After retiring from his playing career at Aston Villa, he was appointed assistant manager to Dean Smith at Villa Park.
The English legend left that role after three years and has yet to take the step up to a managerial position since.
Terry is now back at Chelsea, coaching in the academy, and continues to dream of managing the club, though he feels that may never come to fruition."I love coaching and after three years, I was ready to be a manager, so I came away and reset with the family,” Terry told Talksport.
"Then I had a couple of interviews and it was quite disappointing. In every interview I came away from they said ‘you have no experience as a number one’.
"I still have a dream, I'd love to go in at Chelsea one day.
"Does that happen without me doing the other levels? No, it probably doesn't. So, realistically, it's not going to happen for me.
"I'm comfortable with that, I'm happy, I've done all my badges, I'm ready. So if anything does ever come up and it's the right opportunity, I'll go in."