Yet the Irishman believes that time spent in the lower leagues could prove to be an unlikely blessing in disguise.
Fenlon left Easter Road by mutual consent in November, chastened by poor form and a fanbase which revolted against him following a League Cup defeat by Hearts. He was replaced as manager by Terry Butcher, who was sacked at the end of last season as a consequence of relegation. Alan Stubbs is now at the helm in Leith.
The former Everton coach has rebuilt the coaching team at the club, while George Craig, Eddie May and Graeme Mathie have also been appointed to backroom roles. Fenlon believes that such a rate of change has been facilitated by relegation to the Championship.
"I was devastated for Hibs, I know the affect relegation can have on a club," said the 45-year-old, who has since become manager at Shamrock Rovers. "From where they were when I left, I could not see that happening. But they went on a run.
"It was disappointing for the supporters because they are fanatic. The other side of the coin is that it might not do any harm to be where they are, in relation to restructuring the club."