Glenn Hoddle, Ruud Gullit and Gianluca Vialli. That is some trio of player-managers to learn your trade from.
Like his fellow former Chelsea team-mates, Frank Sinclair's move into football management may have come a bit quicker than he thought - or indeed wanted.
But although his introduction to the dual role has been far from smooth, the 41-year-old is relishing trying to steer Blue Square Bet North strugglers Colwyn Bay away from the relegation zone.
Sinclair, who is also still combining regular work as a pundit with his new role, told BBC Wales Sport. "I'm coping fine. I have an understanding chairman, and an understanding wife as well - which helps.
"It's hard work but I have had a good career and it's the right time for me to be stepping into a role like this.
"It's time-consuming but I am really enjoying it. I have a big challenge on my hands but I am just going to do my best to keep the club in the league."
The Bay finished in mid-table last season in their first campaign in the Blue Square Bet North, but they were a club in turmoil when Sinclair was appointed as Lee Williams' successor in early February.
Williams had only been in charge for four games, but had lost all four after replacing Jon Newby. Newby's exit had been prompted by a run of two wins in 10 games.
Sinclair's reign started brilliantly. Improved performances and a four-game unbeaten run lifted the gloom around the Welsh seaside resort.
And while he had the option of delving deep into his memory banks to tap into the tactical nous of Hoddle or the unpredictable flamboyance of Gullit, the reason for the initial upturn in fortunes was simple.
"It was about the spirit," he said. "We got the belief back in the players that we can achieve something and get out of the relegation zone.
"It was getting the spirit back in the changing rooms. We had missed that since Jon Newby got the sack that was the main thing I wanted to do.
"I have brought in better players and I have brought back players that care about the club. Fraser McLachlan and Danny Meadowcroft, and people like that who are Colwyn Bay through and through and I think that will help."
Since their bright start, the veteran defender has since found life a bit tougher.
Defeat in his fifth game in charge - 2-1 against a young Histon side - sparked a sequence of three consecutive defeats.
And although a much-improved display in Wednesday's 2-2 draw at mid-table Gloucester, has once again given renewed hope, the Bay remain deep in the mire.
Sinclair's side are four points behind Corby but have two games in hand on their main rivals.
The Welsh side also have two games in hand on Histon, but are a further four points behind them, with Stalybridge a further place and point ahead.
Sinclair will also be missing one of his key men for the half of the remaining games. Namely himself.
He scored Bay's second goal against Gloucester and was also on target in the loss to Histon. But his experience and pedigree have been vital keeping the club in touch this season.
However, a red card in the home defeat against Altrincham - his third of the season - means he must serve a five-game suspension.
But Sinclair remains confident.
His ban will at least give him the chance to co-ordinate from the touchline - not that he says he has struggled juggling playing and managing.
"I've not really found it a problem," he said. "I have always been a leader and a talker and have been a skipper at lots of the clubs I have been at.
"The main difference is making substitutions and tactical changes on the pitch, but sometimes it is an advantage as you see things differently when you are out there. It has worked in the past. The decisions I have made worked well at the start."
And Sinclair will seriously think about calling time on a 23-year career at the end of the season.
He will be taking his Uefa B coaching licence with an eight-day intensive course with the Welsh FA in the summer.
"I still feel fit and fresh but I'll see where we are," he said.
"The coaching is the next step but I have to earn the right to keep this job and for me to do that I need to keep the club up.
"We played some lovely stuff against Gloucester and, if we play like that for the rest of the season, I am sure we will stay up."