It's impossible not to love Connor O'Leary. The humble Australian surfer has been an underdog for most of his career. Clawing his way onto the CT in 2017, he finished Rookie of the Year along with an impressive runner-up finish against Owen Wright at the Fiji Pro.
However, despite his breakout debut season, O'Leary has had his share of setbacks too. After falling off Tour in 2018 and failing to requalify he found himself back on the QS, starting over. Things were going well, with O'Leary on track to requalify heading to Europe when he suddenly lost his major sponsor.
"I just kind of had to wear it," O'Leary says. "It all ended up being about myself really. I had to think, ‘Ok this isn't about anyone else this is all on me now, and if you want to do it you gotta put your head down and finish it off.' And yeah, it motivated me to go alright, This is now or nothing."
Heading into Hawaii without a major sponsor to fall back on not only amplified the pressure to perform but also pushed O'Leary to examine his approach to competing at the CT level.
"I feel like falling off the year before and going back on the QS and starting from scratch again looking back on that again, to be honest, was a blessing in disguise in the sense of saying to myself, ‘I need to continue improving with my surfing, I need to keep evolving."
Hailing from Cronulla on Sydney's south side, O'Leary recently relocated permanently to Lennox Head on the North Coast of New South Wales after becoming engaged to a local girl and former Women's QS competitor, Stephanie Single.
The proximity to world-class waves, consistency of the area, along with his fiancé having grown up there were more than enough reasons for O'Leary to make the move north.
"There's a lot of options. In such a small town, there are so many places to surf so it keeps me surfing as much as I can every day. My trainer lives in Lennox [Head] and the High Performance Centre is just up the road. I'm accessible to a lot of great things up here."
Putting down roots in Lennox Head has been a welcomed distraction for O'Leary in 2020 as he along with the rest of the surfers on the CT have had to endure an unusual year. The COVID-19 pandemic has forced O'Leary to re-prioritise his goals and the time away from competition has allowed him to hone his equipment with long time Channel Islands Surfboards shaper, Matt Penn and educate himself on what boards work and why.
"With Matty Penn at Channel Islands who has been my shaper in Australia it's always been like, ‘these boards work, I've only got two weeks until the next event let's just stick to that.' Whereas now because there has been so much more time to play around with things it's like, ‘Ok what is the board going to go like if we do this or do that?' That's been really good to educate me to know more about my surfboards and what works for me and what doesn't. I've been trying to tweak things that I've been riding but more so to improve my boards and go to another level."
After fighting his way back onto the CT and off the back of an epic winter at home, his first in a decade, O'Leary is eager to head to Hawaii and pull on his competition jersey and compete once again and prove he deserves to be counted.
"I feel like there's a lot of times in my career where I haven't given myself enough opportunity and came in and gone, ‘Oh I should have done more of this.' So, I just want to give myself as much opportunity I can in every heat and go from there. Just to show everyone that when I surf freely and relax that's when I surf my best."