The thing about the passing of the years is that you spend a heck of a lot of time worrying about turning a certain age before finally reaching that age and wishing you’d spent less time fretting about hitting that age in the ruddy first instance. As the great Ben Hogan once uttered: “as you walk down the fairway of life you must smell the roses, for you only get to play one round.”

Gordon Sherry has played a few rounds down the seasons but in his eventful, rich and varied sporting life, this gentle giant from Kilmarnock has no regrets. He was the alluring Ayrshireman tipped for superstardom, a 6ft 8" bundle of enthusiasm and golfing prowess who was, quite literally, going to be Scotland’s next big thing. It didn’t quite work out that way, of course, and the amount of words written about Sherry’s struggles in the professional game, following a shimmering amateur career, would fill the British Library.

It’s 20 years now since Sherry, as the reigning Amateur champion, played in the Masters of 1996. This time of the golfing season always stirs the senses. If you’re not meandering down Magnolia Lane, then you’re having a reflective waddle down memory lane. And Sherry has plenty of memorable moments to look back on. Life is for living, after all. It has ups, downs, twists, turns, birls and twirls and the words of his late coach, the celebrated, straight-talking swing guru Bob Torrance, still ring clear in Sherry’s mind. “The last time I went to see Bob before he died, in May 2014, he was really complimentary about me to the girl who was with him in the hospice,” reflected Sherry. “He was really struggling and I ended up breaking down and was in floods of tears. He said ‘ah think you’ll find it’s me who’s dying so why are you greetin’?’ But after that he said ‘anyway, you’ve still got the happiest days of your life ahead of you’. And that’s it. You can’t spend time looking back and regretting things. I look back at what I did as great experiences and you hope there are more to come.”

Sherry’s golfing experiences are bountiful and his Masters memories are as up-and-down as some of Augusta’s undulating fairways. His 1995 campaign was an annus mirabilis as he won the Amateur Championship, finished fourth in the Scottish Open, wooed golfing greats Jack Nicklaus and Tom Watson during a practice round for the Open and helped GB&I win the Walker Cup. By the time the Masters of 1996 came round, Sherry, like Augusta’s radiant azaleas, should have been ready to spring into life. It didn’t quite work out that way, of course. “I do a lot of key note speaking and a big part of it is telling people about my shambolic preparations for the Masters,” said Sherry. “I felt like Man United until I got on the first tee and I realised I was Killie. Augusta was my first competitive round of the year. It was insanity. I was being dragged and pulled by management companies and sponsors and the media. I was totally distracted. In hindsight I just wish I had someone to say ‘right, how do we prepare you to play next year because you’re turning pro and we have to get you ready’. The period of waiting to play at Augusta hindered me and it shouldn’t have. It should have been the opposite. It should have been great preparation for turning pro.”

Standing on that first tee on the Thursday, Sherry was given the kind of shuddering wake-up call usually reserved for army recruits in the barracks. “Fred Couples said to me ‘any good results recently?’ and that’s when it dawned on me. I realised I hadn’t played in any competitions that year. How did I feel? Well, my mum reads The Herald so I’d better not swear. Put it this way, it was terrifying but I went from nervous to raging in a second because the starter announced me as ‘on the tee from Scotland, England … Sherry Gordon.’

“I don’t remember swinging the club but somehow I nailed it down the middle. I only remember walking off the tee and my caddie, Turnberry George’ saying ‘you did well there’ and I said ‘what, not to kill anyone?’.”

He may have missed the cut with rounds of 78 and 77 but Sherry will forever cherish that Masters adventure. He’s had more of them. As manager to the 1988 Green Jacket winner, Sandy Lyle, he gets an access all areas pass to Augusta’s intriguing, intoxicating nooks and crannies. “Sandy was my hero,” said Sherry, who will turn 42 this Friday. “I still find it amazing that I’m working with him. People say ‘you must be disappointed how your career has turned out’ and I’m like ‘really’? When I played in the Masters, I should have been all over Sandy and said ‘can I be in your pocket for a week?’ I know that now. If Sandy would just knuckle down a wee bit more, sharpen up his short game and his putting he could clean up on the Champions Tour and could still do very well at the Masters. It’s very strange telling my idol to get a grip. It’s bizarre and Sandy probably just wants to say ‘oh go away Gordon and stop pestering me’. I just want him to do well.”

Keeping the company of greats is something Sherry is used to. It’s given him a nice keepsake too. His well-documented practice round with Nicklaus and Watson ahead of the 1995 Open at St Andrews, during which Sherry made a hole-in-one on the eighth, is seared on the memory.

“It was a dream-like scenario,” he said. “The ball I made the hole-in-one with is still in Kilmarnock and my mum and dad have hidden it so my dog doesn’t chew it up. I remember I got it out of the hole and I was about to throw it into the stand and Tom (Watson) said ‘don’t throw that ball, we’ll get Jack to sign it’. He was excited. I said ‘will you sign it too?’ and he said ‘yes, but get Jack to do it because he doesn’t sign golf balls’. I hadn’t seen Tom for a long, long time but at the 2011 Open I was last in the queue at one of his book signings. I got up to the table, he looked up and just started laughing. The first thing he said was ‘remember that practice round with Jack in 1995, what a day that was?’ It was fun for everybody and Tom was, and still is, a class act.”

Management, coaching, after dinner speaking, business consultancy, father of five and occasional golfer? It’s a pretty good gig. “And I’m going back to Augusta,” he added. “I’ll be on the range, in the clubhouse, following Sandy. It’s not exactly the end of the world is it? As Bob would say, ‘it’s better than digging the road’.”

That road may not have led to golfing superstardom but the journey has, and continues to be, extremely fulfilling.