It's an incredible rise, one which Calum McFarlane himself describes as a "whirlwind".
He was not a professional player, and has never been a permanent manager before. But he worked his way diligently up through the grassroots game to the elite level - and now, again, he is Chelsea's caretaker manager following Liam Rosenior's sacking on Wednesday.
The 40-year-old will begin his second spell in temporary charge at the grandest surroundings - Wembley. McFarlane has only previously visited the ground as a spectator.
In his initial two-game spell in January, McFarlane replaced Enzo Maresca. His first senior match at the helm was a 1-1 draw at Manchester City, against Pep Guardiola, who took charge of his 1,012th match.
He takes over again at a time of pressure of Chelsea, on a run five league defeats which has pushed them out of Champions League contention.
In the background, there have been fan protests - the continuing tension highlighted by one of McFarlane's former grassroots clubs receiving abuse on social media since he was put in caretaker charge.
Having been promoted from Under-21s manager to first-team coach under Rosenior, McFarlane said he was "gutted" about this week's events. He could now get a six-game spell in charge if they reach the FA Cup final.
"It's a whirlwind, but what happens, happens," he said. "I know it's been tough recently but there's a lot of talent.
"Some of those players in there are some of the best players in the world for their position. There's still a belief within us. We can turn this around and get our season back on track."
The softly-spoken McFarlane is an enigma. He has only a small social media presence. He has established a successful football coaching career away from the limelight.
He grew up in Forest Hill, south London, and in his words, was a "failed footballer", who moved into youth coaching.
Alongside part-time roles at Crystal Palace and Fulham's academy, McFarlane started coaching Lambeth Tigers.
There were two boys from Norway at the club who just happened to be the sons of former Tromso player Thomas Hafstad.
"In 2012, I spent a year in London observing academies at different clubs in England," Hafstad, who played 260 games for the northernmost football club in the world, told BBC Sport.
"Instantly, I could see Calum was a very good coach. He listened to the players - young boys of 11 and 12 - and really understood how to work with them."
Hafstad, now Tromso technical director, said it was easy to see McFarlane "would be a great asset".
"Even then, he had a strong knowledge of the game, but what stood out most was his man‑management," he added.
Hafstad took McFarlane to Tromso, initially as as an Under-14s coach.
"He did very well in two years with us," said Hafstad.
"He moved up to coach the under‑19s and even took first-team sessions. At the time, we were in European competitions, so it was a strong period for the club.