He has found solace in discovering that his career has lived longer in the memory of Dutch football, with the Scot unveiled as the manager of De Graafschap yesterday.
The 58-year-old has felt comfort in the embrace of that country before. His last job was as manager of Go Ahead Eagles in 2012 and Calderwood also spent 10 years as a player at Sparta Rotterdam, Willem II, Roda JC and SC Heracles.
That spell would make the Netherlands a home from home, a sentiment which only grew every time that he was overlooked for a post in his homeland. The latest was at Morton when the struggling SPFL Championship club instead appointed Kenny Shiels.
His reign at De Graafschap will begin in earnest on Monday with a league match against Jong PSV, the Eindhoven club's reserve side, as well as an attempt to gain promotion through the play-offs.
"I really am delighted to be back in football," said Calderwood. "When it's your whole life and you're sitting in the house for week upon week without a job it gets boring.
"When I stepped in at Go Ahead Eagles, I had to try and win the first six games. We did it and we got into the play-offs. People notice things like that and it's pleasing that they remember you."