Having followed in the footsteps of mentor Jose Mourinho at Porto to forge a reputation as one of the finest young bosses in world football, the Portuguese took the reins at Stamford Bridge at just 33 years of age.
He would last only nine months in that post before taking on another Premier League challenge across London at White Hart Lane.
Villas-Boas fared a little better with Spurs, making it through one full season before being moved on, but left English football aware that he had made several mistakes.
He told those in attendance at the WebSummit in Lisbon: “England was bad for me, I was not flexible in my ideas.
“I learned to be more flexible when I went from Chelsea to Tottenham. I always thought more in the long run without thinking in the short term.
“I was thinking about the future, but the results were irregular.”
Villas-Boas has since spent time in the dugout at Zenit St Petersburg and Shanghai SIPG, with the most recent of those spells coming to a close in November 2017.
He has moved into motor sport since then, taking part in the Dakar Rally, but still sees football forming part of his future – potentially in the Bundesliga, with Goal having revealed how he has previously been considered by Borussia Dortmund.
“I'm learning German now, it's a market that pleases me and I need to know the language,” he added.
Villas-Boas will be well prepared for any challenge he takes on, but he believes there is still a lot more that football could learn from other sports when it comes to preparing players for elite competition.
He said: “It does not happen in the US, the NBA or the NFL. The players spend eight hours in the centres.
“It was important to do the same in football - training in the morning, controlling nutrition, analysing opponents, for example.”