How To Outbrave Yourself And 'Just Do It'

Jill Doupe, 66, (left) stands tall and uninjured in the ring. She flew to Mexico last January when she was 65 to pursue her boxing passion. This story is about potential. Video below.

By Ray Glier

Jill Doupe, 66, flew from her home in Kitchener, Ontario to San Miguel de Allende, Mexico last January and climbed into a boxing ring against a 38-year old woman. It was supposed to be a three-round bout, but Jill’s opponent wanted to end it fast.

The woman charged out of her corner at the opening bell. Doupe said the woman she only knew as Evelyn, “was fighting as if she was in a bar brawl.”

In the makeshift ring set up in the parking lot of a shopping center, Jill said she was back on her heels at first, then settled in defensively, and kept the woman from landing a staggering blow. There were some punches that glanced off Jill’s body and that is where the real trouble came into play.

Doupe (pronounced ‘Doop’) was fighting two opponents.

The woman named Evelyn and the ageism of the referee.

“The referee kept asking me in the first round ‘Are you okay? Are you okay?’,” Jill said. “I said ‘I’m fine, let’s go, I’m fine’.

“I think judges were being overly cautious because of my age and the age difference between me and her. Even if I was slightly hit they were concerned and that was annoying.”

Jill in red in the second round before the referee abruptly stops the fight. She is not injured and still moving well. Evelyn has lost her aggressiveness because of fatigue.

Doupe has been hitting a boxing bag for fitness since 2009 and sparring since 2021. She knew better than the judges how to handle herself in the ring. Jill works out at SydFit Health Centre, owned by Syd Vanderpool, a world super middleweight champion. When Vanderpool first saw her hit the bag he nicknamed her “Jill The Jackhammer”.

She didn’t get to show all the skills of Jill The Jackhammer in Mexico, which was a huge disappointment. Doupe let Evelyn punch herself out in the first round and the Mexican grew tired. Jill was beginning to set up punches and then the fight was halted in the second round by the fear Jill was too frail because of age.

“If they would have allowed us to get to the third round, I had a chance,” she said.

Before the fight, the promoter tried to talk Doupe and her coach, the boxer Nihal Grewal, into making it into an exhibition match. Jill refused and then the referee and judges took matters into their own hands.

“I came all the way to Mexico for a real fight. I did not want an exhibition match where there's no winner in an exhibition match,” Doupe said.

Jill is skeptical of the claim she is the oldest woman to box. She was there for the fun and challenge.

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This story is about a lot more than older people being disparaged.

It is about having the dynamism to get into boxing as a sport in your 60s. Boxing was a fitness activity for 12 years for Doupe. Then it became a proper sport when someone else got into the ring to trade punches. It was a complete immersion with professional coaching by Grewal on how to stand toe-to-toe with another fighter.

Boxing was Doupe’s brand, her culture, her showing off a personal orthodoxy of hard work.

For the rest of us, it showcases our potential for any activity. How many times have you discarded an idea for a new fitness hobby because you thought it impractical, or too rigorous? It's ok to leave the pocket.

“If you told me that I was going to be boxing and doing the things I'm doing today, I would never have believed you in a million years,” said Jill, whose main hobby before boxing was horseback riding. “Like anything else you start, you build on it slowly, and then you realize, gee, I can do this if I work at it. I can get there. 

“I love the whole process. That’s what people should embrace. To be good at anything and have fun, work at it.”

It’s scary right? Having somebody come at you with bad intentions is not how you want to spend retirement.

“It came from just building confidence slowly over the years,” Jill said of her fearlessness in the ring. “The more skills I learned and the more practicing we did, you definitely build up your confidence. And then I just got to a point where I was like, you know what, I really want to use this in the way it's meant to be used.

“I wanted to have an opponent across from me because it's so different than just hitting a bag, it's a totally different experience. I had all these skills in my pocket and I wanted to see if I can execute in a real situation.”

That’s it! Right? This is about a new experience. It doesn’t have to be boxing, or cliff diving. It can be a track & field event, or senior baseball, or ice hockey.

But you have to learn the ropes, so to speak.

“I didn't realize how technical boxing was until I started it, and then you really start to have an appreciation for how difficult it is,” Doupe said. “It's probably the hardest sport I've ever done in my life. There's just so much to do and the learning took a long time, like it's not something that happens overnight, because there's so many bits and pieces to put together.”

Did Doupe ever worry about a serious brain injury? This week, after all, is the 50th anniversary of The Thrilla In Manila and who knows how many brain cells were battered in that ruckus.

“That never really crossed my mind,” Jill said. “I guess it’s like someone getting in a race car, off they go, and they don't think about what could happen.”

Doupe didn’t have much time to think in Mexico when Evelyn came at her without form or function. Jill’s coaching kicked in immediately.

One of her fundamental defensive moves is to go into a "high guard”. She could hear Nihal shouting high guard from her corner.

“It is a good position to defend from as it just requires small, quick movements without leaving yourself too exposed anywhere because you try and sit as low as you can in your stance,” Doupe said.

There was some consolation. She was swarmed by autograph-seeking fans after the bout. The promoter had announced that she was the oldest person to ever make a debut fight (she was 65 at the time) and the crowd became delighted in the Canadian.

Jill is skeptical of the “oldest ever” claim, however, Boxing Canada Executive Director Christopher Lindsay told Josh Brown of the Waterloo Region Record he believes it is a Canadian record.

What's more, the promoter told her she was an example for women in Mexico who seldom get to act on their dreams.

Still, what would make Doupe happier is another bout. It is hard to find someone to fight in Masters boxing in Canada because opponents have to be within 10 years of age and within 10 pounds. At 66 that puts Jill on a whole level by herself.

So what explains her?

“It's about your mindset, you have to do it,” Doupe said. “People my age will make excuses. They'll say they don't have enough time. You know, they're just busy. They’re nervous they won't be as good as anybody else.

“I always say to them, ‘You know what, you have to start somewhere, and all you have to do is show up’.”

What’s wonderful about Geezer Jocks is that once you show up and come back, people will notice. Pretty soon you will wonder why you didn’t join the tribe earlier.

Jill is skeptical of the claim she is the oldest woman to box. She was there for the fun and challenge.

Jill on the bag at SydFit Health Centre.