The former Leeds United and Aston Villa manager was speaking on Thursday's Off The Ball Roadshow
David O'Leary said his life as a manager was often "lonely" and admitted that working as an assistant coach never really prepared him to take the top job in management.
Speaking on Thursday's Off The Ball Roadshow in the Helix, the former Leeds United and Aston Villa boss said that his time as a manager was rewarding, but at times he found it difficult to cope with the isolation.
"I enjoyed it, I was used to pressure," he said. "But management can be very hard and the first thing that hits you is that you can be a good player, but it doesn't mean you're going to be a top manager.
"Where it first hits you is that first day when you get onto the training pitch. It's a lonely place as well and it's somewhere that you're tested. Loneliness in management, that's what it was all about."
He highlighted the fact that he spent some time as an assistant coach at Arsenal, but that it didn't full prepare him for life as manager.
"I remember working for George Graham, I couldn't believe he asked me to work as his number two, I learned so much from him.
"But nothing makes up for when you have to make the decisions. You can be doing that role for 20 years and still not be ready for it."
He also added that there was more of a learning curve at Aston Villa when he joined after having had so much success with Leeds United.
"I was told at Leeds that they wanted to me to be a coach and that there would be a board of directors that would look after everything financially.
"So I never attended the board meetings. Where I learned more about the off-the-field stuff was at Aston Villa. You had to go to the board if you wanted anything. I was so raw going into that first board meeting at Villa.
"You learn more about the other side and what you have to prepare. It was an easier role at Leeds because you only had to look after the football club."