He never did return to his original plan.
The 39-year-old is the Stampeders offensive co-ordinator, and a man who's considered one of the brightest young minds in the Canadian Football League.
But while his job seems a million miles removed from a medical profession, he'll tell you it was only ever about football anyway.
"The reason I wanted to go to med school was to stay involved in football," Dickenson said. "I was hoping maybe be a team doctor. I thought that would be a pretty good job to have."
Dickenson's Stampeders will battle the Toronto Argonauts in Sunday's 100th Grey Cup, earning their spot with a victory over the Lions that many credited to the young coach and his ability to strategically pick apart the B.C. defence.
Now the former Stamps quarterback is being touted as the next CFL head coach, despite the fact he's very young in his coaching career.
"I love where I'm at, what I'm doing, honestly I don't really feel like it's in the super-near future," said Dickenson. "I'm not that concerned about it to tell you the truth. I was much more goal-oriented as a player. As a coach, my No. 1 priority is to be in a good situation and win football games and be happy.
"I'm not concerned about accolades or money, I'm really not," he added. "I want to be in a nice city, involved in an organization that I respect and that we're going to win a lot of games. You can check off all those with Calgary."
Dickenson interviewed for the Hamilton Tiger-Cats head coaching position this past off-season, but he said he went for the experience, and told Stampeders head coach John Hufnagel he wasn't going anywhere.
Dickenson starred for the University of Montana, where he was known as "Super Dave" and "The Legend of the Fall." He's one of just two players in the school's history to have his jersey retired.
He played five seasons for the Stampeders and won the CFL's most outstanding player award in 2000.
He played five seasons with B.C., winning MVP of the Grey Cup in 2006, before Hufnagel brought him back to Calgary for one final season before he retired from playing — and Hufnagel said Thursday, it was all part of his plan to make Dickenson into a coach.
"I knew how bright of a mind he possessed," Hufnagel said.
He originally worked with the running backs before being named quarterbacks coach and then in 2010, the team's offensive co-ordinator.
"I wanted Dave to be the play-caller, but I did not want him to have the responsibility of being the offensive co-ordinator, not that I didn't think he wouldn't be able to handle it, I didn't want the pressure on him," Hufnagel said. "If we struggled offensively, I wanted people to blame me, not Dave."
Dickenson said the move from player to coach was a smooth transition, and the added responsibility of being the offensive co-ordinator has sat easily on his shoulders.
The victory over B.C. that vaulted the Stamps into the Grey Cup felt "maybe not quite the same as a player, but it felt pretty darned good," Dickenson said, through his Montana accent that's as prominent as it was when he first arrived in Calgary.
"And I was very happy to wake up with no soreness the next morning. So it did feel really good," he added laughing.
Dickenson said his workload is greater than it was as a player — which will cut into his time to enjoy any Cup festivities.
"Been working a lot of hours, as a staff coming on the road it's difficult, basically you've really got to make sure the guys are prepared, and feel like you want to give them the best chance to win," he said. "As a coach, I don't know if I'll have the same chance to enjoy the Grey Cup, as a player I always took in as much as I could."
Dickenson's players have been praising the young coach at sessions with reporters this week. Running back Jon Cornish and quarterback Kevin Glenn talked about his competitiveness, receiver Nik Lewis spoke of his ability to relate to the players.
Dickenson, who graduated high school with a perfect 4.0 grade point average and earned a 3.84 average in his pre-med studies, said his approach to the profession comes from his parents, who were both teachers. His mom taught math and his dad taught history.
"I think (coaching) is just teaching. And you can't teach people the same. You have to decide how they learn and try to focus on what's best for that guy. I learned from my folks and that's basically how we grew up.
"Coaching to me isn't about yelling or degrading anybody. It's about finding a way for them to learn and figure out a way to do it together."
Both Hufnagel and Argos head coach Scott Milanovich were quarterbacks in their playing days as well, and Dickenson believes there's an insight to the CFL game that quarterbacks possess that makes them well-suited to coaching.
"You can only see certain things from behind centre, I do believe that," Dickenson said. "Nobody else is seeing the game from that vantage point. Since the quarterback handles the ball every play, I believe everything is generated from that position.
"I do think there is something about ... having an awareness, pressures you go through, a lot of people counting on you ... that can translate into coaching as well."
Dickenson's offence — ranked among the top in the league all season — will be matched up against a defence that you'd think he'd know well. Toronto's defensive co-ordinator Chris Jones coached in Calgary for four seasons before leaving for the Argos prior to this season.
"I just know he's very creative and he's not afraid to do anything," he said, on what to expect from Jones. "We'll both have some new stuff and it doesn't really matter what we call, it's whether our players can execute the thoughts, and whatever they see they've got to react to it.
"We certainly like our plays, I know they like their system. But it's still players win games, and coaches just don't get in the way."