He ended the 2013/14 season with Wealdstone but at the end of May came news that he'd signed for Heybridge Swifts to play for his mate Jody Brown, and it is friendship with Brown that has brought about all the other moves.
Brown left Swifts for Grays Athletic within five weeks of signing Little, and he did just that again, taking the former Claret with him. During the first half the season he was playing less but getting more into the coaching side and that led to his next move when Brown landed the Welling job in the week before Christmas.
Brown immediately took on Glen as his assistant manager but, alas, it was doomed to be a short lived move when Brown was sacked last week after just nine games in charge.
Things had got difficult at Welling and after a 1-0 defeat against Torquay Brown had words for the fans who were critical. "We lost 1-0 and the fans think it's my fault," he said.
"Fair enough, they've paid their money but we've lost to a goal when it's a five on two breakaway and, if they think that's down to me, that shows their level of football knowledge, I suppose."
The board reacted, claiming they had to act quickly which meant Brown was shown the door along with Little.
But, Glen has now gone back to Grays as player/coach, and this is a place where new manager Mark Bentley has having what can only be described as a positive effect.
They were losing 2-0 at half time last Wednesday against Hampton & Richmond, Bentley brought himself on as a substitute, leaving Little in charge on the touchline. The manager scored a goal and then had to go in goal himself when his goalkeeper was sent off. Once in goal he saved a penalty as his side came back to win 3-2.