He remains in the hunt to make his Olympic dream become a reality. And if Kieran Woolley gets to Tokyo, it will cap one hell of a journey.
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The Minnamurra teenager has faced not one, but two major setbacks in the past couple of months.
The lengthy Olympic qualification process is gruelling enough and the 16-year-old is doing it while nursing two fractured wrists.
"I was competing over in Rio de Janeiro in an Olympic qualifier [STU Open] late last year and I fractured my left wrist in the warm up," Woolley said.
"I didn't even realise until two weeks ago, so it had been fractured at least four weeks. Three nights after I got the cast for my wrist, I broke my other wrist."
Despite the setbacks, Woolley showed few signs of pain on his way to a runner-up finish at the recent Australian Park Skateboarding Nationals in Gympie.
Woolley competed with two wrist braces on and said his mates told him that he "looked like a bandaged bear".
"I couldn't go as hard as I wanted to in the national championships because of the grabs and I was scared of falling off on them," he said.
"But I could still do some of my good stuff and I managed to get second - I was super stoked with that."
Woolley has returned to the Illawarra to enjoy some family time, but he continues to skate every day.
The next stop is the WS Lima Open in Peru in mid-March. And Woolley knows it's an important one.
Woolley sits in 25th place in his open men's skate park category. The qualification process began in early 2019 and the top 20 in his class go to Tokyo 2020.
"I'm looking pretty good right now," he said.
"I'm heading over to Peru next month and it's the first qualifier for this year. It will super good to see everyone and I'm working really hard to get ready and heal my wrists before the competition. I believe my left wrist will be healed and my right wrist should be fine - but we'll play it by time.
"Hopefully I keep doing well in the qualification events. If none get cancelled. I think there's five more events before Olympic qualification is finished.
"It would be such a big achievement for me to make it, I've worked so hard on it over the past couple of years. It's one of my dreams, it would be crazy."
It would be such a big achievement for me to make the Olympics. It's one of my dreams, it would be crazy.
- Kieran Woolley
And Woolley may not be the only family member to eyeing off the Olympics... one day. Younger brother Daniel is also showing great potential on a skate board.
The 12-year-old recently stepped up into the open men's street division and secured fourth places at both the Etnies Street Series round in Aura and the Queensland State Championship.
"My brother's been killing it," Woolley said.
"He's 12, turning 13 soon, and he's been up against professional skaters and doing insanely well. 'Danno's' been working really hard, I'm so proud of him."
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