Chris Lakey attempted the Oxfam Trailwalker almost 10 years ago.
He has been carrying the weight of not finishing that trek for the years that have followed.
"I got to about 88 kilometres and my legs failed me," Mr Lakey said.
The Oxfam Trailwalker is a 100 kilometre event that starts at the serene Dandenong Police Paddock Reserve and ends at Heidelberg Park in Melbourne.
Teams of four people have 48 hours to travel together through the 100km of bush trails.
Oxfam Trailwalker spokesperson Anna Wemyss said the event is one of the most inspiring team challenges in the world.
"It's not a relay, teams have to start together, stick together and finish together - it's tough, but with the right training and attitude, teams are amazed with what they can achieve," Ms Wemyss said.
Mr Lakey's team, Team J Mac, features himself and three of his closest mates - Ashley, Chris and Mal.
The team name is an homage to another close mate, Justin.
"JMac was very keen to do the walk and we ran into his mum and she said he obviously forgot that it was his sister's wedding that day.
"He's a bit dispondent and he was super keen. He even got shoes for it, so we jokingly said we'd name the team after him," Mr Lakey said.
The 100km event takes place from March 27 to 29.
As Ms Wemyss alluded to, training is pivotal and it's something Team J Mac is well and truly in the swing of.
"Our biggest challenge is that we do all the right training.
"Having done it once before, it is a major, major strain on your body.
"We will have to sacrifice eight or nine hours per weekend from now on to get the training right," Mr Lakey said.
Team J Mac is hoping to raise $3000 for Oxfam, with money raised from all teams going towards Oxfam Australia's work to support communities living in poverty around the world.
An initial target of $1600 is set by Oxfam for teams to participate, which Team J Mac is close to raising.
Mr Lakey said all four team members, himself included, love a challenge.
"I want to conquer the ghosts of 10 years ago.
"One guy from footy is using this as a driving force to keep fit," Mr Lakey said.
"The fact that it is 100km and that we can push each other along is great."
Trailwalker events will be held in Melbourne, Brisbane and Sydney.
Oxfam is organising two more fundraising treks this year, one through Sri Lanka and the other along central Australia's spectacular Larapinta Trail.
"People who want to participate in these life-changing experience aim to raise $2500 each and have the opportunity to meet with the communities who are being empowered through this support," Ms Wemyss said.
Mr Lakey and Team J Mac are under no illusion that the challenge to complete the Melbourne Trailwalker is real.
"Your calves, hammys and everything else will be yelling at you.
"The four of us will need to pull each other along and you have to push through in the dark and cold and fight your inner demons.
"We are really looking forward to it," Mr Lakey said.
Team J Mac is planning to start their trek at 6am on Friday, 27 March and walk until 3am.
To donate to Team J Mac or learn more about the Trailwalker events, visit trailwalker.oxfam.org.au/my/team/35529