Instead, Sidebottom took a good, hard look at himself and lifted his standards to become one of Collingwood's finest players of the modern era.
"Maybe I was kind of drawn to the rat pack a little bit when I was younger," retiring star Sidebottom said on Friday.
"My upbringing - I was one of the boys, I have four older brothers, love to have a beer and I guess I probably struggled finding the right balance.
"I feel like I've always put everything into my footy but there were some things away from footy that I had to change."
Sidebottom believes meeting his wife Alisha was a turning point.
"I had to make some changes. I was a professional footballer - I wasn't a part-time footballer," Sidebottom said.
"I was just doing what was required. I wasn't going over and above.
"I was also in my early 20s, and there's a lot of distractions out there as well, and friends and family.
"My friends weren't doing the same as what I was doing - a few tradies back at Shep (Shepparton) - often I'd get sucked into going back home on the beers with them or whatever it was.
"But also, I think I wouldn't change anything as well. I've had such a great career and one that I'm proud of."
Sidebottom has played 373 AFL games - the second most in Collingwood history behind Scott Pendlebury.
The classy midfielder decided 2026 would be his last season before this year's Anzac Day match - a stage where he was twice best on ground.
Sidebottom wanted to expend his energy on enjoying football, rather than agonising over a decison.
"I've made the decision and now I can just give everything I've got for the last remaining games," he said.
A member of Collingwood's 2010 premiership side as a 19-year-old, Sidebottom kicked a famous goal late in the 2023 grand final to help seal the club's next flag.
He is daring to dream of a fairytale ending.
"Every team that I've ever run out on the field with I've always believed we can win and I think this group's no different," Sidebottom said.
"We've always got 23 out there, like everyone else. We're very well coached, and I believe that what we've got here's good enough."
That starts with Saturday's MCG blockbuster against high-flying Hawthorn.
"To be honest, I'm just looking forward to playing it," Sidebottom said.
"It's been a big week of all about me a little bit so it's nice to get on and worry about the team and play some footy."
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