It is part of what he describes as his "backwards" career path, one that has led him to the point of lining up against the Ibrox club in tomorrow's Ramsdens Cup Final at Easter Road.
In an era when anyone displaying a degree of talent is swept into a youth academy before they have even started shaving, Anderson's route to full-time football as a winger with Raith Rovers has been so varied that it almost induces twinges of nostalgia.
His meandering career has involved periods in Junior, amateur and part-time football, alongside studying for an engineering degree, working as a project manager, and a subsequent stint as a labourer. Unsurprisingly, it is a story worthy of further inspection.
A bright, articulate Glaswegian, Anderson was just 15 years old when he was signed by St Mungo's amateur team to play for their under-21 side. He would stay only a year before moving to Harmony Row, the storied Govan side that boasts Sir Alex Ferguson as its most famous patron. Anderson would put down roots there for the next five years, before moving to Junior football with Kirkintilloch Rob Roy. "They were the only team that showed any interest in me," he admits honestly. From there it was on to Stenhousemuir, until he got made redundant from his job as a project manager with an engineering firm, a move that led to him signing full-time - for less money - with Hamilton Academical.
"If I hadn't been made redundant, I'd probably have followed a completely different path," he adds. "Ronnie MacDonald [the former Hamilton chairman] was honest with me. He knew I'd been made redundant and said that's why they were offering me the deal. Effectively, I had to take a pay cut."
He lasted just a season at Hamilton - a period that included a return to Stenhousemuir on loan - before being let go in the summer of 2012. This time it was Raith who took a chance on him, the past two seasons seeing him finally establishing himself as a full-time player.
It seems a long way from the days when he was labouring for an electrical firm. "I appreciate being a full-time footballer," he adds. "My brother slags me. He's in the engineering trade as a QS [quantity surveyor]. He asks what I do and I say, 'Trained, had a bit of lunch and came home at 3pm'. He says that's terrible. But I do appreciate it. I've had to work for it.
"I was at Queen's Park when I was 13 and they never kept me on. Falkirk also said I was too small. I could have worked all the hours under the sun with the labouring, but this has worked out for me."
It is a far cry from the routes taken by most of the Rangers players who will line up against Anderson and his Raith team-mates tomorrow. "I'm sure they all came through the ranks at clubs and were bred into football," he adds. "That can work to their advantage - I never had a first touch when I joined Hamilton. That has developed over the years, doing it every day, but they are more comfortable on the ball than I would have been at their age. I never played pro-youth. I never played tidy, nice football. So I was used to the elbows and the pushing. I just got on with it. That probably helped me."
It was at Harmony Row that Anderson was first watched by Rangers fans, although probably not particularly attentively. The team used to play their matches on the artificial pitch in the shadow of the Ibrox main stand, the 1pm kick-off giving hundreds of loitering, early Rangers fans something to watch as they waited for the turnstiles to open for their own match.
"Our home pitch for a couple of seasons was the astroturf across from Ibrox," he recalled. "Then Sir Alex Ferguson gave us money and we moved to the pitches in behind Braehead. But to start with, I played all our home games in front of Ibrox.
"We would kick off earlier if Rangers were at home because of how busy it got, but you would still have a few hundred fans turning up early and watching some of our games. The guys were selling scarves, the burger vans were going and fans would watch us because there was nothing else to do.
"I could never have imagined back then that I would one day be playing against Rangers in a cup final. Never. I would look across at the stadium and imagine what it would be like to play on that pitch. Even playing at Ibrox empty in a charity game would have been great. This final isn't at Ibrox, but even then it will be a great experience in front of a full house.
"I thought the best it would get for me would be playing in front of 400 people against Auchinleck Talbot. But I've kicked on from my time in the Juniors and long may it continue."