Advice

Success lessons from underdogs

David and Goliath. Lyft vs. Uber. The Philadelphia Eagles vs. The New England Patriots. If the Super Bowl taught us anything, it’s that the guys with the fanciest jerseys and supermodel wives, don’t always win. Make no mistake about it though, the other guys don’t always win either, but there are lessons to be learned from the underdogs in the equation.

They try harder

Some years back I worked with a man whose nickname in the workplace was Avis (the fact that I worked in an environment where things felt as secretive as the CIA is a story for another time). He joked that while he was always the #2 guy on the totem pole, he was the one who always tried harder. Avis launched the classic “We try harder,” campaign back in 1962 when they were competing with the top rated rental company, Hertz. Their logic and messaging worked for decades. Some people don’t need the slick or top-rated, some people prefer great service or a personal touch.

“They have to work harder, so they know how to keep working,” said Rebecca Kiki Weingarten, AKA Coach Kiki, an executive coach and founder of Tradecraft Coaching in NYC. She’s also my sister, and I asked her to weigh in because she specializes in career shifts and transitions, and had mentioned that sometimes the top executives have a harder time shifting gears mid-career than the more average folks.

Coach Kiki said, “in business, underdogs have the gift of persistence. Even if they have a great success, they don’t keep hanging onto it or living off of it.” She also explained that by being persistent “you’ve shown that you have a thick skin. Nobody believed in you anyway, so you can come out of left field and own the room.

“You have the idea and everyone will tell you that it will never work, but you can also replicate it time and time again until it does.”

They have internal motivation

Many people mock the current trend of giving kids trophies simply for showing up. Coach Kiki put it into a business perspective — the underdog vs. the person who’s used to winning – whether or not they deserve it.

As for underdogs, “They have the grit and can withstand the frustration. Somebody who gets the trophy just for showing up, won’t know how to react when they don’t get the trophy. They wonder what happened and lose interest.

“The underdog isn’t doing it for the trophy. They find internal motivation and they’re going to keep showing up.”

They practice

Coach Kiki referenced Philadelphia Eagles tight end Zach Ertz, who had the game-winning touchdown at the Super Bowl, who kept talking about how the team’s greatest strength was the fact that they always practiced. “I mean, each and every day we go out there, we love to practice, and I think that’s the foundation of this team,” said Ertz. As Coach Kiki put it, the takeaway here is that “you have to keep working toward the next success. Someone who’s not an underdog doesn’t know how to deal with adversity as well.”

They keep going

How do you know when it’s time to quit? “If you have set an idea or parameters or milestones in advance, you’ll know when to give up. It’s a personal decision,” Coach Kiki said.

She also stressed that if it’s a philosophical thing or a justice issue, you’ll hopefully keep going. If your motivations are financial, on the other hand: “There are different things you have to believe in. I’m a firm fan of (the Winston Churchill quote) ‘Never ever give up if it’s important and certainly for the greater good.’ ”

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Rachel Weingarten is a marketing & brand strategist and president of 729.marketing. She's a pop culture and trends analyst who frequently writes about business and style and the business of style. Rachel's a sometimes professor, teaching personal branding on the graduate and undergraduate levels. She leads corporate seminars on topics including evolving communication and spirituality in the workplace. Rachel is also the author of three award winning non-fiction books.

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