"I was also MC-ing a show here," he said.
A couple of months later, he took a call from Mrs Jackson who floated the idea of him taking on the festival director's role.
"I was really excited because it was such a great event."
He had done about 18 months with the busking festival, which attracted about 250,000 people over 10 days - so knows about big crowds.
Part of that role had been spending three months of the year travelling overseas seeking and booking acts. While that sounded just fine, it was tough for his wife, Claudine, and two youngsters.
So, for Wairoa-born Mr Pickering the answer was easy - he accepted the job and prepared to move back to his home province. "Opportunities like this are rare and I'm really excited by it. We love Hawke's Bay and it's really great to be back."
He said the annual summer festival event was now a major national and international event and at the point where it needed careful strategy and direction.
The prospect of handling such an event was not daunting - "it is exciting - I love it".
He said one of the strengths of such festivals was the support of the community and he would be looking at getting locals involved more, as well as ways of getting more younger people involved.
Mr Pickering said while the groundwork and foundations for the Toyota Winter Festival were effectively all in place, he was working closely to put some "finishing touches" to it. He said the event would grow, with some facets of it likely to find their way into the summer event.
"And I'm under way on the 2017 festival now - I came in to a truckload of emails from people who have already booked accommodation and they want to know what is going to be on the programme."
He is also already looking at the 2018 event which will be the 30th anniversary.
He described events organisation as "slow-burning" as they came to fruition six months to a year after being sparked up.
As a teenager, back at Wairoa College, he got interested in the arts and performing through the late Judy Galvan and has both acted in and directed shows, and that is set to continue.
"I haven't done any acting since 2011 but I've already jumped into a show at Theatre Hawke's Bay in September."