Guy Whittingham was 24 when he exchanged the parade ground for the training ground and signed for Portsmouth.
But if Whittingham was a late arrival in the professional ranks, he soon made up for lost time.
Over the next 13 seasons, he scored 158 goals in almost 450 games for eight different clubs including Aston Villa, made his mark in the Premier League and appeared in two FA Cup semi-finals.
And now the man who was spotted by Pompey while playing for the British army in 1989 is passing on his knowledge to a new generation.
For in his role as the Professional Footballers' Association's regional coach for the south west, Whittingham is guiding youngsters at 15 clubs through their early coaching qualifications.
And the man who scored a record 42 goals for Pompey in the 1992-93 campaign also helps senior professionals along the road to more advanced coaching badges.
"Only 15 per cent of academy scholars will still be involved in league football at the age of 21," said Whittingham, 43. "So it's absolutely vital they have something to fall back on if they don't make the grade.
"At the end of the PFA course they will have a Level Two coaching badge which will enable them to coach in the community. We also help young professionals work towards Level Three and be qualified to coach in universities, colleges, schools and club academies.
"England's failure to qualify for Euro 2008 has highlighted the need for quality coaching at all levels so it's important that as many exprofessionals as possible are out there passing on their knowledge and experience."
Alongside his PFA coaching crusade, Whittingham keeps up to speed with Port-smouth's Premier League fortunes as a matchday summariser for BBC Radio Solent. He also features on the station's midweek phone-in.
But with Harry Redknapp's surprise package tucked in behind the Premiership's big four, pundit Whittingham is keeping his feet firmly on the ground.
"Even though we're fifth in the table there are fans out there who are moaning and groaning because we've drawn our last three league games at Fratton Park. They need a reality check!
"Pompey have made incredible strides over the last couple of years and if the new stadium goes ahead they will have the potential to develop even more but we're not ready to challenge the big boys yet."
Whittingham's two spells at Fratton Park sandwiched five years in the top flight with Aston Villa and Sheffield Wednesday and he wound down his career in 2001 after a spell with Wycombe.
Not bad going for a man who thought he had missed the boat as a teenager after playing a handful of games for Yeovil.
"I had trials with one or two clubs but nobody picked me up," he recalled. "So in 1982, I decided to give the army a go. I served in Germany for two years and started playing for the army team when I came back.
"Our coach tipped off Portsmouth and Alan Ball, the manager at the time, was keen - then he got the sack. But John Gregory came in and signed me."
The highlight was an FA Cup semi-final against Liverpool in 1992 when saw Portsmouth lost on penalties in a Villa Park replay.
"The first game was at Highbury," recalled Whittingham, who also had loan spells with Wolverhamprton Wanderers, Watford, Peterborough and Oxford.
"We drew 1-1 and I have a picture of Ronnie Whelan scoring the equaliser with the High-bury clock showing just two minutes to go. We were that close!
"Then nine years later I played for Lawrie Sanchez at Wycombe and reached another cup semi-final, also against Liverpool."
So near but so far - although Whittingham had better luck in his quest for life at the top when he joined Villa for £1.2 million a year after his first FA Cup near miss.
"Pompey will always be my club but I'll never forget that it was Villa who gave me a chance in the top flight.
"Until I went to Villa Park I never quite realised what a big club it is and the same applied to Sheffield Wednesday, where I had four marvellous years.
"At the time I could never imagine Wednesday dropping into League One.
"But at least they are back in the Championship now and hopefully it won't be too long before they are back where they belong."