Yesterday, Mr McGregor (61) retired from the National Bank, an organisation he joined in 1966 in Otautau after completing his school certificate and opting to enter the workforce.
"My father knew the bank manager so we thought we'd have a try," he said.
The punt paid off and he was taken on as branch junior - running errands, delivering mail, processing cheques and lighting the fire each morning.
He progressed to the teller's bench about a year later, then became a head teller in Invercargill in the early 1970s before taking on a series of executive roles at branches in Invercargill, Timaru, Christchurch and Queenstown, relocating each time on the bank's orders.
"In those days, they just told you where to go."
Positions Mr McGregor held included senior banking consultant, and head of international, ledger and lending departments. He moved to Wanaka in 1994 and became branch manager, until the bank was segmented into departments.
He has since served as personal banking manager, commercial banking manager and - his current role - business banking manager.
He has seen some "amazing" changes in his career, including the shift to decimal currency the year after he started and the introduction of computers.
While there was far more contact between staff before the bank was segmented in the late 1990s, there was still a "pretty special fraternity" among bank employees.
Mr McGregor never felt tempted to jump ship to another bank, and said a lot of his loyalty stemmed from the leadership of National Bank's former long-serving chief executive Sir John Anderson.
"He had no great ego, he had a real empathy with his staff and he surrounded himself with people who had that same philosophy."
The bank's "terrific culture" and care for its staff also "breeds a sense of loyalty", he said.
Mr McGregor was "quite contented" with his decision to call time on his career.
"The bank's been great to me; it's put me in some pretty special places ... I just feel the time is right to just relax for a few months."
He hoped to begin some voluntary work next year, and possibly some "completely different" part-time work as well.
He also planned to buy a bike and get fit, travel, devote time to his new role as president of the Wanaka District Club and take up bowls.
Mr McGregor has been sent off in style with multiple farewell celebrations involving current and former staff and clients.
He has not severed all ties with the National Bank, though.
His wife still works three days a week at the Wanaka branch and his daughter works for the bank in Invercargill.
