As a prep player, Flanigan himself was on the receiving end of similar counsel from his father Jim Sr., a former linebacker who was drafted by the Packers in the third round of 1967.
"I learned so much about the game just by having the opportunity to be around all of those professional athletes," Flanigan said. "It was a wonderful experience to meet the Packers and to see firsthand their approach to football at that level."
As a homegrown Green Bay fan, Flanigan could be found more often than not spending his football Sundays sitting in the family section at Lambeau, decked from head to toe in Packer yellow and green.
"My father was on the team from 1967 through 1970. It was really exciting as the entire Green Bay area was involved in one way or another with the Packers. There was a tremendous spirit of community and of rallying around the team whether or not they were doing well on the field. And of course, the big games of the season for all those involved with the Packers were the times they played the Bears."
In fact, young Jim never viewed the Bears as anything but ‘the enemy' until he was an undergrad at Notre Dame.
"Because the school was so close to Chicago, quite a few of my friends there were Bears fans. They'd go in for the games, or at least have them on radio or TV. When Chris Zorich, who I knew, joined the Bears, I saw things in an entirely different light. Maybe that Chicago team wasn't so bad after all. But it was strange to be rooting for them when Chris was on the field."
Almost inevitably, the Bears selected Flanigan in the third round of 1994 draft. Although his family was thrilled that he would be joining the ranks of the pros, the specifics of where he was going caused considerably less excitement.
"It wasn't that my parents were upset that I was headed to Chicago, it was just that they'd hoped I'd sign with another team-like the Packers. I sort of chuckled when they had to come to those Bears-Packers games and root for Chicago for a change. Or I assume that's who they were cheering for."
Flanigan played 7 seasons (1994-2000) for the Bears, compiling 41 sacks over that span.
During his time in Chicago, Flanigan became involved in various business ventures and started his foundation as a way to give back to the community.
"It was rewarding on many levels," Flanigan said. "I was excited by all that such a large city had to offer. It was like nothing I'd ever experienced growing up. Northern Wisconsin doesn't have many major metropolitan areas or so many options for things to do with your time. I made a lot of friends and definitely enjoyed my years living there."
The Bears cut Flanigan in 2001 and he returned to Green Bay where he was glad to play for his hometown team.
"What goes around comes around, I guess. At last, my parents could go back to wearing green and gold," he said.
His time in Green Bay didn't last long, as the Packers cut him later that season. He latched on with the 49ers, where he remained until he retired in 2003.
"You get to a point in life where your focus changes. In my case, I just wanted to spend more time with my family. My wife was expecting and I felt that I wanted to be around the house more. I must admit that I really missed the competition, but you can find that in business as well, it's just in a different arena."
These days, Flanigan can be found scouting prospects, counseling recruits, and prowling the Combine. ‘It's a lot easier being there when you're not the one who has to work out.' He and his family live in Green Bay, not far from the senior Flanigan's residence.
"It's good to be home," Flanigan said. "I loved my time in Chicago. I made some great friends and had wonderful experiences. I wouldn't trade those years for anything. But when all's said and done, I was ready to head home and take things in a new direction. I'm lucky that my career is sports related so although I've left the game, it's really not that far away."