Jackson was away with his wife at the time on a short break and AFC Wimbledon asked if he wanted to come for an interview upon his return.
The former midfielder had been left saddened by the way things had ended at Charlton, where he’d spent 12 years as a player, coach and manager, but the prospect of taking charge of the Dons intrigued him.
Within two weeks of leaving The Valley, he signed a contract at Wimbledon and now has set his sights on getting them straight out of League Two.
“There wasn’t loads of time to dwell and think about the past, the future,” Jackson tells Standard Sport. “I loved what was being said, what the chairman’s vision for the club was. It’s very aligned with my own ambitions and it seemed a really good fit.
“The whole Wimbledon story is a fairytale really and there’s an attraction from that story alone. After being relegated last season, the ambition is to bounce straight back and I am a young manager who is very ambitious myself.
“I feel like I’ve got a lot of unfulfilled ambition and energy at the minute. Everything fell into place and it just felt right coming here.”
Jackson was sacked by Charlton just six months after being given the job on a permanent basis. The club were 22nd in League One when he took over and he guided them to 13th.
“I knew it would end one day, but it wasn’t the way I obviously imagined it,” says Jackson. “It’s always difficult when it comes to an end, and quite sad.
“Having an affiliation that long with a club when it comes to an end it is quite sad and also [there’s] frustration that I didn’t get an opportunity that I deserved, in my opinion, to really put my stamp on it, perhaps get the help that I needed and the time that I needed to mould that club in my fashion.
“I’m quite sad about how it ended, but I look back on my career and time with the club with just complete pride and nothing but good memories about how it all went.
“I feel honoured to have played for them, captained the club, coached and then ultimately managed them. It will always be a special club to me.”
Jackson now, though, is looking to make his mark at Wimbledon and it has been a strange time for him. For the first time in over a decade he is ‘the new kid’ and spent the first few days laying out his philosophy to players.
“We barely spoke about football in that first meeting,” says Jackson. “Literally it was about what I expect from them, the standards that I expect and the respect they need to give me and each other.
“They are just the non-negotiables you need I think to have a good environment to work in. It’s about the basics of being good people and having good standards about yourself.
“You can have as many good players as you want but if you haven’t got that collective unity and that group ethic, that spirit, I don’t think you are really going to get anywhere.”
We need to make Plough Lane a fortress. I’d be a liar if I said my ambition wasn’t to win promotion
Jackson has implemented changes, improving the training facilities, tweaking the travel arrangements and altering players’ food after training.
“I am just trying to make the place feel and look more like an elite sporting environment,” he says. “There are certain things you don’t need millions of pounds to implement. They can be small things in your grasp - like training pitches and nutrition.”
Jackson hopes that will manifest itself on the pitch as a hard-working team who play attacking football. The 39-year-old grew up watching the famous ‘Crazy Gang’ and he wants the supporters to have a team they’re proud of.
“We will try and get the ball down and play. We want to be an energetic team that goes and gets after the opposition,” says Jackson.
“We want to play exciting football, especially in front of our crowd at home. If we are going to have any chance of success we need to tap into that environment we’ve got there.
“We need to make Plough Lane a fortress. I’d be a liar if I said my ambition wasn’t to win promotion.”