400 Football League games later, however, Flynn will lead the Exiles to Crewe Alexandra at the weekend as their manager after the sacking of Graham Westley, albeit with the club teetering on the edge of being relegated back to non-league.
But the wilderness of the non-league scene is exactly where the lifelong association between Flynn and Newport begun.
Given a reprieve by manager Tim Harris and a chance with the first team after his youth team axing, Flynn also found employment as a postman.
Thanks to his form with the Exiles, a nickname earned rather than chosen after years spent out of the city as a reformed club without a home, Flynn impressed as a midfielder with an eye for goal. In the non-league pyramid at least, this postman did always deliver.
A switch to full time football was the dream, achieved with a transfer to Barry Town, a move that changed the course of Flynn's life.
There was to be no future in shelf stacking or letter delivering for Flynn after joining the full time Welsh Premier League side, as he went on to make over 400 Football League appearances for the likes of Gillingham, Wigan and Bradford City.
He returned to his first club and first love Newport County five years ago, helping to steer them to a promotion 25 years in the making.
Flynn was 'heartbroken' when the club released him as Terry Butcher axed 11 players, after Newport's millionaire chairman Les Scadding opted to walk away from the club.
He soon returned when the Supporters' Trust succeeded Scadding, working in various roles including as a club ambassador, in marketing, and as a first team coach.
He even found time to get in a few games for Welsh League third-tier side Undy, so it was no surprise this season when Flynn came out of retirement to help the beleaguered Exiles.
Flynn's career at County, and in football, was almost over before it started.
"I got kicked out of the youth team. The youth team manager Glyn Jones asked me what I had done at the weekend and I said I had played for Pill. He said 'I know, I saw in the local paper you scored a hat-trick.' So he kicked me out for breaking his rules," he recalls.
"I went away crying, it killed me. But the next day Tim Harris rang me and said 'come and train with the first team.' I had just started working as a postman and I had been stacking shelves in Tesco. so it was a relief.
"I earned a contract though and then a move to Barry, which meant I went full time.
"But I always looked out for Newport, for my entire career and I played over 400 games in the Football League.
"It was hard to leave the club and the city. I had to do it to better my career, to better my life."
Flynn, generally a bubbly and talkative character, struggles to express how he feels about his hometown club.
"It is really difficult to put it into words what it means to me, it is everything," he said.
"It is the togetherness of the city, the good days, the bad times, throughout the years. We have seen the fans of this club come together and drag it back to where it came from again.
"The enjoyment on children's faces when they come to games, seeing them being part of it and become the future fans of the coming years.
"The club for me is everything, it is a lot more than just football. And I think every fan around the country who supports their team will understand what I mean.
"I want my kids to see me do well for Newport, I am a Newport boy and seeing this club be successful is everything I want."
Flynn says the task of keeping Newport in the Football League is not impossible, even though they are 11 points adrift with just 12 games remaining.
"It is not impossible, it is going to be hard, it is going to be tough, I am not going to dress it up as something it isn't, but we will keep fighting," he said.
"We will keep going until the end as that is what the fans of this club deserve. The players will be under no illusion about what this means to the fans, to the club and to their careers. Nothing is impossible."
When Newport County threw a teenage Michael Flynn out of their youth academy for defying club rules, he feared he would spend his life doing his part time job, stacking shelves in the local supermarket.