The former Fareham Town player fortunate enough to pick the brains of ex-Liverpool, Real Madrid and Chelsea boss Rafa Benitez and former Portsmouth and Millwall manager Kenny Jackett
He's picked the brains and observed Rafa Benitez’s training sessions of and was an occasional invited visitor to Pompey's training ground to get a close look at the workings of Kenny Jackett.
Both of which would have seemed improbable opportunities for former Fareham Town player Jaymee Highcock following his Aldershot release in 2007.
But would become a reality for the former Henry Cort Community College pupil, 32, whose forged a coaching rise through the unusual route of American university football.
Highcock, who was appointed Fairleigh Dickinson University assistant head coach last March, has built up a star-studded list of contacts from within the game across his 14 years in the States.
During a highly successful five-year spell as head coach of William Penn University men's and women's teams, he recruited former Newcastle and USA international DeAndre Yedlin's best friend.
It was through that move the 'best experience' of Highcock's life arrived as he had the chance to spend a couple of days getting a close look at the training methods of former Liverpool, Chelsea, Real Madrid and Inter Milan boss Benitez.
‘I became really good friends with DeAndre Yedlin,' said Highcock.
‘I stayed with DeAndre and went into Newcastle for a few days and I got to meet Rafa Benitez and all the staff.
‘It was the best experience of my life to meet Rafa and those guys.
‘Rafa was a top, top man, so nice and so friendly. Everyday he would call me into his office to have a chat - it was really good.
‘He told me all about his time at Real Madrid, completely open and honest, and sent me an email afterwards telling me to keep doing what I was doing in my career and that I was good.
‘He reached back out to me afterwards, it was really nice.
‘You learn more from being around Rafa Benitez for two days then any sort of coaching course.'
Highcock also struck up a friendship with ex-Pompey boss Jackett, having taken his UEFA licence courses with his son Ryan.
He regularly exchanges messages with Jackett and would visit the club's Roko training base when returning home from America to visit his father.
It's another opportunity Highcock is privileged he has been provided with. And it allowed him to build a relationship with other members of Pompey's coaching staff.
Speaking to The News prior to Jackett’s departure from Fratton Park, Highcock added: 'I’ve just become good friends with Kenny, I text him all the time and we speak.
'With my dad living in Fratton as well - I usually come home at Christmas or the summer, then go and spend time with Kenny and go in for training on the odd days.
‘He’s super helpful (Kenny), he is really invested in coaching the game and helping people.
‘He just opens the door, tells me what they’re working on, what they’re looking for and lets me into scouting reports and everything.
‘Kenny’s training sessions are always very detailed, he’s a super nice guy and I couldn’t speak highly enough of him.
‘I’ve formed a really good relationship with Portsmouth.
‘I’ve been really blessed.’