And for Harry Garside's next act, Olympic gold.
For the last 67 months, dating back to 2019, the Australian boxer has set himself a different challenge.
He's even overlapped them, the prolific social media user taking great pride in his "100 days of rejection" series that saw him ask awkward and inappropriate questions in public, deliberately aiming to be turned away.
The lightweight broke a 33-year Australian boxing medal drought when he claimed bronze in Tokyo.
He impressed out of the ring too, with painted nails and talk of wearing a dress to the opening ceremony sparking conversation.
Keen to challenge stereotypes and seek out the uncomfortable, Garside cut short his fledgling professional career to return to the amateur ranks and chase a historic gold in Paris.
"To come back and try and win that gold, that's really uncomfortable, right?" he said.
"So the 67th (challenge) is quite a simple one; it's coming to my second Olympic Games.
"I'm filled with excitement, but filled with heaps of nervousness.
"I could have just put my hat on that bronze medal and gone, 'yeah, I'm happy with that'.
"I'll always be the man in the arena and always put myself in the firing line."
The 27-year-old would undoubtedly draw crowds but hasn't committed to building on a 3-0 professional record after Paris.
Either way he'll continue to put himself out there, and have fun doing it.
"There's a quote I love: 'There's no evidence in this world to prove this life is serious'," he said.
"The Olympics; we love it but if you can just take back a bit of control in your life, have a bit of fun.
"I want to continue my sporting career being the best person I can be and then continue growing (in retirement), it's not a final product."
The boxing program, featuring a Games-best 12 Australians, begins at Roland Garros on Saturday.
Garside, fifth seed in the 63.5kg division, has a first-round bye before meeting Hungary's Richard Kovacs on Monday.
Super heavyweight Teremoana Teremoana also begins on Monday, slated to fight Ukrainian Dmytro Lovchynski before a potential second-round meeting with Uzbekistan's defending champion Bakhodir Jalolov.
In her second Games, medal hopeful and captain of Australia's 12-strong boxing team Caitlin Parker (75kg) begins her campaign on Wednesday against Mexico's Citalli Ortiz.
