First, he will journey to Wellington to help lead the Caversham attack in its Chatham Cup quarterfinal against Wellington Olympic in the capital on Sunday.
That is going to be a key match but, following that, Jackson (22) has a week-long trial with the Wellington Phoenix, the country's only professional football team.
Jackson said it was undoubtedly going to be a big next few days.
''It is all I have been thinking about to be honest. Just what is up ahead. But I can't get too excited and have to remember just to play my natural game.''
Jackson returned in May to Dunedin after spending four years in the United States, attending Marshall University on a football scholarship.
The university is famous after a plane crash in 1970 wiped out its American football team.
Jackson played for the university's football side which played all around the country in the Conference USA competition.
He said the football was of a high standard and he had changed his game somewhat.
''I had to learn to adapt a lot. The game was just a lot more physical and you had to be on your game the whole time.
"You'd come up against these big, strong, bruising centrebacks that I wasn't used to.
''But I slowly got used to it. The assistant coach we had there really helped me a lot with tactically what to do.
''Most of the time I played up front although I had a few games in wider positions.''
The former Logan Park High School pupil graduated from the university with a degree in business and marketing. He has just started a job selling insurance for Combined Insurance.
Jackson had been keen to try to make it in the United States professionally in football but, as a foreign player, it was hard going with many established stars coming in from Europe to finish their careers in the Major League Soccer competition.
In something of a twist, his path to the Phoenix trial started in New York.
His agent bumped into a Phoenix representative in the Big Apple, showed him some tape of Jackson playing, and eventually it has led to the week-long trial.
But before then Jackson has the big match for his club team.
Caversham has made a habit of making it through to quarterfinals of the competition but then stumbling.
Jackson though is quietly confident the men from Tonga Park will still be in contention for silverware come Monday.
''They are not going to be easy but in some ways they may underestimate us a little bit. If we are strong at the beginning and get off to a good start then we will be right in it.''
Jackson has an English twang when he speaks and he actually hails from where football started.
He was born in Chester in northern England and lived in north Wales when he was little.
He moved to New Zealand when he was 13.
''My parents came out here for a holiday when I was about 9 or 10. They loved it so moved out here a few years later and have never looked back.''
He is a permanent resident of New Zealand but was in the United States when the rest of his family took part in a citizenship ceremony to become New Zealanders.
