Just curious, was there ever a time when NHL players were actually holding down other jobs and playing/practicing at night? I suspect if yes, it was in the very nascent stages of organized league play?
During the pre-NHL days it was pretty common for players to have regular jobs and also play hockey. Their employers would make accomodations during the hockey season.
In 1907, Cyclone Taylor was lured to Ottawa by the promise of a civil service job, which was the beginning of his career with Canadian Immigration. He played pro hockey for more than a decade while working for Immigration.
Eddie Gerard signed with the Ottawa Senators in 1913, but only after being promised that he could keep his government job.
Frank Nighbor, who played until 1930, was a partner in an insurance business in Pembroke, ON during his hockey career. I would guess he focused on hockey during the season, with Pembroke being too far from Ottawa for a regular commute at the time.
Lionel Hitchman, a defenceman from the early days of the NHL, was an RCMP officer. When he joined the NHL, his career as a Mountie had to be confined to the off-season. Frank Boucher and Lorne Chabot were also members of the RMCP before joining the NHL, but did not continue with it after they became NHL players.
I think during the 1920s, as the NHL expanded into the US and the travel schedule became more demanding, hockey became basically a full-time job during the season. Players still frequently worked another job or had separate business interests during the offseason.
In the off-season former Penguin George Konik worked as an engineer in Minneapolis. He was a Flin Flon Bomber whose rights were owned by the Rangers. Realizing his chances of making it to the NHL were slim he accepted a scholarship at the University of Denver instead, and won three NCAA championships.
He played in the WHL for a time, and then finally played in the Rangers' system for a couple years before being traded to the Penguins in 1967. He got his first and only NHL experience when the league expanded.
After that one year with the Pens he was acquired in the Intra-League Draft (precursor to the Waiver Draft) by the Seals. Unhappy with their contract offer and the prospect of playing for the worst team in the league, he retired and went back to Minneapolis to work as an engineer full-time.
He later became a naturalized US citizen and played in the World Championships for Team USA.