The 27-year-old came through the youth ranks with the Scottish Premiership champions and made his debut in 2008, coming on as a late substitute during a game with Falkirk.
And while he featured against Barcelona in the Champions League later that same year, he failed to make much of an impression in the first-team as in just over two years with the club, he had made just three starts and 14 substitute appearances in the league for the Bhoys.
And he explained that after sensing that his chances would continue to be limited, he felt that the best thing for his career was to move on.
"I was in and out the Celtic team under Tony Mowbray and then Neil Lennon came in," he told the Evening Times.
"I spoke to him and he was quite keen for me to stay but it got to the stage where - and I was a Celtic fan and loved being at the club - I had to start being a footballer.
"I wanted to play football, I ended up going to Swindon and enjoyed a couple of years down there. I have never really looked back since.
"Plenty of folk would have said I'll stay at Celtic as a fan, it's a big club and you are well looked after, but I didn't want to be one of those guys who is 24 year old and has played 15 or 20 games."
After impressing for the Robins, he joined Birmingham City on loan in 2012. And he clearly did enough during the spell as the move was made permanent at the end of the campaign.
Since then, the utility player has made enough of an impression to make over 100 Championship appearances for the Blues, and his consistency helped him move into Gordon Strachan's thoughts, who handed him his international debut during Scotland's friendly with Czech Republic last week.
While he may have often doubted whether he made the right decision leaving Celtic Park, the fact that he has found regular first-team football elsewhere and has been given a chance for the national team would arguably vindicate his decision to part with his boyhood club.