The Clara man has known many highs and lows as a player with Offaly, and in management with Tyrrellspass, Westmeath and the Yeats County, but nothing could ever match success with his own.
Winning the Allianz Football League Division 4 final was a good start but Flanagan cannot get carried away when he his higher goals for the team.
Yet only seven months ago, he was plotting a second campaign with his charges in Connacht.
“I keep saying and I will always say that it was an extremely difficult decision to leave Sligo” says Flanagan.
“It was the biggest decision in football that I’ve ever made. I’ve never previously walked away from a team in my life. I found it very difficult to do so, but the lure of my own county was just too great.
“I’ve always been saying that Offaly football is better than where it has been in the last couple of years. I just want to be part of bringing it forward.
“My heart probably ruled my head to a certain degree because the Sligo people were exceptionally good to me.
“There were plans already in place for the following year, but when the question was asked of me about Offaly, I couldn’t turn it down.”
Flanagan’s influence has certainly been positive and the manner in which the forwards combined to rip table-toppers Longford to shreds at Croke Park certainly bodes well.
Although there was silverware bagged from that encounter, the return match in O’Connor Park on Saturday is by far the more relevant when it comes to gauging where the Faithful are according to Flanagan.
“Going forward, it’s the most important game we’re going to play for the development of the team for the next number of years and I just feel that we need to get a result.
“League football and championship football used to be completely different, but over the course of the years it has become a lot closer than it used to be.
“The likes of Dublin have won their third League in a row and they can make a natural progression on to championship level. I don’t think there’s as big a divide as there used to be, but having said that, there is something special about a championship.
“If you’re not prepared mentally and physically, you are going to suffer on the day and I think the mental side of it is our issue at this moment.
“We need to come down from where we were after the League final and be fully prepared for Saturday coming.”
The budgets in Offaly don’t extend to the employment of professionals to assist in this department.
“Unfortunately, the only psychologist they have is me, whether they like it or not. We can get a lot of stuff done in an on-field situation. There is a reality too in that we played quite well on the day, but Longford might have stepped off the mark with 10 or 15 minutes to go and that allowed us to build the scores that we did. The bottom line is that we are all focused totally on the fact that we need to win a championship match.
“We keep pointing out the fact that in the development of this team, and we’re talking about a two-to-three-year plan, this is a very important game.”