. At seven years old, he started to tell everyone around him he was going to be a professional football player (not necessarily for the Dallas Cowboys, though), and he achieved that goal with a strict mentality built on grit, hustle, and determination.

Woodson first found himself reflecting on his humble beginnings while sitting at the locker room. It was January 31, 1993, in Pasadena, California at Super Bowl XXVII.

Woodson found himself sitting on a stool in a room with 52 other men preparing to play the biggest game of his life at a ripe 21 years old. It was his dream come true. He was surrounded by football veterans; he was going over every single adjustment that needed to be made to win the game.

“I sit there looking at my teammates, the guys that have been battling with me since March… and all that doubt that I had when I was in the locker room is gone. I knew the preparation was there. I knew those 53 men were ready to go,” Woodson said. “It’s about today. It’s about this game, and if you’re ready. I am fully prepared for this moment both physically and mentally. It’s game time.”

Because in that moment, Woodson was thinking about his life—not the game.

“There’s so much anxiety, so much nervousness. 50 million people were about to tune in and watch that game. My family, my friends, everyone. It’s the focal point. It’s the Super Bowl,” he said. “And I found myself thinking about where I come from.”

Woodson thought about his mother, and what she used to instill in him and his siblings. He didn’t have a father figure, but his mom bred him with a taste for competition and motivation to make an impact on his own.

“She used to always tell us, ‘I’m not about just being content in life,'” he said. “‘I’m not just about being committed. I’m not just about being compliant.’ She said ‘I want to be compelled, I want to give and serve. I want to serve you and serve others.'”

Woodson today lives by that set of four Cs. He considers it a way to keep score—it keeps him on track to everything he wants to accomplish.

And though he knows there’s nothing he could do in corporate America that could take him back to that feeling at the Super Bowl, it is those heightened, climactic football moments that prepared him for how to overcome obstacles and be fully ready for what’s ahead.

“Here’s a little taste of Super Bowl Sunday for those of you who are too young or didn’t experience Super Bowl XXVII,” Woodson said. “We went on to win that game 52-17. It was one of the greatest experiences of my life. But that experience, and what I went through in the locker room, paved the way for the rest of my life.”

Woodson today has a pretty impressive resume that goes beyond being a local legend and sports hero (as if that wasn’t cool enough).

Though the transition from the NFL to a post-playing career is often labeled as difficult, he’s found consistent success. He joined ESPN as an NFL analyst in 2005; founded CounterFind, which provides turnkey brand protection software to sports, music, and entertainment brands, in 2015; and started at commercial real estate firm esrp in 2017.

Coincidentally, esrp is located at the Dallas Cowboys’ world headquarters at The Star in Frisco. As a partner, he helps with the firm’s overall vision, growth, and strategy, bringing “innate leadership skills and passion” to meet clients’ real estate needs. It’s, obviously, an extremely different path than what he used to be doing day-to-day at The Star.

But Woodson considers his football experience to be the primer for what he ultimately wanted to achieve.

“There’s certain things that you have to go through as an entrepreneur. There’s certain moments you have to go through in your life. When I started CounterFind, some of those same moments came back to me,” he said. “I had to reflect on where I came from, where I’ve been, and what I want to accomplish in my life. It was the same thought process of, I gotta grind.”

It all lies in discipline. Just being content and “having a job” after the NFL merely wasn’t an option. He knew he was going to get criticism moving from the football world to the tech world, but playing in front of millions of fans perfectly prepared him for that.

On and off the field, he’s always willing to “run through the fire” and be who he truly wants to be.

“For all entrepreneurs listening in, to the naysayers, the doubters, and the family members who said you can’t do it: Damn that. You can do it,” he said. “It’s on you. It’s all about your own work ethic. Don’t rely on everybody else. Rely on yourself and keep pushing through. That’s where I am today.”

Oh, and you can always start the day by putting your shoes on.