Scotland will plays ten Tests this season starting against Argentina at Murrayfield on Saturday week and Gregor is closer than ever to pulling on a dark blue jersey at the age of 29.
And, having once been regarded as the one of the brightest stars of his generation, Gregor is determined to maximise his potential this time round.
"I don't want to be looking back at the age of 40 asking myself 'what if'?," said Gregor in today's edition of The Scotsman.
"I've grown up a lot since I left Watsonians [in 2000]. They were my first Premiership club and while it was a big step up I'd had it on a plate ever since I was a teenager graduating from Moray to Dundee High FPs. There I was able to trade on my size to get on teams.
"So far as Watsonians are concerned they meant a lot to me as I played under coaches Andrew Ker and Dave Cockburn to the extent of watching for their results each week on the internet while in Italy with Parma and Viadana.
"But for not progressing further I accept a lot of it was my fault in that I didn't apply myself. That changed with the five years in Italy where the style of play is a lot tighter which meant I had to commit myself more to being in the rucks and mauls and as a consequence of the extra discipline I felt I was ready to come back to Scotland this year when the opportunity arose."
Added Gregor: "I've picked up a lot of experience including from taking advantage of the ten-month Italian contracts to cram in a seven-a-side tournament programme in the USA to club rugby in Australia while I also had a spell of pro rugby league before leaving Scotland although recent times have been quieter.
"All the while that has meant learning opportunities including improved lines of running from League and now that coach Hugh Campbell has given me a chance of Scottish domestic rugby again at Glasgow I'm working especially hard on weights and in boosting fitness levels. I am absolutely chuffed to have been given a chance to measure myself against the players in the Scotland squad and if that goes a bit further then nobody would be prouder."
"That's the best guarantee I can give because while in Italy it was always in my mind that I dreamt of playing for Scotland although the closest I would get would be travelling to Rome for the Six Nations clashes when the home side latterly included Roland de Marigny, a former flat-mate.
"Always there was the thought that I was in a backwater so far as the Scottish team was concerned which is why I determined to make the most of any appearance for Glasgow having turned down offers to go to the English club scene instead." Gregor has come a long way from when he overlooked the football trials in his fresher year at Elgin Academy and instead received some life changing advice.
"My PE teacher recommended rugby since I did not know the football trials had taken place a week earlier and I took to the oval ball straightaway."
Football's loss could be Scottish rugby's gain...eventually.