However, the decision to take the superintendent's job for Collinsville Community School District was not one Green took lightly.
"At this stage in my career, the grass isn't always greener," Green said.
Green, 58, signed a three-year contract at the Collinsville School Board's March 10 meeting. He will begin his tenure in Collinsville in July.
When the news began circulating in Greencastle, the Greencastle School Board was notified of Green's new position Friday afternoon.
"The hardest part about leaving is leaving people behind," Green said. "I'm going to miss the students, the staff, the community. Everybody's been so supportive of education."
The wheels on the decision had been turning for some time. Green had two interviews for the Collinsville job, and notified the Greencastle board when he knew the other district was seriously interested.
When Collinsville made him an offer, he still did not immediately accept.
"I said, 'I don't know. I'm going to need some time to think about it,'" Green said.
He then took four or five days to consider the decision, weighing the impact it would have both professionally and personally. Upon agreeing to take the job, he made sure not to delay Greencastle's search.
"Once they decided, I said, 'I do not want to hold up the process at Greencastle,'" Green said.
Green said in Collinsville he sees a larger, suburban district with a different set of challenges from Greencastle. While he did allow that the political climate for public schools is currently more favorable in Illinois than Indiana, he knows financial constraints are nationwide.
"Financially, times are tough for everybody," Green said. "Schools are not immune.
"However, (the Illinois) state government is not trying to start a charter schools system or a voucher system," he continued. "At times when things are tight, you take away money from public schools? I don't think that's right."
He said Indiana's attempts at education reform aren't entirely misguided, though.
"Do we need reforms? Yes, we do," Green said. "Not everything the state's doing here is negative, in my opinion."
On the local front, Green had glowing things to say about his nine years in Greencastle.
"I'm especially proud of the academic gains students have made. That's a result of the teachers, students and administrators working hard," he said.
He spoke specifically about the staff development program and the technological gains GCSC has made in nine years. The technology and building improvements have been achieved without raising taxes.
Green also expressed his confidence in the school board to find a replacement, saying he would be involved with the search in whatever way the board requests.
"I've been blessed here with a good school board and good school board members," Green said. "There hasn't been a single board member since I've been here who didn't put the students first."
The Greencastle School Board will begin the search for a new superintendent at its next meeting. The next regularly scheduled public meeting of the board is April 13 at 7:30 p.m. at Ridpath Primary School.