Last season, pre-season was a combined affair with the handful of reserve team players joining in with the first team preparations. Now, as well as his retained regulars, Colin is orchestrating a regime for the 11 former under-19 players that were retained by the club.
These promising youngsters will form the nucleas of Colin's squad for the coming season and Colin certainly enjoyed plotting a programme to get the boys in tip-top condition.
"I've got a little programme mapped out and I've enjoyed working through and deciding what we're going to do," smiled Colin.
"The proof of the pudding will be if, come the start of the season, they look physically fit. They might look it, but it's a case of lasting a game. That's what pre-season games are for though.
"During the next five weeks, as much as they're learning I'll be learning as well. I'll try to put into practice all I thought was good about pre-seasons I've done.
"The bad thing from their point of view is that I was always pretty fit and enjoyed pre-season. I enjoyed hard work and could be horribly cheerful throughout it..."
The Tottenham X1 side, which will comprise reserves and first team players, has four domestic friendlies lined up, plus a tournament in Jersey which features the likes of Manchester United and Barcelona.
Colin insists the young boys must be on top of their games in order to feature in these fixtures.
"We've got a couple of nice games. We're taking a team down to Cambridge and Southend, which one or two of the first team squad will be involved in as well.
"These boys should be pushing to get in that team and really test themselves. That's the first hurdle for them, to get themselves into a position where we say they are ready to go and play in front of a paying public against first team players and see how they get on."
Colin Calderwood is relishing the experience of planning and proceeding with his own pre-season programme with his now much-bolstered ranks.