07/17/2013 10:51 am ET Updated Dec 06, 2017

Woman Who Swore She'd Never Run Tackles the Ultimate Obstacle

LeeAnn Webster

One of the reasons I started my website is that I wanted a place for women to come together and dream. We women need to know that we don't have to hang on to an old dream that has stopped nurturing us -- that there is always time to start a new dream. This week's story is about a woman who gained 20 pounds after moving to a new city, and decided to make a change after seeing an unflattering photo of herself. LeeAnn signed up for an 11-mile obstacle course, and kicked her workout into high gear. She finished the race with flying colors, and has gone on to complete almost 50 races in all. You go girl! -- Marlo,

By Lori Weiss

Like many women, LeeAnn Webster was a yo-yo dieter. She'd taken off forty pounds in her 30s and managed to keep them off for a number of years, but when she found herself in a new city, surrounded by a new circle of friends -- her social life began to tip the scales.

"I was forty years old and I'd just moved from Los Angeles to Chicago," LeeAnn explained. "Chicago is such a friendly city, so I was socializing a lot. And there was a great pizza place right across from my apartment that was open until 5 AM. So I'd go out with my friends and come home to a neon sign with a $5 giant slice calling to me. It was kind of like being back in college. New city, new friends. I guess you could say I put on the freshman 15 plus five."

"But then I saw pictures of myself at The Kentucky Derby and I thought, 'Oh, no. I'm not going back there!'"

So LeeAnn decided to do something she'd never done before. She signed up for a race. And not just any race. LeeAnn committed to competing in Chicago's Men's Health Urbanathlon -- an 11 mile course with obstacles that included a ten foot military wall, giant tractor tires and the stairs at Soldier Field. And while her goal was simply to get back in shape -- the competitive course would end up taking her life in an entirely new direction.

"I thought the race was a good excuse to hire a trainer," she explained. "But I knew most of her clients were runners, so I told her in our first conversation, 'Listen sister, we have to get this weight off, but I am not a runner, so we're not going to run. And I'm not giving up beer, bacon and cheese.'"

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It Ain't Over: LeeAnn Webster

"But I had to get my heart rate up, so instead of running, she'd give me intervals to do on the treadmill. I had the treadmill on an incline of 15 and I was holding on for dear life. She kept telling me I had to let go and that I should just lower the incline and run for a minute -- that it wouldn't kill me. But I was pretty sure it would!"

In the meantime, LeeAnn's friend, who had signed up for the race with her, gently reminded her that the Urbanathlon course was eleven miles and that she really needed to think about the idea of running.

"I thought I could just meander through the obstacles," LeeAnn laughed. "I never considered myself an athlete. I remember somehow getting signed up for a softball league when I was eight or nine and being so nervous at practice that I would get stomach aches. And that was the end of my athletic career. But my friend convinced me to try a two mile run and I didn't die -- and that was really my goal. Although she says I was grunting a lot!"

That two-mile run gave LeeAnn the confidence to take the next step, which for her, was a five-mile run with her trainer. Once she saw what she was able to do -- and the weight beginning to melt away -- she began running three days a week. By race day, she'd set a personal record of nine miles.

"It took me two hours," she said with a smile, "but I felt like a frickin' rock star!"

LeeAnn was ready to take on just about any obstacle, which was good, because she had lots of them in front of her. It was an October day in Chicago, which meant the weather could easily go either way, and on this day, the temperature suddenly dropped to the low forties and there was the possibility of rain in the forecast.

"I have to admit, I felt that little girl with the stomach aches creeping in," LeeAnn recalled. "I had no racing experience and 70 percent of the participants were men. And I began to question what I'd gotten into, how long it would take me, and whether there would be beer at the end."

"The first obstacle involved these huge tractor tires that we had to climb over. That's when it occurred to me that maybe this was not the best choice for a first race. I was sure though that I was prepared for the monkey bars. I'd practiced with the kids at a local park! But then I fell off of them -- twice. The good news was, they let me do push-ups instead and I'm really good at push-ups."

As the race went on, the obstacles became more and more difficult and the woman who swore she'd never run, couldn't wait to get back on track.

"And then it started sleeting," she said. "We're like a quarter mile from the finish line and it's sleeting! It's muddy and it's gross and we still have to climb over a ten foot wall and taxi cabs!"

"But the moment we crossed that finish line, I knew I was a different woman. I have never felt more empowered or more proud. All these years, I thought I could be the funny one or the smart one, but I never thought I could be an athlete, and now I was. And I realized that if I could do this in one area of my life, it had to filter to others. That's when I began to wonder what else was possible."

In the four years since LeeAnn ran that first race, she has gone on to complete 44 more. She's taught herself how to swim and ride a bike competitively and competed in marathons and triathlons. On August 4th, she'll be competing in her first half Ironman competition. And she also began to look at the other obstacles in her life.

"It made me start to look at what I was doing professionally," LeeAnn said. "I was working in marketing for an international law firm. And I began to question whether that was what I wanted my life to be about. At the end of the day, I wanted to be able to say I inspired someone to do something different. So, I thought, if it seemed impossible to run two miles and now I'm running marathons, why can't it be possible to start my own business?"

And that business is now up and running -- literally running. LeeAnn has become a motivational coach -- challenging her clients to get out there and take that first step.

"You're not going to get up and run a marathon tomorrow, but you can run a 5K in a few months. You can begin with a block, then a quarter mile, then a half mile."

"What I've learned is that you can limit yourself by thinking you're only capable of so much. I never thought I could be an athlete, so I never tried to become one. But now I know that anything is possible. The worst thing is to live your life thinking, 'If I'd only tried.' The saddest thing is to wonder."

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