Five Stories of Failure—That Actually Led to Success

Roadtrip Nation
4 min readJan 21, 2020

“Everyone fails.”

“Don’t be afraid to fail!”

“Get to failing!!!”

Okay, so let’s say after hearing your mentors repeat these phrases until their faces turned blue, you finally listened: You took a chance, you went after one of your goals…and you failed. Now you’re at the bottom of the hole you’ve dug, looking back up like, “HEY, guysI did it! I tried! That was fun! Now throw me a line!”

After an epic failure, how do you pull yourself up by your bootstraps and turn your life around? Well…and hear us out here….sometimes you don’t. Sometimes, you just have to keep on digging until you eventually hit China.

Here are our five favorite examples of Roadtrip Nation leaders who encountered major failures, yet kept on pushing until they hit pay-dirt:

1. Jeff Adams, Paralympic gold medalist

The Gaffe: Going into the final turn of his first race at the 1992 Barcelona Paralympic Games, wheelchair racer Jeff Adams was in a breakaway with two other athletes. “This is it,” he thought. “Three medals, three of us…this is the best day of my life.”

Except that it wasn’t — Jeff hadn’t properly checked his wheelchair before the race, and as he approached the finish line, his right wheel broke.

The Gold: Jeff ditched his broken chair and limped through the rest of the race, finishing in last, but finishing nonetheless. It was a failure, yes, but it was also a study in perseverance — and a sign of things to come.

Four years later, he’d learned his lesson, put more time and care into his equipment, and brought two gold medals home from the Atlanta Games. Pretty sick souvenirs, if we do say ourselves.

2. Nicole Baldwin, founder, Biao Skincare

The Tank: Nicole Baldwin had the opportunity of a lifetime: After starting a small skincare business while serving in the U.S. Army, Nicole had attracted enough business and attention to win her a spot to pitch on the show “Shark Tank.”

But right before she was about to go onstage, she saw some images of herself from her deployment to Afghanistan. Suddenly, her mind went blank—a consequence of her then-undiagnosed PTSD. When she finally pulled herself together to pitch, all of the Sharks passed.

The Triumph: Nicole knew that no matter what, she still had the best skincare products on the market. So she refused to give up, and decided to tackle her PTSD and her dreams head-on. She took on another daunting task—entering MSNBC’s “Know Your Value” pitch competition for a 10,000 prize—but this time, she was upfront about her PTSD. She wanted to show other female veterans an example of someone who was trying her best to work through her trauma and take on life.

She won the prize.

3. Craig Brewer, director/screenwriter, Hustle and Flow

The Flop: In his first attempt to make “the great American movie,” director Craig Brewer ended up shooting $30,000 worth of film that was so bad, it never even saw the light of day. Literally, it’s still sitting undeveloped in storage somewhere.

The Flow: After coming dangerously close to giving up the dream, Brewer decided to reshoot the movie on an even smaller scale, using his home as his set and his family as his extras, capturing it all on a digital camera. The resulting film made a splash at a Hollywood festival, and helped him network with the big-shots who would later produce his breakout hit “Hustle and Flow.

4. David Neeleman, founder, jetBlue Airways

The Canning: In 1994, David Neeleman landed his “dream job” working under his idol at Southwest Airlines. Five months later, the CEO took David out to a nice steak lunch and personally fired him. Reason given: Neeleman had a habit of loudly and passionately informing his superiors of all the ways in which the airline could do better.

The Comeback: Because living a good life is the best revenge, David took all of that loud enthusiasm and put it into founding his own airline, jetBlue, which is now one of Southwest’s biggest competitors.

5. Dave McGillivray, director, Boston Marathon

The Collapse: Dave McGillivray didn’t just “not finish” his first attempt at the Boston Marathon — he literally collapsed at mile 16 and had to be taken to the hospital. After that catastrophe, he put in a ton of work over the following year, got himself in peak running form…and got the stomach flu the night before the race.

The Culmination: OH, you thought after all that hard work, the stomach flu was gonna keep Dave down? Nah— after nearly giving up at mile 21, he got a miraculous second wind, finished his first marathon, and was officially hooked on running. Not only did he continue his involvement with the Boston Marathon—he’s now the race director and has run the race every year since — but he also founded DMSE Sports, which has put on over 900 races and raised millions for causes he cares about.

For almost 20 years, Roadtrip Nation has been traveling the country to interview people who love what they do. Using their advice and guidance, we’re showing people everywhere that it’s possible to turn their interests into careers they’ll love, too.

Want to learn more? Check us out at!

A version of this story was originally published on the Roadtrip Nation blog.



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