Touted as a coaching prospect when the star quarterback retired in 2009, the 40-year-old is in his third season as offensive co-ordinator and his fifth year on the coaching staff of the Calgary Stampeders.
There are several reasons Dickenson is comfortable in a subordinate coaching role. He believes there's more he can learn about running an offence in the CFL and there's more to absorb from the vast experience of head coach and general manager John Hufnagel.
The Stampeders retained the same coaching staff and most of the starters from the team that reached the Grey Cup final in 2012, so Dickenson can continue to have a key role in what could be a successful team again.
He's also not ready to uproot his family from a city they love to advance his career. That said, Dickenson doesn't doubt his abilities to command an entire football team on the field.
"Personally, I think I'm ready," Dickenson said Thursday at McMahon Stadium. "I'm not worried about it, but I think I'm ready if it comes about.
"I'm not in a hurry to head coach. I like what we've got. I'm not as goal-oriented as a coach as I was as a player. I want to be with a staff, with an organization, with players who make my job fun and who feel like we can win."
The Stampeders host the B.C. Lions on Friday in a CFL pre-season game.
A Grey Cup winner with both the Stampeders (1998) and the Lions (2004, 2006), Dickenson still holds the CFL record for the highest pass completion percentage in a regular season (73.98 per cent).
He was named the CFL's most outstanding player in 2000 while a Stampeder and was also the most valuable player of the 2006 Grey Cup.
The business of sport, player or coach, is about achieving the next level and its championship in order to gain the next level and that championship.
So it seems counterintuitive that Dickenson, whose personal goal as a player was to be an NFL starter, isn't angling his way to a headliner job as quickly as he can.
"Lots of thing that are important to other people, aren't important to me," Dickenson explained. "Money and prestige aren't something I care about.
"I've got enough to live well. I want more enjoyment, a family type of atmosphere and I want success. I can get all three and then some here. That's why I like it.
"Definitely as a player, I wanted to go to a certain level. Here, head coach is the top level, but I feel it more revolves around winning as a team."
After living the nomadic life of a professional football player for 13 years, Dickenson says his wife Tammy has the final say in any prospective move. His two children are in elementary school.
"When I played, she said 'we'll go where you need to go,' Dickenson said. "I think it's fair to change that up."
After Dickenson interviewed for head coaching jobs with Hamilton and Saskatchewan in 2011, he and the Stampeders agreed to a two-year contract extension. Dickenson says he told Hufnagel then he would not look for another job during those two years.
That commitment ends after 2013. There will be off-season openings on the football coaching carousel and the Ottawa Redblacks will join the CFL next year.
Dickenson shrugs and says he's looking at the team in front of him and not at the horizon.
"I will say it's not like anyone has offered me a job as a head coach," he said. He then joked "I've interviewed and obviously not very well."
"I've also been pretty honest with those guys in that I really do like being in Calgary," Dickenson continued. "It would take a great situation for me to look elsewhere."
When the Lions released him in 2007, the University of Montana star returned to Calgary. Post-concussions symptoms forced Dickenson to announce his retirement in February, 2009.
Hufnagel wasted no time incorporating Dickenson into his staff. Dickenson coached Calgary's running backs that season and was named quarterbacks coach for 2010.
George Cortez's departure prior to the 2010 season left Hufnagel without an offensive co-ordinator. Dickenson was handed play-calling duties on game day, but not the title.
"I had a lot of confidence in Dave being able to handle the offensive co-ordinator position, but I didn't want to put that weight on his shoulders," Hufnagel recalled.
"I more or less just met with him every day and the staff, but I knew he was going to be an excellent play-caller and he grew from there."
Calgary's offence led the CFL in points, offensive yards, first downs and rushing yards in 2010. Quarterback Henry Burris was named the CFL's outstanding player.
Dickenson was officially named offensive co-ordinator in 2011 when the Stampeders tied for second in points and were second in first downs, net yards offence and net yards rushing.
Calgary ranked first in touchdowns and rushing touchdowns and second in several other offensive categories in 2012.
Dickenson has evolved from installing Calgary's offence and running it to countering what the opposing team's defensive co-ordinator is throwing at him.
"It's getting a better feel for how defensive coaches call a defence against myself as the offensive co-ordinator and play-caller and try to have some answers for that," he explained.
Dickenson is also arming himself with the skills he'd need as a head coach should that day arrive.
"I watch Huf pretty closely on how he organizes things in the day, when he's hard on guys, when he backs off on guys," Dickenson said.
"I've been very fortunate to work with a head coach who has basically done everything. He's kind of a path I'd kind of like to try to follow, maybe not the U.S. route as much, but a guy who is certainly a good mentor for me."